What Happened in 2021 — Another Annual Review
Five Celebrations, Five Lessons, and Five Intentions
Every year I sit down to unpack a full reflection of the past year—all the victories, the setbacks, and the lessons. I find every minute spent working on these annual reviews is rewarded many times over.
I’m writing this reflection for myself in an attempt to make sense of it all. This may be way more detailed than you asked for, so feel free to skip around to any sections that interest you.
I choose to share this review with you because:
Each vulnerable action is a small step towards integrating the public and private versions of myself.
Our future conversations are now framed around helping each other reshape the world and become the best possible versions of ourselves.
By holding each other accountable, our mutual success becomes exponentially more likely.
I might inspire you to dig deeper during your own reflection.
I’ve broken this review into three sections with five reflections each:
Celebrations (what went well and why?)
10/10 recommend marrying your favorite person.
When my objective is to have fun, I’ve already won.
Innovation follows imitation and interpretation.
Investing is a relationship business.
We are here to ask the big questions.
Lessons (what didn’t go so well and why?)
Write first or write not, because there is no writing later.
Friendships are plants that require watering.
Training is way more fun than exercise.
Everything is urgent if you don’t have boundaries.
You can’t see depression from the inside.
Intentions (what am I carrying forward to next year?)
Track what’s important and I will improve what’s important.
Embrace the seasons of life.
I don’t need to receive love to give love.
Feeling can be more powerful than thinking.
Don’t be afraid to ask for help.
If you are considering doing a similar reflection, I would love to pay it forward. Drop your email below and I’ll send you the Annual Review Worksheets that I used to create this reflection.
1. 10/10 Recommend marrying your favorite person.
Marianna and I got married in NYC in August. I’ve been mentally committed (and ecstatic!) to spend the rest of my life with Marianna since before we got engaged. I figured we were just getting an official stamp. I expected nothing whatsoever to change. That was my official line when people asked me what it feels like to be married—same, same.
I am starting to recognize that ritual has the subtle power of cementing a partnership. I notice small but meaningful shifts in my planning and language. Her happiness and fulfillment are now our happiness and fulfillment. I thought I was giving freely before; now, I have a better sense of what that feels like. I’m maturing as a person and somehow our bond seems to grow stronger every day. I still have much to learn and am excited to see how the experience evolves.
As I grow older, it occurs to me that maximizing optionality is just a great excuse to delay deciding what you really want out of your time on this planet. Life is a big buffet of opportunities—you have to give up some things you want to get what you want most. It’s hard to achieve anything ambitious or meaningful without commitment (and burning most of the other boats with a gentle “no, thank you”) along the way.
2. When my objective is to have fun, I’ve already won.
I never thought I would say this . . . I played more live poker than online poker this year. Online poker cash games seem to be drying up. I went on an online poker sabbatical in June and have not jumped back into the online streets since.
Meanwhile, live poker games are thriving. I used to detest playing live poker due to the slow pace, the casino environment, and the energetic drain of strong personalities. I see now that it was my attitude that was the issue.
I now treat poker recreationally, as if I’ve already won. I sit down to play with the sole objective of having fun. Unsurprisingly, when I relax, I play better and enjoy the experience more. I play live-streamed games in Austin with a fun cast of characters once or twice a week. It’s cool to review the game tape afterward and see all the things I could have done better.
I’m certainly playing to win but I’m less fixated on being the best. Poker is not quite in the back seat, but it’s no longer driving the car, either. I see poker taking the role of a social catalyst in my life. Poker is now just another vehicle in which to travel, challenge myself, and connect with interesting people.
3. Innovation follows imitation and interpretation.
Teaching is a great way to discover what you don’t know. For years, I taught the performance frameworks of others, attempting to integrate the kludge of pieces I picked up in my journey.
I became too much of a problem-solver—meeting everyone where they were instead of doubling down on what I do best. I found it easy to justify an overly-holistic program as a means for accelerated learning—a dangerous trap, given my love of growth. As always, the solution is focus: more wood behind fewer arrows.
I found clarity after creating our executive group coaching program, Team Performance Training (btw, we’re offering Cohort 3 in February!). I could no longer lean on my pattern recognition in a group setting. To catalyze real transformation, I needed to design a curriculum of maximum leverage. That brought up the question: where is my point of greatest leverage?
We now anchor Team Performance Training around three pillars:
Visualize: get clarity on what you want and be specific on how to get it
Prioritize: allocate your resources of time, attention, and energy in an optimal fashion
Systemize: create organizational habits and a culture that ensures continual process improvement
When you feel stretched thin, go deeper.
4. Investing is a relationship business.
I dedicated much more time and attention to investing last year. I actively managed my equity portfolio and made lots of long-term bets in venture capital, crypto, and some weird stuff that defies categorization. It is still early but it seems like all the tuition (time, attention, mistakes) is starting to pay off.
Venture capital has always been an obsession of mine. This year I decided it was about time to enter the arena. I invested in four single-partner funds and wrote ten angel checks. Valuations are high across the board but I expect a well-constructed venture portfolio to outperform public markets in excess of the illiquidity premium.
I applied a smart beta approach to crypto by overweighting emerging protocols achieving developer network effects. There seems to be no substitute for getting your hands dirty and bumping up against reality by pressing all the buttons: bridging, staking, and farming. Currently, farming stablecoins and pegged pairs seem like the best risk-adjusted places to deploy cash. Numbers go up in a bull market which is nice. Interested to see how sustainable the returns are long-term.
It is challenging to walk the fine line between investing and gambling in such a reflexive market. Increasingly, it seems that alpha is concentrated behind walled gardens in private chats and forums. This means being deep in the streets and streams—you have to share event-driven value to access value. I want to maintain a better separation from short-term prices but being a passive HODLer feels irresponsible with how much alpha is out there. Am I foolish for trying to triumph in this zero-sum space, or foolish for doing just about everything else?
My returns on financial capital seem to be a lagging indicator of my intangible investments in social relationships. Seeds take time to sprout but bear fruit for a lifetime. The best deals I participated in this year were generously shared (and evaluated) in a small investing group I started called Investor Brain Trust. I feel incredibly grateful to call such brilliant minds and generous souls my friends. If I continue to cultivate relationships with friends of integrity and deep domain expertise, the returns will take care of themselves.
5. We are here to ask the big questions.
All personal development is a Trojan horse to contemplate the existential. There is a meta-ladder at play. Internalize that you can do whatever you want and you start to wonder—what do I really want anyway? What do I want to want? How do I decide what I should want?
I used to shy away from philosophy and spirituality out of misguided skepticism and perceived pragmatism:
Why study that which is unknowable?
If there is no objective answer, how is it actionable?
I now believe that the unanswerable questions are the most important questions to ask. Inquiry reshapes the paradigms that influence how we think, what we believe, and what we pursue in subtle but powerful ways. I am particularly interested in studying Buddhist thought these days, with meditation as a nice compliment.
The trap of materialism is turning spirituality into just another project with hopes of greater happiness or well-being. These expectations just lead to further suffering.
Can spirituality be a practice for its own sake, my path without progress? Time will tell.
1. Write first or write not, because there is no writing later.
My goal was to publish one article per month. I only published four this year. I am very proud of what I did publish but disappointed in the lack of prioritization and consistency. My writing came in bursts of activity. If I felt busy, stuck, or uninspired, I could go weeks without even opening up the document, losing all sense of momentum. Ideas have a half-life. If left alone for too long, enthusiasm and curiosity begin to decay.
Writing is an always important but never urgent activity. Writing is my forcing function for inquiry. I discover my beliefs and clarify my thinking through writing. When I’m deep in a piece, the world becomes rich with metaphor, every interaction and observation transcendent.
Yet there is always something less ambiguous and more immediately rewarding to do. Rationally, I know what a critical role writing plays for me. Emotionally, perhaps the timing isn’t right to wring a few drops out of this dry rag I call a brain. The most dangerous distractions are those that can be easily justified in hindsight.
Writing is my primary interface for open-sourcing my knowledge to guide fellow travelers on the path. I want to hold this objective of clarity in mind without becoming too results-oriented. This means treating writing as a practice, free from expectations.
If the desired outcome is to build the identity of a writer, I need to internalize the daily habit of writing. The key to rebuilding a fragile habit seems to be “make the bar so low you can’t say no.” I want to get away from writing when it is convenient and transform it into a default. My goal is to write for thirty minutes every day before using my phone or accessing the internet. I’ll also be going back to the well of what seems to work best: co-writing sessions, social accountability, and asking for feedback.
2. Friendships are plants that require watering.
This past year, I simply felt overwhelmed and stopped reaching out as much in my friendships. I pride myself on creating memorable experiences, but I fell into a pattern of social passivity. Trying to get a group of friends to commit to a plan felt like herding cats—so I stopped trying to herd.
Cognitive dissonance is a hell of a drug. When you fall off or pull back on a habit, your brain is quite adept at making up plausible excuses. Not only was I no longer trying, I felt fine about it.
Zoom fatigue is definitely a thing. Many of my friends live across or outside the country. After spending my day talking with my clients and team on Zoom, I was less motivated to catch up in front of a screen. (Is it just me or is this whole metaverse thing a bunch of bullshit?) I was always reinvigorated after seeing friends, even virtually, but somehow “let’s do this again soon” became “wow, has it really been six months?”.
Marianna and I went fully nomadic in 2021 with six different home bases. In hindsight, this lack of stability made the year more difficult as well. I realized how much Marianna and I thrive in a supportive local community and how much we miss our NYC/Brooklyn family from the last several years.
When I played online poker most evenings, a lack of definitive plans was a win-win: have fun or print money, all good either way. Now that poker has taken a back seat, the gap is more obvious.
Many of my favorite moments involved large unstructured pockets of time away from alarm clocks. Every retreat, unconference, and group weekend trip was a big win. I now have so much gratitude and admiration for everyone who brought these events to life. For me, pre-commitment seems to be the most effective way to create these unstructured pockets. I started blocking time every Friday afternoon for “planting flags.” If I make a group reservation or buy tickets, that acts as a forcing function for the touchpoints necessary to make invites.
I do think that social friction has diminished in the last few months as we reemerge from our cocoons, and I feel better knowing that I’m far from alone here.
Think about the reframe: the friends you want to see feel too overwhelmed or unmotivated to make plans and are secretly praying you will make the first move. It is uncanny how often I text something lame like “hey—thinking of you” and the friend says they have been meaning to reach out. Consciousness creates reality; we are all just floating in the quantum foam.
3. Training is way more fun than exercise.
I put exercise on “maintenance mode.” We created a makeshift home gym while traveling or did bodyweight exercises with whatever props we had on hand, following along with our personal trainer or yoga instructor via Zoom. Don’t get me wrong—it was way better than nothing. But exercise began to feel like a chore. I was just going through the motions, “checking the box” whenever my calendar told me it was time.
This sense of obligation bled over into my discipline in other areas. Stop pushing yourself and your capacity diminishes. The initial flinch wins out more often. Your sense of exertion is caused by a lack of exertion.
I used to be skeptical of using competition to generate motivation to exercise. Most people who sign up for a marathon to start running drop the habit after the race. But I overlooked an important detail: structured progression feels meaningful. I competed in my first Spartan Race with friends and the experience left a deep impression. Training is way more fun than unstructured exercise, especially when you have friends and training partners to push you.
A question I keep coming back to: what are you progressing towards? There is no growth without goals.
Having target weights on your lifts is essential, even though the target itself doesn’t matter. I’m signing up for tennis/pickle-ball leagues, mid-distance bike races, and obstacle-course races around Austin for the spring. If you want to join or you have other ideas for a friendly competition to train for, let’s squad up.
4. Everything is urgent if you don’t have boundaries.
Our collective attention spans seemed to take a huge hit this year. I worry that my ability to sit quietly and think deeply has deteriorated. I struggled at times to maintain a balance between doing “deep work” and taking advantage of finite opportunities in volatile 24/7 markets. The excuse of seeking the alpha (I perceive to be) just lying on the ground conveniently seems to appear the minute I encounter an unpleasant or ambiguous task.
All around us, the world is shouting at us to move faster. Most urgency is actually a distraction. Due to opportunity cost, suboptimal actions are a waste of time, attention, and energy. Thus, many things that look productive to an outside observer are actually counterproductive.
Checking my phone so often and pressing F5 on prices has to be detrimental for both my mental health and my bottom line. Hang out with traders staring at one-minute charts and your timescales will shrink as well. Whether we’re in a bull, bear, or crab market, there has to be a better way to live.
Say it with me now: “I am not behind.” I want my time preference to approach infinite, not zero.
All behavior is contextual. If I change my environmental container, my behavioral patterns will follow. I know a few of you want me to get tactical, here’s your time to shine.
I’m experimenting with four interventions to reduce phone use and restore sanity:
Phone outside of the office during the day. Phone stays on airplane mode until lunch.
Reduce phone use cases. Use an analog alarm clock and a laptop for 2FA. Use a scrubbed iPad as a phone replacement if necessary.
Remove Twitter/Telegram from phone, use Freedom to set schedule/time limits on laptop.
Move all portfolio tracking from phone to laptop. Delete apps, block coin-tracking sites in the browser. Set up price alerts (no alert, no need to check).
5. You can’t see depression from the inside.
I’ll just come out and say it—I experienced depression this past year. The exact timing is difficult to pin down, but there were multiple multi-week stretches where I felt depressed. I doubt most people noticed. I certainly didn’t notice. Depression is only obvious in hindsight. It is important to document your warning lights, the canaries in your cognitive coal mine to alert you when you are feeling off.
Everyone’s experience with depression is different. I want to share my own experience in case there is someone reading who can benefit, and so I can maximize my chances of intervening earlier next time.
While I was depressed, my world was painted in shades of gray. Nothing excited me. Climbing the greasy pole of achievement no longer seemed worth the effort. My mind generated plausible explanations, e.g., “It’s all just status games and empty prestige anyway,” or “I’ve worked so hard for so long, maybe I just need to chill out.” This is a good tip-off: not being motivated by something is normal, not being motivated by anything is depression.
I was overcome by a general sense of unease. From the outside, I was living the dream, a life that would have made eight-year-old Chris truly proud. Something was always missing but I could never put my finger on what that thing was.
A reliable warning light is any avoidant behavior, seeing things as threats or obligations instead of opportunities. The key for me seems to be to take the smallest possible action to flip myself from avoidance to approach.
How did I snap out of my depression? When I could no longer deny it. At one point, I started having difficulty remembering words and finishing sentences. I became concerned about cognitive deterioration and started reading journal articles and making lists of brain specialists (normal, I know). I spoke with my physician and he mentioned it may just be a sign of fatigue and depression. It immediately clicked. “Holy shit, I’m depressed.”
I remember just how incredibly relieved I was to discover that I was depressed. It is a strange sensation to play back the tape of depression with a massive grin plastered on your face. I was speaking normally again within days.
People don’t talk about subjective experience enough in this business. It’s all hustle porn and delayed gratification. I don’t care how successful capitalistic culture tells you that you are—if you are unhappy, unfulfilled, or having a negative influence on those you love, you aren’t succeeding.
So I’ll say it. Your subjective experience—it matters. If you don’t feel great, stop putting on an eyeless smile for your partner or team and talk to them about it. If you don’t love what you’re doing with your life—while acknowledging the necessities of supporting your family, being responsible, etc., etc.—then do something else.
There are a million paths to the top of the mountain. No dead ends, just scenic detours.
1. Track what’s important and I will improve what’s important.
All improvement is seeded with awareness. I see it over and over again. Anything you track (habits, diet, exercise, sleep, relationships, investments, business metrics) improves over time just by tracking it. I give the advice to track all the time, but this year, I rarely put it into practice.
It brings up the obvious question—if it works so well, why didn’t you do it? Great question.
After seven years of minimal architectural changes, I took my habits and routines for granted, even when they became inconsistent. I fell off my monthly review habit which turned out to be a forcing function for my tracking—never underestimate the power of needing to fill in an empty cell on a spreadsheet. I also got stuck in the frame of over-optimization, not wanting to start tracking until I had figured out “how to do it right.” A great recipe for never starting.
This is the year of tracking everything important to me. This tracking will not be part of some over-elaborate, color-coded, automated system. My tracking will be ultra-mediocre but directionally correct. The perfect lightweight system emerges after many iterations of stripping away everything but the most essential details.
2. Embrace the seasons of life.
I now understand how important it is to have others in mind. I am ready to put my desire for eternal youth aside and become an elder figure for students. I feel like I’ve lived several lifetimes worth of experiences, and now have lessons and teachings to share with younger people in leadership and mentorship roles.
Younger people? I hear it now, “If you feel old now . . . .” I know, I’m only thirty-five, I still have much to learn. But that learning is no longer central to the narrative and neither is the sense of scarcity or entitlement that comes along with that centrality.
For years, I was obsessed with personal development—forever chasing the horizon of achieving my full potential. I am grateful for that work and how far it has taken me. But, at this point, further optimization now feels myopically self-obsessed and a bit hollow. With maturity, I realize that I often treated others as supporting characters in my hero’s journey instead of kindred souls, travelers on the same path.
In order to bring this transition into fruition, I need to completely shift my identity and disassemble my notions of time well spent. Personal impact does not scale but it sure feels good.
3. I don’t need to receive love to give love.
How do I support these kindred souls? My first step is always to open-source my knowledge like I am attempting here. But this writing is still on my terms, the perceived consciously aware of the perceivers. I need to escape my comfort zone and desperate grasps to maintain control.
I want to give with a sense of abundance and no expectation of return. I want to give in the way that is most needed rather than in the way I’d prefer it to be. This all begins and ends with love.
It’s hard to underestimate the power of reciprocity: we reflect back what we receive from others. When I am with someone who radiates love and non-judgmental presence, my higher self comes to the surface. I would like this state to be my default and a freely-given gift to anyone I interact with.
Opportunities to serve are all around us. But these opportunities have a knack for presenting themselves at inconvenient times and in inconvenient places. So we (willfully or not) overlook them. Our ego pulls the veil right over our eyes while whispering comforting reassurances in our ears. We see a momentary glimpse of light but flinch away, retreating back to the shadows on our cave walls.
I’ll still flinch away most of the time. But I hope to choose love more often.
4. Feeling can be more powerful than thinking.
After identifying as “intelligent” for three decades, my rationality is overdeveloped at the expense of my instincts. This is a tough pill to swallow: all my compulsive consumption is hampering me more than it’s helping me. As Marianna eloquently puts it, “the more rational you are, the easier it is to rationalize whatever you’re doing.”
What is the key to right action? Silence. Stillness. The answers are already there. In order to accelerate, we must first slow down and listen.
This year I intend to cultivate my intuition by getting in tune with my body and listening to what it is telling me. The more I trust my intuition, the more I will be able to trust my intuition.
How does this work? My intuition compounds with internalized experience, creating a positive feedback loop. Trusting intuition generates more environmental feedback, leading to a well-calibrated intuition. Evidence that trusting intuition works leads to moving faster with more conviction, thus things working out more often.
For now, this means putting down the popcorn and hopping in the arena. Practically speaking, there is no longer room for hesitation. I see a potential alliance member across the room and I walk over and introduce myself without first generating a few options of clever opening lines. Failures of commission rather than omission. No egg on my face means I’m doing it wrong.
5. Don’t be afraid to ask for help.
We all have our irrational but deep-rooted fears. One of my biggest fears is appearing weak or incapable in front of people I respect. I’ve jumped through many rings of fire under the gun of a self-created deadline, struggling to maintain a perception of competence in the eyes of others.
Asking for help? That's for the weak. I got this, I have it all figured out. I don’t need your shortcuts. I actually prefer standing on this side of the velvet rope, thank you very much.
“Do one thing every day that scares you.” I know I could probably double my business and my bankroll by sending just one text per day. Yet the very thought terrifies me. It’s absurd. And, in recognition of the ridiculously talented and supportive friends I have somehow managed to surround myself with, it is downright stupid.
I called these intentions for a reason. Despite my client-facing admonitions to give yourself no wiggle room, I crouch behind this ambiguous notion of trying.
The truth is, I need your help. Despite the 186 “I’s” so far in this review, “I” can’t achieve any of these things alone. Perhaps this is why I chose to end here, even as I reconsider whether to hit publish. To plant the seeds of me coming to you as a friend and asking you for your help, just as I hope you will not hesitate to ask me.
Because if you read this, and I don’t ask you for your help, I will know that you know. Public accountability is the sledgehammer of productivity—it’s messy but it sure gets the job done.
Thanks for reading. Eternal gratitude for those who have made this all possible. Thank you for caring, believing, holding me accountable, and being an inspiration.
Best wishes for the year ahead. I hope that you find whatever it is that you’re looking for.
If you are interested in conducting your own annual reflection, you can download my Annual Review Worksheets for free. I’m also offering a Mid-Year Review and reVision Workshop in June if you would like to be guided through the process.