Earl Lee


2022 Reflection

2022 was filled with a lot of ups and down, the most in the past few years which says a lot given those were COVID years. I’m very grateful, though, because the highs were good and the lows a good lesson and time for reflection. I want to share a couple learnings and the goals I had set for this past year as well as outline the ones I am setting for this upcoming year.

I. Life

Like most graduates coming out of a top university, I spent the better part of my early 20s putting in the hours and thinking a lot about how I could accelerate my career. Fortunately, I also found an amazing friend group in D.C. where I spent the first four years out of college. I still keep in touch with most of them to this day and remember those days very fondly.

Somewhere along the way, though, the strength of those relationships withered. This was partly a function of external factors—friends would leave D.C. for new jobs or graduate school, including myself—but a part of it was also internal. Entering my mid to late twenties, I felt compelled to leave the familiar and sought to strive for more. That led to pursuing an MBA, exploring venture capital, and, eventually, founding my own company. Along the way, I met a few close friends and greatly broadened my horizon and network.

I can’t help but feel in retrospect, though, that I could have done more to invest in relationships both old and new.

I think there were opportunities where I could have gone out of my way to spend time with friends that I didn’t take which I wish I had now, whether this is as simple as reaching out and organizing dinner or more involved like setting aside time to commit to a trip. This lack of effort grew acute during the past couple years as a function of COVID and founding my company. In the business of work it’s easy to forget to tend to other areas of your life.

There were some opportunities, like a trip to Hawaii, I did take which in the moment felt like a big commitment with uncertain outcome—would I actually enjoy the it?—but in retrospect were easily some of the best decisions I’ve made. As an introverted ambivert, I tend to dread the activation energy of doing something social but almost always am glad when I do.

Growing older, I realize these opportunities dwindle. Life commitments accumulate, we settle into our communities, and spontaneity and new friendships dwindle. In comparison, the opportunity to work never goes away.

I used have a Chrome extension that would count down the number of days until I’m 30 every time I opened a new tab. Behind that motivational, or, some would say existential, ticker, were career goals I had in mind. Now that I’m 30, I realize I should have been thinking more broadly than that. I should have thought more deeply and further into the future about what my life goals are.

This isn’t to say don’t work hard. I pride myself in putting in the work, but it does make me more conscientious about the trade-off between making time and headspace for family & friends and career. It also forces me to prioritize what really moves the needle and delegate effectively.

II. Excellence is in the Nuance

Recently, I saw a breakdown of how the Argentinian goal keeper was incredibly deliberate with his actions and behaviors from the moment it became known that there would be a penalty shoot out in the 2022 World Cup Final. Everything from testing the boundaries of how a referee will enforce the rules to throwing off opposing players with ostentatious celebrations after each block, every little detail was intentional. I completely missed it as a naive viewer.

I think about how this applies to my work, everything from designing a product to winning deals against competitors. When a situation seems simple and straightforward (just block the ball after it’s kicked), there’s probably infinite depth to dive into and stack the odds in your favor (how do I influence where the ball is kicked, and how well it is kicked?)

Another way to look at this is that when something seems like a foregone conclusion, there’s likely still room to turn the tides. The past year I worked through a few of these examples:

  • Beating a Series B company backed by Sequoia and a16z to sign a key founding hire as a Seed company with relatively less well-known investors.
  • Winning over an initially skeptical decision maker in our most important account which turned into our first paying customer.

Through these experiences I realize I can be even more open-minded and embrace a growth mindset more deeply than I have in the past. It’s difficult to see the room for improvement when you’re frantically trying to spin a number of plates ranging from product development to hiring to winning customers, but that’s often when it’s most important to dive into the non-obvious crevices of nuance to see where you can unlock markedly better outcomes than by simply staying afloat or going through the motions.

III. 2023 Goals and Themes

My goals for next year are simple:

  • Invest in my relationships

    • Move to NYC by March 2023
    • Host 1 dinner a month
    • Hang out with 1+ friend a week
  • Be open and direct about how I feel and what I think

    • Give more compliments to people, they’re free to give and valuable to receive
    • Ask the deeper and uncomfortable questions that tap into emotion and motivation
    • Front the difficult conversations because the longer you wait the lower the chances they resolve positively or the longer it takes to reach the inevitable
  • Achieve a certain ARR goal for HeadsUp
  • Gain 6 LB of lean body mass and end up comfortably around 145 LB while lean (12% BF)

    • Bulk from January through March aiming for 0.75 LB per week (or about 250 to 375 calories above maintenance so 2,450 to 2,575 calories per day)
    • Cut from April through June aiming for 1 LB per week
    • Lastly bulk again July onwards

The guiding principle for my next year is to focus on the basics and build:

  • Invest more in my relationships (friendships, family, team members)

    • Default to yes and get past the activation energy
    • Be upfront and honest as early as possible
  • Embrace the growth mindset

    • Imagine it’s day one
    • Pause, reflect, and recognize the nuance
    • Don’t overthink things, wait on others to make the first move, or wait until you’re comfortable; reps are beneficial even when they go poorly
    • But plan ahead when it’s important
  • Rest in order to grow (sleep, nutrition, letting the mind wander)
  • Reduce unnecessary things and avoid the incremental (purchases, activities)

Books I read in 2022

Recommendations followed by an asterisk.*


  • Minor Feelings, Cathy Park Hong (2020)


  • *The Captain Class, Sam Walker (2016)
  • Zero to IPO, Frederic Kerrest (2022)
  • Amp It Up, Frank Slootman (2022)


  • *The Ride of a Lifetime, Bob Iger (2019)
  • *Eleven Rings, Phil Jackson (2013)
  • Crying in H Mart, Michelle Zauner (2021)
  • eBoys, Randall Stross (2000)
  • Power Play, Tim Higgins (2021)


  • How Not To Die Alone, Logan Ury (2021)