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Some things I learned and was wrong about in 2021

It’s my birthday! Someone asked me to write a letter to myself about the things I learned this year and in doing so, I realized just how many things I’d been wrong about. I like that feeling :) This is that list — sharing in case it sheds some light on my thinking or offers solace to others navigating similar waters.

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You can make yourself interested in anything.

• As long as you’re curious, everything is interesting if you dig deep enough

• I’ve historically been very wrong about what I wanted to do: I thought I wanted to be a cinematographer, a product designer, a writer, a software founder, etc. I clung to these titles as my identity and was opposed to other paths for stupid, superficial reasons, claiming “lack of interest” and massively limiting myself (e.g. I’d have laughed and made a face at you 4 years ago if you’d have told me I’d find b2b saas fascinating in the future)

My path isn’t going to look like everyone else’s but that doesn’t mean it’s interesting.

• Trying your hand at lots of different career games is the best way to avoid “playing the associate game” in any given industry while growing your ambitions

• You can’t actually know whether a career path is right for you until you try it— taste-testing > advice because until you try, your heart will always second-guess you

• I prefer operating in the extremes — either being pushed way out of my comfort zone or occupying spaces where I can be entirely unfiltered. Sitting somewhere in the middle means you can never fully relax but aren’t totally sure why — this has a dampening effect on developing your intuition

All my spikey bits that made my circular self hard to fit through a square-shaped hole have become significant advantages once I managed to squeeze myself through.

• What I mean: I was an art kid. I storytold myself into being a tech kid in order to weasel my way into this industry. Now that I’m in, my art background has become my competitive advantage: it allows me to see abstract qualities in people that others might miss and make things that feel compelling to people

• General rule of thumb: if you’re sheepish about some quality of yourself that is perceived as irregular in your environment, it’s probably possible (and potentially powerful) to harness it as a competitive advantage

I care a lot about making the world more beautiful and soaking in its beauty.

• Pragmatic solutions are almost always only as successful as their packaging

• I find illegible, illusive, and enigmatic things and people the most beautiful. In my mind, the magic of them is such: there exists a space between the truth of the thing and your understanding of it. This space gets filled with stories you tell yourself about said thing that are spun entirely out of your own memories

Getting up on the public stage (e.g. the internet/social media) is only worth it if you have a goal in mind.

• It’s important to build durable competence in something before you start performing the act of self. Performing of any kind freezes your development — choose your roles wisely and know where you want them to take you

Failure exposure therapy is the main thing most people need to do big things.

The speed by which you do one thing is the speed by which you do everything.

• Collecting data points is almost always more globally productive and personal pace-increasing than introspection

The easiest way to forgive or accept someone is to see them as a tragic figure.

People with taste will always have a job, their title just might change.

1. Similarly, creativity isn’t some elusive thing — it’s just dot-connecting old ideas in a new, interesting, and/or unconventional way

Software will make almost all of us generalists, with a select few extremely spikey specialists (basically artists).

Bringing kids into this world isn’t selfish, actually.

I am extremely lucky to be in spaces with some of the most brilliant, optimistic, and high-agency people alive today.

• I have designed my career going forward to make the most of this fact

• Talent is real, intelligence is real, not everything is nurture. I was wrong about this

• If you feel hopelessly less smart than the people around you (a good sign!), find ways to focus on how you can contribute as opposed to constantly falling short in comparison

Some qualities that make someone exceptional in my eyes:

• Curiosity

• Consistency/obsession

• Contrarianism (especially about people, e.g. extending reputational lines of credit to unknown/disliked people! I think a lot of people are currently overindexing contrarianism towards ideas)

• Understanding the question behind the question

• Having a heart-led reason why you’re doing a thing (spite is fine too, this doesn't have to be altruistic — any personal-experience-built emotional investment will do)

• Ability to make people feel good around you

• Writing well, quickly

• Fast processing speed and ability to update beliefs/identity quickly

• Having an early rock bottom experience and persevering (more of a commonality than a quality)

I am often not asking the right questions and I know it. Despite that, my favorite questions to ask others right now are:

• Where were you when you had the idea for your current thing?

• What has most impacted your taste in ideas?

• Whose words echo for you?