My 2021 Review

2021 was a breath of fresh air compared to My 2020 Review.

Quality time with friends, family, and co-workers lifted my spirits as I rejoiced at the return of trips with friends, birthday celebrations, family vacations, eating out, live concerts, and that unmistakable office buzz. We enjoyed being physically together, even if six feet separated us at times.

In January, I hopped on a one way flight to Dallas. My lease in San Francisco was up, my roommate had moved out, and I wanted a change. Going home presented an opportunity to reconnect with my parents and rediscover my focus. It ended up being one of the most productive months in recent memory, and the perfect way to kickstart the year.

But most importantly, I also wrapped up the year on a high note by publishing this review on December 30th so I can finally relax on New Year’s Eve!

Table of contents

  • On home
  • On cycling
  • On merging minds
  • On startup growth
  • On traveling
  • On writing and reading
  • Memorable moments

On home

As only one definitively past the peak of youth would say, buying a home in San Francisco was a big move. I explained why I wanted to mortgage away my future in a previous article, but suffice to say it was a calculated choice.

I snuck in at the end of the much-needed market correction (downturn) triggered by COVID, buying a new condo right in the center of the city. But of all the things I should be grateful for — like continuing the wonderfully convenient trend of being able to walk to work — I’m still endlessly amused that the address 555 Golden Gate Avenue is as SF as it gets. I hadn’t considered whether it was a factor in the buying decision — probably best not to think about it too much!

Finding a home was a challenge, but ultimately nothing like furnishing it. Without any expiring lease agreements in my near future, I could finally invest in quality furniture and quite a lot of it indeed. For months, life was summed up as working during the day and furniture hunting at night. We’ve slowly but surely whittled down our “(FUN)iture” doc, but new items keep sprouting up in the doc like weeds.

For anyone who’s stepped into my primitive dwellings of the past decade versus the new home, they’ll quickly recognize a changed man. There’s an alarming number of furniture photos from different angles on my phone, I have this growing desire to fill every empty space with houseplants, and Architectural Digest videos dominate my YouTube history. Ah, the joys of a home.

On cycling

Instead of titling the section “fitness”, I thought it better to be specific, since cycling has become my primary source of exercise and competition as well as the only sport my battered joints can survive.

2021 was the year I unlocked the true secret to cycling faster.

It wasn’t the oatmeal and homemade energy balls, interval training, heart rate monitor, aero tuck, or drafting. Although these, amongst others I’ve learned, are all great strategies to pick up the pace.

No — the best way to get up that hill faster is…

… getting a significantly lighter bike.

I jest! Mostly. Everybody knows there’s no real shortcuts to consistently increasing your speed outside of deliberate training. But the first time I took the new carbon fiber frame for a spin, I really did feel like I was pedaling on a cloud.

How obnoxious I must sound when I painstakingly differentiate between my old “city bike” and my “real road bike”. The new bike also signals the start of the slippery slope that ends in a garage full of expensive bikes collecting dust, otherwise known as the n+1 principle:

While the minimum number of bikes one should own is three, the correct number is n+1, where n is the number of bikes currently owned. This equation may also be re-written as s-1, where s is the number of bikes owned that would result in separation from your partner.

With a lighter bike in tow, I picked up the intensity in the second half of the year and hope to ride, so to say, that momentum going into 2022 . I didn’t finish a century (100 mile ride) or break 9 minutes on the hill sprint, but I did enjoy a beautiful 60 mile ride to and from Half Moon Bay and hauled my butt up Hawk Hill dozens of times. Good progress for next year’s goals!

On merging minds

Bridget, my partner, asked me if she’d show up in the review. She’ll either be irked or flattered when she realizes she gets an entire section instead. For as big a part she’s played in making 2021 a fantastic year, it was actually unfair to set aside just one section.

We passed some important milestones in our relationship. We spent time long distance, survived an extended vacation with my parents, moved in together, and even started texting each other’s mom directly.

I relied on her more than ever this year as a thought partner, confidante, and home design consultant. And we’re thoroughly convinced that our minds have merged, with some exciting science lending credence to our claims. So in what can only be described as “stupid things couples do”, we make it a game to shout out the thoughts the other one might be thinking a split second before they can say it aloud.

On startup growth

Persona’s year can be summarized in one word — growth.

Growth is a double-edged sword. On one hand, you get revenue, recognition, funding, and opportunities. We tend to tout and fixate on these. On the other hand, you have more pressure, competition, onboarding, communication, and knowledge transfer. We tend to ignore these and let them fester.

We’ve grown quickly every year, but year three felt markedly different. I summarize my time at the startup as a series of key inflection points, and this year brought the biggest one yet.

For the first two years, I knew all my co-workers in a meaningful capacity, many as friends. The cross-team collaboration required of my functional role combined with incumbent knowledge as an early employee meant I had the privilege to work closely with everybody. As we’ve raced past the hundred-person mark this year, I don’t know everybody anymore. There’s people I’ve never even introduced myself to! I’m the first to admit that I should make more of an effort to reach out proactively, but it’s no easy task to build and maintain so many relationships.

This hundred-person inflection point is scary for two reasons:

  1. More complexity, less control- I like to get things done and do them well. Generally, the more factors I control, the better the results. This likely demonstrates poor/unscalable leadership or control freak tendencies, but I can own up to that. As the number of people and processes increases linearly, any given individual’s control decreases and communication needed to get anything done increases exponentially. In short, getting things done becomes much harder much faster. While these challenges are inevitable and expected, the real challenge is adapting my own behavior from when the entire company fit on a small couch to now a hundred-plus organization. We try hard to keep teams small and de-coupled, as popularized by Amazon’s two-pizza teams, to combat this complexity.
  1. Stratification- This one scares me more because it often goes unnoticed. I see people falling into this trap all the time, myself included. As more people join the company, implicit “generations” form based on when you started. The human need for connection and storytelling is strong — you bond with those whom you share the most in common. This often manifests as innocuous statements like “Remember that time we…” or “It was so much better before…”. In private, it spurs camaraderie. In public, it stratifies and slowly pushes apart groups that know and don’t know what you’re talking about. It’s incredibly difficult to fight, but well worth it since it’s a primary way that the startup’s culture stays cohesive over time.

Navigating the growth stage comes down to finding new and clever ways to operate as if you were still that ragtag bunch on the couch, all while optimizing the transfer of knowledge across the company.

I like to draw upon some simple adages.

Repeat, repeat, repeat

One thing we product managers love to commiserate about is how no one seems to absorb what we tell them about the product. Why?

  1. There’s so much going on that nobody is absorbing 100% of what you’re saying at any given time.
  2. Our product surface area is expanding rapidly as we build multiple standalone products on top of the platform.
  3. New people join every week and the knowledge gap between them and existing folks widens. We need to communicate at the lowest common denominator.

I still find myself getting annoyed at repeating myself over and over again, but I also continue to marvel at how critical it is to keep doing.

Teach while you do

I recently joked with one of our early engineers that we’re just professional teachers these days. Truly, the most powerful way to scale ourselves is to teach others. I originally wrote that “Teaching is more important than doing”, but realized that’s not quite right. The reality and more difficult duty is that we need to teach and do at the same time. At this stage of the company, our ability to tackle the most complex problems from the front is as valuable as ever, but we also need to guide and empower others to be able to accomplish at least the same if not better. The earlier and more senior you are, the more important it is to internalize.

On traveling

One of the great pleasures of 2021 was being able to travel.

While we didn’t leave the US, it was rejuvenating to resume the annual trips with friends that I looked forward to like the seasons of the year and escape the daily monotony of being cooped up in a small space. There’s simply nothing I love more than exploring new places with old friends. So I’m happy to now share this cringey rhyme.

Our first time in Hawaii, but certainly not our last.

We relaxed in LA and Vegas over July 4th, golfing as the fireworks blast.

A cloudless sky in Minneapolis, with a jaunt to the Renaissance Fair.

Walking and eating our way around Seattle, whose summers are beyond compare.

Long weekends in Santa Cruz, Mendocino, and Monterey kept us near.

And now we’re old enough now to look forward to many a wedding next year.

On writing and reading

In January, I challenged myself to write and publish an article on Medium every day of the month. I’m proud of what I accomplished and learned a great deal about recreational writing and my distinct style within it, which I dutifully summarized in a follow-up article.

Though I failed to consistently write publicly in the following months, I constantly reference and revisit the thoughts that had finally been organized into coherent write-ups. I was recently collaborating with a co-worker on a how-to guide for working with third-party vendors that power our product, and got the ball rolling on our discussion by drawing upon tips I’d laid out in my Vendor Management article.

Yet the best part is not what I gain, but hopefully what I in some small way can inspire. As unexpected as it was gratifying, after Bridget’s dad, Emile, heard about my writing, he starting blogging about the memories of his own life. He’s lived a rich nine decades, not to mention written many books as a professor, so I’m ecstatic to be a part of an exclusive group who get a glimpse into his journey. As is much of starting to write, Emile fittingly started the blog with this:

I am making a start on a path that has no immediate destination.

Now we’re waiting for the ninth entry!

Inspiration to write often comes from what I’ve read, and I managed to read a book or two. While I still challenge myself to read a certain number of books, I primarily use it as a reminder to find interesting reads as opposed to worrying about quantity, especially as the selection of books I actually want to read shrinks. I’ve eased up on the Outliers-type self-help and behavioral economics books for two reasons:

  1. I’ve read so many books in the genre that I recognize the same core message repackaged across different examples.
  2. Now that I’m old enough to have some actual life experiences, they teach deeper and longer-lasting lessons than learnings from a book.

Therefore, I’ve taken an interest in biographies, history, and societal commentary (with a scattering of sci-fi as always).

My non-fiction highlights:

  • Can’t Hurt Me- Few books have had a bigger impact on me. In hindsight, I had been in a rut when I read this but hadn’t yet grasped the cause-and-effect. It was a wake-up call that helped me refocus on goals I’d unknowingly put off. Can’t Hurt Me is an easy-to-read autobiography written by “the toughest man alive” who embodies mental resilience and does us a favor by sharing his story. But more importantly, it was exactly what I needed at the time. A blurb won’t do it justice — I plan on writing more later.
  • World After Capital- A thought-provoking read about technology and society. If there’s one thing I appreciate about venture capitalists, it’s that they tend to share interesting insights into trends and the future. Whether or not the author’s predictions come true, it’s worth understanding why and how technology is pushing us from the Industrial Age to the proposed Knowledge Age, in which the scarcest resource to optimize for shifts from capital to our attention.
  • A Short History of Nearly Everything- This is a brilliantly-written and well-researched book on an ambitious premise. It’s Homo Sapiens, one of my favorite books of all time, but with a deeper dive into the science and copious amounts of wit. Not every page or historical figure is riveting. After all, the great challenge of science is that it’s largely uninteresting until suddenly it isn’t! But if I had read this in lieu of science textbooks in school, I may have chosen a different career.

Memorable Moments

As is tradition, I’ll end with some additional 2021 highlights and a gratuitous collage of our home-cooked meals so people think we’re good cooks:

  • Birth of my niece, Iris 💮
  • Camping in Bothe
  • Our first caricature
  • Bridget’s 30th birthday party
  • LANY and Brett Young concerts
  • First TAMS trip with +1s
  • Persona’s holiday party

Best wishes for a happy and healthy new year!

--

--

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store