What a year for gratitude! 2020 was the COVID year. (Or was it the first of the two COVID years, plural?) In any case, there were headwinds!

And yet, I have plenty of gratitude. I mean, obviously, it was a horrific year. But I’m taking a Stoic approach — control what I can control.

When I started this gratitude practice in 2007, I was stressed, trying to figure out how to be an entrepreneur and not at all confident that I was on a path that would work out. So I started trying to balance that stress and worry by collecting things that happened to me that I was grateful for, aiming for 52 of these per year. These good things are a measure of my life’s direction.

I committed to myself that if I couldn’t find an honest 52 that I’d give up my entrepreneurial dreams. (So far I haven’t had to do that.)

Here are my prior lists:
2015–2019, 2013–15, 2012, 2011, 2010, 2009, 2008, and 2007.

Managing Shelter-in-place. Knock on wood.

Well, let’s just start with the obvious. Sarah and I were sheltered, for the most part, in our NYC apartment with our dog, Eloise.

1. Health. No one in my immediate family caught the virus. We all kept our jobs. There were no family tensions about how to stay safe. Knock on wood. I hope this continues in 2021.
2. My downstairs neighbor’s fridge. They spent most of this time with family in Virginia. So we took care of their favorite plant in exchange for using their fridge. We ate so well and that fridge was a key place to store overflow foods. At one point we were storing thirty pounds of blueberries there.
3. Sarah. Normally I wait until the end of this post to make a big deal about being grateful for my partner Sarah. But, please, on the vast majority of days we were the only two people we saw face to face. And I’m so grateful that we both took this time in stride and with good humor. In normal years, she is my best friend but this was a whole different level of being together.
4. Hugging my mom. We saw her four times during the pandemic, masks on. The first time we didn’t hug. And that was a mistake. I’m so grateful for each of the hugs after that.
5. Long Island Bar burger. Simple pleasures. This is my favorite Brooklyn burger and I’d meant to go in last January, but I didn’t. And then they were the first restaurant in the neighborhood to close down. I thought I’d lost my chance forever. But then they re-opened and Sarah and I went on our first proper date in months, sitting at a sidewalk table, cocktails, hours of conversation even though we’d been talking to each every night for months. Plus the burger was perfect.

There are many more examples of managing in the sections below.

Thinking Differently

A lot of my self-improvement effort was on learning to think differently.

1. Now or Never. COVID threw all my plans for a loop and highlighted and then trained me to act now or assume the opportunity will pass. Now or Never was the name I gave to 2020 when I did my annual review.
2. Upside. I started a work idea where I try to turn everyone I work with into entrepreneurs for their area of responsibility and then split the profits with them. Overall, very pleased with this way of working.
3. Be More Myself. A friend thinks I’m already the most myself person he knows. And yet, I know that I am hiding a lot of myself almost all of the time. Opening up, quieting my inner critic, giving myself permission to be different than other people— these are all things that I did a lot of work on this year, successfully.

Time with People

1. Boston. During the pandemic we spent a few days with my brother-in-law and family in Boston. At first it was supposed to be a quick visit and then we just kept extending the trip because we were all so hungry for human contact. They are the only people we expanded our bubble for this year.
2. Basketball with one of my nephews. I haven’t shot a basketball in years even though I played competitively and watch religiously. Heading up to Boston, my nephew, age 11, challenged me to a game saying I’d do fine, even if I was rusty, and that all he’s been doing is practicing for 90 minutes every morning, then coming home and doing pushups, sit-ups, jump rope and pull-ups. That’s all. He was amazingly good and it was inspiring to watch what a dedicated beginner could do based mostly on hard work, YouTube and NBA 2K. At an age where I was still learning to dribble without looking at the ball, he has cross overs, step backs, finishes with both hands, and counters if you try to take away any of his moves. He learned all this in a few months.
3. Scotchrepreneur. My favorite founders group normally meet face to face every two months to drink Scotch and address our biggest problems. But this year our meetings were all over Zoom. Still one of my favorite ways to spend time.
4. Laura’s Baby. Our friend, and frequent travel buddy and often inspiration for my own business, had a baby early in the year and we just barely squeezed in to see the tired mom and the newborn.
5. Eloise Painting from Joan LeMay. Joan came over for dinner and came with a painting she’d done of Eloise. She also did a portrait of our last dog. So in the future, when people can visit again, any visitor to our apartment is going to see two custom paintings of dogs, plus get a greeting from at least one dog, and from that understand that Sarah and I are definitely dog people.
6. Costa Rica. Terrie and I did a company retreat to Costa Rica. It actually was really helpful for strategy and I came away with a lot of clarity about Coach.me. We’d meet in the morning and afterward I would got mountain bike riding. I think I rode five days in a row. Given that we went into shelter in place right after, I’m so grateful that we squeezed in that trip.
7. Casual Thanksgiving. We cooked a Thanksgiving-ish meal just for the two of us, but with 20% less pressure. I have to keep that in mind. A touch of casualness made the day about 5x more enjoyable.

Coach.me

1. Certification. A thing that happens when you are iterating a lot is that you end up with a lot of useful features of mediocre craftwork. I end up in that boat often, but always with the ambition that version two will be world class. I think we’ve done that with our new Habit Coach Certification, now on its fourth class of students. Very grateful to Kendra for leading the instruction.
2. Commencement. This was a great idea done on a whim. What if the cherry on top of our certification was a fantastic commencement ceremony complete with a well known commencement speaker? Well, we had Gretchen Rubin (Happiness Project) and Leo Babauta (ZenHabits) last year, and George Mumford (Mindful Athlete) right at the start of this year. Our European coaches had previously only experienced commencement through the lens of American movies, but I play pomp&circumstance and Kendra reads the names of each graduate. It’s cool.
3. Open Coaching Directory. After years of only allowing habit coaches, we opened our directory to coaches of all stripes and as a result, met a lot of coaches, and connected a lot of clients to them.
4. 46 New Year’s coaching sessions. I love January because it’s when people are most realistic about how much work is required to achieve something meaningful. And every year I do a round of coaching sessions that end up being incredibly inspiring (for me).
5. Although I tell people I’m no longer a programmer, I did generate 140 commits to the main Coach.me app. Actually, I’m going to stop telling people that. I like programming and often build really useful software on my own.

Medium.

Dang, thank you Medium. What a year. Drafting off of their growth, we reached 70 million reads across a huge spectrum of personal and professional development advice and tutorials.

1. Better Humans. Terrie Schweitzer ran this publication with love and discipline and a lot of curiosity. This is self-improvement for curious people. If you ever worry that self improvement is a scam, then ours is the publication that you should read. Terrie puts a lot of work into making sure that you can trust what you read.
2. Better Programming continued to be a keystone to the overall programming community on Medium. It is by far our highest traffic site. And Zack Shapiro did a great job building tools to make our editing processes more efficient along with picking articles that people wanted to read.
3. Better Marketing is where I go to learn. I felt like I couldn’t help our coaches unless I was better at helping them promote their businesses. Niklas Göke started the pub and then mid-year Brittany Jezouit took it over and has grown it significantly. This is the publication on Medium that I read most often.
4. Frankenstein. It probably seemed random for me to put this book onto Medium last year. But I was testing an idea which turned into me helping the Pragmatic Programmers put their entire catalog of programming books onto Medium. I’m an advisor to Medium and I think this little experiment turned into a much bigger win that will play a real role in helping Medium succeed.

Zwift

1. The best thing I bought in 2020 was this Smart Trainer for my bike. It lets me ride inside and connects to virtual bike courses on my laptop. So when the virtual course starts going up hill, the resistance on my rear wheel gets harder to match. That’s the “smart” part.
2. I use Zwift for my virtual bike rides and that got me into bike racing where I go against other virtual riders, even including the strategy of drafting them. It turns out drafting is a painful dynamic because it’s constantly tempting you to sprint if you ever find yourself losing the draft. That’s what makes bike racing differently challenging and painful than what I’d experienced in running racing. (Running is evenly paced with a gradual and predictable increase of pain until the moment you collapse at the finish line.)
3. I won a virtual bike race. Only one so far although I’m often second or third place now. Winning was a big improvement from where I started.
4. In total, I rode 1700 indoor miles thanks to Zwift.

#Upside

Going back to work, clarifying my Upside concept, led to a lot of interesting work. Habit Coach Certification is the biggest one, already mentioned above. But also:

1. Moneyball. An app to help authors make more money on Medium. We’re using it internally and have a few Medium authors as paying customers More soon. Connor Montgomery and Zack Shapiro were my excellent collaborators.
2. Better Marketing Community. A Slack community for marketers trying to build their portfolios and get new gigs. Brittany Jezouit’s work.
3. Slim.to is a URL shortener for marketers. It’s the first time I’ve done an Upside project with someone I didn’t already know. And so far it’s going well and I think we’ll bring a useful tool into the world. Dylan Roy is my collaborator.

Bought a second house.

Technically it didn’t close until January. But we bid on it in July, won the bid in August, went into contract in October, and basically did a lot of the work that was necessary to do this in 2020.

1. Being able to afford this was a big financial goal and so achieving it was a big financial win. Credit goes to a combination my favorite Coach.me financial coach, Scott Maderer, YNAB, NerdWallet’s retirement calculator, and our Financial Planner.
2. The house. It’s cool. You get a lot of house in the country compared to what we paid for our NYC apartment. There are acres of land and I’ve already started carving my own mountain bike trails and drawing up plans for a productivity lab. You’re all invited (I mean, ask first, but probably you are invited.)

Bought an RV

A couple of years ago I spent four months in a borrowed campervan. I love this lifestyle.

1. This year I bought a used 22' RV on a Chevy Van chasis. So it’s technically still #vanlife. These tiny spaces are so personal because everyone needs different tradeoffs. What I decided was that I wanted a bed I never had to make (queen size in the back), an indoor place for my bike so that I didn’t have to worry about theft or weather (overhead space above the cab), a bigger desk (full dinette).
2. My first trip was to the Pine Barrens which is where the mob in Boardwalk Empire drops bodies. It’s also a relaxing place to go mountain biking.
3. Then Sarah and I took a trip up to Maine.
4. And then third, I took a westward, meandering MTB trip, getting all the way to the edge of Missouri and liking the trails in Ohio best.
5. Like many things in the pandemic, purchasing this RV was a huge hassle because various government agencies were not operating at full capacity. So I have so much gratitude for the seller, Tim, who was completely easy to work with during a process that should have taken an hour and actually took two months.
6. Also props to HipCamp and Harvest Hosts for making it easy to find places to stay. In the mountain west, you can almost always boondock for free on government land. But that’s not really possible on the east coast and so Harvest Host gives access to stay on the property of many farms and wineries. These are great when available. And then HipCamp lets you find spots on private land when there isn’t a nearby HarvestHost. The infrastructure for van life gets better every year and these were the two big upgrades since last time I was on the road.

My Two Favorite Books Were:

1. Qualification. This was a graphic novel about a person addicted to 12 step programs. I think about this story a lot because of how easy it is to fall into the trap of doing self improvement work without actually solving any of your root problems or reaching any higher level goals.
2. Ursula K. Le Guin’s book of essays, No Time to Spare: Thinking About What Matters. I wanted to spend time with the wisdom of older people, especially women. And this book delivered big time. It’s less about trite advice and more about just a confidence and way of being.

Best TV

Hey, we were home a lot.

1. Sex Education.
2. Tiger King.
3. Scott & Bailey. This is the one people probably haven’t recommended to you.
4. Unorthodox.
5. The Witcher

Best Movies (46)

1. Tenet. I wanted to experience a “movie, movie” and this delivered. Sarah’s review, “It looked like it was expensive to make.”
2. The Queen’s Gambit. Read this backstory from David Paul Kirkpatrick.
3. Enola Holmes.
4. The Old Guard.
5. Self Made.
6. Echo in the Canyon.
7. Ghostbusters at a drive in.

Oh, Hey, Politics

1. I’m glad we got a new president. I wasn’t sure we would. I voted, donated, helped, worried.
2. GOTV works! Thank you Georgia. Stacey Abrams did a lot, but a lot of people helped. I think Georgia flipping was so reassuring that, yes, with tons of work, things can change. Lets just never stop doing tons of work!
3. BLM Protests NYC. These were really inspiring, with the entire city rallying around an issue of moral clarity. Given how divided this country can seem, it was a charge to be inside a movement where, even New Yorkers blocked in traffic, were clear that change was necessary. (BTW, there continues to be a lot of resistance to change and so this movement is still very necessary)

Favorite Picture at a National Park

1. I only made it to one, Acadia. With Sarah.