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.