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My 2020 Year in Review

January 12 2021 – 03:39pm

As I was thinking about my upcoming income report for December 2020, I realized I had a lot to say about the year itself. Last year I included my review within an income report, but this year I’ll try doing a review of the year itself. (Little of this will be about finances. You’ll find that stuff in the income reports.)

The elephant in the 2020 room

The elephant in the room is of course that 2020 sucked big time for the world. I’m lucky, 2020 wasn’t so bad for me.

I’ve never liked to characterize entire years as “bad” or “good,” but part of the reason 2020 wasn’t so bad for me was that I had a couple of the most heartbreaking and horrible experiences of my life during the two years leading up to 2020 (read the last two chapters of Mind Management, Not Time Management, if curious).

In fact, if I had to characterize 2020, it was my best year in several years. A couple multi-year projects came to fruition in 2020: I finished MMT, I got settled in a permanent apartment in Colombia. Both of those projects were full of trials, and both – once completed – immediately changed my life for the better.

Mind Management, Not Time Management launch

The biggest thing that happened in my business in 2020 is of course the launch of Mind Management, Not Time Management. It was a decade in the making: The impetus for the book came when I was writing Design for Hackers in 2010, the title for MMT came from a blog post I wrote in 2012, and I had been struggling to get a grip on the book idea since 2015.

Mind Management, Not Time Management is off to a great start, and much of that is thanks to all the self-publishing experience I already had under my belt. The Heart to Start organically sprang from the process of writing MMT, but in many ways it was designed to get a feel for self publishing in preparation for the larger project that would become MMT.

Building on self-publishing experience

I can’t imagine how difficult it would have been to launch MMT without the prior self-publishing experience I had built through HTS and various short reads. Seth Godin was right when he told me back on episode 77 that you learn by doing.

Thanks to that prior self-publishing experience, I had already dealt with the technical challenges of formatting an ebook. I had already gone through the Amazon KDP publishing process, and considered the oft-overlooked metadata. I had already navigated the murky waters of publishing wide. I had already been down countless marketing rabbit holes – sometimes investing dozens of hours trying out a tactic, only to decide it wasn’t worth pursuing. I had already spent more than $50,000 on ads, and gotten a handle on where my efforts and money were best spent.

Nailing the title

Of all the self-publishing experience I already had upon launching Mind Management, Not Time Management, the most valuable was that which helped me decide on the title. Though I had originally written that title for my 2012 blog post, I hadn’t recognized that it would make a good book title. There were countless other titles I had considered or that I was certain I would use.

It’s only after cutting my teeth by marketing a mid-length book, in The Heart to Start, as well as numerous short reads – and reflecting on the experience of having a successful title with Design for Hackers – that I was able to recognize how bad my other titles were, and that I was able to recognize that a really great title had been sitting right under my nose.

I had to see how hard it was to sell 20,000 copies of HTS, despite impeccable reader reviews and lots of ad spend, and how surprisingly-easy it was to sell How to Write a Book, before I could get a feel for that right mix between making a statement with your title, and tapping into existing concepts in the collective conscious.

Learning my lessons on hardcover and audiobooks

I also learned from the experience of launching an IngramSpark hardcover for HTS that it probably wasn’t a good idea to launch MMT with hardcover as the only physical option. Thanks also to my experience producing the audiobooks for HTS and other short reads, the audiobook production for MMT has been that much easier. Of course it’s also easier to produce the audiobook because of all the experience I’ve gained, through producing the podcast, in writing for audio and performing voiceover.

All that to say self publishing really is a jungle. After several years getting lost, I feel as if I have a clear map. The landscape will continue to change, but it’s still an asset I can use for life.

Self-publishing income climbing

As I talked about in the November income report, my overall profit has remained flat for the past three years. But, I’m very happy that the self-publishing portion of that profit has been climbing.

Self-publishing money is the best-feeling money

This is the best-feeling money that I make (a close second would be the money I make from Patreon support).

When I make affiliate income, such as that from Active Campaign, I know I’m selling something I didn’t make. When I sell a course, I remember that I don’t particularly enjoy building courses. In the rare cases when I do some kind of consulting, I bristle at the thought of selling my time.

When I sell a book, it feels good all around: I know the reader is getting their money’s worth, I enjoyed making it, and it’s something unique that came from exploring my own curiosity. I know I’ve already done the work, and I feel confident there are more sales where that came from.

So to both have the experience under my belt to navigate self publishing, and to have a substantial portion of my income come from the books I publish, is a really good feeling. I feel like I reached a new level on both of these dimensions in 2020.

Investing in my ideas

I’ve always aimed to invest in my own ideas, but I made progress in this quest in 2020. Thanks to reading The Naval Almanack, I came to recognize that I am in the business of leveraging media. There is almost no limit to the number of people I can reach. What determines whether I reach them or not is how well I adapt my ideas to the media where I can reach them.

Twitter revival

One medium where I can reach a lot of people is on Twitter. I learned in 2020 it also happens to be a medium where I can get feedback to make my ideas better.

Can you suck at Twitter and still be a good writer?

At the beginning of the year, I came to the realization that I had been on Twitter for nearly fourteen years, but that I had not been using Twitter well. Sure, I had over 20,000 followers, but it wasn’t uncommon for me to publish tweets that got no engagement at all. In fact, I was losing followers.

Twitter is words, and I’m a writer. If I wasn’t good at Twitter, what did that say about my writing? On the surface, it looked as if thinking about Twitter wasn’t worth the effort. After all, I clearly wasn’t getting traffic or making sales from Twitter. But I posited that effort put into Twitter would not pay off linearly. If you’re leveraging media, inputs do not directly lead to outputs. It makes sense that there would be a tipping point after which you go from no results to a lot of results. Looking at popular accounts such as James Clear’s and Mark Manson’s, it was clear there was activity happening on Twitter – but my tweets were not good enough to attract that activity.

The best breakthroughs start with first principles

I thought back to other breakthroughs I had had in my career as a creator. Two that came to mind were the articles I wrote that were popular on Hacker News and that led to a book deal, and the Summer of Design email course that brought my email list from 5,000 to 30,000 subscribers. I realized that in both these cases, I had studied the medium at hand, and taken a first-principles approach to coming up with something new.

I was leveraging media, and Twitter was the medium I was primarily leveraging. So, I invested a huge portion of my attention and energy into studying Twitter, studying short-form writing, and studying media theory and history. I bought Ed Latimore’s Twitter course and I watched a Twitter webinar with David Perell and Matthew Kobach. I read books about rhetoric, and – after publishing my third book – I finally read some books about writing. I also read and am reading media theory classics, such as Understanding Media, Amusing Ourselves to Death, and The Image.

What I changed about my Twitter approach

The highest-impact things I did specific to Twitter were that I started paying really close attention to my Twitter analytics to see what was working and what was not working, I stopped composing tweets on Twitter itself and started composing them in a separate text file or even wrote them by hand, and I disciplined my Twitter usage so I wouldn’t be constantly checking it throughout the day.

It took a long time to see results. For several months I was still losing more followers than I was gaining. I believed I still had a lot of inactive or irrelevant followers from fourteen years on the platform, and I needed to attract fresh, active, and relevant followers before I’d see things turn around.

Slow then sudden improvements

Slowly, I started to see improvements. I started with a 1.0% engagement rate in February, 1.4% in March, 2.0% in April. Still, I was losing followers – even slightly more followers as my engagement rate improved.

If there was one turning point in my Twitter revival, it was the day I launched Mind Management, Not Time Management. I published a tweet storm I had spent a lot of time on. I incorporated into that thread everything I had learned throughout the year, not to mention the decade worth of insights distilled from the book itself. When I started trying to improve at Twitter, it wasn’t unusual for one of my tweets to get fewer than 1,000 impressions. The first tweet in this thread has over 130,000 – with a 12% engagement rate.

Well, did I gain any followers?

Leading up to that day, I had started adding a modest number of followers. In July I added 67. In August, 91. In September, only 12. But in October, when MMT launched and I published this Twitter storm, I added 634 followers. In November, I added 113 followers. In December, 251.

In raw numbers, my Twitter revival isn’t terribly impressive: I gained about 1,500 followers. When you already have 20,000, that doesn’t seem like a lot. But I have far more engagement than I did at the beginning of the year. My dashboard for the past 28 days shows my average at 2.7% – remember, I was at 1.0% in February 2020.

Though the number of followers I have hasn’t changed a great deal, my tweets are getting more impressions. Before I began this Twitter revival, a bad tweet of mine might have gotten 1,000 impressions. Now, my tweets get about 2,000 impressions at a minimum, with tweets over 10,000 impressions once in a while, and of course that thread with over 130,000 for the first tweet.

Twitter as an idea lab

My efforts to improve at Twitter were never all about Twitter. I merely saw Twitter performance as a proxy rating of my skill as a writer. I set up systems to monitor which of my ideas resonated. I iterated on ideas that did well, tried different angles on ideas that didn’t do well – often abandoning them if they did not, and I built my best-performing tweets into larger works such as Love Mondays emails and podcast episodes.

I think I’m a better writer for it. Mind Management, Not Time Management is better thanks to the self-publishing experience I had built, but it’s also better thanks to the effort I put into writing better tweets. I used Twitter as a laboratory for testing insights and turns of phrase that are within the book, and it’s no coincidence I’m seeing those same insights and turns of phrase highlighted and shared on social media as people read the book.

Stopped podcast interviews

In preparation to launch Mind Management, Not Time Management, I stopped interviewing guests for the podcast. This gave me more space to think about and improve upon the ideas in the book. Through the essay episodes that remained, I also got to share those ideas to promote the upcoming book.

At this moment, I don’t have plans to interview guests again. I learned a lot through my guests over the years, and I built a lot of relationships that made launching my new book easier. However, I really enjoyed having the extra space to think deeply about my own ideas, rather than feeling the need to think about the ideas of a steady stream of guests.

Will I do interviews again? Maybe.

There are still some people I’d like to connect with and interview, but the number of people is too low to justify releasing an interview every other week again. Additionally, many of the people whose ideas I would like to explore are impossible to interview – either because I couldn’t get them to agree to an interview, or because they’re dead.

Maybe it’s not that kind of show anymore?

The podcast market is maturing, and my goals for the show are maturing. Much of podcasting has shifted from the “interview” genre to a narrative genre, complete with sound effects. The interviewers who remain have more talent and interest in the art of interviewing than I do. As such, they have built very large platforms that can attract huge guests.

The number of downloads of my podcast episodes continues to be more-or-less flat, and I’m okay with that. It helps me share my ideas, and I have a good number of listeners who really enjoy it.

It’s possible I’ll do a series of interviews – maybe even in 2021. But such a series would be based even more so than before upon pure curiosity and interest in talking to those people.

Stopped podcast sponsorships

Along with my decision to stop interviewing guests, I stopped taking sponsorships for the show. I had interest from at least one very-well-known company, but when I looked at the opportunity costs of taking their money – and the way sponsorship money “felt” – it wasn’t a fit. So, I burned my boats and shut down sponsorships completely.

This means I don’t make money from sponsors, but it also means I don’t have to manage the process of on-boarding sponsors and writing, recording, and inserting their spots. Continuing the theme of leveraging media, this reduces complexity, and frees me up to make my content better, which may in turn help my message reach more people. Fortunately, I have enough support on Patreon to keep the show going.

SEO Revival

To invest more in my ideas, I also directed my attention back to this blog. I made some quick tweaks such as removing comments and speeding up loading time by removing unnecessary scripts and reverting back to standard fonts.

But I also decided to start thinking about SEO again. Not so much from the standpoint of optimizing existing posts or doing any special tricks. Rather, I wanted to start once again thinking about the content I’d write here from an SEO perspective.

From the start of this blog in 2004, I often thought about what search terms someone might use to find a post of mine. I didn’t think about that hardly at all the previous several years. When I did think about it, it was mostly about attracting people who were searching for podcast interviews of my guests. However, I’ve found that there’s very little of such traffic.

I haven’t yet refined my process for deciding which search terms are worth writing for, or for evaluating how well my predictions pan out on what is or isn’t worth writing about. But, I’m thinking about these things as I go.

Newsletter improvements

I made a lot of tweaks to my Love Mondays newsletter throughout the year. I also made a lot of changes behind the scenes – to the process I use to produce the newsletter.

The main change I made within the newsletter is that I no longer share a tweet nor a highlight within the newsletter itself. I now write a short article – which is often based upon a tweet that has done well.

I also added what I call “ABCs”: Every week, I share two of the following three things: an Aphorism (aka quote), a Book, or a Cool thing. I wanted to add some quick hits of “variable rewards” to the newsletter for people in a hurry in their inboxes.

The link clicks for Books and Cool things also give me surprising data about what my readers like or don’t like (How to Take Smart Notes was the most popular Book, with 4.94% of opens leading to clicks. Stephen King’s Different Seasons was the least popular, with 0.48% – a 10x difference! The Molkeskine Volant was the most popular Cool thing, with 6.75%. The charity Iodine Global Network the least popular, with 0.77%.)

Newsletter process automation

I made huge improvements to the production process of the newsletter. I have what is now a pretty sophisticated Airtable spreadsheet in which I can sort through past tweets and Aphorisms that have done well on Twitter. I can also collect and write descriptions of the Books and Cool things. Once I have a newsletter drafted, I plug it into the spreadsheet, select my ABCs for that week, and Airtable rolls it all up into raw Markdown. From there, it’s a little cumbersome than it needs to be to schedule in ActiveCampaign. That’s part of the process I wish were easier to improve.

After a newsletter goes out, I can collect in the spreadsheet data about open rate and click through rate on my Bs and Cs (I found it hard to motivate readers to interact with Aphorisms – such as through a “click to tweet” link). I use this to continuously evaluate the performance of content, which helps me decide in what direction to go with future content.

Barbell Strategy

A major shift in strategy I made in 2020 was to think about using the Barbell Strategy in as many areas as possible.

After reading the book deeply to write my The Black Swan book summary, I realized that as a creator, I am harnessing randomness. It’s unrealistic to expect my progress to smoothly go up-and-to-the-right. Creative work happens in Extremistan. You need to expose yourself to explosive opportunities, while staying in the game long enough to get lucky.

85% sure bets, 15% wildcards, ignore the middle

The Barbell Strategy is basically: Invest the majority of your resources in “sure bets” – places where you know you won’t lose your investment. Invest the rest of your resources in “wildcards” – places where you very well might lose your investment, but where there is potential for unlimited upside. Meanwhile, ignore the “middle” – areas that feel safe and shoot for incremental returns.

the barbell strategy

The Barbell Strategy is primarily used in an investing context. In fact, after the recent fantastic stock market rally, I’m in the process of rebalancing my portfolio to use the Barbell Strategy to preserve what I’ve earned, while still staying exposed to future potential gains.

Barbell Strategy for content

But I’m also applying the Barbell Strategy to my content creation. Thanks in part to guidance by Alex Birkett’s article about a Barbell Strategy for content marketing, I’m splitting up my content like so:

I’m trying to apply this mentality to other areas as well. For example, my experiment with meditating an hour a day is an application of the Barbell Strategy for time management. In my reading, I’m trying to read scientific articles, or classics of theory (as well as some fiction). I avoid middle-of-the road business books.

Note-taking / Zettelkasten

I worked hard this year on developing a note-taking system that works for me. A lot of people call it a Zettelkasten. After reading How to Take Smart Notes, I looked at the Zettelkasten concept from a first-principles perspective, and designed something that worked for me.

Where I was note-taking-wise

I already had well over 15,000 highlights saved in Readwise. I had in the past experimented with the “commonplace book” of index cards, as I had learned about from Ryan Holiday – however, writing by hand on index cards wasn’t for me.

I started to feel the pain as I tried to keep track of my research notes while finishing Mind Management, Not Time Management. They were strewn about in a Scrivener file. I hated the idea that they were locked away in this project file, where I wasn’t likely to look for them in the future.

Leveraging technology for creativity

I’ve long tried to live my creative life on the edge of what is possible with technology – to leverage technology to enhance my thinking, while being careful not to allow technology to disrupt my thinking. I had already done that by designing my business and life in a way that allowed me to move to Colombia. A byproduct of that decision was that I was forced to do most of my reading on Kindle – which has led to my massive database of highlights.

Now I’ve taken that a step further where I have processes for distilling things I’ve learned, capturing ideas, and connecting them all together in a database from which I can quickly retrieve quotes, prior research, and ideas. I talked about the system I’ve settled on a little in an income report, but I’m currently working on an article where I can share in more detail.


I’m not big on making plans, projections, or goals for upcoming years. I’m more reluctant than usual to do so for 2021. Besides the fact that uncertainty in the world didn’t magically end at midnight on December 31st, also because I just recently finished a massive project.

I’m just coming off of a month-long break from the podcast, as well as my usual attempt to disconnect from my day-to-day work and revisit the question of what I want to be doing day-to-day. I am feeling tempted to wander a bit. I am thinking about some book ideas for my next non-fiction book, but I’ve also been exploring some fiction ideas, too.

I do know that I want to keep pushing on the theme of investing in my own ideas. I want to keep testing ideas on Twitter, and sharing ideas in my newsletter and podcast. I do want to think more about how to take my email list from flatline to a bit of growth. But, I have no predictions, no revenue projections, no goals. Just keep doing what I’m doing, one day after another, as I have done for years – though probably with a detour or a set of new tires once in a while.

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This post is filed under Business.