Dec 31, 2023
When I first started doing annual reviews, it only required just a few minutes of scrolling through photos and group chats.
It has now evolved into a four-hour-long ritual that includes reviewing my color-coated calendar, summarizing Kindle highlights, and deploying ChatGPT to synthesize all this information.
This year’s retrospective required multiple cafe visits equipped with noise-canceling headphones and alarmingly large cups of coffee.
The latest addition to my overly rigorous routine involves answering a list of questions that I’ve been collecting throughout the year.
The first prompt asked, "What did you change your mind about this year?"
"Uncertainty isn't a problem that needs to be solved."
- Phil’s pithy response
2023 was the year I grappled with contradictions.
Can I stay ambitious while still being kind to myself?
Can I be consistent while still being spontaneous?
Can I be thoughtful without over-analyzing?
My response to all of these would be, “Yes, but I’m not yet sure how.”
Despite caffeine coursing through my veins, I’m perfectly at peace with how unsatisfying, ambiguous, and imprecise that answer is.
I think it’s a sign of personal growth.
When you've been hardwired to always chart the path ahead, any inkling of uncertainty can be perceived as some sort of personal failure.
I need to plan better. I need to be more prepared. I need to have answers.
Coming to this realization after a 20-step annual review process is an irony that doesn’t escape me.
Looking back on the decisions I’ve made, the content I’ve consumed, and the topics I wrote about, my evolving relationship with uncertainty emerged as a central theme.
To cap off the year, I want to reflect on how this transformation impacted the three areas I spent the most time thinking about:
Decision-Making
Friends (and Feelings)
My Definition of Happiness
Along the way, I'll share key lessons, fond memories, and awesome content I consumed that guided me throughout 2023.
Decision-Making
Q: What was the hardest realization you faced in 2023?
A:Realizing I had fallen short as a leader and decision-maker
Let's address the challenging aspects of 2023 first, so we can end this reflection on a high note.
This year really tested me as both a leader and a decision-maker, particularly in my role leading a new team.
Under normal circumstances, a growth team already encounters a lot of uncertainty—you launch experiments, see most of them fail, and hopefully double down on the few that show promise.
But we also faced uncertain economic conditions, company-wide layoffs, and multiple personnel changes that introduced new levels of lingering unsteadiness.
As a leader, I've always taken pride in providing energy and clarity but this year demanded a caliber of leadership that I didn't consistently deliver.
It’s easy to blame things outside your control, but I can't overlook my own decision-making mistakes and unforced errors.
I never had trouble saying “I don’t know” until everyone around me started to feel anxious about what comes next.
Over time, my desire to feel certain overwhelmed my ability to exercise sound judgment.
I found myself opting for more concrete and tangible choices, even if they weren’t the best ones.
I rushed decisions, not out of a desire to be more decisive, but to avoid the discomfort of uncertainty.
I blindly followed business school platitudes like "move fast and break things" or "do what the data tells you” which work well when applied judiciously but harmful without considering the details of each situation.
It turns out that answers to difficult strategic questions don't come from a SWOT analysis or a rigorous ROI-prioritization exercise. But I still deferred to established processes and the opinions of others because I couldn’t trust my own judgment.
Faced with uncertainty, I hopped on the life raft of “I’m doing what I’m supposed to.”
I realized all this after a lot of difficult conversations and soul-searching.
A few key insights also started to reshape my understanding of leadership:
"When you struggle to make a decision, you’re conflating the fear of decision with the implementation. You often know the right decision, you just don’t want to make it" - Matt Mochary on The Tim Ferris Show
"It’s a cognitive bias for many people, whereby we believe that the sooner we start fixing a problem the sooner we’ll solve it" - Hasard Lee in The Art of Clear Thinking
"Think deeply to move quickly" - Marty Cagan citing mantras from Amazon and Stripe
This year, I learned that bringing clarity doesn't mean eliminating uncertainty; it means helping your team explore and manage it effectively.
My team didn’t need guarantees of inevitable success; they needed confidence that decisions were well thought out.
To do this, I had to learn to embrace uncertainty not as a hurdle to overcome, but as an inherent aspect of complex situations.
Things improved slowly.
We spent less time trying to forecast results, recognizing that time spent improving precision could be better used launching and observing outcomes.
We started treating roadmaps and OKRs as tools to communicate goals and expectations, instead of inflexible plans that had to be strictly adhered to.
We refocused our experiments to prioritize learning over merely hitting quarterly targets at all costs.
By moving away from rigid processes and strict rules, we embraced a flexible approach that acknowledged the presence of uncertainty instead of putting on “certainty theater.”
Foundational to all of this was a personal commitment to always exercise discretion instead of hastily clinging to apparent certainties.
I forced myself to assess my motives and decision-making with questions like "Do I feel rushed to make a decision?", "What discomfort am I avoiding?", and “What do I know is true versus what do I hope is true?”
It’s still a work in progress but I’m encouraged by the results.
P.S. For a deeper dive into this topic, check out a talk I gave in November, where I explore these lessons further.
Friends (and Feelings)
Q: What gave you the most energy this year?
A: Quality time with people I love especially when I feel more connected with them
One of the best things decisions I made in 2023 was starting a Highlights Journal where I record any memory that fits the simple criterion of “I want to remember this!”
It's filled with spontaneous encounters, inside jokes, and little moments of joy.
"My best friend got engaged!" - Jan 28
"Watched Borat on my phone because we couldn't get the TV to work" - April 15
"Spent 4 hours at Dishoom drinking chai and catching up. The waitress gave us a free meal because we seemed like such good friends" - Jun 26
"Our group wandered into a random dive bar in Midtown still open at 3 am on a Wednesday" - Aug 30
"Cooked brunch and watched Oppenheimer (still not sure how I feel about calling it Bombs & Bagels)" - Nov. 27
Almost all the entries in my Highlights journal involved spending time with close friends and loved ones and reviewing these moments put a huge smile on my face.
I also noticed that I have an increased capacity to recognize and appreciate these moments.
I’d attribute that to deliberately working on myself emotionally this year.
In addition to working with a mental health coach, I also invested a ton of time trying to learn more about how our brains work.
Here are a few takeaways
"Your biggest distractions are the stories you tell yourself: anxiety and worry about the future, regret, and guilt about the past…These narratives distract you from accepting reality for what it is and just doing what needs to get done." - Ben Bergeron on The Danny Miranda Podcast
"Shame is the intensely painful feeling or experience of believing that we are flawed and therefore unworthy of love and belonging." - Brené Brown on The Tim Ferriss Show
"When we feel disconnected, it’s easier and less painful to shut down our emotions and simply attack when our needs are unmet...The longer partners feel disconnected, the more negative their interactions become. Avoiding emotion sets their relationship for more disconnection. Marriages don’t usually fail because of increasing conflict, it is decreasing affection and emotional responsiveness." - The Psychology of Breakups by The Psychology of your 20s
For a long time, much like my relationship with uncertainty, I treated emotional regulation as an exercise in eliminating and suppressing negative emotions.
I would criticize myself whenever sadness, disappointment, or fear broke through my facade of perpetual optimism.
I learned to not categorize emotions as either good or bad. Instead of trying to overanalyze my feelings, I gradually saw the value of just listening to how my body was responding.
Some emotions can be challenging, but we need to remember that they’re temporary. Avoiding, minimizing, or altogether ignoring them can stop us from engaging on a deeper, emotional level.
While I'm still on this journey, I'm beginning to see the positive impact this approach has on the relationships that mean the most to me.
On Defining Success
Q: What do the people you most admire have in common?
A: They embody qualities I aspire to have—dependability, optimism, curiosity, and supreme confidence.
For those who read last year's review, you might remember a section about experimenting with new routines.
Revisiting it now, I notice a pernicious, unspoken assumption of having the "perfect" routine.
I went a little overboard.
My mornings start at 6 am with meditation and journaling, followed by a pre-planned workout that also involves listening to podcasts at double speed.
After an Andrew Huberman-endorsed cold shower, I tackle the most important tasks I have for the day in a calendar block named "Peak Flow State Work" (cringe).
I would have an egg white omelet for lunch every day except for the weekends (when I’d get to “cheat” and have whole eggs) before powering through meetings in the afternoon.
I’d have dinner promptly at 6 pm, prepare for the next day, and watch an hour of YouTube before bed at 10 pm.
Like my parents, I'm a creature of habit indoctrinated with a protestant work ethic. But instead of watering our potted plants precisely the same way every day, I adhered to scheduled workouts, hitting my macros, and scheduling EVERYTHING so no time gets wasted.
I enforced these rules thinking they’d make me the person I wanted to be—disciplined, consistent, and reliable. However, this approach led to a mindset where even minor mistakes seemed like a dangerous regression toward complacency.
I convinced myself that living life to the fullest meant optimizing every second of every day, but what to what ends?
And if I don’t know the answer, why was I so certain these rules would lead me there?
Routines provide a ton of concrete benefits but we should treat them as foundations rather than the rule of law.
If deviating from the plan means I can feel more energized, more productive, and happier, I should leave the certainty of following a regiment.
Fortunately, I have some fantastic role models around me.
What they have in common is they’re extremely thoughtful and intentional about how they want to live their life. Their passion and energy are consistent regardless of what their calendar actually looks like (or whether they even use their calendar).
The happiest people I know aren't constrained by expectations or comparisons. They're actively defining their own vision of success, embracing what’s next with infectious enthusiasm and curiosity even if it’s uncertain.
Because their identities are tied to their "Why" ("because it's cool!") rather than their "What”, they’re able to focus on achieving goals while also enjoying the journey.
They balance being grateful for the present while maintaining excitement about possible futures.
When something doesn’t go their way, they possess the self-awareness to learn from that experience and the resilience to adapt and continue.
And they do this without judging themselves, other people, or the experience itself.
Everything is relative. There are no perfect solutions, just tradeoffs.
And much of what I've learned this year supports that perspective:
"Nothing’s ever as good and bad as it seems." - Morgan Housel in The Psychology of Money
"A good day is one filled with demands and pressures, yet navigated and adapted to successfully. It feels good to be present, engaged, and learning. A succession of such days leads to a successful life." - Light Watkins on All the Hacks
"The pathless path, an alternative to the default path, embraces uncertainty and discomfort. It’s a call to adventure in a conformist world. It's a reminder to laugh amidst chaos and trust in facing an uncertain future." - Paul Millerd in The Pathless Path
Seeing so many of my friends take bold steps to define their path has inspired me to do the same.
But that's a story for another day (so be sure to subscribe 🙃 to stay in the loop).
Conclusion
Q: What surprised you most this year?
A: How often Bookie comes up in random encounters.
In line with this theme of uncertainty, working on Bookie makes zero sense from an ROI perspective.
Writing is time-consuming. Assigning words to partially shaped thoughts is hard. And it’s not clear what the reward is for taking clumsy snapshots of my brain and sharing them out into the world.
But I've been pleasantly surprised by how often this blog comes up when I meet new people. It's led to new friends, deep conversations, and some really interesting opportunities.
I’m reminded that life's unpredictable and sometimes we're better off just doing what feels right and worrying about constraints and returns later.
Your kind words and genuine reactions to these blog posts keep me going.
I'm excited to continue writing and share more exciting updates soon, but in the meantime, thank you all for reading and being a part of such a wonderful year!
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