My 2022 Review

14 min readDec 31, 2022

Introspection — Photo by Tingey Injury Law Firm on Unsplash

I turned thirty this year, and for a hot second considered writing a review of the past decade. These annual reviews, however, are thoughtful enough and getting longer every year anyway (My 2021 Review).

I even forced a year-end relationship retro on Bridget while we were on vacation, which wouldn’t have gone so well if I hadn’t caved in to her blue bubble demands and bought an iPhone in February.

Staying on brand with these reviews, 2022 was a very introspective year for me. I’m grateful for many conversations with friends, family, and co-workers about the next decade both personally and professionally.

On life stages
On cycling
On marathons
On people
On roles
On startup mentality
On reading and writing
Memorable moments

On life stages

Not to be overly dramatic, but 2022 marked another inflection point in terms of planning my life in longer horizons. As a student, I merely had to think about next semester. As a young adult, I considered the next two years at most. But now, I need to think in five year increments. I’m no better at predicting the future, but now I know more about what I do and don’t want.

Our closest friends are getting married and starting to have kids. We attended seven weddings this year alone! Besides being memorable opportunities to reflect and to celebrate loved ones, we also learned plenty about each of our wedding preferences. If I had my way, we’d have a casual backyard BBQ with a smattering of toasts. Skip the verbose ceremonies, plated dinners, best man / maid of honor, and bridal parties. But got to have the late night snack!

On a more serious note, the weddings also served as natural opportunities to reflect on my own relationship with Bridget and what the future holds in store for us. We had important discussions about our own timelines in the next five to ten years, and I’m excited and grateful to embark on that journey together.

But the most immediate change in our lives is the corgi puppy we picked up on New Year’s Eve. Apologies in advance to our friends and family for the late replies and ragged appearance in early 2023! Bridget and I had joked about getting a dog starting last year, but I knew it was inevitable when we started watching videos of other people’s corgis on Instagram before bed.

Willow & Mango 🌻🥭 on Instagram: "Oh... Hey 👋🥭 * * * * #corgi #corgilove #corgipuppy #corgilife…

Willow & Mango 🌻🥭 shared a post on Instagram: "Oh... Hey 👋🥭 * * * * #corgi #corgilove #corgipuppy #corgilife…

www.instagram.com

We can’t wait to introduce you to our pup soon, but no guarantees on an Instagram account.

And if I wasn’t already hyperaware about getting older, I also continued the trend from my late twenties of discovering how eerily similar I am to my dad:

My rapidly receding hairline 🧑‍🦲, sigh.
My leadership style — I’m not the most vocal or motivating, preferring instead to lead by example behind-the-scenes.
My tendency to binge — whether reading a book, watching a show, or playing a game. I’ll stay up way past bedtime.

On cycling

In what I hope is a continuing trend, 2022 was the best year of cycling yet. I hit my goals:

climbed Hawk Hill in under nine minutes
completed the right of passage in cycling known as a century (a 100 mile ride)

But more important than hitting arbitrary numbers, I started riding with a group of fellow cyclists that call themselves the SF Cyclomaniacs, a fitting name that captures their enthusiasm for the sport. I was introduced when I reconnected with a college classmate, and it’s been humbling to discover how little I actually know about cycling — and especially bikes, as I was fortunate enough to have obtained my bikes from a high school friend who also moonlights as my mechanic.

The primary group activity is a 6:30 AM meetup at the entrance to the Golden Gate Bridge to haul our butts up Hawk Hill every Wednesday. It’s a great way to push through the mid-week slump, and doubles as an outstanding opportunity to enjoy the San Francisco sunrise.

I really found my groove with cycling this year. I have a great group to ride with, a mental map of all the routes in the north bay (which continues to amaze me as one of the best places to cycle in the world), and a new level of fitness to tackle even more challenging but rewarding rides.

I even squeezed in some mountain biking in Mammoth!

While it was a great experience riding my century solo, now that I’ve gotten a taste of group riding, I set my sights next year on completing a group event like a double century or a multi-day trip.

On marathons

To be clear, I’d never run an actual marathon! My poor knees would crumble. But I did surpass four years at Persona in October, and as the saying goes:

Startups are a marathon, not a sprint.

So I wanted to reflect on the marathon so far and what else is in store.

Celebrating four years of eating all the food at Persona

The four year mark is a major milestone in startup land. It tells a rich story, including, but not limited to:

Against the odds, the business is still ALIVE
You’ve been around long enough to make an impact
You have a rolodex of fun stories to tell new employees
You fully vested your initial stock grant

The last point is the least important to me, but much to my surprise, was the one that forced me to think most critically about my future at Persona.

Why?

It came down to one question- do I want a new four-year stock grant or a one-year grant? I won’t get into pros/cons here, but this seemingly innocuous question triggered a more important question- how long do I realistically see myself at the company?

Which then triggered more questions:

How has the company changed in the past four years? How will it change in the next four?
Why am I still at the company? Am I still having fun?
What else do I want to accomplish before my time is up?

I spent months contemplating, ultimately arriving at the conclusion that I still have miles to run in the Persona marathon, but also acknowledging that:

I don’t know what I’ll do after crossing the finish line. One thing I realized early on was that I don’t want to be CEO of a venture-backed company. Other than that, I know more about what work excites me but less about how to build a career out of it. I care less about titles and climbing the ladder than I ever thought I would. And I don’t see an obvious “next play” professionally (to borrow some LinkedIn lingo). This both scares the part of me that’s always envisioned myself as a high-powered exec and excites the part of me that’s always sought and embraced risk.
I’m not running as fast as I was at the start. I’d been wanting to take a three month break to rest and recharge, and I was finally able to squeeze in five weeks off this past summer. I actually avoided the emails and Slacks this time, and the break contributed significantly to staying sane this year. A longer chunk of time off served as a valuable reminder to create intentional points of change for myself — to have something to look forward to in the never-ending marathon. Better yet, it provided an opportunity for other talented folks that can run much faster than me to step up in my absence.
I’m likely closer to the end than I am to the beginning. There’s a lot of different reasons to unpack here, but the takeaway is ultimately the same. I don’t feel the same levels of excitement as I did in the earliest days. The company has evolved so much over time, and I’m in a different stage of life now than when I started. It was initially frightening to internalize this, but putting it into perspective was also freeing and helped me prioritize how to best spend my remaining time, however long it may be.

On people

The first two years at Persona was heads down building the product, last year was building the company, and this year was all about people.

When asked what kept me up at night, I consistently found myself answering with some variation of “the product isn’t the hard part, it’s the people”, or “I spend most of my time on people problems”.

People problems are a different breed of problem. They’re emotional, messy, and personal. They trigger countless rounds of investigation, questioning, and listening. They require copious amounts of tact and deep thought about potential second/third order effects. And they have an unfortunate knack for backfiring spectacularly.

We’re constantly moving people from team to team. Experimenting with different roles and responsibilities to spark increased performance. Meticulously putting folks on projects that have complementary strengths and weaknesses. Rigorously debating who can or should lead initiatives. Intervening when there’s too much friction between groups. The org chart is an ever-changing jigsaw puzzle.

We’re constantly forced to pick between two tough options

We go to extraordinary lengths to put folks in different positions to succeed when conventional wisdom suggests we let them go. It’s astonishing how often it’s worked out, but it doesn’t change the fact that we invest a lot of blood, sweat, and tears to make it happen and increase the odds of success. People-first is our number one value at Persona and I’m proud we’ve stayed true to it despite the tradeoffs.

I find myself surprisingly adept at identifying and diagnosing people problems, although resolving them is a different skill entirely. I’ve always had strong intuition on how well groups are working together and can build trust quickly across different personality types- these are the type of generalist skills that allow me to tackle all sorts of problems with all kinds of people.

The irony is, I don’t even directly manage anyone anymore! There are number of factors related to the organization and my role, but I don’t think I’m a great manager either; I hate dealing with poor performance, I’m not politically savvy, and I’m conflict avoidant. But I do care deeply that everyone is able to do their best work because a company is only as good as its people. I’m more mentor than manager, more dotted line than solid line.

On roles

Breadth, depth, and prestige. Every role optimizes for different combinations of the three. At Persona, I started with breadth and depth, believing prestige was the next step. Over time, I traded off breadth and prestige for depth. And in the inevitable next iteration of my role, I want to prioritize breadth again.

Different role iterations and possibilities

The closest thing to an interview I had to do for Persona in 2018 was a phone call with an investor. I don’t remember much about the call, but one thought shared after the conversation always stuck with me:

Generalists wake up one day at a startup and realize they don’t have a role at the company anymore.

There’s different flavors of this statement, another one being:

The people that you got here aren’t the same who’ll get you to the next stage.

These statements ring true as startups grow, but they paint too binary a picture. There’s opportunity to create value regardless of role:

There are so many holes of different shapes and sizes in the company as we try to accelerate through the growth stage, which generalists and folks who’ve been around longer are acutely aware of and are constantly plugging in the background. There’s more to do than ever, and having an extreme bias for action and a can-do attitude never goes out of fashion. Yes, we need more specialists now, but that merely changes the expectation for generalists. You need folks who can operate in the rapidly increasing number of seams between teams and specialists, creating cross-functional systems that scale.
Arguably the most important aspect of my role these days is not doing the work and leading by example in the trenches, but rather being a culture bearer and historian. I kickstarted an internal company podcast to capture the stories that have shaped the company (inspired by a similar effort at Shopify), which had been on my backlog for the better part of two years. And on a recent intro call with a new hire who had worked at GitLab, a leader of the remote-first movement, she dropped so many great suggestions to improve remote work that I immediately pointed her to our ops team. I assured her we didn’t have a tedious process and we value feedback and bias for action whether you’re in week one or the CEO. So I was ecstatic to see us implementing her suggestions by end of week! Sharing context about the past and how we work is critical to perpetuating core behaviors that have driven our success.

The key is embracing change. I don’t necessarily know how to solve problems any better than others, but I’m not afraid to make change. And if there’s one thing I’ve learned as the company doubled again this year, it’s that much of scaling successfully is mental. There are no silver bullet processes that magically make everything easy. Prioritize the right fires, invest the time and effort to listen to problems, collaborate on solutions, and communicate that you’ve thought deeply about the consequences, and progress will come. The act of making a change is often more important than the change itself.

On startup mentality

After years of free capital being plowed into every startup with a passable pitch deck, 2022 was a reality check for startups. Inflation and the Ukraine war were black swans that burst the grow-at-any-cost bubble — a much needed reset of expectations.

The startup mentality that building a successful startup is insanely hard was forgotten amidst the tailwinds of the last couple years, and I have some 🌶️ takes unpacking it:

Folks in tech, including myself, have gotten entitled and soft. Take remote work as an example. I shared why I prefer in person work in My 2020 Review. And after two more years of hybrid, I think remote work spoiled us. We expect increased flexibility, comfort, and productivity. Call me a pessimist, but I don’t believe you get more of one without trading off others. I’m the first to admit that I’ve traded productivity for increased flexibility and comfort over the years, but it was a conscious and communicated decision.
The odds are always stacked against you as a startup. You have to fight for survival and seize every possible advantage, all of which require some level of personal sacrifice. You need an edge and mental fortitude to withstand the ups and downs. If that’s unbearable, think carefully about whether you’re in the right situation instead of complaining!
Tech employees are undoubtedly some of the best paid and privileged personnel, and we’ve been able to demand more from employers because of recent market dynamics and COVID. Historically, the pendulum has swung too favorably for employers to get away with equating real people as mere “resources”, and it’s a good thing work will never be the same — change is progress. The pendulum now shifts back in favor of employers as we enter an economic downturn, and after swinging wildly in favor of employees, that’s also a good thing.
Some of my co-workers are also my closest friends, and work would be far less enjoyable without them. I’m careful to distinguish, however, that Persona is not my family. At the end of the day, we’re trying to build a business. And too much emotional attachment blurs the line between professional and personal. I have a reputation for being very serious at work. Not only is it just my style, but it’s also a tradeoff I’m willing to make to funnel the bulk of my energy into building the company.

Success is highly correlated with effort and sacrifice. Everyone has different priorities that dictate what they can put in to the startup, but the startup mentality never changes, so we should make those tradeoffs intentionally.

On reading and writing

While I didn’t read many books this year, I still read plenty and managed to write a bit:

Technically- the author writes simple explanations of tricky technical concepts. What’s a data lake? What does GitLab do? What are microservices? I’m so impressed by the crisp writing and whiteboard visuals. Communicating complicated concepts simply is one of the best indicators of clear thinking, and I try to emulate the author’s style as much as possible!
Tim’s monthly retros- these are unfortunately gated to Persona folks. Tim is an engineering leader I’ve worked closely with over the years, and he started writing a monthly retro that spans a range of topics on process, culture, and people. It’s quickly become one of the share-outs I most look forward to each month. His writing is a key reason why he’s able to drive complex decisions to quick resolutions, and the retros are a great way for the team to get into the head of someone they respect and admire. Periodically look back on what’s happened in order to chart a clearer path forward.
The All-In Podcast- during the course of five weeks over the summer, I cranked through dozens of these hour+ long episodes and gained a wealth of insights on the economy, tech, and politics. I’m not the biggest fan of venture capitalist personalities, and there are plenty of cringeworthy moments that remind the listener they’re listening to the fireside chatter of a highly privileged group. But all in, I find the debate and steelmanning to be rigorous and comprehensive in unpacking the nuance of the issues.
Technorealism- the first article I wrote this year was also one of my favorites. I’d never stopped to challenge my own rose-colored lens on technology. We too readily paint tech progress and leaders as unequivocally positive for society. That’s changing now, and THAT is unequivocally a good thing.
Speed > process- letting go of the need to layer process on top of everything I touch is one of the biggest mental shifts I’ve noticed over the years. Startups have but a few powerful advantages, and moving fast is the most important one of all.
Abstractions vs models- as we work more remotely and rely on written documentation to communicate, word choice becomes increasingly important. These particular words had bothered me at work for so long, I decided to write about them.