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!

The power of choosing the right verb in living the life you want

I’ve always appreciated Merlin Mann’s careful use of language. I think he was the first person I ever heard explain the difference between “busy” and “time constrained.” Another one of his favorites is the difference between “expensive” and “costly.” I admire precision in language. In this same vein (and following yesterday’s article) I’ve discovered my own pet peeve when it comes to one verb in particular — find.

“Yeah I’d love to meet! Let me find some time in my schedule and I’ll get back to you.”

“10 Ways to Find More Meaning in Your Work!”

The word find is pervasive. Everyone is constantly searching for and sometimes finding the time to do things. Finding the time to go to a meeting. Finding time to setup a call. Finding time to work on that report. Looking for and often failing to find a time to work on that important but not urgent project. Busy, busy, busy. Finding, finding, finding.

Find insinuates that what you’re looking for is hiding from you and it’s simply a matter of discovering its location. At the same time, there’s a tinge of uncertainty. Something that must be found may end up being too well hidden. The excuse of not doing it is baked right into the verb — the time simply couldn’t be found! You tried! Who has ever heard of blaming someone for looking but failing to find? It’s not your fault!

The other context in which I see find inappropriately thrown around is when it comes to having a sense of meaning at work. Lifehack/personal development bloggers love to give advice about finding meaning at work. In their eyes, tips and tricks are what’s standing between you and the last rock you need to turn over to find the professional/personal meaning that has been hiding from you. Somehow meaning is some kind of discrete entity that is waiting for you to come get it if you just look hard enough.

It’s bullshit.

I’m trying to ban the word find from my vocabulary. When I say find what I should probably be saying is make. To find is passive. Finding has an excuse built into it. Finding absolves you from needing to make choices. Finding goes hand-in-hand with being too busy. Finding isn’t hard work.

Making, on the other hand, is active. It connotes making a choice. It’s deciding that something is important and doing what you need to do to make space for it. It’s being in charge of how you spend your time and attention and taking the vigorous action to do what needs to be done. It’s often difficult.

It even feels different when people use it in conversation with you. Which of these feels better as the recipient? “I’d love to hop on a call — let me make some time and get back to you,” vs. “I’d love to hop on a call — let me find some time and get back to you.” It’s subtle but the former feels like someone who is prioritizing our time together and not looking to slot it into an otherwise open part of their schedule.

Ultimately, I think the difference between find and make is the difference between feeling like you’re being buffeted about by the demands on your time and attention and feeling like you’re in control of where you direct your time and attention.

Active creators of their own reality make. Harried responders find.

Things I learned when I stopped writing every day

Awhile back, I used to write and publish something on Medium every day. The idea was to ideate, draft, edit, and publish in about 30 minutes. It was enough time to formulate some thoughts beyond the most surface layer of a topic, but not so long that sitting down and doing it felt too arduous to actually do (usually). I’m lucky to be a pretty quick writer so it usually meant I could crank out a couple hundred words without breaking much of a mental sweat.

Eventually I decided to stop that practice because it felt like it was potentially keeping me from writing something more “worthwhile” or “substantial.” Most days my only writing would be that thirty minute article that was drafted, edited, and published in the same sitting. Part of me felt guilty for not using that time to work on articles that can’t be written in one session. That I wasn’t building the muscles necessary to grab ahold of a more difficult or obscure topic and run it to ground over several, or many, writing sessions.

I have several pages of notes and ideas for articles and writing projects that can’t be tackled in the span of a thirty minute writing session. I hoped that relaxing my daily writing schedule would provoke me toward making meaningful progress on these projects.

Nope.

The truth, is that I havne’t been working on any substantial piece of writing. The time that I freed up by not writing and publishing every day has gone everywhere except toward writing more substantial pieces.

I try to treat everything I do like an experiment but somehow this experience has felt more like a personal failing as an aspiring writer and intellectual. I’ve been embarrassed to not publish anything for this long. And the longer I went without writing the more important it became in my mind to write something worth the delay. Which only raised the stakes which only made me less likely to actually write. Hello, negative feedback loop.

But a slight shift in mindset helps me realized I’ve learned some things:

• Writing, like most things worth doing, benefits from momentum and momentum is more about frequency/consistency than quality. It’s impossible to write the best thing you’ve ever written every day, but even writing something so-so every day has residual effects that spill beyond the boundaries of that individual writing session. I stopped writing every day because I felt like I was “using up” time and words that could be better spent on tougher pieces of writing. Turns out when I stop doing that I tend to stop writing entirely.

• Writing is part of my identity and when I don’t do it I don’t feel like myself. I’m decidedly average at a lot of different things that are relevant to my professional life. Writing is one of the few things I can point to and say, “You are good at this.” So when I don’t do it I’m basically handicapping myself in my quest to make a positive impact in the world.

• Writing generates more ideas. Somebody who doesn’t write frequently might think that writing consumes ideas but my experience is the opposite. It’s a very rare writing session where I don’t add two or three topics to my “spark list.” Writing prepares my mind to have ideas and make connections. I start seeing creative ideas and concepts everywhere. When I’m writing and publishing everyday it’s like they know they have an avenue to being made real so they pop into existence easily and in high numbers.

• Much of my work requires wading through ambiguity and uncertainty. Working with clients on a day-to-day basis, often in highly emotional contexts, means that a lot of my work is amorphous and hard and its hard to feel a sense of progress. Writing is a process with a beginning, middle, and an end. It starts with nothing and results in something. When I’m not writing I don’t get to feel those I-made-something-feelings very often. Those feelings feel good. I need them.

I feel like I’ve written a version of this article before and I’m sure I’ll write another version of it at some point in the future. I don’t seem to be the type of person who can learn a lesson once and have it really locked into my psyche from then on. But that’s okay. I’m a slow learner.

These daily(ish) articles aren’t going to follow a specific format or theme any more than my mind and daily life seems to follow a specific format or theme. The barrier for inclusion will be low because I want to be able to successfully write about anything and make it interesting (as long as we’re comfortable with a very liberal definition of interesting).

Forgive me this self-indulgent foray back into being a writing person and I’ll do my best to prevent this little project from veering into such navel gazey territory in the future.

You gotta cut me some slack, though — it has been awhile.

Focusing on the how in the quest for great work

I think meaning exists at two very different scales. The more common and overarching “macro” meaning that lives at the organizational level and the equally important meaning that is derived on a moment-to-moment basis while doing almost anything the right way (let’s call it “micro” meaning for now).

Consultants and the organizations in which they consult spend a lot of time talking about the first one and a lot less talking about the second one. Macro meaning is generally pretty easy to identify and talk about. It’s about doing good in the world and creating a positive impact in your community. It’s the difference between a non-profit bringing clean drinking water to the people of the world and a company bottling clean water from Michigan while its residents continue to drink poison from their taps.

Most people want to feel like their work has meaning (even if there is a significant dose of cognitive dissonance that must be managed). When you spend as much time at work as most of us do, the idea that what we do doesn’t matter is a quick recipe for disengagement and apathy. Macro meaning tends to live at the organizational level and when we talk about it we are mostly talking about organizational purpose. It’s all about what the organization exists to do and whether we believe that is worthwhile.

I’m more interested in the other kind of meaning, though. The smaller one. The one that exists at an individual level and is built and re-built hundreds of times throughout the day. Moment-to-moment, activity-to-activity, thought-to-thought.

This kind of meaning is what’s built when the way in which you are working and interacting aligns with your values. It’s the decisions you make about how to tackle a piece of work or how to have a conversation with your boss or how to show up in a meeting. I’m having trouble defining this feeling with words, so instead I’ll share a couple examples from my own work life.

I know how dangerous distractions can be when trying to do something that requires concentration and focus. When I take action to limit distractions during an activity (like writing this article) I feel like I’m doing it right. It’s easier not to turn on Do Not Disturb or put my devices in Airplane Mode or not switch over to Twitter the second I get stuck with what I’m trying to write. But every time I setup my environment in a way that allows me to do what I need to do well and I avoid the temptations to break concentration I feel like what I’m doing is more meaningful. If it’s worth the extra effort to do well then it must be worth doing.

Another example from a typical day; when I show up to meetings on time, or ideally, a little bit early. Not every meeting is one that I look forward to (shocker, I know) and the temptation is to stroll into those just as it’s starting or even a little bit afterward. Every time that happens, though, I can feel the cracks forming in my meaning foundation. I think it taps into a feeling that I don’t have any volitional control over my time and attention so showing up a little bit late is the (lamest) act of subconscious rebellion. Showing up early, ready to go, and fully focused for a meeting isn’t always the easiest thing, but when I do it I feel like my work has more meaning and that I’m showing up the right way.

One last example. On any given day there is almost always a mix of actions I could take but the overall order of operations is completely up to me. Very few things must be finished today. Things could get moved to tomorrow, later in the week, and truthfully, could probably never get done and the world wouldn’t stop spinning. When I’m not feeling connected to my work and it’s not feeling meaningful in any way, the way I tackle those tasks is often dumb. I’ll look at everything I need to do and I’ll do the easiest thing first. Then I’ll do the next easiest thing. I essentially take everything I need to do and reverse sort on Difficulty. That wouldn’t be a huge deal if nothing new was being added to my list but because I work in a company (kind of two, actually — The Ready and my client) there are always new tasks (e.g. emails and Slack messages) that are entering my consciousness and getting kicked to the top of my reverse sorted Difficulty list. The next thing I know, I’ve spent 8 hours doing easy (and mostly unimportant) stuff while surfing along the top of my email inbox and Slack notifications. The clean inboxes at the end of the day come at the cost of having to actually do anything difficult or worthwhile or meaningful.

In all three of these examples the common theme is having control over my attention. When I make deliberate choices about how to spend my attention I generally feel like my work has more meaning. When I let my attention be buffeted by things outside my control it feels like nothing I do matters. That’s why having a conversation, responding to an email, and writing this article could all be opportunities to build a sense of meaning in my work, or they could all be opportunities to destroy a sense of meaning in my work. It’s not the what but the how that matters.

I think a surprising amount of the organizational dysfunctions we see in our consulting and you probably live on a day-to-day basis can be tracked back to that sense of moment-to-moment meaning that happens at an individual level. When you multiply that feeling, or lack of feeling, across hundreds or thousands of people in an organization you get some effects that are far more than the sum of their parts and why extremely minor shifts in how we all approach our work may be more of a solution than it first appears.

I have a lot more to say about this but let’s end it here for now.

What do you think? When do you feel like your work has the most meaning? When do you feel like what you’re doing doesn’t matter at all? What am I missing from my description?

The State of the Apps & Tools: 2018

A craftsman has a paradoxical relationship with his or her tools. On the one hand, tools are the primary conduit through which their skill and passion are made manifest in the world. From this perspective, tools are incredibly important and the careful consideration of them makes perfect sense. On the other hand, a true craftsman knows that their skill and ability isn’t contingent upon the quality of their tools. They know they can take supbar tools and still create beautiful work.

All of this is to say that I think about the tools and apps I use to do my work a lot. I use the former perspective when I’m trying to feel okay about trying my third email app in three months and the latter perspective when I need to berate myself to focus on what actually matters (i.e. my actual work).

To indulge my “tools are important!” side for a little bit I thought I’d write a summary of the key pieces of software and hardware I’m using as I go into 2018. It’s always interesting to see what stays the same from year-to-year and when I’m successful in introducing a new tool that actually sticks around for the long haul.

So, let’s get to it.

Hardware

MacBook (Retina, 12-inch, Early 2015, 8 GB RAM, 250 GB storage)

This computer is entering what is probably going to be it’s last year of service. In the fall I’ll start looking for a replacement as this one will have reached the three-year mark. All-in-all, I love this computer. I’ve had a few of the well documented keyboard problems earlier in the year but am currently riding a nine month wave of keyboard bliss (knock on wood). It’s getting a little long in the tooth when it comes to anything computationally challenging at all but I’m either becoming more patient in my old age or its pokeyness just feels normal now. When it’s time to upgrade I’ll have to decide whether I want to keep rocking the lightweight MacBook or go with something a little bit more powerful. I think it’ll partly depend what my reliance on iOS/iPad is at that time.

iPad Pro 12.9" (first generation, Wi-Fi & Cellular, 256 GB) with Apple Pencil and Smart Keyboard

I went through long swaths of 2017 using this as my primary computing device. If the Google suite of apps weren’t unecessarily neutered (why are the advanced sharing settings different on iOS?!) I’d be able to use it almost 100% of the time. Whenever I use my iPad exclusively for a long period of time I start to feel like I’m living in the future. However, every time I come back to using my MacBook I feel like I can work smoother and quicker. Basically, I shift back and forth between using my iPad and my MacBook as my primary device on a pretty regular basis. The Apple Pencil is great and some of the best client reactions I’ve gotten in awhile were in response to the hand drawn slides I pulled together and the real time drawing/note-taking done during a meeting while connected to a projector.

Unfortunately, this iPad is currently having some issues that prevent it from staying reliably connected to its Smart Keyboard. I’ve taken it to an Apple Store and swapped out the keyboard several times, all to no avail. So, if I want to keep running this iPad experiment I think I’m going to have to make a new purchase fairly soon. I’m thinking about downgrading to the smaller Pro size as 12.9“ has felt slightly unwieldly at times. I think the 10.9” might be perfect.

iPhone 7 Plus (256 GB)

In many ways, my phone is the cornerstone of my work and personal life. I really enjoy the Plus size and have been impressed with its overall resilience. I like to use my iPhones without a case (or more specifically, I consider Apple Care+ my case) and so far I’ve only needed to seek assistance with a cracked screen once over the nearly 2 years I’ve owned this phone. I think I’m going to skip this most recent generation of iPhones and take a hard look at what’s released this fall with an upgrade likely to happen around then.

Apple Watch (first generation)

I love my Apple Watch. I use it all the time, including while I sleep. It makes me a more active person and while it may feed my unhealthy connection to notifications, I do feel like it adds more value to my life than it does detract. I’m very anxious to update to one of the newer models (not sure if I’ll get the LTE version or not) since I’m still rocking one of the original slow ones. Considering how much I like this version I’m a little afraid of how much I might like one with better battery life and quicker response times.

Kindle Paperwhite

The minimalist in me likes to do all his reading in iBooks on my phone or iPad. The reader in me likes my Paperwhite. I’ve decided to lean back into my “use the best tool for the job” mentality and that means my Kindle has re-entered my life with a vengeance.

Software

One thing I’ve learned about myself is that I have two primary “modes” that I seem to alternate between every couple weeks. One mode I already mentioned above — the “use the best tool for the job” mode. When I’m in this mentality it means I’m using primarily third party apps (often extensively customized to meet my preferences). I probably spend about 70% of my time in this mode.

My other mode is what I call “default” mode. When I’m in this mentality I’m all about keeping my needs as simple and minimal as possible. I’ll use the default apps and settings and try to minimize my reliance on third party apps or fancy workflows of any kind. I’ll often find myself switching to this mode when everything feels overwhelming and I feel the need to get back to basics. I probably spend about 30% of my time in this mode.

I used to berate myself for switching between modes because there’s always some switching costs in doing so. In some ways, it can become a distraction and a crutch (often it’s a sign that I’m avoiding real work) but I’ve decided to become a little bit kinder toward myself. I think having these two modes helps me stay fresh and aware of both a.) what my actual needs are and b.) new developments that might make my work better or easier to do. Therefore, in the section below I’m going to share both categories of apps when appropriate (Default Mode first, then Best Tool for the Job Mode second).

Web Browsing (Safari)

I use Safari everywhere because I’ve never been annoyed enough by it to seek out something else. I like the design and I like that it seems to sip battery power across all my devices as compared to Chrome. I keep Chrome around for emergencies but it never feels as good to use as Safari so I rarely let it come out to play. I’m thinking I may give it another whirl, especially when I’m in Best Tool for the Job Mode but for now I’m a Safari man across macOS and iOS.

Email (Apple Mail/Airmail)

Airmail has lots of great preferences that allow me to really craft an email experience that works with my productivity workflows and the way my brain works. I like being able to kick emails over to Things extremely easily — something Apple Mail doesn’t make as easy. I also appreciate that Airmail has versions for iPhone, iPad, and my MacBook that all look and work about the same.

Maps (Apple Maps/Google Maps)

I want to use Apple Maps more and more, but articles like this make it tough to not use Google Maps. I do think Apple Maps has gotten significantly better since iOS 11 (the turn-by-turn driving directions especially) but it’s hard to beat how much more information is easily reached via Google Maps.

Notes (Apple Notes/Bear)

Gosh, I love Bear. I’m not 100% sure why, either. I’m not a huge fan of tagging systems (I tend to prefer folders-based systems) and I don’t even really use Bear’s all that much but for whatever reason I happily pay for a yearly subscription to this app. I think it’s just really well designed and incredibly stable. As with all my key software, it has great versions for all my devices, too.

Music (Apple Music/Spotify)

Last year I spent most of my time in the Apple Music ecosystem before switching back to Spotify in the last few months of the year. I like the design of Apple Music better but I can’t deny that Spotify’s recommendations are much, much better. This year I’m going to try to stay as completely within Spotify as possible so my end-of-year report is actually accurate (what can I say, I’m a sucker for automatically generated year-in-review reports).

Twitter (Official Twitter app/Tweetbot)

Every time I get all excited to use default apps I’m always really excited and motivated until I get to Twitter. God I hate the algorithmic timeline that the default app pushes on you. It fundamentally changes how I view and use Twitter (for the worse). I can’t help but think that there will come a day when this is the only option I have for Twitter but until then you’ll find me using Tweetbot (and more or less being a timeline completionist) the vast majority of the time.

Calendars (Apple Calendar/Fantastical)

Nothing beats Fantastical when it comes to easily adding events with natural language. On the other hand, the default Calendar app has some nice integration with Siri (pulling information out of my email and other apps) and features like Travel Time that I find myself longing for when I use Fantastical for too long.

Task Management (Things)

There is no default app that replaces Things. I’ve tried using Reminders as a simple task management system but I always seem to come back to Things within a few days. Things drives nearly all of my productivity and it’s in the place of honor (far right position in the dock) on all my devices.

Shared Lists (Apple Reminders/AnyList)

Until recently I used Reminders for all shared lists but on the advice of The Sweet Setup I decided to give AnyList a try. So far, I like it quite a bit and it has taken over the shared list job in my life.

Longform Writing (Apple Notes/Byword)

I debated whether this was still a category worth having as Bear has seemed to cannibalize a lot of the writing that I used to do in Byword. However, considering I’m writing this article in Byword right now I figured it was worth keeping, for now. I like that I can publish to my Medium account directly from the app and I think that’s what has helped keep it around instead of just using Bear for all writing. When I’m in Default Mode, Apple Notes becomes the place where I do all writing, including longform.

Other Software I Use A Lot (Slack, Trello, MindNode, Day One, Reeder, Deliveries, Dark Sky, Instapaper, Apple Files, AutoSleep, Moment, Exist.io, Keynote, Google Docs, Insight Timer)

MindNode, Day One, Dark Sky and Instapaper have all been in active use for years. I’ve tried alternatives in most of those categories but always come back to these apps. I’ve gone pretty deep into the iCloud Drive world, hence the use of Files. In fact, I don’t even have Dropbox on any of my devices anymore.

A Word on Notifications and Other General Setttings

• Do Not Disturb: I have DND set to turn on from 10:00 PM to 7:00 AM on all my devices. I would love, love, love Apple to introduce DND by app at some point in the future. For example, being able to set all my communication-centric notifications to start appearing around lunch time while allowing utility-centric or system-centric notifications to appear earlier.

• Notifications, in general: Like with my software preferences, I seem to have two modes when it comes to notifications on all my devices. When I’m deep under the influence of Deep Work and Flow and feeling like I need to focus intently, I’ll adopt a notification strategy where I basically eliminate all of them. At other times, I like keeping all my notifications on because it helps me feel connected to the rest of the world. With as much travel as I’ve been doing and with the fact that my family and my girlfriend all lived far, far away I tended to keep notifications on. However, even in this mode I will feel no compunction about manually flipping on Do Not Disturb when I need to sit down and really focus on something (like writing this article, for example).

• “Military time”/24 hour time: I use a 24 hour clock on all my devices because I think it’s simpler than the AM/PM system. There’s never any ambiguity and I appreciate the simplicity.

• Tap to click: I’m all about settings that allow me to make things happen with less effort. Therefore, my trackpad settings on my MacBook are set to tap to click. Unfortunately, I’ve seemed to have built impossible to remove muscle memory that always makes me do a “for real” click. I’m trying to re-learn!

• Highest sensitivity settings on trackpad and mouse: Keeping in line with my preferences for settings that allow me to do more with less movement, I have the sensitivity settings for my trackpad and mouse setup to be as responsive as possible. Apparently that isn’t super common because it’s the #1 thing people comment on if they use my computer at all.

• Camera privacy slider: In the past year I got skeeved out enough about the possibility of hackers doing nefarious things with cameras to buy a privacy cover for my MacBook. I got this one and it looks good and works well.

2018 Intentions

In general, I hope to do less fiddling with my setup this year. When I do feel the urge to switch modes, I want to do so mindfully and as swiftly as possible. I’ve done things like collect all the apps I like to use in each mode into a single folder so that when I decide to switch into that mode it’s easy to update my homescreen and get myself arranged (as opposed to hunting for each app each time I want to switch modes). Hardware-wise, it’s likely that every major component of my setup will get upgraded this year. That really won’t change much other than making it more enjoyable to use the software I’m already using. There is a small part of me that keeps getting tickled by the idea of getting an iMac for my home office but so far I’ve been doing a good job of tamping that thought down.

Curious about anything I didn’t go into enough detail about here? Leave a question below and I’ll collect them all into a Part 2!

My 2017 in Books

2017 was a strange year of reading for me. I re-read more books this year than I ever have before while also reading the fewest number of books and pages since 2014. At the same time, while this was still a “down” year for me, I still managed to get through 60 books — which taken at face value is a decent amount of reading to get through in 365 days.

I definitely went through stretches this year where I wasn’t reading consistently. When I’m on top of my reading game, I’m usually reading for anywhere between 30 and 90 minutes a day with intermittent audiobook listening throughout. I worked through the backlogs of a couple podcasts this year and that cut into my audiobook time (looking at you The Adventure Zone). I also had a hard time focusing on anything, especially books, when I was working through some post-concussion symptoms last spring. Luckily, I picked up the pace in the second half of the year and was able to get back to my usual pace.

I know it’s not all about the sheer number of books or pages read. However, I think it’s important for me to be reading as much as possible. Instead of slowing down and taking copious notes or really trying to digest every little part of the books I read I treat it more like a waterfall that I choose to stand under. I let it wash over me knowing some of it will stick and some of it won’t. When it comes to great ideas I think it’s more important to expose myself to as many as possible. It’s a numbers game — therefore, I read as much as possible.

The Best Thing I Read This Year

• Grant by Ron Chernow: Chernow is a master biographer. Every single one of his books I’ve read (Alexander Hamilton, Washington, Titan, and now Grant) has been excellent. I read this immediately after having read Walter Isaacson’s new book on Leonardo Da Vinci and it was fascinating to juxtapose these two authors. Chernow is such a better biographer. It’s not even close. Isaacson writes like a journalist and his biographies feel like long magazine articles. Chernow is a goddamn biographer and his books feel exhaustive and complete.

The Most Challenging Things I Read This Year

• Blood Meridian by Cormac McCarthy: McCarthy holds the honor of writing the book that has emotionally affected me the most, The Road. I’ve never read anything that has been anywhere close to as successful at making me feel uncomfortable. Blood Meridian may be a close second, though. The violence and depravity described in this book gave me visceral reactions of revulsion. I’m pretty sure I’ve never muttered, “Jesus…” or “What the…” under my breath so many times for a single book. It was good as hell, though.

• The Rise and Fall of the Third Reich by William Shirer: Incredibly long, utterly depressing in many ways, and showing its age in places (i.e. treatment of homosexuality). Oh, and there’s something about reading about the rise of Nazi Germany in today’s political climate that is very eerie.

The Most Fun Things I Read This Year

• Harry Potter and the Deathly Hollows by JK Rowling: I’m only what, 10 years, late on this one? Better late than never, right?

• The Ghost Brigades & The Last Colony by John Scalzi: This series is like candy in book form.

• Leviathan Wakes and Caliban’s War by James S.A. Corey: Same as above. Pretty fun sci-fi that doesn’t require me to think too hard. I think the TV show is pretty okay, too.

Most Likely to Re-Read

• Why Buddhism is True: The Science and Philosophy of Enlightenment by Robert Wright: My meditation practice continues to be a source of joy and frustration. When I read this book I was pretty far away from my ideal meditation routine and I’d love to read this book again when I’m deep into a regular practice. I think I will get a lot more out of it when I’m not reading it simply as an intellectual exercise.

Things I Re-Read This Year

The only new additions to this list are The Phoenix Project(which I actually read for the first and second time this year) and Team of Teams. Everything else I’ve read three or more times, at least. I think Essentialism and Deep Work will continue to be yearly reads.

• The Phoenix Projectby Gene Kim, Kevin Behr, and George Spafford

• Essentialismby Greg McKeown

• Team of Teamsby Stanley McChrystal

• The Way of Zenby Alan Watts

• Flowby Mihaly Csikszentmihalyi

• Mindfulness in Plain English by Bhante Henepola Gunaratana

• Deep Workby Cal Newport

The Most Underwhelming Stuff I Read This Year

• Zen in the Art of Archeryby Eugen Herrigel: I don’t know if underwhelming is the right word, but in the afterword you find out the author was a Nazi. That soured me a bit on this otherwise interesting book.

• The Art of Learningby Josh Waitzkin: Tedious and shallow, in my opinion.

Looking to 2018

At the very least I’m committed to reading at least 52 books/18,000 pages this year. My stretch goal is to hit 70 books/24,000 pages. There are a few ongoing series that I’d like to finish out before starting anything truly epic. I also think I’m also going to stay away from doing a bunch of re-reading this year. Other than that, we’ll see where the year takes me. I generally don’t make long lists of highly detailed reading plans. I just throw books into my To Read list any time I stumble across anything interesting and when it’s time to start something new I just scroll through the list until something catches my eye. Do you have any suggestions for me? What are you going to read this year?