Recapping My Second "Month of Write" and Looking Ahead to a "Month of Read"

In February I conducted my first Month of Write and was very disappointed. In April I decided to take another crack at it quicker than I had initially planned in order to see if I could get the bad taste of February out of my mouth. Whereas in February I didn’t really have a plan other than “write more,” in April I specifically wanted to see myself get up at 6:00 AM everyday, sit down at my iPad or computer by 6:15, and write consistently from roughly 6:15 to roughly 7:30 (I originally intended to do 7:45 but quickly learned that that end time unnecessarily complicated my mornings).

As you might expect, April went much better than February.

First, a few objective stats:

• Words Written: 17,702 (compared to 6,500 in February)

• Days Written: 18 (compared to 13 in February)

• Published articles/newsletters: 7 (compared to 3 in February)

And now a few subjective reflections:

• I started really strong. The first week of this month I was an absolute machine. The routine felt incredible. I felt like a real writer. I was focused and energetic and just so goddamn writerly.

• Each week’s writing total went down. The second week was okay, the third week was spotty, and the last week was a travesty. 

• This decline was not super surprising. The first couple weeks of any new habit are always the easiest. It’s once the novelty starts to wear off that you really start to run into problems.

• I started to get distracted by work urgency as the month went on. I had several early morning meetings where it felt like I had to use the time I set aside for writing to prepare. I need to figure out a way to keep my intense job as constrained as possible into normal work hours.

• Even as my output tailed off across the month, I did a pretty good job getting up on time everyday. I would just sometimes get sucked into reading or looking at my phone or working on “regular work.”

• Finally, I started to wrap my arms around a large writing project in a way that I haven’t in a long, long, long time. I wrote around 7,000 words that I didn’t publish but I’m excited to keep nudging forward.

And a few more lessons (how is a “lesson” different from a “reflection”?):

• I created a process for daily writing that I’ve never used before but I really like. Basically, I create a separate file in Ulysses for each day. I then do all of that day’s writing in that sheet, regardless of the “type” of writing I’m doing. At the end of the writing session I can copy and paste what I created into it’s final resting space. For example, a typical day might contain a couple hundred words that are a journal entry that eventually lives in Day One, the first two thirds of an article I’m eventually going to publish on my website, and the beginning of an outline for an issue of The Deliberate. I’ll copy and paste these various chunks to the places they need to go but I’ll leave behind the “master” log of all the writing I do each day.

• It’s a really nice way to have a sense of progress since I can see each day’s note in the sidebar and see how many words I wrote.

• It lets me set myself up for the next day’s writing by ending each day’s writing session by creating tomorrow’s document and pre-populating it with my ideas or thoughts about what I could write about.

• The writing association with Tycho that I’m trying to build is slowly getting stronger. As I tailed off in my productivity last month I realized I had gotten sloppy with putting my headphones on and turning on Tycho as quickly as possible. 

I’m really looking forward to the day where I can make writing a larger part of my day job. The only way to do that, though, is to make writing a larger part of the rest of my life. Developing these skills and putting more of my ideas out into the world is what will allow me to eventually make that jump to more of a writing-focused career. The nice thing about my current writing routine, though, is that it’ll serve me just as well now as it will in this fictional future state where I can write all day. So, until then, if it’s between 6:15 and 7:30 in the Eastern American time zone then my butt should be planted in front of my desk, Tycho should be bumping in my ears, and I should be making words appear in Ulysses.

Month of Read

I have four Anchor Habits that I try to do everyday: exercise in some capacity, meditate, write something, and, most enjoyably, read something substantial. We’re now into May and I’ve given each of these habits (and writing twice!), except for reading, a month of their own. The time has finally come to rectify that. Welcome to the first Month of Read of 2020!

This month creates a bit of a conundrum for me. The basic idea was that although I try to do these four Anchor Habits in a minimal capacity everyday, I can be extremely hit or miss on them. I thought that by really focusing on one of them per month would help me get more consistent. And so far, that hypothesis has been right! However, I’m already incredibly consistent with my reading habit. As of this writing I’m rocking. A 62 day streak of having read at least 15 minutes per day. Reading is a part of my day that already feels like a reward and it’s pretty deeply baked into my daily routine.

So, what to do in a month where I’m supposed to really focus on it?

My initial inclination was to give myself a specific focus or restriction. Something like, I can only read fiction, or poetry, or I have to read something deliberately difficult, or read slower, etc. Something that would push me out of my normal comfort zone. However, for each of my other Focus Months where I was focusing on a habit for the first time, I kept it deliberately simple and basically just had the intention of, “Try to do the thing more than I normally would and see how you feel.” So, in the spirit of simplicity I’m going to do the same thing with this Month of Read. I’m just going to read as much as I can (which is kind of what I already do but I’m sure I can find some parts of my day where I could switch over from something low-quality, like browsing Twitter, to reading) and actually track the amount of time I spend reading in a time-based reading log (which is not something I normally do).

At the end of the month I’ll have a better sense of how much time I spend reading in a month where I’m really trying to spend as much time reading as possible. In the remaining two months of 2020 where I’ll focus on reading again, I’ll put some kind of variation or focus or restriction on the intention to make it more interesting.

Feel free to follow along in this Notion card to see how I’m doing during the month: https://www.notion.so/samspurlin/Read-as-much-as-I-can-every-day-3c855fdb064a43fa9e04577663543283

Carving Out Your Space to Contribute

Why do I sometimes feel ashamed of the stuff I like to read and write about? Is that shame trying to tell me something useful or is it keeping me from contributing valuable ideas to the world? 

Productivity Pornographer or Philosopher?

On the useful side of things, it’s definitely keeping me from participating in the “productivity porn” and “hustle porn” racket. There are definitely parts of my personality that are drawn to those topics in a way that I know isn’t helpful or healthy. I know that writing about productivity for the sake of productivity is not anything the world needs more of. There are too many people already hawking suspect productivity advice that papers over problematic views about the world and the role of work in our lives. I mean, I like reading and writing a good productivity hack as much as the next middle-aged white knowledge worker guy but that’s not exactly elevating the discourse about meaningful work. I like candy bars too but I’m not about to eat a candy bar only diet.

Speaking of elevating the discourse, I think that’s the other vector into my shame about what I feel drawn to write about. There are some folks who take an incredibly philosophical point of view and tone in writing about work and personal development that I find both admirable and completely unattainable with my writing and thinking ability. In my darker moments I look at someone writing and thinking at such a high level about this stuff that I feel like I shouldn't add anything if I can’t operate at that level. 

Considering I just articulated two ends of the same continuum, there’s obviously a lot of white space in the middle where I could probably feel pretty comfortable exploring. I know I’m not going to write absolute drivel about 10 productivity hacks to supercharge your productive productivity (even if I sneak a quick look at those articles from time to time...) and I’m not capable of writing a far-reaching philosophical treatise on the nature of work and the human condition. That doesn't mean those are my only two options, though.

Charting My Place in the Middle of the Continuum 

To stay away from the drivel end of the continuum, I think it helps to articulate that I specifically ascribe to a definition of productivity that’s broader than simply the amount of work you’re able to get done. It’s much more about overall meaningful engagement with the world — work or otherwise. It’s about feeling like an active agent in the world rather than a passive object. Anything from “tips and tricks” to life philosophies that help you feel more engaged with the world falls into the realm of productivity to me.

And on the other end of the continuum I don’t think it’s particularly helpful to keep the discourse around meaningful engagement with the world at the level that only philosophy professors can engage with. To the extent that I can use my experience in the academic world to bring those concepts and ideas down to a level that’s more digestible to the average person then I am providing a useful service. I’ve been out of the academic world long enough to know that what often passes as good writing in academia is utterly impenetrable to even very bright people and that making ideas accessible can be incredibly valuable.

As a reminder to myself and a public stake in the ground, these are the areas where I have something to contribute and I should be pushing myself to publish as much as possible on:

• Everything I’ve been thinking about with reformed workism and deliberate attention

• Everything I’ve learned about the reality of being an employee in an organization — legacy, self-managing, small, large, or otherwise

• The intersection of organization design and the individual experience of work

• The connection between using tools and software to make yourself a more effective agent in the world

• The remnants of my academic training in positive psychology and how it applies to individuals and organizations

• My own personal experiments/experiences with how I’m applying these concepts to my own life

Shame is the ultimate in unhelpful emotions when it comes to trying to make a positive impact on the world or do anything that remotely opens you up to potential rejection or judgment. For a long time I don’t think I really understood that a lot of my creative blockage was being caused by the shame I felt in either contributing to the anti-intellectual and unhelpful productivity hack genre or being unable to elevate my thinking and writing to the almost equally unhelpful “productivity philosopher” level. Now, I think I’m finally starting to realize that my advantage and gift is being able to explore much more of the continuum while staying away from either extreme end.

Shame and Comparison

In an effort to make this a little bit more generalizable and less navel-gazey, I have to imagine that this dynamic I just walked myself through is something that other folks experience, too. At its heart it’s a problem of comparison. The transparency of the internet has given us a much wider pool of people to compare ourselves to and believe it or not, there’s a lot of incredible people out there in the world. The most useful advice I’ve heard about this dynamic is that it’s profoundly unhelpful to compare your backstage to other people’s front stage. Meaning, you only have access to the polished final project that people project into the world (no messiness to be found anywhere!) whereas you're intimately familiar with all the personal discord that accompanies everything that you produce.

That’s why I love seeing “behind the scenes” content from the creators I really like. Show me your process. Help me understand that you don’t just crank out stuff that I adore with never ending productivity and effortless grace. Show me your struggle so that mine feels a little bit more normal.

Finally, the other piece of advice that I read somewhere a long time ago that sometimes soothes me in moments of uncertainty is that even if it seems like someone has already done what you’re trying to do, they haven’t done it in your voice. The writers and creators I follow most closely are not constantly sharing brand new ideas. Many of them cover well-trodden ground. However, it’s their voices and personalities that keep me coming back and interested in what they’re doing. That can be a difficult generosity to extend to ourselves but when I’m able to do so the quiet, doubting voice in my head is placated and I can actually focus on doing what I want to do.

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Personal development is an expedition, not an exercise in perfection

I don’t think personal development is an exercise in trying to reach some idealized state. Or at least, not some kind of universal idealized state that’s the same for everyone. I’m not interested in personal development because I’m trying to become more like somebody else who I think is admirable in some way. I’m interested in personal development because I’m trying to better understand and learn about myself. I believe that most of us only have visibility to a small sliver of our own personalities, capabilities, and general self-knowledge. Who “I am” is a bit of a black box, I think. I see the parts that are brought out of the shadows by the demands of my normal day-to-day life and the challenges I experience navigating it. But I get the sense that this is only a small portion — that there are parts of me that exist but I don’t regularly see or experience because they aren’t generally needed to navigate my normal life. I want to find those hidden parts. I want to understand those under utilized parts. And that’s why I pursue personal development. I want to see and understand and interact with the parts of me that are below the surface.

Or let’s try another metaphor on for size: an unmapped territory. The visible parts of me and my personality are like an extremely well-mapped neighborhood. There’s a ton of details on the map and it’s extremely precise. But as you get further from the center it starts to get a bit fuzzier. There aren’t as many road names and the features are more vague until eventually, once you get far enough away from that extremely well-mapped center, it simply shows fog and here be dragons. Personal development as I conceptualize it, then, is the systematic series of forays into that fog to update and add detail to the map that is me. It’s looking at that fuzzy map and the warning of dragons and asking, “Do there actually be dragons? Let’s see if we can find them.”

This is deliberately in contrast to a deficit view of personal development where I’m constantly trying to become better because I’m not enough. Or, because I’m not close enough to some sort of ideal person (or writer or athlete or consultant or whatever aspect of my identity isn’t feeling up to snuff at the moment). Approaching personal development from this angle is a qualitatively different, and I would argue less pleasant, experience. I’m certainly not immune from falling into this kind of comparative mindset. It’s easy to look at someone and immediately use them as some kind of measuring stick that almost always seems to find you wanting. That’s not a fun way to go through life and if you look at personal development through that lens I wouldn’t be surprised if it wouldn’t be attractive to you.

Limit work in progress in all the things — including your good intentions about yourself

But, let’s say that for whatever reason you’re already of the mind that personal development is an inherently rewarding experience and that being on a quest to better understand yourself is attractive to you. In my experience, one of the most difficult things about thinking this way is being overwhelmed by the options in front of you at any one time. And if your reading diet has as many non-fiction books in it as mine does you are constantly finding good ideas for things you’d potentially like to try. If you’re like most people, those ideas end up floating around in your head in some kind of liminal state for awhile until you eventually forget about them and go back to whatever your current default behaviors are. If your lucky, you might try something different long enough to slightly adjust your default behavior. If your like me, however, you’ll spend most of the time feeling like your failing at enacting new behaviors because you have too many in your head at once and no real clear commitments about what you told yourself you would do. 

Luckily, there’s a thought technology that comes from our understanding of how work flows through a system that I think is useful in this context, too: limiting work in progress. Somewhat counterintuitively, the most work in progress that exists in a system the less smoothly it flows through that system. By limiting yourself to less pieces of work in progress (with everything that still remains to be done waiting to be pulled from a backlog) you’re able to do much more than if you tried to do everything at once. This applies to personal development intentions, too. Trying to do everything at once is a recipe for frustration and for not actually changing much of anything.

A great tool for visualizing and limiting work in progress is a Kanban board. A kanban board is a simple tool for showing a list of work items sitting in a backlog, a list of work items currently being worked, and a list of work items that have been completed. These “work items” move from left to right through the system such that anybody can walk up to the board (or load it on their computer) and see the state of the system. They can see the work that’s yet left to be done, the work that’s currently happening, and everything that has already been accomplished. Why don’t we use this same idea for personal development endeavors, too?

What if instead of getting inspired by something you read in a book or article and immediately try to implement in your life (likely on top of whatever inspired you last week or the week before) you captured the idea and put it on a backlog? Then, on a regular cadence you could consult your backlog of ideas and promote a reasonable number to “active” status. As part of promoting something from the backlog you’ll also do some thinking up front to understand what it is you’re actually trying to do. Like a good scientist, you’ll have a hypothesis about what will happen and you’ll have a sense of what metrics you’ll need to look at to validate or invalidate your hypothesis. At the very least, you’ll know that on a certain date you will look at an experiment you were running and ask yourself a few questions like, “How did it go?,” “Did I learn anything about myself?,” “Does this tell me anything about what I should do next?”

That’s what I’m trying to create. An approach to help you capture, process, and implement personal development intentions so that you can come to better understand yourself over time. A system to help you keep from being overwhelmed with all the ideas you have about things you want to try or ways you think you could be “better” (however you want to define that word). By bringing some structure to this whole process I can spend more time and energy actually trying new things rather than trying to hold it all in my head. Holding it all in my head means I inevitably forget good ideas and almost guarantees that I feel badly about myself as I try to do a bunch of half-formed ideas/intentions at the same time — seeing very few of them to completion and generally feeling like I’m not doing “enough.”

Don’t (just) build habits, uncover insights about yourself

Over time, as I do more and more experiments/experiences I’ll occasionally shake loose an insight that helps me better understand myself. While these insights feel blindingly obvious when they occur to me, they’re also the type of thing that are likely to be forgotten faster than I would like. That’s why I want to capture them and keep them somewhere where I can regularly review them. This body of insights about myself and the world is my best articulation of who I am and a visual representation of my growing self-knowledge. It’s the map that I want to be adding more and more details to as I do more forays into the unknown.

The whole point of caring about personal development and doing experiments is to knock loose, uncover, craft, or otherwise get my arms around these key insights about how my brain works, what my personality is, why I think or believe the way I do, etc. These insights, then, can shine a powerful light on interesting paths to pursue in my personal development efforts. Which then creates new insights (or tweaks previous ones). The cycle continues. And because there’s no specific end point that I’m shooting for, no idealized state of perfection, I’m glad the cycle continues. The cycle itself is full of meaning and excitement.

Is finding joy in this cycle something that’s completely unique to me? Is it only interesting to a very small number of people who are similar to me? Or is it something that can be taught to anyone who has a little bit of curiosity about themselves and how they interact with the world? I honestly don’t know but this is the path of inquiry that I’m going to explore until I figure it out.

"Month of Sit" Recap & a Look at April

Is there a better time to try to develop a healthy meditation practice than during a global pandemic? 

My March focus for my Intensity/Simplicity theme was my meditation practice. As a reminder, I’ve decided to take each of my four daily habits (Read, Write, Move, and Sit) and focus on one at a time each month for all of 2020. January I focused on Move and tried to run a bunch. In February I focused on Write and tried to write a “shit ton.” March, then, has been focused on Sit.

Like with the other two months, I didn’t step into March 1st with a specific goal in mind. I figured for this first go around with each of the habits I would just try to see what it is like if I made a general intention to do each one “more.” In the case of January I think that worked pretty well. I definitely ran more than usual, at least. February was mostly a failure. I would put March somewhere between the two. As I sit here today on April 1st I see I have a 73% completion rate on actually sitting down and meditating every day. That comes out to 8 days missed out of 31. In February I missed 19 days so I definitely took a step in the right direction.

As part of this experiment I also re-read Mindfulness in Plain English to help ground me in what I was trying to do — and why. I did that in the first couple days of March with the vague intention I would read some other meditation-related books throughout the rest of the month but that never actually happened. I did re-subscribe to the Audio Dharma podcast and while I don’t listen to everything that shows up in that feed there’s usually at least one or two talks I’ll listen to each week. 

I did a combination of completely silent meditations using the app Enso as a timer and some guided meditations using Calm. The purist in me thinks the guided meditation craze ala Headspace or Calm or 10% Happier or Wake Up and the rest of the Relaxation as a Service companies is kind of a cop out and that you don’t “need” anything other than a place to sit and some quiet to meditate. However, in the absence of a teacher I do think I picked up a couple techniques via the guided meditations that helped. 

Finally, I had a vague intention to not only meditate “more than usual” but to find a place in my daily routine where it could become just an automatic part of my day. I played with a couple spots and I think I’ve landed on in the morning after I read/have coffee as my favorite timeslot with just before bedtime as a backup. I definitely learned that the later in the day it got before meditating the less likely I was to actually do it. 

Now, with all the arguably unimportant preliminaries out of the way, did I actually learn anything about myself by meditating more than usual this month? Honestly, no. But that’s okay. I have enough on-again off-again meditation experience to know that 30 days of extremely limited meditation (between 10 and 20 minutes a day) is not enough for anything to “happen” (to the extent that anything ever happens in meditation). I didn’t expect to become enlightened or have some kind of breakthrough — and I didn’t. I did notice that on days when I meditated I felt calmer and more in control of my emotions. I’m not sure if that’s a result of simply having done a thing I intended to do (I can get similar feelings from writing or reading or exercising) or was a result of the actual meditation experience itself. At the end of the day, it probably doesn’t matter.

April: Month of Write (Redux)

The nice thing about coming up with some kind of experiment or personal development program is that I get to make the rules. I had a general intention to spend the first four months of 2020 rotating through the four daily habits I mentioned earlier. Having done Move, Write, and Sit that would mean April is a Month of Read. However, I’m going to call an audible.

I’m still really annoyed about how poorly my Month of Write went in February, so I’m going to hold off on doing my first Month of Read and do another Month of Write instead. This time, though, I’m putting a little more structure into play. No more am I just going to vaguely try to “write more.” Instead, I’m specifically trying to sit at my desk and try to write from 6:15-7:45 AM everyday this month. The topic of the writing doesn’t really matter but the goal is to more or less keep my fingers moving for the vast majority of this time. Personal journaling and other stream of consciousness writing is what I’ll turn to if I’m not making any progress on an article for SamSpurlin.com or The Ready or The Deliberate or any other major writing project.

Basically, I’ve paid enough lip service to the idea of being a prolific writer and if I don’t figure out how to build it into my days, even though I have a very demanding day job, then I’m never going to figure it out. The day job may be demanding, but it’s flexible (and stands to benefit from my greater writing output, too). My life is also the simplest it’s ever going to be. It doesn’t necessarily get easier from here. I’m not married and I don’t have kids. If those things are in my future then it’s not like there’s some future writerly state where I’ll have more time or attention to dedicate to this. If I can’t lock in the practice now while I’m relatively free to do as I please then I’m worried I never will.

Along with the specificity of “sit at my desk from 6:15-7:45 AM everyday and try to write,” as a goal I’m putting in a bit more scaffolding to help me accomplish this.

First, I know my phone is the central character here who can foil my plans. If I look at email, Slack, Twitter, or Reddit before sitting down to write I’m much less likely to actually get it done. Therefore, part of my process is to not get my phone off its charger until after I’ve finished my morning writing session. The problem is that I generally use my phone as an alarm clock. However, with that setup I’m guaranteed to touch my phone mere seconds after I wake up; right when my willpower is lowest and I’m most likely to convince myself that looking at Twitter for a few minutes will “help me wake up.” The fix is simple enough, though. I bought an analog alarm clock so now I have no reason to touch my phone immediately upon waking.

Second, I can sometimes dilly-dally when it comes to making coffee in the morning. This is usually caused by getting lost in my phone but the resistance to getting up and actually making the coffee might be bidirectional with the phone problem. To that end, I’m making it as easy as possible to make coffee in the morning while still meeting my annoyingly high standards (fresh beans, pour-over or AeroPress) by filling the electric kettle the night before, putting beans in the hopper of the grinder, assembling the AeroPress or pour-over cone, and getting a mug out of the cupboard. It’s not much, but I’m hoping the fact that all I need to do is push a button and twist a knob to get hot coffee and prepped grounds will make it easier to actually get out of bed and to the kitchen.

Finally, I’m really taking seriously the idea that I can create an association with a specific type of music and a specific kind of work. I already listen to a ton of instrumental electronic music while I do other work and the band Tycho is my absolute favorite. When I sit down to write every morning I’m going to turn on my Tycho playlist and that’s the only thing I’m ever going to listen to while working (and I won’t listen to Tycho outside of these morning writing sessions, either). I’m hoping that I can get to the point where hearing a Tycho song immediately puts my brain into a state that’s particularly conducive to writing. 

I’ve been operating under this program for the last week of March and have been averaging somewhere between 2000 and 3000 words of fresh prose each morning — so the early returns are certainly promising! The trick, though, as with all monthlong experiments, is to keep this momentum going when getting up “early” and writing for 90 minutes is no longer the fun new thing and is instead “just a thing.” 

The End of My First "Month of Write"

Welp.

That didn’t seem to go very well.

My month of writing as much as humanly possible (actually, I guess I called it a “shit ton”) has come to an end and I can’t help but feel I mostly failed. Before the self-flagellation begins let’s start with the objective facts and then I’ll dive into a bit about what happened and what I think I learned.

This month I wrote approximately 6,000 words (plus whatever this article ends up being) spread across one issue of The Deliberate, one issue of Brave New Work Weekly, two published articles on Medium, and 10 journal entries. I did this writing spread across 13 days. The word output isn’t what’s getting me down — it’s the fact that I basically only managed to write for 50% of the days in a month where my primary focus was to write as much and as consistently as possible.

There were definitely some external factors at play that somehow didn’t manage to make their way into my daydreams about what this month was going to be like (funny how reality has a way nosing it’s way into everything). The past couple months have been perhaps the most hectic and stressful I’ve ever had while working at The Ready. I’m putting in far more hours than I want to be in order to make some (ostensibly) short-term projects successful. We’re expanding our scope at the client, I’ve been leading an initiative to work with external writers at The Ready, and my partner and I have been hiring and training a new member. I’ve also been on the road for much of the past month with trips to NYC, Charleston, SC, and Dallas, TX all happening in the past three weeks.

I don’t share these external forces as excuses. Only as useful context for understanding why it was difficult for me to accomplish what I had set out to do with this experiment.

I had hoped to build a set writing routine into my default day. Perhaps carving out an hour or so in the morning or maybe closing out my day with a strong writing session. I didn’t have strong feelings about when it happened, I just wanted to see myself prioritize writing every day. WIth a 50% completion rate that obviously didn’t really happen. I didn’t really stick with any specific time of day long enough to truly understand whether I could’ve made it work for me. I seem to find it difficult to write first thing in the morning but I’m so cognitively drained by the end of the day evening writing sessions don’t really happen either. It seems that the only way I’ll write as much as I think I could or should is if I bake it into the prime part of my day. Perhaps in calmer times that will be possible but when spinning as many plates as I was this month there was no way I was adding another plate without causing some catastrophic problems for myself.

It wasn’t 100% negative, though. One thing I learned over the past month was that I have an underdeveloped process — and respect — for the brainstorming, planning, researching phase of writing. Early on I wasn’t giving myself credit for days where I simply outlined a potential article or pulled together notes but I quickly realized that was stupid. Writing is more than sitting down and drafting prose and if I don’t give myself mental credit for doing the stuff that allows me to draft then I’m shooting myself in the foot for no good reason. Along with the mental permission to consider outlining/mind mapping a legitimate part of my writing process I also realized I don’t really have a robust process for taking an idea from a nugget to a fleshed out article.

My bailiwick is smallish ideas that can be captured in 1,000–2,000 words. A blog article, basically. I don’t want to just be a blog article writer, though. I want to be able to push an idea across many writing sessions and many rounds of revisions before I share it with the world. If everything I write has to be conceptualized and drafted over the course of one working session then I’m really putting a ceiling on the type, amount, and quality of the writing I can produce. I think I have a newfound respect for figuring out how to do all the work that surrounds a productive session of actually making prose appear on the screen.

In my remaining two “Months of Write” that I have in 2020 (tentatively scheduled for June and October) I have a couple ideas that I’m batting around.

1. Shooting for a specific word goal.

2. Working on one “piece” of writing the entire month.

3. Picking a specific part of my day and making the focus of the month the installation of a writing routine in that part of the day.

4. Forgoing all public writing for the month and just exploring ideas in complete privacy for a month.

While my guardrails for this month were deliberately broad and pretty vague, I’m wondering if I might benefit from some tighter constraints the next time around.

And while I didn’t hit 100% on this month’s aim of writing everyday I do feel like I learned some things about how I can become a better writer and I’m looking forward to taking another crack at it in a couple months.

I’m Sam and I write about time and attention at The Deliberate and help organizations become more adaptive at The Ready. I Tweet and post really mundane pictures on Instagram.

In February I'm Going to Write a Shit Ton

Month of Focus #1 is done and in the books. Over the course of January I focused on my daily habit of getting some sort of exercise. Specifically, I tried to walk and run as much as I could. It wasn’t a perfect month but I did manage to have a relatively high level of consistency and saw myself improve across a couple metrics.

Moving onto February I’m shifting my attention to a new daily habit, writing. I have long known that I am a better version of myself when I’m writing consistently. Of all the potential creative outlets I could do it’s definitely the one I’m most skilled at and derive the most satisfaction from doing. It acts as the best conduit I have for channeling diffuse feelings of unease or frustration or confusion into something more useful. Just as nobody has ever regretted going for a run or getting some exercise I’ve never regretted spending some time writing.

While the therapeutic benefits of writing are real and valuable enough to make it an important part of my daily routine on its own, writing has also been the cornerstone of nearly every good professional thing that has happened to me. Or at least many of the good things that have happened. I definitely got into grad school on the strength of my writing. I definitely got an interview at Undercurrent back in the day because I had a large body of writing to point to when my actual consulting experience was lacking. Most of the “big breaks” that have happened in the transformation projects I’ve worked on have happened after I sat down and wrote a heartfelt letter to the client about what was going on and what I thought we needed to do.

When I think about the evolution of my career I know that I want writing to play a larger role in it. I love the consulting work I do right now, but I’m not sure I’ll love it forever. I want to write books. I want to write articles for my own website and for magazines and for anywhere else where smart writing is regularly being published. I look at someone like Ben Thompson as both a professional and intellectual role model as someone who makes an independent living primarily off the strength of his writing.

Words are my friends and writing is a salve for my anxious mind.

And just like my real, flesh and blood friends, sometimes I don’t do enough to invite them into my life as much as I should.

So, here I am sitting down and saying that for the month of February I’m gonna write as much as I can. I’m not here to set a bunch of specific goals or make any grand pronouncements about what I will have produced at the end of the month. I just want to spend more time writing this month than I normally do. Just as I had some simple guardrails for last month’s experiment (try to run/walk a lot, everything counts, listen to your body and don’t get hurt you idiot) I need to develop some guardrails for this month:

• Write everyday — even a little bit

• Don’t worry about hitting a word count

• If you have extra time, energy, or attention, write

• Public writing is good

• Private writing is good too

• Try to do it early in the day but don’t be precious about it

That should help keep me on the straight and narrow, methinks.

And since this is a bit of a visioning/chartering exercise, let’s capture some hypotheses about how I think this month is going to go or what I might experience over the next few weeks:

• The first week is going to be fun and I’m gonna write all sorts of stuff that I end up sharing with all of you and feeling really proud and happy about it

• After the first week I will have exhausted all the really low hanging fruit that I was excited to write about and it’s going to start feeling like a pain in the rear

• I’m going to end up writing some really weird shit at some point

• Hopefully I’ll break myself out of the habit of only writing things that I can draft and edit in one working session and instead work on some stuff that takes longer to do

• At the end of the month I will have written more than I probably have in years and I will also be willing to move onto my next Focus Month

My plan is to keep adding to this Twitter thread with everything I publish over the next month. That’ll be an easy way to follow along if you’re curious about what a focused month of writing ends up looking like.

My name is Sam and I like words. I write them here and at The Deliberateand on Twitter. I also say them into a microphone on my podcast, Fields of Work.

Introducing Focus Months

My yearly theme is Intensity/Simplicity. I want to do intense things but I want to do them simply. I’m not interested in getting intense about details at the margins. I’m much more interested in marrying intensity with the essence of a thing.

As part of this intention I’ve decided to take my four Anchor Habits (daily writing, reading, exercise, and meditating) and focus on each of them for a month at a time. With four habits and twelve months in a year, I’ll have an opportunity to go deep with each of them three times in 2020 (yay math!)

The idea is that I’ll continue to do my three other daily habits at a consistent, yet minimal, basis while I use whatever extra attention/energy/motivation I might have to really go deep with the chosen habit. I have a couple ill-formed hypotheses I’m pretty sure I’m testing:

• Focusing on one intention for a month will help me uncover new levels of appreciation for it.

• The more interesting experiences lay below the surface (i.e. after you focus on it for longer than a day or even a week)

• Limiting the number of personal development decisions I need to make will leave more time and energy for actual personal development.

• Doing one thing for a month will mean I’m tired of that thing by the end of the month and will have lots of motivation and excitement to do the next thing.

That’s the plan.

January — The Month of Move

I decided to kick this experiment off by focusing on my daily exercise habit (or as I tend to call it, my Move habit). The basic idea was that I would try to run, walk, or otherwise exercise as much as I reasonably could throughout the month of January. I had a couple guardrails in place:

• Speed doesn’t matter.

• Walking counts.

• Consistency even over session-level intensity.

• Listen to your body — don’t get hurt you idiot.

So, what did I actually do?

• Walked or ran 52.79 miles

• Did an hour and 42 minutes of strength workouts

• Did just over an hour of yoga and foam rolling

• Played in 3 hockey games

• Had 7 “zero days” (where I did nothing)

In the middle of the month I got sick for a couple days, but surprisingly (stupidly?) still managed to go for a walk on each of those days. I only really got waylaid in my plans to workout consistently in the last week of the month when I had some really intense responsibilities at work. It wasn’t ideal to string together a series zero days right at the end of the month but if we consider February 1st to be an honorary member of January then I actually ended pretty strong.

Overall, I feel pretty good about this first foray into what I’ve now decided I’m going to call Focus Months.

Other than the work week from hell I was able to keep a pretty high level of consistency all month. Perhaps most surprisingly, I actually saw myself improve my running (objectively and subjectively) even across the relatively short timeframe of a month. I started looking forward to my runs and even managed to go for significant stretches where I wasn’t hating every step.

One of the things I’m keeping an eye on during these Focus Months is whether focusing on one specific habit or area of personal development might have impacts on other parts of the complex system that is me and my life. I noticed I had an easier time being more mindful of my eating (in both food choice, portion size, and consistency of tracking) than usual. Knowing that I wanted to workout more than I normally do made it easier to put somewhat better fuel in my body on a consistent basis. I’m guessing each type of focus will have somewhat unexpected spillover effects with other parts of my life.

I’m going to chalk up this month as a success and put my focus toward my next Focus Month, writing.

I’m Sam. I write about attention at The Deliberate and I help organizations at The Ready. I help nobody on Twitter.

How to Engage With an Overwhelming World

What’s the best way to navigate a world of infinite information? Should we manually create highly curated informational ecosystems for ourselves or should we dip in and out of the overwhelming stream while trusting algorithms to surface the interesting, relevant, and necessary? Is there a clear best answer for everyone or is it a matter of personal taste? Does it hold true across all types of information, or can you vacillate between these two approaches depending on the source?

When thinking about different ways to engage with the world I think you can plot them on a 2x2 graph where the two axes are Algorithmic Curation to Human Curation and Few Sources to Many Sources. The Algorithm/Human axis describes the way in which you decide what to engage with. On the Algorithm end of the continuum you’re relying on recommendation algorithms to learn your preferences and serve up the most relevant and interesting content automatically. These are things like following people Twitter recommends to you, using the first-party Twitter app with it’s algorithmic (rather than chronological) timeline, and letting YouTube recommend the next video you should watch. On the Human end of that continuum you have the individual practice of deciding what to engage with and how. This is things like using a third party Twitter app (like Tweetbot) that allows for a purely chronological timeline, being extremely selective about who you follow, and having only a set number of news sources that you turn to for information (like a home delivered newspaper or a specific magazine).

The other axis describes the amount of informational sources you will consider when designing your informational ecosystem. Folks on that end of the continuum are simply interacting with very few sources of information whereas folks on the other end of the continuum tend to surround themselves with many different sources of information or interaction.

You can then take the 2x2 chart and describe each of the quadrants: The Surfer (Algorithmic & Many Sources), The Minimalist (Human Curated & Few Sources), The Uninformed (Algorithmic & Few Sources) and The Overwhelmed (Human Curated & Many Sources).

To better understand to more interesting Minimalist and Surfer approaches, let’s take a quick detour into The Uninformed and The Overwhelmed, first.

The Uninformed

The Uninformed has the mindset of The Minimalist but the approach of The Surfer. They have a small number of sources that they don’t ever really engage with and haven’t really curated. They mostly go through the world without really thinking about the informational ecosystem around them and without having ever made deliberate decisions about what to pay attention to and what not to.

The Overwhelmed

On the other hand, The Overwhelmed is interested in many different sources of information but they try to engage with them on a purely human curation level. Meaning, they probably spend most of their time being distracted and deathly afraid of FOMO. They don’t want to miss out on anything so they are constantly engaging with everything all the time to make sure nothing slips through the cracks. It looks manic and desperate and is a guaranteed path to burnout.

The Minimalist

The Minimalist practices extreme curation around the information she lets into her life. She’s generally not interested in having algorithms provide recommendation or curation. It’s all about reducing the sources of information as much as possible and keeping the vast majority of the noise outside of her well-curated cocoon. It’s all about engaging deeper with fewer things and doing everything within her power to not be distracted by anything new and shiny. Occasionally a new source of information may wiggle its way into her consciousness, but that is a relatively rare occurrence.

This approach gives you an intense sense of control. Since your informational ecosystem is so limited it’s easy to feel like you’re “caught up” or “up to date” (as long as you don’t think too much about all the potential sources of information that aren’t part of your system). Distractions tend to be fewer and infrequent which allows for a narrower or deeper appreciation for the sources of information and topics you follow (e.g. reading The Economist from cover-to-cover versus browsing your Twitter timeline).

On the other hand, though, it can be surprisingly easy to get obsessive about curation. Since the larger informational ecosystem is outside of your control you’re constantly having to re-evaluate whether something new could or should become part of your limited suite of information. Additionally, even if you only follow a select few sources of information it can be surprisingly easy to get overwhelmed (how many people have died under the ongoing crush of a single New Yorker subscription?)

The Minimalist approach often means forgoing the potential for new connections (both in terms of people and ideas). It’s not about looking widely at all the available sources of information or potential connections. It’s about figuring out the bare minimum of information you need to get by and then basically ignoring everything else.

The Surfer

The other approach to navigating our overwhelming world of potential information is to embrace the immensity of the situation and deliberately “surf” along the top of it. The Surfer embraces algorithms as the best way to surface relevant and interesting information. He may follow thousands of people on Twitter or Instagram but doesn’t worry about being any sort of “completionist.” They dip into the stream from time to time as the situation dictates it.

The Surfer commits to nothing. Everything is potentially available to him and he trusts the algorithms and AI to show it to him at the right time, regardless of the source. He wouldn’t subscribe to The Economist, but he would read an article from The Economist that someone recommended on Twitter or showed up in Apple News.

This approach has less overhead than the Minimalist. He doesn’t have to spend time evaluating and vetting and testing various sources for inclusion into his highly curated life. He just has to occasionally push the Like/Dislike, Thumbs Up/Thumbs Down buttons to feed the algorithms along the way. He’s constantly being exposed to new things (well, within the confines of his specific filter bubble) and can more easily make new connections between ideas and people.

The Surfer, however, is at extreme risk of getting distracted and sucked into unproductive uses of time. The algorithms he trusts to elevate the relevant and interesting can often easily overcome his willpower. The services who provide and design these algorithms are not interested in giving him just the right of information and sending him on his way. They want to consume as much of his attention as possible and will do anything to get it.

In addition to a real sense of “playing with fire” The Surfer is at risk of creating a filter bubble around himself. The algorithms that are trying to extract as much of his attention as possible aren’t interested in showing him things that might turn him off or cause him to do something else. The Minimalist, on the other hand, can deliberately choose to incorporate sources of information that run counter to her general inclinations or beliefs in an effort to have a more well-rounded view of the world.

I’ve tried to write about both of these approaches in a very even-handed way because I actually think both can be incredibly valid ways of interacting with the world. They each have pros and cons (probably more than I’ve described above) and they both can be used productively and successfully. If that’s the case, though, how do you choose which one is best for you?

I’ve found myself vacillating between the Minimalist and Surfer approaches over the past few weeks and I’m planning on diving deep into the pros and cons of each of these approaches in future articles. In the meantime, though, I’m curious about how you think about creating your informational ecosystem. Is this framework interesting? What would you like to see me (or someone else) explore with it?

Hi. I’m Sam and I write about attention and work and organizations. Follow along on Twitter and maybe subscribe to my newsletter, The Deliberate?

The Year of Intensity/Simplicity

In lieu of a New Year’s resolution I like to select a theme to help guide me over the coming year. A theme is kind of like a resolution in that it is an attempt to somehow be different (maybe even better!) than I currently am but it differs in that it lacks the clarity or specificity of an actual goal.

This is by design since the downfall of my previous attempts at picking and sticking to a New Year’s resolution always seemed to hinge on the fact that what seemed urgent and important on December 31st lost its potency by the middle of summer (if it was lucky to last even that long). A year is a long time to focus on one specific personal improvement intention so I’ve experimented with a shift to a yearly theme over the past few years.

The nice thing about a theme is that it’s broad enough to apply in many different situations. If done right, it acts as a filter that all your decisions and experiences go through. It’s like wearing sunglasses all the time — your eyes are protected by the dark glass and eventually you just kind of forget they’re there. I mean, your theme shouldn’t fade entirely into subconsciousness but you don’t really want to be thinking about all day everyday, either. Instead, it just acts as a guardrail to help keep your decisions headed in a way that they may not go otherwise. And other times it’s like a helpful and cheerful parrot sitting on your shoulder and constantly asking, “Does this align with your theme? Does this align with your theme? Does this align with your theme?”

Anyway, enough about themes. They are good and you should pick one (or two).

Last year’s theme was The Year of Deliberate and I wrote about it a whole bunch in another article. You should read it. It ended up being extremely successful and helpful.

Now, onto this year’s theme.

I’m not a very intense individual by nature (in most, but not all, things). I was a pretty good youth/teenage hockey player but looking back at my career with the benefit of hindsight I can see that I wasn’t really that intense (at least by elite hockey player standards). I wasn’t a particularly intense student. I was lucky to get by on natural talent in most things and could work hard when that wasn’t enough. But working hard isn’t intensity. Even now, in my work as an organization design consultant and writer I can see large swaths of my day-to-day work where I could benefit from doing what I’m currently doing… but in a slightly more intense way.

Over the past few months I’ve been trying to notice when I find myself intrigued or repelled by somebody in a social or professional setting. Almost universally I’ve realized the people I find the most interesting in most settings are intense about a thing (or at most, a couple things). When you talk about the thing with them you see them find another gear. They scoot to the edge of their seat or set their drink down so they can more move their hands around with greater theatrics or they start drawing things on scraps of paper — you get it.

You might think the opposite of this would be people who are super calm and chill all the time. I don’t think that’s quite right. I think the opposite of the intense person is the person who just doesn’t care about much of anything. No strong opinions. Somebody who couldn’t talk your ear off about a thing (even if they think you’d think the thing is boring — I love when people have obsessions over weird stuff).

Just to be clear, on this continuum of INTENSE to MILQUETOAST I think I fall more toward the intense end than the bland end. Anybody who has gotten me going about GTD or the Detroit Red Wings or org design or whatever sci-fi book I happen to be reading at the time know that I can pour on the intensity from time-to-time. There’s something about the last couple years, though, that make me want to take this dedication to intensity more seriously.

I think it may come from a sense of doing too many things at too mediocre of a level. I love being busy and I love new projects and I have a hard time telling anyone (especially me) no. It’s hard to be particularly intense about a few things if you have a ton of stuff going on, though. Looking at it through this lens, then, I realize that I want to try to say yes to fewer things and then do them with a newfound intensity.

But I also want to explore intensity in other parts of my life. How do I up the intensity in my relationships? What does it look like to be an intensely attentive partner? An intense son? What does it look like to bring intensity to a conversation with a stranger and a conversation with a lifelong friend? What topics would I want to broach, how would I want to show up emotionally, how can I be a better version of myself by turning up the intensity a little bit?

And what about my personal habits? What would a more intense commitment to health look like? More intensity with my writing? With meditation? With committing to simplicity and minimalism?

The nice thing about this theme is that I’m not really undertaking it as a grand effort of fundamentally changing myself as a person. I actually think I’m pretty great. I do work hard. I do care about people. I can be empathetic to a fault. I want to do the things I already do… but I just want to do them better.

But wait, there’s more.

I could wrap up this article right here and call it a day but I think I want to try something a little different this year. With a single word or concept yearly theme you can run the risk of over-indexing on it. I’m sure it doesn’t take too much imagination to see how I could potentially go off the rails with a yearly theme of “Intensity.” For that reason, and because I like the idea of a partially paradoxical yearly theme, I’m going to add another word — “Simplicity.”

Simplicity is about operating from first principles whenever possible, removing unnecessary distractions, and staying as close to the essence of the thing as possible. Intensity without simplicity could be disorganized. Intensity with simplicity is focused. Intensity without simplicity could have you chasing rabbit trails — intensely. Intensity with simplicity means doing the right thing consistently.

On the other hand, you can look at simplicity as being in opposition to intensity. A lot of times the simple thing is the easy thing and very rarely is the easy thing the intense thing. In my case, I think it will be helpful to filter my desire for intensity through a secondary lens of simplicity. I’ve already seen some very early positive returns that this dual focus can have. In the middle of December I decided that I was tired of seeing my yearly weight graph ever steadily going up and to the right. Like many folks at the end of the year I decided that 2020 was going to be a year where I took my fitness more seriously.

I had already been noodling on this Intensity/Simplicity theme for a little while at that time so my first impulse was to ask myself what it would look like to get intense about my fitness. All sorts of things started coming to mind — getting a trainer, finding the best gym, finding some sort of elaborate program to follow, etc. However, once I added simplicity to the equation I realized that I would be better served by directing my intensity into as simple a plan as possible (namely, eat more reasonable portions and run). I’m still being intense about it but I’m actually being intense about the right things rather than something ancillary like joining a dope gym or hiring a trainer.

I’m looking forward to navigating this creative tension throughout the year. Asking myself whether a given decision or situation is calling for my simplicity theme or my intensity theme — or perhaps a hybrid of both — is going to be a lot of fun.

What does your upcoming year look like? What’s your theme?

I’m Sam. I help make the future of work more human and adaptive at The Ready. I help humans take back their time and attention at The Deliberate.

Looking Back at a Year of Growth, Grief, and Calm

In 2019 I tracked (deep breath): sleep duration, sleep quality, the average time I went to bed, steps, running + walking distance, body weight, number of meditation sessions, duration of meditation, heart rate (average, waking, and exercise), the amount of time spent on each of my devices, the number of times I picked up each of my devices, the number of journal entries I wrote, number of workouts, days of reading at least 15 minutes, days I wrote, the video games I played, the TV I watched, the movies I watched, the number of flights I took, the number of miles I flew, the number of airports I visited, and the music I listened to the most. Before you write me off as a complete lunatic, I did all of this with a weekly routine that takes no more than fifteen minutes every Sunday morning. Almost every single metric on this list was passively collected by the various devices, apps, and services I surround myself with. My role was simply pulling it together into a spreadsheet each week so I could see patterns and interact with the numbers enough to get a feel for what was going on.

When I sat down to plan this article I saw two clear paths in front of me. The first path was to dive deep into the numbers for each metric. I have the numbers so why not cleave as close to them as possible and stay firmly in the realm of the objective? The other path is to let the data I collected over the year act as the background music for some more subjective reflections. Part of me thinks that’s a waste of perfectly good data but I know, actually, that this is the more meaningful way to do a yearly retrospective.

For the past couple weeks I’ve been marinating in everything I collected over the past 12 months. In some cases I’ve been liberating it from apps that aren’t part of my weekly metric collection routine (Goodreads, Flighty, etc.) and in other cases I’ve been looking for patterns and stories that are living just under the surface of the numbers themselves. With all these numbers starting to settle, like a snow globe coming back to its rested state, some insights are becoming clearer. Feelings about what went well and what didn’t. What over the past year brought me a sense of accomplishment and what is tinged with shame. The things I look back upon fondly and those events and activities that my self-protective ego has already expunged from memory.

My aim is to marry these two spheres of experience — the subjective and the objective, the emotion and the data, into a coherent sense of what I experienced over the past year. With this, then, comes the ability to feed and grow the aspects of this year that I want to carry into 2020 and hopefully avoid repeating mistakes of 2019.

Revisiting 2019’s Theme

Without rehashing last year’s article where I go into the weeds about why I selected this as my theme, the basic idea was that I wanted to spend the year doing “everything” more deliberately. I had noticed some bad habits starting to take root that all orbited around a lack of focus, concentration, and just an overarching sense of floating through my days. The aim was to have a theme that helped eliminate the float and instead anchor myself in deliberate action.

The centerpiece of last year’s theme was something I ended up calling Anchor Habits; the four daily habits that are necessary for me to feel good about any given day (read something substantial, write something, meditate, and engage in some kind of deliberate exercise). I tracked each of these behaviors all year long and gave myself an “Anchor Point” for each one I completed; which means each day could have a potential of four Anchor Points. If I successfully hit all four Anchor Habits in a day I called it an Anchor Day and tracked that, too.

A couple lessons from trying to do this for a full year. First, I was right that these four habits are the bedrock of a good day. When I did them I felt good about myself and the world. When I didn’t do them I felt off. Second, it was surprisingly hard to hit Anchor Days. Most weeks I only had one or two. Some weeks I had none. I had a perfect seven Anchor Days in a week only once.

This focus on Anchor Habits was a key component of my Year of Deliberate, but it wasn’t the only thing I did in 2019 to try to teach myself to have more control over my attention. A couple other highlights include starting a newsletter about “managing attention in a complex world” (conveniently titled The Deliberate), continuing my practice of recurring office hours (a way for me to deliberately practice connecting with strangers in a short period of time and building my network), dabbling with “hyper scheduling,”and starting a podcast with my brother where we explore our vastly different experiences in the world of work.

Each of these projects, in different ways, were exercises in becoming more deliberate. More deliberate with my time, my writing, my community, and in spending time talking to my brother.

The thing about a yearly theme, rather than a new year resolution, is that it’s supposed to permeate across your life. It may spark some discrete projects, as it did for me, but it is a background process that’s running in the back of your mind at all times. Ideally, it’s subtly influencing decisions in conscious and subconscious ways throughout the entire year.

The rest of this article I’m going to share some reflections and data that seem separate from the Year of Deliberate, but probably aren’t if I were to hold them up to the light for closer examination.

Overarching Feelings from 2019

Pride in professional growth

In many ways 2019 was a banner year in my own professional growth. After a very up-and-down 2018 (difficult project with a ton of travel, a longer than planned idle period that messed with my confidence, etc.) I felt like I was the most on top of my game I’ve ever been. I can’t go into too much detail without violating client confidentiality, but basically I was very successful in selling the work The Ready does at a very large organization that sorely needs the help we provide. In addition to having my first taste of success in selling a substantial amount of consulting work, I acted as the “lead” on the project for much of the year. This isn’t an actual role that we have at The Ready but because of some creative staffing we had to do in the middle of the year I was more or less the common anchor that held the project together during that time. This has challenged and pushed me in ways that were brand new but also have made me a much more confident and capable consultant.

A brush with grief for the first time

I’m a very fortunate 32 year old. There has been very little personal grief in my life up to this point. Both of my parents are relatively young and healthy. While I have lost a grandmother, it was when I was a baby and too young to remember (and my grandpa remarried a woman who is the only grandma I’ve known). This changed in 2019 when we lost my Grandpa Ed in October. While not entirely unsurprising (he was 93) it was still a very intense and very sad time — both the couple of weeks leading up to it and in the immediate aftermath.

I had never been faced with that kind of grief before and I feel like it opened up a part of me that had never been exercised before. It brought me closer to family, gave me a much more intense appreciation for life, and opened me up to talking about emotions that I’ve never before let out.

Comfort and joy in routine

Looking back at 2019 I’m struck with how calm it was in comparison to other recent years. 2015 was marked by the decision to move from California and start work with Undercurrent (and then The Ready) in New York City and all the tumultuousness that moving across the country and starting a new job entails. 2016 and 2017 were years of learning how to live in NYC, learning how to be an organizational consultant, deep impostor syndrome, keeping a long-distance relationship alive, tons of travel, and generally drinking from the firehose of experience. Late 2017 meant moving to another new city (Washington D.C.) and 2018 meant 6 months of full-time commuting to San Francisco followed by 6 months of physical and emotional recovery that the previous 6 months demanded. Compared to the previous four years, 2019 was downright calm. Working on a predominately local client meant my travel was drastically reduced. With my travel drastically reduced I was able to form a daily and weekly habit that helped me stay centered and productive most of the year. In these routines I have found more joy, calm, and stability than I have in a long time.

Meaningful Data from 2019

Moving out of the realm of the subjective and into the world of data, here’s what stood out to me from 2019.

Less reading, but very okay with it

I know I read a lot. Part of me is afraid that even writing this section comes across as some kind of humblebrag because I know I have to be in the 1% of folks with how much reading I do. Nonetheless, I think there’s something interesting worth diving into with regards to my reading stats from last year.

In the last four years I’ve finished the following number of books: 62 (25,188 pages), 72 (26,215 pages), 60 (20,562 pages), and 75 (24,509 pages). In 2019, I read the fewest number of books (60) and pages (18,518) since I started tracking. What’s notable about this number is the feeling that it elicits (or doesn’t) within me. Namely, not much. In fact, I’d be very okay seeing that number go down in 2020.

Up to this year, I think I read almost compulsively about topics related to my field of work. I felt behind and out of my league with basically everything I was doing so reading — and the fact that I could do it quickly — became my biggest and best weapon for getting up to speed. So, for the past four years I’ve read voraciously and borderline compulsively. 95% of those hundreds of books have been non-fiction and read at a sprint. I’m done with that, I think. So done, in fact, that I bought myself a subscription to Blinkist and I’m going to try to do as much of my non-fiction “reading” there as I can. Instead, I’m going to shift as much of my reading as possible into the realm of fiction and let myself take a bit of a breath and a beat when it comes to non-fiction books related to my line of work.

Up in exercise — but also up in weight

2019 was the first year where I started tracking whether or not I did any “deliberate exercise” in a given day. The definition of “deliberate exercise” was left pretty vague and I allowed it to have a pretty low bar. A walk counted. Getting a massage counted. A “real” workout obviously counted. Basically, I wanted to string together as many days as possible where I made a deliberate decision to do something at least moderately physical. I ended up giving myself credit for 223 days where I did just that.

What this didn’t translate into, however, was improved health. In fact, I continued my ever so gradual yet consistent trend to getting heavier (from 2015–2019 I’ve averaged 203.6 lbs. to 207.4 and currently weigh around 210). I’m going to continue this tracking into 2020 but I think the main takeaway is that I can’t expect this to be enough to lose weight or be particularly healthy. Making a bare minimum decision around doing some kind of daily exercise is table stakes and I need to bump it to a slightly more intense level, and take a look at my eating habits, if I want to end this troubling bodyweight trend.

I should write more — but I actually wrote a lot?

One of the most ubiquitous feelings I live with is the never ending sense that I’m not writing “enough” (whatever that means). My professional identity, to the extent I had one before and during grad school, was mostly as a writer. I wrote literally hundreds of articles on the various incarnations of my website over the years from 2009–2015. Ever since starting work with The Ready my writing output has fallen off a cliff (having a demanding full-time job can do that to you). Somehow I have failed to adjust my personal expectations to account for that. As a result, unless I’ve recently published something there’s a good chance I’m mentally beating myself up for not writing more.

This is where a robust year-end retrospective process can come in pretty handy. As I was going through all my data from the last year I realized I wrote 8 articles for my personal Medium account, 2 articles for The Ready’s publication, 35 issues of The Ready’s newsletter, and 26 issues of my newsletter, The Deliberate. That’s not even including the 118 personal journal entries I wrote throughout the year, too. There’s no way I can look at that output and keep up the story that I don’t write. Could I write more? Of course (and I intend to in 2020). But should I be beating myself up as if I didn’t publish anything this year? Of course not.

Conclusion

I could probably write a paragraph or two about every category of data I’ve collected over the year. That would be interesting to a grand total of one person (me) so I think I’ll wrap up this year’s review here. If you’re interested in taking a look at the spreadsheet I used to collect most of my personal data this year, you can check it out here. If you see anything interesting or want to ask any questions, please shoot me an email (samspurlin@gmail.com) or catch me on Twitter (@samspurlin).

Now that the review is more or less finished, it’s time to decide how I want to use this information to steer my behavior and intentions in 2020! I’ll be sure to link to that article here once I finish it. In the meantime, thanks for indulging me and good luck in 2020!

My name is Sam and I help organizations fight bureaucracy at The Readyand people fight for their attention at The Deliberate.

Seeking Calm and Stability in Tools

Looking back on the technology I used in 2019 the word that most comes to mind is, “unsettled.” This is surprising to exactly nobody who has followed my writing for any length of time, as a frequent theme of mine is wrestling with two fundamentally different approaches to software: Default Only and Using The Best. 2019 found me flip-flop between these two polarities a couple times.

On the one hand, I think this is partly a result of Apple continuing to push the capability of their default offerings forward. I went for large swaths of 2019 using the basic Apple apps across all my devices. What they lacked in customization and power features they made up for in hardware integration (think streaming the Podcast or Music apps on my Apple Watch) and psychological “purity” (“I’m using all Apple stuff so everything *should* work really, really well.”)

On the other hand, I spent almost as much time using my tried and true toolkit of premium third-party apps where the vast majority were either paid for up front or required an active subscription. When I was in this mode I felt like I had crafted a working environment where every tool was helping remove friction from my life even if they weren’t as deeply integrated to the actual hardware that I like to use.

The see-saw year eventually found me landing on the latter (the Using The Best mindset) as what I’m going into 2020 with. As much as I love the “purity” (I really don’t like that word because of what I feel like it’s saying about me as a complete Apple lackey but I’m having trouble finding a better one…) of going with all first party software Apple just had too bad of a year with their software quality across the iOS 13, iPad OS, and macOS Catalina launches for me to feel safe about that. Additionally, I’ve decided that part of what I love about using Apple hardware is all the great third-party apps that either give me functionality that Apple’s apps can’t or broadens the hardware’s usefulness into niche situations where Apple doesn’t have a solution. I want to make sure that ecosystem stays viable and vibrant. If I only use first-party apps that means I’m not helping those small companies and indie developers who make software I love stay in business.

Ultimately, that means I’m going into 2020 with this basic stack:

• iPhone 11, iPad Pro 10.5, 27” iMac

• Notes: Bear

• Writing: Ulysses

• Calendar: Fantastical

• Task Management: Things

• Email: Airmail

• Read Later: Instapaper

• Habit Tracking: Streaks

• Podcasts: Overcast

• Music: Spotify

• Password Management: 1Password

• Weather: Carrot Weather

• Twitter: Tweetbot

• Drawing & Handwritten Notes: GoodNotes

• Books: Mostly Apple Books but still a bit of Kindle

• Maps: Apple Maps

• Journaling: Day One

• RSS: Unread (with Feedly as backend)

• Key Utilities: AutoSleep, Deliveries, TV Time, PCalc, Nomorobo, Unread, Flighty, GG, Apollo, UpHabit, Timery, Calm, Bobby, Grocery, and Notion

I feel like this is the software that allows me to most smoothly move through the world and have the impact that I want to have. If there’s something on this list that you’d like me to write about in more detail please let me know in the replies below.

At the end of 2020 I want to be able to pull up this article and think to myself, “Yep, that’s basically what I used all year.” I don’t want to get back on the see-saw that I spent much of 2019 on. I know I’ll have to resist the siren call of the default apps around WWDC and the launch of iOS 14 when the allure of new features and updated first-party apps will be the strongest… but at least until then I want to move forward without ever thinking about what software I’m going to use to do my work.

What about you? What does your tech stack look like going into 2020?

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My name is Sam and I write about technology, work, and the better use of our attention. If you like these sorts of things, you should subscribe to my newsletter. It’s called The Deliberate.

How I'm Going to Do My Annual Review

I love taking time at the end of the year to pause, breathe, and try to make sense of what I’ve experienced over the past 12 months. Obviously, this could, and probably should, be done during any time of the year but without fetishizing the turning of the yearly calendar too much I think December is as good a time as any.

First, I’m going to look at all the various sources of data I collected over the year. For me, that means the things that I capture on my Personal Metrics Spreadsheet every Sunday as well as other passive sources of data collection. Some of these are things I’ve deliberately collected over the past year, like my body weight and sleep data. However, there are lots of ways to generate data over the course of a year that probably don’t seem like data at all. Things like, all the photos you’ve taken over the year, or Screen Time data passively collected by your iPhone, your Amazon orders, the digital books sitting on your iPad or Kindle, etc. I think it’s super helpful to start with whatever data you have access to at the beginning of any kind of retrospective. Overall, I’ll probably end up reviewing some combination of the following data:

• Sleep metrics

• Body metrics (weight & heart rate)

• Steps and running/walking distance

• Meditation sessions & duration

• iPhone usage

• Journal entries

• Video games played

• Books read

• Music listened to

• Photos taken

• Flights taken

• Articles published

• Purchases made

• Previous calendar events

• Podcasts listened to

• New experiences (personal & professional)

As I go through all of these data sources I’m going to be asking things like:

• Is there a pattern or theme here?

• How does this compare to previous years?

• What am I noticing?

• What’s surprising me?

• What’s not surprising me?

And as I review this data I’m going to be keeping a separate list called, “Steering for 2020.” Basically, anything that comes to mind about how I want 2020 to be different from 2019 will get captured on this list. By putting something on the list I’m not mandating that I’m going to do it — only that I’m putting it up for consideration.

Once I review everything I can from 2019, which I’m expecting to take several days to do, I’m going to let it sit in my brain for a couple days without thinking about it deliberately. I want to give myself time to make sense of the patterns and themes that maybe weren’t obvious at first glance. Once I’ve let everything stew in my brain for a couple days I’m going to review my “Steering for 2020” document, add anything that seems to be missing, remove things I no longer want to consider doing, and do some stream of consciousness writing about my yearly theme for 2020.

My yearly theme is designed to help me take whatever I learned or experienced in 2019 and use it to help me have a better 2020 without getting bogged down in highly specific resolutions that inevitably lose their luster after a few weeks. A theme is meant to be a relatively nebulous and amorphous lens through which I can filter many different types of decisions and situations over the next year — with the ultimate goal of helping me live better and more deliberately. I already have an idea of what I think my 2020 theme might be, but it’s always possible that I’ll land on something else as I go through this review process. And even if I don’t, then I’ll have a bunch more data and a deeper understanding about why the theme I’m thinking about feels like the right one for 2020.

Over the next few weeks I’ll be writing about some specific aspects and insights from my own review process as a way to keep myself accountable to actually getting it done and to give you a peek behind the curtain of how one person does it.

This whole approach to reviewing my previous year is very much a work in progress and I’m always taking inspiration from the way other people approach it so please don’t hesitate to share your own system or point me to other bits of writing that you’ve found helpful.

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I write a free newsletter about the deliberate cultivation of attention in a complex world. It’s called The Deliberate and if you like things like yearly reviews, themes, and the quest to live “better” then I think you might like it. Subscribe or check out the archive.

A few quick thoughts on WWDC 2019

I’m not a software developer but I always eagerly await Apple’s annual Worldwide Developers Conference. I love seeing what Apple has been working on for the past year and what I can expect, software-wise, from the devices that play increasingly important roles in my professional and personal life. In no particular order, here’s what stood out to me this year as particularly interesting:

1. Apple TV adding support for PlayStation 4 controllers was completely unexpected but a really awesome move. Apple TV has always seemed extremely overpowered for what most people use it for and without a bundled controller no video game producer was going to create anything that required one to play. I’m hoping this pushes some more high quality games to the system. It looks like this support is being extended to iOS/iPadOS, too, which just turned my already incredibly capable iPad Pro into an extremely capable gaming system.

2. The separation of iOS and iPadOS into two separate systems is a great sign. It made sense for them to start in the same place as they tried to figure out what the iPad was even good for. That made sense in 2011. Not so much in 2019. It always seemed a little silly that so much of the iPad UX was just a big iPhone. It was holding the platform back in so many ways and now that they’ve been unshackled from each other I’m interested to see how they better evolve to fit their unique use cases. When I travel I’m iPad only and I’m very, very close to going iPad-only in my everyday work, too. If iPadOS means a more capable iPad then sign me up.

3. While iOS/iPadOS represents a splitting of one OS into two, I’m equally interested in the Project Catalyst stuff that is aiming to bring iPadOS and macOS closer (I realize that’s a huge over simplification). It’s not hard to see that the Mac is a somewhat neglected platform as compared to the attention iPhones and iPads get nowadays. If it’s easier for developers to bring their iPad apps to the Mac I’m very interested in seeing what comes out of that. There are plenty of great iPad apps I use everyday that I’d love to see on a Mac.

4. The privacy angle that Apple has amplified over the past few years and really leaned into recently is becoming more and more attractive to me. I’m already naturally drawn to a tech stack where the same company builds the hardware and software even though I’m often tempted away by more polished, customizable, or niche apps. But this privacy stuff is giving me another arrow in my quiver when convincing myself that it’s worth going all-in on Apple whenever possible (e.g. I’m writing this article in Pages, which I don’t think I’ve ever done before).

5. I’m glad Apple learned its lesson from the “trash can” Mac Pro and basically created the equivalent of some kind of industrial equipment for knowledge workers. I will never buy this machine but I’m glad it exists.

6. Dark mode is good. I already use it in every app that offers it so having a system-wide option is welcomed.

7. The latest episodes of Upgrade and Accidental Tech Podcast have some good recaps and commentary on the keynote. I highly recommend checking them out — especially ATP just to hear Siracusa talk about the long awaited Mac Pro (seriously, he’s still using a 10 year old Mac Pro and has been waiting for an update ever since the trashcan Mac Pro of 2013).

8. Something about the Goodnight Developers video made me want to start developing apps. That’s a bad idea, right? I’ve dipped my toe ever so slightly into the software development world a few times in the past (like, ever so barely) and I think I might just like the idea of being a developer and not the actual work that goes along with it. I don’t know. It’s on the Someday/Maybe list.

What stood out to you? What are you most looking forward to?

Reflections on My Digital Detox: Week 2 and 3

The first week of a digital detox can be a lot of fun. I think it’s mostly a matter of novelty and the stark difference between your new reality and business-as-usual. For that reason, I kind of feel like a digital detox doesn’t really start until week two, at the earliest. That’s when it stops being all fun-and-games and your brain starts getting really good at giving you reasons to go back to the way things were. I’m very much in that headspace right now as I’ve just wrapped up my third week of my digital detox so I wanted to share some of the insights I’ve found interesting so far.

It’s surprising how little I miss podcasts right now.

If you asked me to predict which part of the digital detox was going to be the hardest I would have said not listening to podcasts. I’ve been listening to roughly the same slate of podcasts for years. In some ways the hosts feel like my friends. On the other hand, I’m fully aware of how easy it is for me to trick myself into thinking I’m being productive when I’m listening to something vaguely intellectual. Podcasts were the primary reason I had almost no silence in my life: Walking to work, walking home from work, driving around, cleaning the apartment, taking a shower... podcasts were always there. I never had space to think my own thoughts because I was always piping somebody else’s into my head.

Now, three weeks into this detox, I haven’t spent much time thinking about podcasts at all. I’m a little conflicted about how or if I’m going to reintroduce podcasts into my daily routine at the end of the detox. I assumed I would but now I’m questioning that assumption.

Social media’s hook into me is validation, not consumption

I used to spend a lot of time scrolling through Twitter but I’ve learned that social media is much more about validation for me. I use Twitter and LinkedIn to share when I’ve published a new article and the urge to check these services after having announced a new publication is intense. I really want to get to a place where I can publish something and not spend the next three hours wondering if anyone has responded to it. I noticed a similar feeling with Slack and email, too. I have the urge to check these things so much because I want someone to have responded positively to something I (or The Ready) have done. Give me pats on the head for the smart thing I shared in Slack! Tell me I did a good job! Maybe someone wants to hire us!

Can I get to a place where I can publish something or do something in public and not be consumed by a need for positive validation from strangers? God, I hope so, because that sounds pathetic when I see it in writing.

Turns out I don’t really have many analog hobbies

A key concept of the digital detox is to not just abstain from optional technologies, but to fill your newly available time with wholesome, ideally analog, activities. That has been tough. Almost everything I like to do requires the use of technology. I’ve done a bit more writing by hand than usual... but actually that has been with an Apple Pencil on my iPad in GoodNotes. I’ve done a lot of reading... almost entirely on a Kindle or iPad. I’d like to get into gardening, but I live in an apartment and Emily might kill me if I buy any more houseplants. I play hockey, but that’s one evening per week. I run, but not very far or very long. 

I remembered that I used to take guitar lessons for a few months in high school — maybe I should do that again?

I need to be careful about replacing optional technologies with more work

Kind of tied to my previous point about not having many analog hobbies, I’ve realized that a lot of what I’ve been doing in my free time could be construed as just another flavor of work. I’ve been spending a lot of my time reading books (often related to what I do for a living), writing articles (like this one), and re-building my personal website. None of these things are really “leisure.” It has felt good to re-establish a writing routine and to work on my personal website, both things I’ve been wanting to do for a long time, but I should probably be a little bit skeptical of whether I’m actually giving myself enough true leisure time nowadays.

Distractions always have a second level

I’m getting much better at asking myself, “What’s actually going on here?” when I’m feeling drawn to a distraction. There’s always something deeper going on than just, “Looking at Twitter would be nice right now.” One of the most common things going on is that I’m simply not admitting to myself I’m tired and need a break. Instead of just standing up, walking away from the computer, and doing something to rejuvenate myself, I’ll find myself getting drawn into a distraction loop. Somehow my fatigue-addled mind thinks flipping between Slack, email, and Twitter is work and that I’m being productive by doing that.

Another second level cause for seeking out distractions is not knowing what I need to do next and instead looking for some kind of stimulus to tell me what to do. This results from not taking the time and energy to actually figure out how to best use my time and vaguely hoping that I’ll stumble across something in my mindless internet wandering that will tell me what I should do. Maybe I’ll get a Slack message from a colleague asking me to do something? Or maybe an email will come in that needs responding to? Both of these things seem easier than actually pausing for a moment, taking stock of my situation (what’s on my to-do list, how much time is left in the day, how much energy I have left, etc.) and making a deliberate choice about what to do next.

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My name is Sam. I work at The Ready where we help organizations eliminate bureaucracy. I write a newsletter about meaningful work and attention called The Deliberate.

It’s Time for a Workism Reformation

Over the past few weeks there have been a few articles describing and decrying the growth of workism, or the quasi-religious commitment to extreme work habits, in American society. Performative hustle, hustle porn, glorification of lack of sleep, and the general all-consuming nature of work are the hallmarks of this harmful workism. 

Reading these articles has been uncomfortable in that I keep seeing glimpses of myself. I do think work is a wonderful arena for creating meaning in my life. I do believe that work should and could be meaningful and that it’s worth striving toward that. I think obsessively about what it means to work hard, be productive, and I’m constantly experimenting with new ways of organizing and completing my work. I love work and I love when other people love their work. Am I part of the problem? Am I just another disciple preaching the harmful gospel of workism?

Toward a Reformed Workism

The workism dominating the news right now seems to be externally focused. It’s all about working long hours, not getting enough sleep, and generally conspicuously performing “hard work.” It’s a type of self-flagellation that is ugly to witness (and experience) but is also impossible to ignore. It’s easy to tell who is worshiping at the altar of workism. If you’re an adherent of this school of workism then everyone will know and you stand to reap the reputational reward this community bestows on its members. Whether through the bags under your eyes, or the hashtags on your Instagram posts, or the 3:00 AM emails you send your team — your allegiance to workism will be known. When the burnout eventually arrives you may be miserable but at least you will have company of your fellow adherents. There is solidarity and community in this externally-facing practice of work.

But what if there was a more internally-focused workism? A workism less focused on the “what” (long hours, burnout, lack of sleep) and more on the “how” (the internal experience of meaningful work)? A workism marked not by how many hours you work but by how much value you could pack into as few hours as possible? A workism all about moving skillfully through your day. Not overreacting or under reacting to anything. A workism where there is deep commitment to crafting a meaningful experience at work but without the performative elements. No pride in burnout. No pride in lack of sleep. In fact, taking these results as signs that one’s approach must change, not that one is on the right path.

To push the religion metaphor to a potential breaking point, Reformed Workism is quiet contemplation and self-reflection whereas traditional workism is big tent revival, put-on-your-Sunday-best, speak-in-tongues and public exorcisms. You can do the former without anybody knowing whereas the latter is more spectacle than substance.

Reformed Workism operates on a micro-level. It’s focused on the moment-to-moment reality of work. It’s the world of Frankl, Csikszentmihalyi, and Seneca rather than Musk, WeWork, and VC-driven booms-and-busts. It is an ongoing practice that must be renewed each day and with each email written, meeting attended, conversation held, and presentation given. It’s the constant decision to choose private excellence and skillful engagement with the world even when those around you are using public exertion as a crude proxy for providing value (and potentially celebrated for doing so).

Open Questions

I anticipate exploring this topic much further in the near future so rather beat it to death in this first attempt at articulating it I’m going to capture some of the open questions I hope to explore soon:

1. If nobody knew how hard or how many hours you worked how would you decide whether you had a successful day?

2. What are the internal signs that you’ve responded skillfully to a situation?

3. What are the personal practices that help with adopting Reformed Workism?

4. What would an organization look like if it celebrated Reformed Workism in its employees rather than Traditional Workism? How would it be different from the typical organization?

5. Is Reformed Workism steeped in privilege? Can folks in terrible jobs experience it? Should they be encouraged to?

6. What obligation does society/government have to create the conditions under which Reformed Workism can exist?

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I’m Sam. I help change the world of work at The Ready. I also write a newsletter called The Deliberate.

Digital Detox, Week 1: Laying Out the Rules and Capturing Some Early Insights

I've had a sneaking suspicion for awhile that my use of a few pieces of digital technology are drastically influencing and reducing my creative output and overall happiness. I haven't been happy with my writing consistency for awhile now and I figured my sometimes questionable tech habits probably had something to do with it. Like my own personal climate change, the conditions that underlie everything have been shifting in such a way that what is imperceptible on the hourly or daily level is actually quite obvious when looked at from a further remove.

I used to write a lot more. I used to feel better about how I use my time. There are obviously many potential confounding variables (no longer being a student, having a full-time job, other responsibilities that come with age, etc.) but there's enough circumstantial evidence that my use of optional technologies is playing a major role in these negative feelings.

I decided to follow Cal Newport’s advice from his recent book, Digital Minimalism, and give a digital detox a try. The idea is simple: For 30 days abstain from optional technology while exploring more analog, and fulfilling, ways to spend your time. At the end of the 30 days, make deliberate decisions about which technology to reintroduce to your life. Simple enough, eh?

I just finished Week 1 so I thought I could dive into specifically what I did and what I've learned so far.

The Rules

The following are completely off-limits (in theory): Twitter, Instagram, Reddit, CNN.com, Apple News, solo video games, podcasts, audiobooks, Medium, RSS. I don’t use Facebook or Snapchat, but if I did they would be on this list, too.

The following had some strict “operating procedures” baked into their usage: email (not on phone), Slack (not on phone), text messages (batched), video games with friends only, YouTube (professional use only), T.V. (with Emily or Red Wings games only), LinkedIn (messaging only).

I was trying to be as complete as possible with everything I consider an optional technology even if there is a massive spread in how problematic the various tools are (Twitter and Reddit are massive time consumers whereas I actually spend very little time texting).

Some Early Observations

This whole experiment is less about the raw amount of time these activities take and more about the removal of “escape hatches” my brain can take when it's frustrated, bored, anxious, etc.

• I see why you need to do this for 30 days. You will inevitably spring “leaks” in your detox and you'll have to get rid of those things, too. My interesting leaks have included, checking for messages/mentions on Twitter and LinkedIn (“At least I'm not looking at the timeline/feed, right?”), becoming an avid reader of The Athletic (I'm torn as to whether this is actually a breach or just reading a magazine), email and Slack a bit, and, hilariously, asking my HomePod to tell me the news. I'm sure I'll find even more absurd breaches in weeks two and three. 

• I'm interested to see what happens when this moves beyond the novelty stage and just starts to become more normal. 

• I haven't explored much in the way of analog leisure other than maybe cooking a bit more than I had been. I've mostly been using my freed up time to read and write. I'm okay with this. I don't think I want any new hobbies. I'd much rather focus on strengthening my anchor habits. 

• Unexpected stress can make it tempting and easy to revert to old patterns.

• It’s not a “purity” thing. Don't give up because you've failed. Plug the leak and keep going. 

• It's working. I feel calmer. I'm spending more time doing more valuable things. I can feel the grip of needing to be in the know and connected all the time loosening. I don't think this is necessarily my new status quo, but the idea of going back to how I was has very little appeal right now.

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I’m Sam. I work for The Ready in Washington D.C. I tweet (but not right now). I write a newsletter about attention called The Deliberate.

Crafting a yearly theme instead of New Year resolutions

I’m not a big fan of resolutions (Merlin captures why pretty well) but I am a big fan of thinking I can be a better person than I have been up to this point and that there’s something, something, about the advent of a new year that fills me with optimism about that whole being better idea. In an effort to keep some coherence between these potentially opposing ideas I’ve adopted a thought technology I’m pretty sure I first heard discussed by Myke Hurley and CGP Grey on Cortex; the Yearly Theme.

Before you accuse me of playing a semantic game in a veiled attempt to set a new year resolution by simply dressing it up in fancy new clothes, let me try to explain their differences as I see them. A canonical new year resolution is generally a goal. It’s a statement of how you want to be different in the future and is usually pretty specific. This is what makes it feel good in the short-term (“It’s so clear and so simple!”) and what sets you up for failure in the long-term (“This turns out to be harder than I thought,” or, “January-Me had no idea what July-Me needed to do so let’s forget this whole thing…”). Meaningful personal change almost by definition takes a long time to accomplish and a resolution seductively simplifies the complex process into uselessness.

A Yearly Theme, on the other hand, is much more open-ended. Instead of a specific decision about how you or your situation is going to be different in the future, it’s a guiding statement or phrase that can help you make decisions across many different situations and scenarios. Its generality gives it more staying power because it can evolve and reveal new layers of meaning as you (hopefully!) grow alongside it. Plus, and this may be the biggest advantage it has going for it, it’s nearly impossible to fail at a theme. You can’t fail your theme in January, or June, or ever. You can just have variation in the extent to which you’re using it to guide your life and you always have the option of reaffirming and refocusing on it if you want to.

How to pick a yearly theme

A good yearly theme starts tickling the back of your head a couple months before you even realize what it is. It’s not the type of thing that you just sit down and make a rational and intellectual decision about. You’ve gotta live with this thing for a year and you need it to resonate with you on an emotional — nearly spiritual — level if you want it to mean anything 10 months from now.

It starts with noticing the points of your life where you feel particularly good about who you are, what you’re doing, and how you’re interfacing with the world. It continues with noticing the points of your life where you feel particularly shitty about who you are, what you’re doing, and how you’re interfacing with the world. The noticing of these individual moments hopefully turns into the noticing of patterns. The noticing of these patterns hopefully turns into profound personal insights about what makes you tick. These insights will form the foundation of your yearly theme.

You can see many of my insights in my 2018 recap article. These will become the launch pad for my 2019 theme: The Year of The Deliberate.

The Year of the Deliberate

I’ll try to keep this short considering variations on this idea are likely to inform nearly everything I write for the foreseeable future (that’s kind of the point of having a theme). The shortest version is that I’ve always been fascinated by what is possible when people deliberately use their attention and that the ability to do anything deliberately seems to be under profound attack in our current environment. On a personal level, which is the level that any Yearly Theme should certainly resonate strongest, I’ve noticed over the past several years, but particularly in the past year, that my best days are driven by a sense of having been deliberate in what I did and my worst days are characterized by the opposite.

In 2019 I almost don’t care what I do as long as I do it deliberately.

Okay, that’s not entirely true. There are four things that are going to serve as my Deliberate Anchor. They’re best summed up by this drawing:

Read = read a book, Write = write anything, Sit = meditate, Move = exercise

This is my easiest measure of whether or not I had a “good” day. When I do these things I generally feel good. When I miss any of these for a significant period of time I tend to feel bad. I created this drawing a couple months ago as I tried to articulate the simplest and most essential way to feel good about myself on a daily basis (see my comment earlier about a good yearly theme starting as a tickle in the back of your head…). Now that I’ve been using this little drawing every day for a couple months I want to see what I can accomplish by really focusing on it.

Like any good theme, though, I suspect the Year of Deliberate will be more than just me achieving my Deliberate Anchor every day. It’s going to come through in my writing — both for myself and The Ready (in fact, I just super soft-launched a newsletter called The Deliberate where I’ll be exploring some these ideas). It’ll be showing up in my own daily habits around media consumption, the news, relationships, and personal growth (I’m pretty excited to share a Personal Development Kanban Board that I’m pretty sure is the #1 reason I was able to kick a 30 year old nail-biting habit at the end of last year) and assuredly so much more that I can’t even think of, yet.

It’s not too late if you haven’t set your own Yearly Theme, yet. The rollover from 2018 to 2019 may provide a nice short-term motivational boost but there’s no rule that you can’t start your Yearly Theme on January 12th, May 23rd, or November 15th! And if you have set a theme, I’d love to hear about it in the comments below. I’ve noticed that hearing other people talk about their own themes can be strangely motivating to articulate and adhere to my own theme so you’ll be providing a service to me and anyone else who makes it to the end of this article.

Have a wonderfully deliberate year!

I’m Sam. I work for The Ready in Washington D.C. I tweet. I write a newsletter called The Deliberate.

Looking Back at 2018

It’s no secret that I track a lot of information about myself. I know every book I’ve read in the past year, every TV show and movie I watched, how much sleep I got, how many times I meditated, how many steps I took… just to name a few. Part of me wants to go through each metric I tracked and dive deep into what the numbers are and what they might mean. God knows I’m not shy about diving into miniscule detail about pretty mundane things. For once, though, I’m going to show some restraint and actually try to extract some themes instead of deluging you with data.

After a couple weeks of reflecting on how the past year went, looking at the various data I collected, and talking with loved ones, here are the three key themes I’m taking from 2018:

1. Self-compassion will be my ultimate productivity hack

I have a hyper-active self-critic who thinks he’s the star of every show. He’s not shy about chiming in. Sale fall through? “Hello, why are you so bad at this?” Have a tough time figuring out what to work on? “You call yourself a productivity expert? You’re a joke.” Write something that didn’t garner much attention? “I always knew you weren’t very smart and now everyone else knows it, too.” It’s truly endless and at my lowest points, emotionally and in terms of productivity, it was because my critic had made himself far too comfortable in my brain.

For somebody as obsessed as me with personal development this is one part of my development that I haven’t really explored. I’m much more comfortable creating new systems and structure that help me take the action I know I need to take. I’d much rather read a book or do some writing or somehow just try harder. 2018 is when I finally started to learn that you can’t berate yourself into self-compassion (I know, right?) and that shutting up the critic in my head will probably do more for unlocking personal and professional growth than literally anything else.

2. I need to make decisions for sustainability

For the first half of 2018 I commuted full-time from Washington D.C. to my project in San Francisco. I would catch a 6:00 AM flight Monday morning (after a 30 minute Lyft to the airport), land in SF Monday morning, spend all day at the client’s office, work normal-ish 8–5 PM days Tuesday-Thursday (while fighting my body’s attempt to acclimate to the time change) and then either take a red-eye flight back to DC Thursday night or fly out early Friday morning and land in DC Friday early evening. Repeat for five and a half months. This is one example of me taking a situation at face value and basically martyring myself rather than seeking some concessions or changes that would allow me to work in a more sustainable way. I put myself in the mindset of a hockey player battling through an injury in order to not let my teammates down. I can’t do that.

This learning is largely around the idea that I have limits, both physical and mental, and although they can sometimes be ignored in the name of “powering through” or making the client happy, they represent a debt that must eventually be paid. In my case, it meant absolutely crashing at the end of May and requiring several months of recuperating to get back to anything close to approaching my normal operation.

I’ve spent most of my life looking ahead to the next thing. College was a finite time ending in a degree and entrance into the real world — so I might as well bear down and really do a good job. My abbreviated teaching career theoretically should’ve been a time where I was focused on the long-term but I think I knew early on that it wasn’t going to be my future and I was therefore simultaneously hustling on multiple side projects. I was teaching during the day, coaching hockey at night, and writing for my website during the snippets of blank space that I was able to carve out each day. Grad school was another unknown with a theoretically knowable end point but I was self-financing through student loans and didn’t have a clear sense of what I was going to do afterward. I had to ignore sustainability in the name of hustling to figure out what the hell I was going to do to justify the incredible debt I was taking on to give myself this experience (hence the copious side projects, organizing TEDxClaremontColleges, starting a company, and non-stop work). Only now, three years into my work with The Ready, am I starting to realize that I don’t need to be killing myself in the name of figuring out the next thing. The next thing is this thing. I need to be growing in my roles and responsibilities at hand — not grinding myself into a dust in order to figure out what I need to do next.

I think part of me has worried that the flip side of not hustling is complacency. 2018 taught me that what I’m actually looking for is sustainability and that until recently I’ve never felt like I could be in a place to work sustainably. I have a lot of bad habits and mindsets to unravel (see learning #1 regarding self-compassion) but acceptance feels like the first step.

3. Action does not (and will never) equal progress

Are you sensing a theme here?

I’ve always been powerfully motivated to be productive. Call it a Protestant work ethic combined with Catholic guilt, a childhood and adolescence spent playing extremely competitive ice hockey where there was always somebody looking to take my spot in the lineup, being the oldest of five boys and always wanting to be a role model for my brothers — the reasons are surely numerous and profoundly psychoanalytic. What it means in practice, though, is that I’ve always been comfortable taking non-stop action toward success. What’s the next action? What do I need to do? Repeat, forever.

Working in a self-managing company requires an ability to pick through a truly overwhelming amount of possible actions (I could literally do anything I want) and pick the best ones given any number of contextual factors (my energy, what the company needs now, what the company will need later, what Slack is telling me, what my email inbox is telling me, etc.). Instead of getting good at distilling this information down to the most essential things to do I’ve gotten too good at capturing every possible thing I could do and then surfing along the top of all of them. Instead of going deep on the most essential one or two projects at a time I’m able to do the most inessential work across 7, 8, or 20 projects all at once. The end result is a ton of work without much to show for it.

This is the lesson that fills me with the most angst. It’s the one that feels like the largest squandered opportunity and the one where I should’ve most obviously “known better.” Without letting my critic get too engaged at this point, let’s just say that this lesson is going to inform the largest part of how I work differently in 2019.

What now?

I’m not particularly interested in distilling these lessons into bullet lists of “things to do” because I think they retain more of their usefulness in their more complex and ambiguous form. Suffice to say I will continue reflecting on these in the weeks and months to come and future writing will (hopefully) peppered with ideas that were born of the lessons above. For now, though, I’m going to get back to the most important project I could possibly be working on, in a sustainable way, while I tell my self-critic to take a hike!

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I’m Sam. I work for The Ready in Washington D.C. I tweet. I write a newsletter called The Deliberate. I take pictures of mostly boring things.

State of the Apps: 2018

It’s no secret that I think a lot about the software I use. Simply put, spending all day in front of some kind of electronic device raises the stakes for the decisions I make around the software I choose to use. If I’m going to spend all day looking at a screen I want to interact with tools that I find enjoyable, well-designed, and help me get my work finished as seamlessly and efficiently as possible.

When I look back at 2018 I’m struck by how many of the tools I continue to use are the same tools I used in 2017, 2016, and even before. I definitely spent a significant amount of time investigating new entries into the market (it’s one of my favorite ways to procrastinate), and reacquainting myself with old friends, but at the end of the day my “official” tech stack looks a lot like it has always looked.

What follows are the major task categories/actions I need to take on a regular basis and the tools I use to get those jobs done. I’ll try to say a few words both about the primary winner in each category but also my experience with any other notable options I tried over the past year.

Before I dive into the specifics, here are the most important principles I’m looking for when deciding which app to use:

1. iOS & macOS compatible: I use both Apple operating systems extensively and I need my apps to seamlessly sync between my phone, iPad, and various computers. If an app doesn’t have a version for the other operating system it’s either so niche that it doesn’t matter or it’s so good I can look past that glaring omission.

2. Well-designed: This is obviously a pretty subjective criteria but it’s something I feel like I can get a pretty good read on after using an app for a couple hours. I’ll try to call out specific examples that I think really exemplify this principle. Basically, if it’s able to spark any kind of joy in me when I’m using it, that’s a good sign.

3. Dark mode, please: I’ve become a big fan of using apps in “dark mode” whenever it’s available. Whether its a true black mode that looks great on an OLED iPhone or just a more traditional dark mode that tends to look better on my iPad or Mac, I will prioritize an app that has a dark mode.

4. Default wherever possible: Given that I’m about to write several hundred words about the apps I use it might be hard to believe that I actually try to use default apps and services wherever possible. I’m a big fan of the interoperatbility and integration you (sometimes) get when you use all Apple devices and Apple software. Much of my tinkering this year was investigating which default apps and services were good enough to replace some third-party app that I used to use.

5. Clear business model: I want to see and understand the business model of any app or service that I use consistently. I don’t want important parts of my workflow yanked from underneath me because the developer can’t afford to keep a free thing going indefinitely. I want to pay for apps and I’m not averse to signing up for a subscription if it’s something I like and use a lot.

Without further ado, here’s the state of my apps as I head into 2019!

Short-Form Note Taking & Reference Storage: Bear (iPhone, iPad, macOS, paid subscription)

This category of app needs to allow me to quickly take notes (usually in Markdown) and then allow me to store those notes in an easily searchable way. For the last couple years, the hands down winner in this category has been Bear. Any time I need to write something that’s shorter than an article it probably starts in Bear. Emails, long Slack messages, notes during meetings… all of these start as Bear notes. The main tweak I made this year was to figure out a tagging system that allows me to review active notes on a regular basis, without having to go through my whole archive. That’s probably an article for another time, but I essentially mirrored the structure of Things in Bear so that it’s easier to find relevant notes for the projects I’m working on at any time.

Honorable mentions in this category are Agenda and the default Apple Notes app. I made a go of switching over to Agenda this year but ultimately decided not to stick with it. I think they are doing some really interesting things with the nature of note-taking and reference storage with Agenda but it ended up being too radical of a shift from my GTD-esque way of thinking about my work. And the default Apple Notes app continues to be a very good app (I especially like that I can just tap my sleeping iPad screen with the pencil and be brought into a new note) but I can’t abide a folder-based organizational structure. I’m a tags man through and through nowadays.

Long-Form Writing: Ulysses (iPhone, iPad, macOS, paid subscription)

For much of the year I was actually doing my long-form writing (like this article) in Bear. Eventually I realized I didn’t like having pieces of writing that require hours and hours of work intermingled with one-off notes, so I decided to seek out an app to house my “real” writing. In the past I’ve used WriteRoom, Byword, and Drafts. All are very minimal and very good word processors optimized for writing. However, I decided to use this opportunity to investigate an app that I see lots of people I follow using — Ulysses. Turns out, it’s pretty damn great. Great Markdown support, dark mode, versions for all my devices, unique but logical organizational structure… I could go on. Technically, Bear is completely capable of handling the long-form writing that I tend to do but psychologically I’ve really appreciated having a separate home for the type of writing where I want to linger over it for awhile.

Calendar: Fantastical 2 (iPhone, iPad, macOS, paid app)

No big surprises here. I’ve been using Fantastical for years and although I made a half-hearted effort to explore the calendaring space a little bit this year, I found myself back in the warm embrace of Fantastical almost immediately. It seems that many calendar apps try to be too many things at once. I don’t want my calendar app to handle reminders (Fantastical gives you that option but it’s easy to turn off). I don’t want my calendar to try to handle my task list. I don’t want my calendar to be in my email app. Ultimately, Fantastical gives me the simplicity I’m looking for in a calendar app with some of the nice bonuses that make it feel professional (like top-notch natural language processing for creating new events and having different calendar “sets” on macOS).

I made a go of using the default Apple Calendar for a couple months of this year and it was mostly fine. Weirdly, I noticed it being kind of slow in updating when calendar events changed in the backend (like when a coworker moved a meeting or changed the description). That’s the type of thing I would expect a default app to be better at, not worse. If Fantastical went away tomorrow I’d be fine running with just the default app and if it continues to improve — and Fantastical stays mostly static — then I could see this being another category where I simply settle into using the default app everywhere.

Task Management: Things 3 (iPhone, iPad, macOS, paid app)

Things is life. Things is everything. Things drives the way I work and without it I would be wandering in the wilderness. That’s not to say that I’ve never had a wandering eye. In the past I think I’ve flirted with every major to-do app on the market: Todoist, 2Do, and OmniFocus have all had their time in the sun. But I always, always, always end up coming back to Things. In the past there was always a little bit of disappointment in that fact because it severely lagged behind a lot of the other major players. Sometimes it almost seemed abandoned. But ever since Things 3.0 came out in May 2017 it feels like a whole new app. Cultured Code is updating it at a torrid pace (it’s at version 3.8.1 right now) and is including all sorts of great features: insanely good iPad keyboard shortcuts, dark modes across all versions, Siri Shortcuts support, etc. It’s a good time to be a Things user.

Email: Airmail (iPhone, iPad, macOS, paid app)

As with many Slack users, it seems like my email usage is getting less and less every year. That being said, email is still an important enough part of my workflow that I want to use a tool that I like. I actually used the default Apple Mail app for several months this year and like with the default Calendar app, it was fine. Airmail could go away and everything would be copacetic (especially since Things introduced a “mail to Things” feature that lets you forward emails directly into your Things inbox). However, Airmail has one key feature (other than just being nicely designed) that keeps me coming back again and again: custom swipes. The important thing to understand is that I treat my email inbox as simple a location where next actions periodically arrive. I almost never respond to an email when I initially read it (unless it’s truly easy and quick to respond to). Instead, I think to myself, “That’s a task I need to take care of,” which means that it needs to show up in Things — because that’s where all my work lives. As I mentioned with regards to the default app, there’s an email address that I can forward an email to that will result in it showing up in my Things inbox. Seems easy and quick, right? It is — except in Airmail I can just swipe right on a message in my inbox and it automatically sends it to Things (with a link back to the actual email) and archives the original email. Perfect.

Read Later: Instapaper (iPhone, iPad, macOS, subscription)

I think it’s vital to use some kind of service that collects and holds things you find on the internet that you want to read or watch. The mental mode I’m in when I’m finding interesting things to read is often very different from the mental mode I need to be in to read something. Instapaper ensures that I always have something ready to read when I feel ready to sit down and dig into something. It’s nice and simple with great typographic options (including a dark mode). It’s easy to send things to it from anywhere, whether I’m on my phone, iPad, or Mac. It may be the oldest app that I regularly use so there’s probably a bit of irrational nostalgia that keeps me coming back to it, too.

I explored Pocket for awhile this year because it seems to be the most popular read later option. It’s good. No major complaints from me other than I think it’s trying to be a bit more than I need it to be. There’s a social component to it that I’m not interested in as well as a discovery feature that tries to guess what you might like to read and serves it up to you. I already have enough interesting content coming at me throughout the day so I don’t need my read later app to get into that action, too.

I also played with the default Reading List feature in Safari. It’s also fine but it lacks the ability to “like” an article and have it be easy to find again, like Instapaper. I use the “like” feature in Instapaper to indicate which articles I might want to include in The Ready’s weekly newsletter that I read so if I went all in on Reading List I’d need to create a new workflow for saving those (probably just a normal bookmarks folder). Not the end of the world, but I’ll stick with Instapaper for now.

Recurring Reminders: Due (iPhone, iPad, paid app)

There’s a class of reminders that I want to set and receive that a.) happen on a recurring basis, b.) I want to be as annoying as possible, c.) I don’t want to see when they aren’t being triggered. I call these my “Daily Guardrail” reminders and they’re simple things like being reminded to “Drink a glass of water” within a couple minutes of waking up, “Water the plants” every week, and “Last chance to do daily #yearofmundane Instagram post” at 9:00 PM every night. These reminders shift and morph over time as I try to develop various habits. Due is great because once a reminder is triggered it will keep going off on a cadence you’ve determined until you indicate you’ve finished the task. I keep the app buried in a folder somewhere so I don’t have to think about it or see it until the reminders pop up and I take the action I need to take to get it to shut up.

For more run-of-the-mill reminders, reminders that I want to trigger based on a location, or reminders I want to use Siri to set, I’ll use the default Apple Reminders app.

Habit Tracking: Streaks (iPhone, iPad, paid app)

There are four things I try to do every day: read a book, write, meditate, and exercise. The app I use to track how well I’m doing those things is Streaks. It’s really simple but has some nice touches that make it satisfying to use. For example, indicating you’ve finished a task requires you to hold down the button for a second or two, instead of just tapping it. I don’t know what part of my brain this is tickling but it feels better to do it that way. Every Sunday I like to look back at the previous week and record how well I did with each of these habits and Streaks makes it easy to go back and see which days you did and didn’t accomplish the habit. For such a simple app it has actually become a pretty important part of my life over the past year.

Shared Grocery List: AnyList (iPhone, iPad, subscription)

My girlfriend and I needed a way to contribute to a shared grocery list and The Sweet Setup recommended AnyList. We’ve since added a few more shared lists (TV Shows to Watch Together, Vacation Locations, Things to Do in DC) and it is doing a fine job of holding those, too. I’ve recently had some frustrations with getting Siri to add items to the grocery list (as a family with copious amounts of Apple devices including multiple HomePods I want to be able to just exclaim grocery store items into the air and have them added to a shared list) but once I realized I could connect the default Reminders app to AnyList that frustration largely went away.

Music Streaming: Apple Music (iPhone, iPad, macOS, subscription)

This is the one category where I probably went back and forth the most all year. Apple Music and Spotify both scratch different itches for me. Starting with Apple Music, I’m obviously a fan of the fact that it’s the default option for an Apple-centric household. It integrates with all my devices, including HomePods, in a mostly seamless and pleasing way. I also prefer its overall design and aesthetic over Spotify. Spotify, on the other hand, is so goddamn good at recommending me music that I like. Plus, it does things like the end-of-year summary that the data nerd in me loves.

However, in the past few weeks I think I’ve mostly negotiated a truce between these two services and have landed on the one I’m going to run with for the time being (and hopefully long term): Apple Music. This is probably an article for another time but what seemed to flip the switch for me was completing wiping my library, turning off the setting that adds songs to my library when I add a playlist, spending an hour re-creating my library from memory, and creating three playlists (The Sound of High School, The Sound of College, and The Sound of Productivity). With a fresh and interesting library that I actually invested some time in creating I felt like I had some skin in the game with Apple Music. Add to the fact that it integrates like a dream with my HomePod and allows me to stream music to my Apple Watch without needing to bring my phone on a run means that I think I’ve made myself mostly cozy in the Apple Music universe and I can try to ignore Spotify and it’s sweet, sweet, recommendation engine…

Twitter: Tweetbot 5 (iPhone, iPad, macOS, paid app)

This category has gotten much more complicated in the past year. With Twitter’s continued slow-motion strangulation of third-party apps (this time through removing the APIs that allow for notifications) I’ve had to slightly adjust my approach to Twitter over the past year. The simplest option, and something I experimented with for much of the year, would be to just use the default Twitter app. I don’t hate it as much as many old-school Twitter users do, but I also don’t love it. What I’ve decided to do is keep it on my devices, buried in a folder, but with some of its key notifications turned on (yes, I know I should probably turn off Twitter notifications all together but I’m not so popular that it’s a.) an overwhelming number of notifications or b.) ever particularly negative). Basically, I use the Twitter app as the notification engine and Tweetbot as the primary way I interact with my actual feed. Tweetbot has had some nice updates recently (on both iOS and macOS) so I think I’ll be riding it into oblivion with the rest of the Twitter die hards who will only let go of our third-party apps when they are pried from our grasps.

E-Books: Kindle (iPhone, iPad, Kindle Oasis) and Apple Books (iPhone, iPad, macOS)

I’m in the weird position of actively using both Amazon and Apple for my e-book needs. It’s kind of dumb… I definitely go through periods of time feeling like I wish I had just picked one and stuck with it for the long-term instead of spreading myself across two devices and services. On the other hand, I kind of like that I don’t give Amazon 100% of my book buying budget. And the lover of default apps in me likes using Apple Books (especially with the iOS 12 update) and being able to consolidate nearly all my work and much of my leisure onto one device. But then the premium experience lover in me likes taking my Kindle Oasis into an environment where a 12.9” iPad Pro or an iPhone screen would suck and using a device that is specifically designed for reading books. Anyway, if you can’t tell I’m pretty conflicted but I don’t actually see my approach changing here anytime soon. I’m probably 70/30 Kindle to Apple Books at this point and if anything it might shift closer to 60/40 or maybe even 50/50 in the future. In either case, Goodreads will remain as my primary way for tracking books I’ve read and still want to read and Audible is really the only game in town for audiobooks.

Podcasts: Overcast (iPhone, iPad, subscription)

Podcasts are another category of job where I did some major experimentation with using the default Apple app. Like the other default apps I made a go of using this year, it is fine. The problem, though, is that my preferred third party option is so much better than “fine” the default app never really stood a chance. Overcast is maybe my favorite app on my phone. It’s filled with nice design touches, is extremely easy to use, and has one of the best features ever — Smart Speed — that lets me listen to podcasts faster without having any noticeable distortion. Plus, it has extremely nice dark mode options and is being actively developed by a guy, Marco Arment, who I feel like I know thanks to the years of listening to him on various podcasts. If it suddenly went away I’d be fine using the default app but I would be very sad.

Time Tracking: Toggl (iPhone, web, subscription)

After years of listening to Myke and Grey talk about time tracking on Cortex I decided to give it a go in the last few months of 2018. I’ve been treating this as a test run to figure out how I want to do it “for real” once 2019 rolls around. My tool of choice has been Toggl and for the most part it has been pretty straightforward and relatively painless to use. I know there’s a bunch of stuff I could be doing with Siri Shortcuts to potentially make it easier to trigger and stop various timers, but I’m running it pretty vanilla right now.

Password Management: iCloud Keychain (iPhone, iPad, macOS, default)

First, let me say that everyone should be using some kind of password manager. For me, for years, that was 1Password. I wasn’t always the most diligent making sure I used strong and non-duplicative passwords but 1Password helped me take my password hygiene in a positive direction. For the past few months I noticed that every time I was prompted to enter a saved password it seemed like it lived in iCloud Keychain, not 1Password, though. So, I decided to see if I could run with just iCloud Keychain as my password manager (like Dr. Drang). So far, it seems like I can. Another third-party app falls to the default option!

Web Browsing: Safari (iPhone, iPad, macOS, default)

Logically, I know I should probably be using Chrome nearly everywhere I can because The Ready is a Google Suite shop and I spend a ton of time in Google’s software. But I just can’t do it. I don’t like what Chrome looks like. I don’t like what it “feels” like. Safari feels like home and I don’t see myself moving away from it any time soon.

Personal Journal: Day One (iPhone, iPad, macOS, subscription)

Day One and I go way back. I have entries in it from 2009! I go through periods of time where I seem to write something every day and I go through periods where I’m much less consistent with my writing. At this point, though, I have hundreds of entries saved in Day One and nearly every day I’m presented with something I wrote on that date in the past. I really like seeing these quick shots of what I was thinking about and struggling with at some point in the past. I have a notoriously bad memory so it helps me remember what I’ve done, what I’ve seen, what I’ve worked through, and what hopes and dreams I had for the future.

Weather: Dark Sky (iPhone, iPad, paid app)

Weather apps are a playground for design. As such, I’m a sucker for exploring the latest and greatest. For much of this year I was rocking CARROT Weather across all my devices (albeit, with the personality setting set way down) and I mostly liked it. However, like with some of my other tried and true favorite apps, I could never shake my first true weather app love: Dark Sky. The precipitation notifications can’t be beat and I haven’t found anything with as classy or agreeable visual design. So, after my long sojourn with CARROT and a few other weather apps, I’m happily back with Dark Sky.

Delivery Tracking: Deliveries (iPhone, iPad, macOS, paid app)

I always seem to have a box being shipped to me. Deliveries lets me know where that box is and when to expect its arrival. It’s a nice bit of peace of mind to know I can swipe over to this app and see where my deliveries are. It’s a simple app that make it easy to add new tracking numbers and good notifications that keep me apprised of what’s going on.

Sleep Tracking: AutoSleep (iPhone, paid app)

The key feature for a sleep tracker that I’m going to use consistently is the ability to work consistently even when I forget about it. AutoSleep does just that as it automatically figures out when I fall asleep and wake up. I’m not in love with its design choices but what keeps me coming back to it is the dashboard view that shows me summary data for several different periods of time, including the last week. I pull out the weekly data every Sunday and put it into my own spreadsheet so it’s important that my app can show me that weekly view.

Recipes: Paprika (iPhone, iPad, macOS, paid app)

I’m trying to do a better job of cooking more consistently and Paprika has helped me take some strides in that direction. It has all sorts of features that I haven’t really explored in depth, like keeping a list of the ingredients you have on hand and various meal planning features, but even just as a way to keep a list of recipes it excels.

Movie Tracking & Backlog: Letterboxd (iPhone, web, paid app)

I don’t watch very many movies, but I like to keep track of the ones I do. I’ve used simple lists in notes apps and other apps specifically for that task but Letterboxd is the one that stuck.

TV Tracking & Backlog: TV Time (iPhone, web, paid app)

Same as above. I don’t watch a ton of TV but I like knowing which series I’ve started, which ones I’m caught up on, and what I want to watch in the future. TV Time does that perfectly well.

Subscription Tracking: Bobby (iPhone, paid app)

As you may have noticed reading through this article, many of the apps I mention above are subscription-based. I don’t have a problem with that, but I do like to keep a handle on how many subscriptions I have ongoing at any one time. This little app does a good job of holding all that subscription information and showing me how much I’m spending on a monthly or yearly basis.

Calculator: PCalc (iPhone, iPad, macOS, paid app)

That’s right, I use a third party calculator. Inexplicably the iPad doesn’t ship with a default calculator and I’m not going to use different calendars on different devices. That means I need something that shows up on each of my devices and PCalc fits that bill.

Ad Blocker: 1Blocker (iPhone, iPad, macOS, paid app)

Safari continues to do a pretty good job of making using the Internet a somewhat reasonable endeavor, but I like to use an ad blocker as well as the native features. I’ve used 1Blocker for a long time and the new version seems to continue in the same vein, albeit with even more customizable options, as the last version. Bonus points for being able to use it across all my devices, too.

Call Blocker: Nomorobo (iPhone, subscription)

I almost never answer a call that comes from an unknown number, but Nomorobo makes sure I never answer a call from a known robo-caller. It’s super easy to have it run in the background and every time it catches a robo-call I feel like I’m getting my money’s worth.

RSS Backend: Feed Wrangler (web, subscription)

Google shut down Reader years ago but I’m still not used to the fact that I now need a separate RSS backend and reader. David Smith’s Feed Wrangler took over from Inoreader this year and it seems to do a fine job. I don’t use it to actually read my RSS feeds — it’s just where I go to add new ones.

RSS Reader: Unread (iPhone, iPad, paid app)

Another one of those apps that I’ve had forever but still seems to be the best option for how I think. It has a delightful dark theme and makes it easy for me to send useful articles to Instapaper which is where I actually do the reading.

Wallpaper Finder: Vellum (iPhone, paid app)

This delightful little app makes it super easy to find interesting and handsome wallpapers for my phone. I especially like the blur tool that lets you take any of the wallpapers and add a neat effect. I like to use the regular version for the lock screen image and then a blurred version of the same image for the home screen (because it allows apps to stand out better). If you like to change up your wallpaper from time to time this app is a no-brainer.

Drawing: Linea Sketch (iPad, paid app)

This is a category I’m still actively exploring. I’m not an artist but I have been in situations with clients where flipping to a drawing app, sometimes while projecting my iPad onto a screen so everyone can see it, and drawing in real-time has been very useful. Right now Linea is my favorite app for doing that but I have a few more I’ve liked (Paper by 53) or still need to investigate (Goodnotes & Notability).

The Stuff I Don’t Have Much of a Choice in Using

Slack

The Ready runs on Slack. Many of my clients run on Slack. I’m increasingly ambivalent about the effect it’s having on me — and work in general — but for now it’s the best we have.

Google Drive, Docs, & Sheets

The Ready also runs on Google apps. As somebody increasingly interested in using iOS-only in my computing life, this isn’t ideal. The Google iOS apps range from okay (Google Drive) to flaming garbage (Docs and Sheets).

Trello

We use Trello at The Ready to publicly track various projects and other work. I still haven’t found a good way to integrate my personal task management system with the way we use Trello at work, but overall I think Trello is a pretty great tool.

Zoom

As a member of a fully remote company I spend a lot of time on video calls. That means I spend a lot of time on Zoom. I wish so much that the Zoom iPad app would allow for split screen usage. What that actually means is that I spend a decent amount of time with Zoom on my iPhone and my iPhone awkwardly propped up against something or Zoom on my iPad and my video going away every time I alt+tab into another app. It’s not ideal, but I make it work.

Looking into the Future

I’m mostly happy with the tools I’m using in my life right now. Does that mean I’ll never try a new app? Of course not. At this point, it’s practically a hobby. Trying new apps and combing through settings screens is one of my favorite ways to relax. But when it comes to the main jobs to be done in my personal and professional life I feel like my chosen tools actually help me do great work. They get out of the way when they need to get out of the way and they help me take action when I need that help.

Looking into 2019 there’s a handful of things that I hope to see happen or am thinking about. First, I really hope Apple decouples the default apps from the yearly iOS update. There’s no reason Mail, Notes, Podcasts, and the other default apps should only be updated once per year. Let those teams ship updates to those apps like any other app. If that were to happen I have a sneaking suspicion that even more of the default apps might make their way into my regular stack.

Tied to that idea, I will continue to pressure the third-party apps I use with the default options whenever possible. I like the idea of running as stock as possible as long as it doesn’t materially negatively effect my ability to work. In some cases, like with iCloud Keychain and Apple Music, that means I use the default options. In other cases, like with Overcast and Airmail, the third-party options remain a better fit for how I like to work. I wonder if at the end of 2019 I’ll say that I’ve adopted more of the default apps?

Finally, I’m going to make a major push to be as iOS-only as possible this year. Partly as an exercise in future-proofing myself and partly as something I think will be fun, I will be prioritizing the apps and workflows that let me do everything from an iPad and my phone. I’m not sure what that means for what this article will look like a year from now, but it’s something I’m keeping an eye on.

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Interested in more? Follow me on Twitter, Instagram, and LinkedIn. Have an app you think I’d like? Let me know!

Use software that sparks joy

In The Life-Changing Magic of Tidying UpMarie Kondo introduced the idea of only keeping physical objects that “spark joy.” I’m not a full Kondo-ite who thinks this advice should be taken to its literal and extreme end but I do think that is a mostly useful and interesting piece of advice that aligns with my minimalist tendencies. It’s a high bar and when applied to the vast majority of the items around you leaves you with a much smaller and curated collection that actually feels good to own. It’s a little hard to explain if you’ve never had a chance to experience it but opening a closet or looking around a room and only seeing items that spark joy is a pretty cool feeling.

While Kondo focuses on the physical world, I decided to take a look at my digital world with the same spark-of-joy-trained eye. As a knowledge worker who spends the vast majority of his day in front of some kind of electronic device (usually an Apple device of some kind) my suite of tools is decidedly non-physical (other than the devices themselves, obviously). Regardless of their ephemerality, I think it’s reasonable to expect to feel some spark of joy with your digital tools, too. If you have any autonomy over deciding what you use to get your work done then noticing which apps and services spark joy for you isn’t a bad way to make some decisions about what goes in your proverbial toolbox.

What follows are the tools I use that spark joy and a few words about the joy they spark.

Note: You’ll notice that I didn’t even try to define what “spark joy” even means. For me, I think it’s some combination of obviously thoughtful design, minimal aesthetics, and a high degree of functionality with regards to how I like to work. Your definition will undoubtedly be different — which is okay!

Overcast is an iOS podcast app developed by independent app developer, Marco Arment.

Overcast is one of those apps that you can tell was crafted with a ton of care. Marco is an opinionated guy and it shows up in the design and functionality of this app. He’s a total audio nut and obsesses over how to make listening to podcasts ever better. The Smart Speed feature is incredible. It imperceptibly takes out silences in the podcasts you listen to without adjusting the pitch of the audio. It also keeps track of how much time you’ve saved by using Smart Speed — so far I’m up to 299 hours. The other marquee feature that Marco pioneered is something he calls Voice Boost. When you have it turned on it somehow adjusts the audio playback so that it sounds better/louder through your phone’s speakers. It isn’t a straight volume boost — he’s actually doing something more sophisticated (that I don’t understand) to make spoken word sound clearer and louder through the phone’s speakers. Like I said, he’s a huge audio nerd.

Instapaper is a read-it-later service originally developed by Marco Arment but currently under new management. It allows you to save and read articles you want to read later from anywhere. I like to separate modalities when I’m working and most of the time when I find an article that looks interesting it doesn’t mean I actually want to stop what I’m doing in the moment and read it. Instapaper allows me to easily save those interesting articles for a better time.

Honestly, I think there’s a nostalgia component to why I love this app. I’ve had it on my home screen ever since my first iPhone back in the 3GS days. I understand if that’s not reason enough for you to also enjoy the app. Luckily, it has some other things going for it. It has a lot of great typography options which is kind of what you want from an app where the whole point is to read things easily.

It has a really simple and clean UI that gets out of the way and lets you do the main thing you’re there to do, read the articles you’ve saved. It makes it really easy to save things into it with browser extensions for your computer and sharing extensions on iOS. It has a simple structure (your list of unread items, your archived items, and items you’ve “liked”) that can grow in complexity (by creating folders) if you need it.

I think this app helped me realize that just because I found something interesting to read doesn’t mean I need to read it immediately. It allowed me to recognize the two different modes related to reading and learning — finding new material and actually sitting down to read that material. They require different ways of thinking and benefit from being separate from each other. I don’t think I realized that until I started using this app.

Fantastical is an iOS and macOS calendar app. I use it instead of the default Apple Calendar app on all my devices.

Fantastical’s main selling point is how good it is at parsing natural language (“Lunch with Emily from 12–1 PM at Panera”) into actual calendar events with all the information filled out. Most other calendar apps have a pretty tedious process for filling in all the information for a typical event. Fantastical lets you do the vast majority of it by simply typing something out the way you would say it to another person.

A few other sparks of joy this app manages to pull out of me are due to it’s cross-platformness (I use it across all my devices), the ease for switching to different time scales (daily, weekly, monthly views), and the idea of having “calendar sets” (at least on the macOS version — hopefully iOS gets this feature someday, too). A calendar set is a group of calendars that always show up as visible together. Since I have visibility on all my colleagues calendars (for finding mutually available time easier) I like to be able to turn on and off certain sets of them very easily (like, my current project team vs. just me).

Bear is an iOS and macOS note taking/writing app.

Bear fills two important writing jobs for me. On the one hand, it’s the app I’ll quickly open when I need to take some notes in a meeting or any other situation where writing some text-based notes makes sense. On the other hand, Bear is also the app I open when I sit down and work on a longer piece of writing (I’m writing this article in it right now).

It has a really clean and simple design that let’s me use it for both purposes without feeling like I’m pushing against the limits of its functionality. It has a pretty robust library of themes to choose from. I use a dark-ish one that has a gray background and white text.

It also has an interesting tagging system (instead of folders) that I really like. This allows for some interesting ways of organizing and retrieving old notes that a more traditional folder system wouldn’t be able to do.

Finally, like any app that has cross-device functionality, it has an absolutely rock solid syncing engine. Something I write on one device shows up on the other one almost instantaneously. I never have to wonder if the device I’m holding has the most current library of notes. They all do, all the time.

Carrot Weather is a really weird app. It’s default settings involve the app being “hosted” by a malicious AI character that talks to you every time you open the app. It’s funny, but I’ve actually turned off all the whimsy and use it in the “Professional” mode (which basically means it doesn’t talk to me or emit any sound effects). I like it because I think it does a really great job of presenting a lot of information without being overwhelming. It also lets you use Weather Underground as the data source for the weather information so you can get hyper local forecasts, which is neat. Lastly, the latest update has given it a pretty incredible series of maps which you can turn on or off at will and layer them to perfectly suit the information you’re looking for.

You can also choose from lots of different app icon versions so you can find one that matches your own personal aesthetic instead of getting stuck with the default.

Airmail is an email client for iOS and macOS. You may be picking up on a theme here, but apps that are really cleanly designed give me a lot of joy. I really like Airmail’s design (although I’d love to have a dark mode). Where it really sparks joy for me, though, is in the swipe customizations. I only do a couple things with any given email: archive it, trash it, or send it to my task management software (Things). I can map all of these actions to various swipes (short left, long left, etc.) so I can very quickly triage an entire mailbox full of email very quickly. I love the way it integrates with Things so I can easily send an email over there and have it create a new task with the information from the email, including a link back to the original email, in the notes field.

Things is my task management software. Anything I need to do, or think I might want to do someday, is managed through this app.

I’m not even sure where to begin with this one. I’ve been using it for so long it has become synonymous with productivity for me. First, I love that it’s completely cross-device so I can use it on anything that happens to be nearby me (iMac, MacBook, iPhone, iPad) and know that everything will be synced across all my devices. When you’re putting thoughts, ideas, and reminders of things you need to do you have to trust that things won’t disappear. I don’t think I’ve ever had any data disappear from Things.

A new version was released a few months ago and it is just a beautifully elegant piece of software. Subtle things like the animations that happen as you interact with the app (my current favorite is the little “x” that kind of rolls/cartwheels into position when you swipe on a task to delete it) to large things like the overall organization to the app — it’s all really, really good. In an update a few weeks ago they introduced a much more robust approach to keyboard shortcuts on the iPad app and I’ve only just scratched the surface in learning these. It’s one of those apps that a pro can go really deep on while at the same time retaining a core level of simplicity and approachability where anybody with a spare thirty minutes could learn enough to have it make a huge impact in how they organize their work. It’s just so damn good.

I’m a fan of knowledge workers adopting a craftperson’s mindset to the way they approach their work. A key part of that mindset is giving a shit about the tools you use. Not in a persnickety if-only-my-tools-were-better-I’d-be-better-at-my-job way, but in the way that a master carpenter knows how his or her tools so well they become an extension of their body. These pieces of software are the extensions of my mind and body that allow me to focus on the work at hand while also getting little bursts of joy throughout the day.

That being said, I’m always on the lookout for new apps or tools that might be a better fit for how I work and think. Share the tools that spark joy for you in the responses below!