My 2023 Review

16 min readDec 31, 2023

According to the Chinese zodiac, 2023 was the Year of 🐰. But for us, it was the Year of the 🐶.

We picked up our new pup, Miso, at the end of My 2022 Review, and spent the first part of the year potty training him and taking photos of every nap.

Once Miso settled into a steady schedule, so did we. I started going back to the office 4x a week (which magically solved my neck cricks), committed to early morning cycling classes, and walked the dog at least once a day.

Then the rest of the year just flew by.

Now that we successfully absorbed the shock of inviting another living creature into our home, we’re ready for another change in 2024. Is it time to start ring shopping?

On being a dog dad
On burnout
On culture, care, and craft
On teams
Quick hits
Memorable moments

On being a dog dad

I didn’t grow up with pets. To paraphrase my parents, “Another mouth to feed? NO THANKS!”

Raising a puppy was a big commitment and a steep learning curve. And while we taught Miso a lot, Miso taught us more:

Patience- I’ve always had a short temper, which reared its ugly head during potty training. Each time Miso peed on the floor, I honestly felt betrayed. He once peed indoors three times in a row and I lost it. I sat him on the couch, seething, and stared at him for fifteen minutes as if he’d internalize my disappointment. He didn’t 😆. Bridget rightly pointed out how my anger was unproductive, and I focused instead on what I could control: systematically tracking his schedule, praising his progress, and resetting my own expectations that accidents happen! Miso was progressing, but the curve was spiky rather than linear, and I had unreasonably high expectations for him and myself. Don’t take progress for granted. Be patient with the process.
Positive reinforcement- 99% of dog training methodology is based on positive reinforcement. Dogs don’t feel guilt or regret, so shaming or yelling at them doesn’t work. Anybody who knows me knows I’m not exactly a fountain of praise, so dog training brought out a side of me I wasn’t sure existed.
Manners- I believe our pets reflect our values. The rules and manners we impart on Miso indicate how we interact with those around us. No dogs allowed in the bedroom or bathroom. No jumping on the table. Wait for the “OK” before going through doors or eating. Greet other dogs and hoomans calmly. Go to the crate when asked.
Parenting- our favorite question to ask our couple friends is, “Who’ll be the stricter parent?”. It often stirs up interesting debate, but in our case there’s no debate — it’s me! It’s fascinating to see Bridget, who would’ve otherwise been more strict, take a good cop approach to balance my strictness. I want Miso to be well-trained, well-mannered, and well-socialized. Maybe too much so. Strict parenting often leverages negative reinforcement, which doesn’t work with dogs, so I’m mindful of not turning into a tiger dad.
Love- I love my furry friend more than I thought I could. He puts a big, priceless smile on my face every day. As DINKWADs (dual income, no kids, with a dog), we have an overflow of love to shower upon our dog. I honestly have to catch myself when I get home and greet the dog before Bridget 😬.

I’ve always wanted a family, and after our first year with Miso, our small family is starting to feel very real. Nothing brings me more joy than bear-hugging Bridget and Miso.

And beyond our household, my sister is having her second child next year. So we’re excited to welcome the little one and spend more time with my three-year old niece, Iris. It’s surreal to see the next generation of my family emerge.

As much as I hate to be the obnoxious pet owner shoving photos in your face, how about just a couple..?

On burnout

Burnout is physical or mental collapse caused by overwork or stress.

During my time at Persona, I’ve had countless conversations about my own and others’ burnout. After going through another round this year, I wanted to reflect on what I’ve learned.

First, I asked myself a couple questions about each time I’ve felt burned out. What were the circumstances? How did I handle it? How did I recover?

I count at least four instances:

December 2018- the full story’s here, but the short version is I had two weeks to find, sign, and integrate two vendors to launch our first major customer in a space I knew nothing about. I ignored everything outside work for the month. And while I frantically cobbled together a plan, the co-founders shipped an absurd amount of code. It was as tense a time as it was invigorating, but we got it done! To this day, still one of my proudest Persona moments. But after already grinding 24/7 for months leading up to this pressure-packed sprint, I was exhausted. The holidays were a much-needed break.
March 2022- our most important gig economy customer escalated a big conversion drop in their sign-ups. It was the most challenging, intense incident I’ve ever been apart of. For weeks, we pored through every possible change and data point, going back and forth with what seemed like their entire company. We never nailed down the exact root causes, but we pushed out a slew of improvements and conversion recovered. I remember being unreasonably frustrated and short-tempered with everyone. If you weren’t directly involved, why were you slacking off and not working on this incident? If you were helping, why weren’t we able to solve the problem? It was a classic lose-lose situation.
October 2022- our biggest customer was at risk of not renewing their contract, and I was asked to work closely with the customer team to get things back on track. I was indignant because I was already slammed trying to ramp up new team members, and I wasn’t excited to work with people I perceived to be struggling. After a series of conversations in which we talked through the pros/cons, what I’d have to take off my plate, and planned different scenarios to transition off smoothly after renewal, I very reluctantly agreed. Looking back, I overreacted. Frankly, I was scared of causing another customer incident and in a deeply introspective mood about work after reaching the four year mark.
March 2023- I was convinced it was time to quit. It wasn’t any one thing, but rather a slow build of many irritants: potty training the pup, dealing with organizational issues, running into scaling problems, recovering from annual planning, jumping on complex sales deals. It was a real existential crisis. I felt disconnected and nothing excited me. I’d look at my calendar in the morning and be filled with dread. And a discussion about upcoming time off was the straw that broke the camel’s back. I put so much into this company, why should I feel bad about taking time off? Ultimately, through a series of convos with those I trust most, they helped me hit the reset button and redefine my why.

Next, I looked for trends.

Conditions: urgent customer escalations, not seeing others put in care and effort which is exacerbated when I have even more on my plate, not working closely with people I admire and respect, not taking care of my body, not having a break to look forward to.
Signs: less engaged in meetings, low energy, less sociable, everything gets under my skin, easily distracted, difficulty focusing, Monday blues but everyday.

Each time I felt burnt out, I realized there was at least one stack.

We can sprint for weeks or even months when we need to get something done. But at some point we’re tapping into our reserves, and periods of intensity are balanced by periods of recovery.

When you stack multiple intense periods on top of each other, you hit the limit exponentially faster. I’ve seen folks with unbelievable limits (easily 10x my own), but they ultimately have limits as well.

In both 2022 and 2023, we had just had wrapped up an intense month of planning culminating in high-pressure presentations at our annual kickoff. I realize now that I was already in a precarious state after kickoff, and it didn’t take much to tip into a downward spiral.

Each burnout was seemingly worse than the previous, so how do I mitigate it?

For the past three months, our Head of Product has been on maternity leave and I’ve been covering for her. I’ve been as busy as I can remember, but not nearly as stressed. Why?

Set boundaries- I’ve been intentional about setting boundaries over the years, treating it as a gradual process and balancing the tradeoffs (e.g. turning off certain notifications, being more comfortable about not knowing every detail).
Separate work from personal identity- make sure I always have an answer to this question.. who am I if I’m not working at Persona?
Relieve stress- establishing a consistent, rigorous cycling schedule and playing a couple video games I was excited about were tremendously helpful in releasing stress.
Avoid stacks- just like an exercise regimen, you have to balance intensity and recovery.
Talk about it- burnout is worse when you feel isolated and alone. My tendency is to bottle up negative emotions, and I’m constantly surprised at how much better I feel after a conversation.
Find the why- when the existential crisis hit me earlier this year, rediscovering why I was still grinding after all these years was the key to getting out of the rut: 1) I’m intensely loyal to the early team, 2) there’s things I still want to learn/do that can contribute to Persona’s success, and 3) this may very well be the most important work I ever do.
Create meaningful breaks- taking any less than three consecutive days off isn’t a meaningful break, it’s just piling on for later. We started counting down to our December vacation when we booked it in July. We created a surprisingly powerful anchor for our tired minds to look forward to. My most productive weeks are the ones leading up to breaks- that’s how powerful the effect is!

I’m incredibly lucky to have passed 5️⃣ years at Persona. But if there’s anything I’ve learned about burnout, it’s not about luck. Burnout can be managed and mitigated. And it doesn’t go away if ignored. Identify the trigger conditions, look for the signs in behavior change, talk openly about it, and make the change.

On culture, care, and craft

These three related concepts came up seemingly every day at Persona.

Culture — the values and principles that guide how we operate

Having a shared set of beliefs is powerful — they’re the superpowers of any company. But superpowers mask hidden weaknesses. These shadow superpowers are not only counterintuitive, they often only surface during times of crisis. This year, we’ve had to grapple with shadows of our culture.

The shadow of a considerate and friendly culture results in avoiding necessary conflict and not taking charge for fear of stepping on others’ toes.
The shadow of high bias for action results in a small group of individuals who consistently end up driving complex decisions and stunt growth opportunities for others.

Incidents are a great example of the above. When the product breaks, we’re scrambling to figure out what’s wrong and how to fix it. During this time, we need folks to jump in with ideas, debate, and take decisive action.

But what happens when there are a lot of people deferring because they think someone else knows better? How do we spread knowledge and empathy if it’s the same people making the critical decisions?

The bigger a company gets, the more important it becomes to understand the shadows. More people, processes, and products create cultural cracks that need to be glued back together.

As a professional glue guy, and in the unique position of being the first hire but not an executive (i.e. I understand the historical context but not necessarily mandating from a position of power), I started pushing myself last year to find more explicit ways to share aspects of our company culture.

I want to encourage conversations at scale about our culture, both good and bad. I want to talk more openly and often in meetings, write more, create podcast episodes, and start a working group to mobilize folks across the company with different perspectives. Culture is set by example, but that shouldn’t be mistaken for being top-down.

Care — committing to shared success and giving it your all

Arguably the most important part of our culture, but also the hardest to scale.

Back in 2021, I wrote about different generations of employees. I’ve come to realize that the perceived divide is driven not by differences in skills or context, but about how much one cares.

The easy answer is that some employees — particularly early ones — just care more. Maybe they feel more ownership, figuratively and literally. Maybe they have less commitments and can put in more hours. Maybe they have more innate bias for action or intrinsic motivation. All can be true, but I refuse to believe we can’t also nurture care.

We’ve tried a lot of different tactics, many of them having to do with getting closer to customers and those we serve, and we’ll continue to do so because our long-term success depends on it.

Instead of asking what’s best for me, ask what’s best for customers, the company, and those around me?

Craft — the skill in carrying out your work

There’s an adage in startups that “people don’t grow as fast as the company does.” While there’s truth to it, outside of picking the line of work you focus on, mastering your chosen line of work is the next best way to scale yourself as the company grows.

Craft means holding yourself to a high standard.

Craft means constantly improving your product and yourself.

Craft means being proud of what you put out into the world.

Craft means loving the tiniest details.

Even when the company is rapidly growing or changing around you, being great at what you do naturally leads to growth opportunities.

One of my favorite indicators of high craftsmanship is diligent bug reporting. No matter how good the software is, there’s always bugs. Users run into bugs all the time but often don’t report them. In a rational sense, reproducing the bug in different scenarios and filing a report isn’t worth the effort. But that’s a slippery slope. What bugs are worth filing and why? When the next person runs into the same bug, will they have that same understanding?

This year I’ve been thinking about craft on our product management team. We have an incredibly talented group of individuals, but we’ve relied too much on talent and done a poor job systematically raising the bar on craft. The good news, though, is that craft is teachable, learnable, and has a clear feedback loop with higher quality products.

On teams

The basic structural unit of a company is a team, so I’ve been thinking about how to make teams more effective and what role I have to play.

This is not meant to be a comprehensive list but I have applied every one of these bullets this year.

Purpose

Define what the team does, who they serve, and why.
Have a clear set of goals for a given period, evaluate the team against it, and iterate.
Consider how the team’s behavior is influenced by incentives — whether it’s the above goals or at the level of wider company strategy. At Persona, our product teams became siloed over time because they were rightfully following the mandate to build standalone products.
Let teams self-organize as opposed to rigidly defining areas of ownership. The team that feels the most pain has the most incentive to invest in a solution. In this way, I’ve seen many teams take on more than their immediate scope and clarify existing purpose or even discover new ones.

Structure

Organize the team by function (e.g. sales, engineering) or mission (e.g. SMB customers).
Make sure the team is the right size to serve its purpose. Better too small than too big, but effectiveness suffers in extremes of both scarcity and excess. I personally do my best work in small teams. In a couple months, with a couple engineers and a designer, we laid the foundation to go after a new market and launched the first iteration of the product this year.
Split out new teams when new purposes arise. Teams naturally try to coalesce, but new ideas need space to break out of the status quo.
Put the right leaders in place. Teams take on the personalities of their leaders and need different types of management to be successful.

Culture

If people don’t weigh in, they don’t buy in. High-performing teams have to be comfortable disagreeing and debating.
Stay connected to the front-lines. As teams get bigger, it’s easy for leaders to make too many assumptions about details. Similarly, it’s easy to treat people as nameless faces or resources on a gantt chart instead of understanding how each individual fits the team.
Experiment! High growth teams are constantly changing. If you don’t feel like anything needs to change, that’s a clear signal something needs to change. The more you experiment, the more you learn about the natural cycle of change. I’ve seen multiple product teams start without standups, introduce live standups, move to async standups, and go back to no standups. On and on as the team evolves.

Process

Get the right people in the room — how do we arrive at informed decisions as quickly as possible? As Persona has grown, trying to engage entire teams has become less effective. Making decisions within or across teams is ultimately about creating champions out of key individuals.
Invest in tools like AI. I’m no AI fanatic, but it’s clear that it’s a game-changer for internal process. We’re implementing AI into our products, but there’s challenges like processing time, vendor roulette, and rate limits (i.e. how much data we can throw at the AI in a given time period) that make customer-facing applications risky. No doubt these will be solved in due time, but I’m more excited about internal applications like summarizing Zoom meetings and code editing via Copilot in the near term.
Beware of too much process.

I’m actively applying the above to the product management team. We’re going through another inflection point as a company, and we haven’t put enough emphasis this year on resetting the team to scale for the next stage. As a group, and over many weeks, we unpacked what was wrong about PM’ing at Persona and brainstormed dozens of initiatives I aim to empower folks to drive in the new year.

More broadly, the PM function went through a reset after Airbnb dropped their PM titles. I’m indifferent about the title itself — I’ve long believed that PMs are too often glorified — but the responsibilities needed to build great products haven’t disappeared. Airbnb bifurcated the primary responsibilities of PMs into business outcomes (i.e. product marketing managers) and product delivery (i.e. program/project managers). That was their hypothesis to improve their teams’ effectiveness and I admire their willingness to change!

Separately, I’ve been mulling over my role on teams, specifically on management. This year, I donned the manager hat again and spent more than three months stepping in for our Head of Product, which was a valuable opportunity to re-evaluate my capacity and desire to manage.

Many of these observations aren’t new but bear repeating:

Management often doesn’t feel like real work. I’m further away from the execution and how the actual work happens is more opaque. If you “manage” to achieve your desired outcomes, it’s genuinely the most rewarding feeling. But when you don’t, you have to dig way deeper to find out what went wrong.
I felt more prepared and comfortable managing the second time around after: 1) taking a half-year break from it, 2) having more experience under my belt, 3) observing and partnering closely with other team leads.
I still prefer a player-coach role. Having a project I can fall back on when dealing with draining organizational or people issues is a great stabilizer.
Don’t conflate management with career progress- it’s just a different path. There’s so many ways to grow outside of management. If you’re interested in management, ask yourself if you’re more energized by solving people problems or product problems?
I prefer coaching and mentoring over management. In other words, I like to teach and facilitate more than direct. Fun fact: I’d love to coach my kid’s sports team one day, but I also know I’ll struggle with the kids that aren’t exactly excelling on the field 😅.
Steve Jobs said, “You know who the best managers are? They’re the great individual contributors who never, ever want to be a manager, but decide they want to be a manager, because no one else is going to be able to do as good a job as them.” This resonates with me more than ever.

Quick hits

A new, experimental section- thoughts that don’t warrant separate sections but are still personally interesting.

Big decisions need time to bake, so start the conversation early. I dipped my toes for half a year before committing to buying a condo or getting a dog. It happens at work too. Our most important decisions were on again, off again discussions over many months or even years. People need space to digest complex topics for themselves, understand the ramifications, and feel enough ownership of the idea to buy in.
At work, I pride myself on replying to messages quickly and directly. A sentence sent fifteen minutes later is often more helpful than three-paragraphs sent a week later. If only I could do the same with my texts!
One monthly reminder I’ve had for the past couple years is to stop comparing myself to others, which has always been a major driver of imposter syndrome. I can’t point to any one thing that made me feel comfortable removing the reminder this year, but I’ve just learned more over time about what truly brings me joy.
It’s no secret why Persona has been successful- 23 of the first 25 employees are still here. There’s fewer opportunities to work closely with that group as the company has surpassed 230+ employees, but I cherish the moments we get to solve problems together.
I only posted one article this year 😕. I like to daydream about taking a break from an operating role and writing full time for a bit. Bridget can attest to how many banal dream jobs I have, but this piece about writers who operate reminded me that the grass isn’t always greener on the other side.
I watched more cycling this year, and it’s been fascinating to learn the dynamics of a team sport that crowns individual winners. Every team has a lead rider and everyone else rides in support of that leader. But team and individual ambitions constantly butt heads, as exemplified by the Vuelta de España controversy.
When hiring, if you‘re not desperately trying to convince everyone else why a candidate should be hired, you don’t feel strongly enough about them. Objectivity is an illusion when you’re the hiring manager.
Pedestrians and cyclists in San Francisco are so dangerously entitled. They always think they have the right of way. And whatever you do, don’t honk at them. Even when they’re clearly at fault, nothing brings out the irrational anger and colorful swearing like honking. Myself included.

Memorable moments

As is tradition, it was painfully difficult to condense the year into a single collage.

Miso’s first camping trip
California Pizza Kitchen nostalgia
Hosting Spark SC at the office
Oyster shucking on the beach
Visiting Greece and Turkey for an over-the-top Indian/Kazakh wedding
Long weekend in Tomales with the fam
Bridget’s first cruise
Christmas in Albuquerque

Wishing you and your loved ones a happy and healthy 2024!