2020 in Review

The year felt like a decade.

Big picture we’re fine, maybe great. We didn’t lose a loved one, our incomes, go hungry, get covid, or suffer unfair treatment from police or institutions. Things can always be worse, and I’m grateful we’re OK.

But California felt a constant state of siege.

Covid, police brutality, social unrest, shops boarded up and tear gas in the streets. Summer covid spike, then brutal wildfires. The election. Kids and parents under the same roof for 9mths straight. The dark covid winter with a growing death-count and incompetence or just indifference to vaccinate the people who need it most as quickly as possible.

We don’t need more words on any of these topics, but it’s context to remind myself just what it was like this year. With that, my review of the things I could mostly control.


I was injury free, and had my best year on the bike: 4,500km + 84,000m climbing. This was the main thing keeping me sane, while juggling work and kids at home during lockdown. Highlights included a big day in the passes around Tahoe, and a 7hr solo birthday ride through Marin and back down the coast.

Over summer I hired a coach from my old gym to add structure to my strength work, and felt good about the improvements. Luckily I’d invested in basic home-gym equipment over the past few years, and avoided the worst of the great kettlebell shortage of 2020. It was a real thing.

In 2019 I completed the 8-wk course for MBSR (mindfulness-based stress reduction), and started to build a habit around meditation. This year I was sporadic in maintaining it, maybe only once or twice each week.

I avoided any alcohol throughout Q1, and felt phenomenal. For most of the rest of the year, the company of friends and a decent wine became an important coping mechanism. It’s crazy how even 1-2 glasses disrupts sleep. I’ve tracked sleep quality using an Oura Ring for the past two years, and targeted 7hrs sleep a night (after years of deprivation).

Looking back at monthly trends does correlate with how “great” I remember feeling on average throughout the year:

Insights thanks to Oura Ring

Insights thanks to Oura Ring

Looking back at the weekly reviews I share with my Elephants, there were a couple of distinct periods of “feeling low”. It’s not fair to call it depressive, but the main word I used to describe it at the time was malaise.

I just felt sad about the world, and relatively powerless to improve it in any meaningful way. Talking with other friends, this seems very common and hardly surprising. I don’t think we’ve even begun to understand the long-term, collective impacts of 2020 on families, kids, relationships, health outcomes etc, which will take years to show up. It’s been hard on everyone, in different ways.

Family + Relationships

We survived! Two working parents and two girls (5yo,3yo) under the same roof since March, with our nearest family +14hrs away. That’s probably the only highlight that matters – along with continued health of our immediate family.

>So cute thinking it would only be a few weeks.

On a positive note, we had more time with our kids than ever before, and maybe ever again. We had a bunch of fun milestones: cycling without trainers and first day on skis (5yo), starting to cook, migrating to real beds, potty-training (for the younger). They brought us a ton of joy despite the daily grind.

My wife is a boss (in the best possible way). We shared a workspace for most of the year. It was the first time I’d really seen her in action in a professional context. The way she balances being a mother, wife and leader at work is inspiring a little humbling. I already knew this, but know I really know it. Huge highlight of the year.

It was the year of the family Zoom. The biggest challenge was feeling distant from family in Australia, and fear in our inability to just jump on a flight for any reason, if they needed us or we needed them. Facetime helped, and storytime with grandma(s) became an almost daily event. But it was the first time in ~8yrs living in California that I’d really felt the distance.

It was a mix of highs and lows with other relationships. The biggest positive change I’ve made in the last two years was forming an Elephants group with 3 other mates. It’s been a wonderful mix of deepening friendship, mutual support and accountability.

One big insight from that group has been the way that consistency and commitment compound the quality of relationships. So I’ve tried to do that in other areas, like a regular hike with another mate, or carving out consistent time to call people. That said, I struggled to stay in close contact with a bunch of people who are important to me, and need to find ways to do better next year.


After 2.5 years at Lyft, I joined some good friends at ClassDojo, to lead revenue growth and monetization. See this thread for why:

I’m grateful for my time at Lyft, working with some incredible people, and learning a ton about building product and a company at scale. It was a valuable change after nearly 7 years as a startup CEO, and helped me level up in a bunch of ways. I’m excited to bring both perspectives to ClassDojo, still under 100 people.

Transitioning roles in a pandemic was very weird. I still haven’t met most of my team-mates in person, and may not for some time. Getting a work visa while on lockdown was even weirder.

Investing: Outside of “work”, I’ve loved continuing to support a few startup founders, with new investments into Ovira and Powerlines Pro. Grateful to both Alice and Dan for including me in their (competitive) rounds. Excited to explore more of this in 2021, along with a few other friends.

Growth + Learning

Finished 14 books, and started but dropped another handful (I’ve realised I should just stop reading when something doesn’t capture me). Top 3 were all biographies, which I love as audio-books:

Took a Reforge course on pricing and monetization, which was OK but did give me some helpful frameworks going into my new role.

Learned a couple new songs on piano, and picked up the guitar again after a few years of hiatus. Also how to deconstruct a road bike, as part of a project to build up a new one.

Learned quite a bit more about the horrendous history of systematic oppression in the United States. I’ve found it difficult to comment as a caucasian foreigner, and found it helpful to discuss this with others in a similar situation. We’ve explored ways to have positive influence, but still don’t have great answers.


I leave this section in to maintain tradition, but feels a bit empty.

We started the year with big plans: hike the Grand Canyon; spend a week with family in Portugal; have a week in Australia with friends; then do some skiing over winter. Like most people, our big plans were cancelled. Still, we did OK.

Sadly, didn’t surf all year (no good reason) and had only a single day of skiing (decent reasons). But I did start flying a kite again. Hoping to do more of each in 2021.

It was a shit of a year, but I’m grateful for so much. I think 2021 is going to be a great year – once we’re all vaccinated!

Looking ahead to a new year

Looking ahead to a new year

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