annual review - 2020



~10 min read


1913 words


The end of the year is normally one of my favorite times of year. The holidays and cold weather means that family gets together and stays inside where we enjoy good food and cheer. It’s also a time when the world outside slows down enough and I’m able to make space to reflect on what happened. I’ve made a habit of sharing some of those reflections on this blog (2018, 2019) and was prepared to do the same thing this year.

I went through the process. I reviewed my notes. I wrote down answers to questions designed to get me to think about the year deeply. The result felt like it was missing something. I had gone through the process as if 2020 was just like any other year. It wasn’t.

So, before I get started, I want to acknowledge just how truly awful so much of this year has been. Yet, even in the darkest moments, there are reasons for hope. Covid has killed too many, yet, vaccines are being approved and distributed. Millions lost their jobs and too many still aren’t working, yet the economy is recovering and the vaccine will help. The killings of Ahmaud Arbery, Breonna Taylor, and George Floyd (and too many others) are beyond words, yet they gave (new) life to a movement for reforms and reinvigorated a national dialogue about justice.

2020 is gone, but it remains with all of us. The events of this year have shaped me and my thoughts. These changes are not something the change of a calendar can wipe away.

Reviewing 2020

Coming into 2020, I hoped to make it a year of the three Rs - respect, reflect, refine. Among my many hopes for the year, I planned to improve my communication skills through public speaking, to take my meditation practice to the next stage with a retreat, and to swim 100 miles. I also wanted to ship a product and earn a promotion.

The only item on this list I did achieve was the promotion, and yet, in many respects, the year was a success. Though it certainly didn’t feel like it at the time (as my journals testify to), getting laid off may just have been “the best possible thing that could have ever happened”1

I did earn the promotion, but the celebration was short lived as I was laid off the next month. Still, it’s hard to argue with how things turned out (though it was certainly not a guarantee, a fact to which my journal entries from the period testify), two main highlights stand out:

  1. I launched Studio Charlie this spring after being laid off in March. While being laid off was not part of the plan, I had talked about starting a business for a while and I suddenly had the opportunity (and reason) to do it! More important than starting the business was making my first sale. Though my vision for Studio Charlie is to be a product company, I was able to start with consulting - proving to myself that I could. If nothing else, it removes that objection for the future.
  2. Joining Olo. There are so many opportunities available at Olo and I’m only just scratching the surface. Really looking forward to 2021.

Personally, the story is a little richer and more complicated. I achieved none of my personal goals and yet, I would confidently call it a success. The goals I’d set out to accomplish were related to my identity. I’m always working to be a better human, and as of late, working on that in public. To that end, I wanted to practice public speaking, meditating, and swimming more in 2020.

I didn’t do any of that (with the possible exception of meditating, but I had an explicit goal of attending a retreat which didn’t happen).

So, why do I call it a success? Well, if my goal was to further define my identity, then I think I did that. Just not how I had expected to.

James Clear defines Identity in Atomic Habits this way:

[T]he word identity was originally derived from the Latin word essentitas, which means being, and identidem, which means repeatedly. Your identity is literally your “repeated beingness.”

There were several areas of my life with considerable repeated beingness.

  • I completed 100+ katas.
  • I practiced meditating 191 times.
  • I published 351 posts this year.
  • I read 30+ books again this year.
  • I logged 195 workouts.

I am most proud of the writing habit I’ve sustained for another year. I didn’t quite hit publishing every day, but I think this may be one of those “shoot for the moon / land among the stars” situations.

Month Posts Days %
January 37 31 119
February 29 29 100
March 33 31 106
April 28 30 93
May 37 31 119
June 31 30 103
July 33 31 106
August 32 31 103
September 28 30 93
October 31 31 100
November 23 30 77
December 9 31 29
Total 351 366 96

Looking ahead to next year, I want to maintain this habit, but I think I’m going to shift it a little. I’ve spent the past few years writing mostly about things I’m learning on a daily basis. There’s plenty to learn, which is why I’ve had no shortage of topics. But I want to evolve my writing a bit and polish it a bit more. I suspect that my volume might drop significantly, but I’ll still consider it a win if I’m proud of the work I’m producing.

I’m conflicted about what the goal for next year should be here. Building an email list may be the right move, but I am trying to figure out the right way to do that. Specifically, there’s a piece I plan to write soon related to the multiple identities we all possess. This site has always been my personal corner of the internet and as such I’ve brought all of my identities to it (some more prominently than others). The problem with that from the perspective of trying to build readership is that there are not many folks who would be interested in reading about everything I write. Perhaps segmented lists. Anyway, for now, this remains an open question and a problem for the new year!

Zooming out, it was also a notable year in some major steps my wife and I were able to take together. Due to the nature of her work, the future is always a little uncertain, but we’ve placed a bet on Chicago and hope we can build our life together here. While it seems everyone else was seeking more space in the suburbs, we bought our first home in downtown Chicago, a few short blocks from the park. Having moved every 6-18 months for the past 8 years, it’s nice to feel like I have real neighbors and am part of a community.

Key Lessons

A few lessons I’ve taken from this year.

  1. This too shall pass. As bad as it seems, time goes on. As good as it seems, it won’t last. 2020 was full of reminders of this.

  2. Consistency pays dividends.

    This year I spent a lot of time on the bicycle. The first few months were slow and steady improvement, then I had a break through and started seeing impressive gains seemingly every time I got on the bike. I’m back at a plateau now (I had 9 PRs in September and 10 in October, 4 in November, and 0 in December), but I’m optimistic that I’ll be able to break through again through consistent effort and smart training. It’s about the long haul.

  3. I work better when I’m on a team.

    I had an opportunity to do some contracting work this year and found it very challenging personally. I struggled a lot with feelings of isolation. I know people who love the flexibility and detachment that is possible with contract work. I am not one of those people and I’m glad I learned that lesson.

Looking Ahead To 2021

I was quite pleased with the guiding light last year’s themes of Refine, Reflect, and Respect provided. With some regularity, I’d return to these themes and ask myself if I was living them. The answer was not always yes, but the reminders were useful all the same.

While the three Rs served me well, I think this coming year will require a more active approach. If I’m going to hit my goal of actually shipping a product by year’s end (and earning revenue from it), I’ll need to practice marketing and sales in a new way. I’ll need to engage potential customers in conversation. I’ll also need to build. All of these things I’ve done in some form or another before, but I also know there’s room for improvement for all of them.

That’s why I’m viewing 2021 as a year of Polish, Experimentation, and Joy.

  1. I’m leading with polish as an evolution of refinement. From one angle, polish is just refinement in new clothes. The distinction I’m making is that it’s often considered a bit shinier. The emphasis is appropriate as I hope 2021 is a bit more outward focused. That said, there will be no polishing turds.2

  2. Experiments are the fuel for the fire. There are a lot of things I don’t know how to do and there’s only so much that can be learned by reading. Experiments offer an opportunity to learn by doing. They allow me to explore a topic first hand, to reveal the edges of my knowledge, and pique my curiosity. By their very nature, many will also fail - and so by focusing on experiments, I’ll be setting myself up to fail more. A well structured experiment ensures that a failure is never wasted. Lessons are still learned and feed into the next iteration.

  3. Joy was not my first pick to round out the trio, but after a year in which many plans were deferred or upended, it feels right to focus on it. Waiting to “arrive” at some future happy state is no way to live. That’s why I want to make sure to enjoy the day-to-day and do things that bring me joy.

On that note - here’s to a very happy and healthy 2021.


  • 1 This happens to be a personal mantra, a line taken from Zen and the Art of Happiness by Chris Prentiss, which I’ve been saying to myself nearly daily since 2014.
  • 2 One of the enduring lessons from Walter Isaacson’s biography of Jobs was the care Steve’s dad took with the internals of cabinetry even if no one else saw. A lesson Steve would learn well and which manifested itself in the form of the internal arrangements of Apple computers (persisting even as they became more and more difficult to open).

Hi there and thanks for reading! My name's Stephen. I live in Chicago with my wife, Kate, and dog, Finn. Want more? See about and get in touch!