The elephant in the 2020 room was COVID, slicing the year into distinct eras: the sliver of time pre-COVID, rudely cut short by early quarantine, leading to summer and fall quarantine when optimism was unreasonably high and things almost felt normal, and slowly crawling into winter quarantine.

I planned on climbing Mount Kilimanjaro in June- that plan and others were upended. But I’m grateful my life wasn’t. I’m still employed, work from the comfort of my own home, get anything I need delivered to my front door, talk to loved ones at the push of a button, walk to my partner’s apartment in under 10 minutes, and live in a city that takes COVID seriously. I don’t take that for granted.

All that to say, 2020 was a relatively boring year to review unless you love cooking, watching TV, and playing video games. If that sounds boring, there’s always the 2019 review! Although it wasn’t all bad- finding out that Costco offers free delivery for orders over $35 through Instacart was easily my best quarantine discovery.

Table of contents

  • On remote work
  • On writing
  • On reading
  • On fitness
  • On tracking habits
  • On leading and managing
  • On COVID
  • Memorable moments

On remote work

For many folks I know, remote work resulted in more productive work, more hours working overall, and less distractions. For me, it’s reverse, and I’ve identified a handful of reasons:

  1. I have a lot of meetings, and Zoom calls drain me faster than in person meetings.
  2. I thrive off the physical and mental energy of others at work, which is also why I love working in coffee shops.
  3. Tapping folks on the shoulder in the office is my second language, which has been difficult to replicate virtually.

The common challenge here is communicating. And as a product manager, when communicating clearly and quickly across teams is my main responsibility, remote work is a unique challenge. I, for one, can’t wait to get back to the office.

One thing that has been true is that the line between work and life is increasingly blurred. I mitigate this as early in the day as possible by setting aside the time after I wake up. Instead of getting sucked in to work by checking Slack and email first, I drink a glass of water, go for a walk or do yoga, make breakfast, shower, review my calendar, check my personal to-do’s, and plan lunch before I sit down for a long day at my desk.

On writing

Is it possible to be a better writer by reading about it? I set out to answer that question by reading two books, On Writing Well and Sense of Style. And the answer was a resounding yes. There are the rules (e.g. you can cut out 50% of the words and still be coherent) and the tricks (e.g. read what you write out loud), but the key for me was critically analyzing good writing alongside the bad. But if you don’t want to invest in two books, this article is a great summary.

As I yet again failed to publish anything but this review in 2020, I set an ambitious goal to kickstart 2021. Every day in January, I’ll write and publish something on Medium. No guarantees that any of it will be compelling, but the mechanism of publishing my thoughts publicly is a powerful motivator. I’m curious to see what comes of it.

One of my long-standing goals has been eliminating vague words like “should” or “could”, and hedge phrases like “I think” or “I believe” from my writing. It’s been a multi-year journey, but I can confidently claim mission accomplished. There’s no vague words or hedge phrases in this post- I just checked! Eliminating them from conversation is a different beast as I’ve discovered a number of valid use cases: when encouraging others to share their opinion, giving critical and constructive feedback, and creating collaborative environments and safe spaces.

On reading

I read twice the number of books- 18 this year compared to 9 last year. Who knew that being stuck at home encouraged more reading?

In my 2019 review, I explained why most educational books are effectively worthless. So to increase the chances of learning and applying the wisdom in these books, I adopted a new tactic. When I read educational books, I read two on the same topic back-to-back. Particularly for a topic like hiring that’s incredibly subjective and generally unsolved, this tactic reinforces shared concepts through repetition while highlighting the differences in opinion and approach. And better yet, it expands the window of time I have to absorb and ultimately apply what I learned.

See Goodreads for all my reads

Here are my non-fiction highlights:

  1. The Phoenix Project- This book surprised me. It’s not only the most well-written book I’ll ever read about IT (albeit, not a particularly high bar), it’s one of the best books I’ve read period. It covers prioritization and efficiency in the world of work, which was already a hard sell for an optimization enthusiast like me. But the author weaved these insights into an engrossing and entertaining corporate drama. The jokes are corny, but the book is brilliant for anyone that enjoys thinking critically about productivity at scale.
  2. The Hard Thing About Hard Things- This had been on my backlog for a while, and it didn’t disappoint. I’m generally skeptical of taking someone’s personal experience as dogma but these types of books are a great way to peek around corners as you go through a similar experience. In this case, I’d recommend it to startup founders, execs, and early folks, in that order.
  3. Recruit Rockstars- This book was recommended to me by a friend who founded a startup. It delivers on core concepts while introducing some new ideas. Recruiting is a ridiculously hard problem. Imagine, in a couple hours (if you’re lucky), figure out if you can work with this person for potentially thousands of hours. Oh, and make sure they’ll be good at what they do (whatever that means). Oh, and if you do that successfully, convince them to join you. In interviewing at least one candidate a week in addition to hiring two people directly onto my team in 2020, I can use all the recruiting help I can get.

On fitness

Another year, another sport picked up. While 2019 was the year of climbing, 2020 was the year of cycling (and walking, so much walking).

At the end of 2019, I tore the labrum in my right shoulder, although I didn’t know at the time. I re-injured it a couple times over the next couple months, and finally got diagnosed in early 2020. I can repair the labrum surgically, but the reality is that climbing was always going to wear my body down. Climbing is a physically demanding sport and serious muscular injuries are common. So based on my highly-decorated injury history and gyms being shut down, cycling was one of the few unexplored sports and one where I had a shelf life greater than two years. In fact, cycling is the perfect COVID activity- it’s outdoors and isolated. I haven’t completed a 100 mile ride yet, but find me on Strava!

There’s a lot I love about cycling. Pragmatically, it’s a legitimate means of transportation. Competitively, you’re first and foremost competing against yourself. Sports have always been a great outlet for my competitive streak. But the truth is, I don’t like winning so much as I just like getting better.

Then there’s the adrenaline rush from speeding downhill or pumping your legs on a straightaway. There’s the fresh air and cool breeze of being outside. And there’s the battle up the hill between your mind and body as a fire rages in your lungs.

“It doesn’t get any easier, you just get faster” — Greg LeMond

Hawk Hill just north of SF

On tracking habits

I finally bought a fitness tracker. While I already track goals, caloric intake, and workouts, I always wanted to unlock sleep. What happens for almost a third of my life? As it turns out, less sleeping than I thought- being asleep doesn’t equate to sleeping well. But few things put me in a better mood than waking up and seeing a high sleep score, as if I worked HARD to earn that good night’s sleep, while a low score encourages me to set aside time to get quality sleep that night.

Average hours of sleep per day

When I bought my Fitbit in June, I was so excited to start tracking how much water I drank each day as a means to encourage more overall intake- my lips are always dry because I’m a full-time mouth-breather. I was also looking forward to finally syncing my calorie tracking with my metabolic burn. But after five months of daily tracking, I realized I don’t need to explicitly do so. I’ve internalized these goals so deeply that I instinctively calculate and consider how many calories I’m eating or have eaten whenever I see food, and my hand automatically reaches for the cup of water at the corner of my desk every hour. That’s the beauty of tracking- it creates better long-term habits by pushing it top-of-mind. And it generates some fun graphs to boot.

Average calories burned per day

On leading and managing

As a product manager, my mandate is to lead without managing. Remote work increased the difficulty exponentially, but 2020 presented other challenges.

First, Persona almost tripled in size. While I still own projects as an individual contributor, I mostly drive progress with and through other people and teams. As an early employee, I take immense pride in setting up other folks, especially new additions, up for success. It’s my sweet spot- I’m at my best as a do-it-all glue guy. But the primary challenge is knowing how and when to lead from a more visible and prominent position versus leading from behind-the-scenes. Do you push or pull? I’m trying to figure it out, and imposter syndrome niggles in the back of my mind. On this, a sobering reminder from many conversations I had in 2020 is the importance of experience and repetition. In tech, we tend to over-glorify youth, intellect, and ambition. People expect success at the snap of the finger, but I personally can’t see the path to get there. On the other hand, I can see success that’s achieved over many iterations of doing the same thing over and over again with slightly different variables. Better yet, there’s a clear path to hack it- find ways to move faster.

Second, managing others is the biggest professional challenge I’ve ever faced. I had the privilege of working alongside a set of incredibly talented individuals that brought their unique strengths, weaknesses, and quirks. And I need to tailor my approach to each individual, pushing and unlocking limits they may not even know they had. Am I a good manager? No way. Am I better than before? Absolutely. Answering tough questions about an unknown future, giving constructive feedback, dealing with lows, and being responsible for the growth of another individual, all foster a deep empathy which I know is crucial to being a great manager.

On COVID

Many pundits smarter and more eloquent than I have shared their thoughts on COVID and what it means for the future, but let me share a couple personal takeaways.

COVID was the “great accelerator”. It compressed years into months. It was fuel on the fire. Sometimes it was for the better; other times it was for the worse. I’m not sure I would’ve been able to spend so much quality time with my partner if it wasn’t for COVID, but I’m grateful for every minute that brought us closer together. Unfortunately, that wasn’t true for everyone. Other trends also accelerated- some that will continue and others that will slow. I’m bearish on food delivery, but bullish on grocery delivery. I’m bearish on full-time remote work, but bullish on hybrid work models. I’m bearish on the stock market, but bullish on tech stocks. I’m bearish on video conferencing as the primary means of communication, but bullish on digital productivity tools and live events. And I’m super bullish on videogames- I got back into it to escape everyday apartment life and connect with friends.

Humans crave connection. We need to connect to something bigger than us. Nothing represents this more than the monolithic migration from trend-to-trend throughout 2020. From gossiping about the latest Netflix reality show to rallying around social justice issues to nervously poll-watching to baking sourdough, we grasped onto every shared strand we could find. I actually spent more time catching up with people this year than any year prior. I proactively sought connection, while I was historically complacent and reliant on the comforting thought that I could always visit in-person.

Memorable moments

As is tradition, I’ll end with memorable moments. 2020 was all about the little things:

  • Thanksgiving with my family and Christmas with Bridget’s
  • Hiking in Half Moon Bay on my birthday
  • Taking a ramen-making class
  • Lake Tahoe for Labor Day Weekend
  • Chinese New Year with my sister and cousins
  • Debating every proposition on the 2020 ballot
  • Fixing my desktop after tinkering with and replacing every single part over the better part of two months
  • Getting a massage and grilling steaks for our anniversary
  • Persona: moving to the new office, park hangouts, office warming, holiday party

And just for fun, a sampling of our many and memorable home-cooked meals:

Best wishes for a happy and healthy new year!

Endlessly curious, always optimizing. Startup and product enthusiast. vincenttsao.com