Baby Steps

“No idea or behavior shift has ever spread more quickly or completely in the history of the planet. In seven weeks, the life of every single person on Earth changed.”

According to Seth Godin, we’ve officially entered Generation C.

As I reflect on the past month and the weeks of shelter in place to come, I’m shocked at the state of things. I’m humbled by helplessness. Saddened by loss. And afraid of a dystopian future.

I’m also overcome with gratitude. We’re lucky to live in the age of the Internet. That COVID-19 isn’t more deadly. That the little grocery store across the street hasn’t closed, and everyone is doing the best they can.

It is a great joy and privilege that I and the vast majority of my family and friends and community are safe and sound. I hope with all my heart that this continues. And I’m sending you warm thoughts and prayers.

One year ago…

I lived in St. Louis, Missouri as the final stop on a scattered vagabond post-college adventure.

I taught chess classes at half a dozen schools for $20/hour, took a few shifts at a local Mathnasium earning $12/hour, and drove Lyft / Uber averaging that or less.

It wasn’t bad. I had plentiful free time and enjoyed working with the kids. I learned about myself and grew enormously from the experience, ultimately culminating in my becoming an adult and understanding what that means.

But I could have easily stayed in that same situation forever—delaying my life journey through inaction or going somewhere else to hide from the challenge of growth.

Instead, I chose to glance at my fear more often and establish a new baseline normal.

I previously wrote about this process in more detail. Basically, it involved confronting and re-shaping some beliefs:

  • I was not ready to found my own company.
  • I was not more talented than peers, just different (and probably lazier).
  • There is little benefit and large potential harm in cultivating a personal vacuum to live in.
  • Commitment is difficult and following through is worthwhile.
  • The hard work of shipping is what ultimately leads to growth.

I’m so, so fortunate I was able to move quickly and arrive where I’m at now. Sure my studio in SF has no laundry, half the size, and triple the rent…

But my earnings have gone up proportionally, I can work remotely without any issues, and I’m loving and making the most of every day.

How do people evolve?

According to Mary Gates in the recent documentary, Inside Bill’s Brain, “Ultimately, it’s not what you get, or even what you give. It’s what you become.”

In other words, you’ve grown to be the person you were yesterday, and you will continue on to become who you are tomorrow.

Your actions matter.

Large and small, they shape your trajectory and fold into your identity. So you should act with responsibility and good intent. Keeping an eye on your values and an eye on the long-term horizon.

A lot of brilliant self-help boils down to this profoundly simple and impactful message. For instance: Victor Frankl, Marcus Aurelius, Jordan Peterson, Dr. Meg Jay, Tim Ferriss.

Good stories also illustrate cause and effect. How a character’s thoughts and actions lead to struggle and growth. The hero’s journey is universal because we empathize.

We crave self-transformation in forward motion, to identify with our superpowers, to experience the before and cathartic clarity of after.

Years ago, I learned with fascination that Oprah “not only grew up poor but also overcame significant obstacles” and was given a very high Forbes self-made score. What an incredible woman and life trajectory and story.

I’m unlikely to amass enough wealth to be noticed by Forbes, but I’ll give myself a self-made score around 7-9. That’s not to say I come anywhere close to Oprah’s 10. (The scale seems closer to logarithmic than linear.) I have had a ton of advantages, piled high both before and after birth, such that it’s doubtful I recognize all of them.

Even with a strong tailwind, however, it hasn’t been easy for me to get where I am today. Things have seemed relatively easy for a few years, but that’s only because I endured the bulk of my personal hero’s journey from ages 10-16.

Because of my experiences confronting and overcoming adversity, I am optimistically biased towards nurture over nature. I enjoy self-help and pondering these things I’m writing about.

Inspiring Friends

I’ve met so many incredible people from all kinds of backgrounds with all kinds of accomplishments.

Here are some of the extraordinary communities I’m grateful and lucky and proud to be part of, in no particular order: Presidential Scholars, Interact Fellowship, alumni of MIT, alumni of Scale AI, current employees of ReadMe, alumni of Pillar, alumni of the Nanites 4092, alumni of Tech Chess, alumni of Delta V, alumni of the Dryden Drop Tower Lab, alumni of Lean On Me.

The funny thing is, after meeting some truly impressive résumés, I’ve come to realize that most folks are pretty inspiring if you just give them a chance.

However, there are certain friends and acquaintances who seem to belong to one particularly interesting class of humans—those who don’t seem to need or want the self-help genre.

It’s interesting because these people are equally thoughtful and balanced and wonderful in all the same ways as folks whom I see as having successfully run the self-help gauntlet.

The bootstrappers are who they are as a result of deep literature-fueled introspection. They’ve performed lots of emotional work and identity labor. They’ve engineered themselves. I’m certainly in this camp, or at least on my way.

Yet somehow, these other people naturally converge on being awesome, seemingly without any effort.

They are often quite thoughtful and introspective people, but thinking about themselves too deeply makes them gag. They are very authentic; they just want to live their lives.

These creatures are rare and beautiful and marvelous. They seem to emanate deep inner peace and happiness. I’m beyond pleased that they exist, and that a handful of them are friends.

No, you probably don’t know who you are.

Climbing Hills

Let’s view life as a series of hills and Dips. This might be a good way to explain how people evolve through their actions.

Some folks climb higher and higher hills. Some choose a steady-state altitude. There’s no right or wrong.

But it’s unfortunate if you’re not currently living the life you want to lead.

This could mean lots of things—that you’re climbing the wrong hill, that it’s the right hill but the wrong time, or maybe that you just don’t like the feeling of hill-climbing.

Living the good life boils down to two components: living the life, and feeling good about it.

The first component is partially outside your control. Living life each day is all about where you start and the opportunities that present themselves.

You have to do what you have to do. There are immediate practical challenges—unavoidable hills.

But, all things equal, we often have the opportunity to take productive action. To move towards the opportunities—hills you want to climb.

I believe the second component, feeling good about the current hill and life in general, is almost entirely within your control: “Success is 95% luck. Happiness is 95% attitude. Which is more likely to come first?” (from college advice).

There’s a nuance here. Just deciding to be happy is only a small portion of how you can control your attitude. Much of it comes from doing things that you’re proud of in a lasting way.

These can be small daily rituals and habits, or big complex multi-year projects. The key is to believe in better and bet on yourself and ship often and crush the inner competition and dance with the fear.

The most important thing is to just climb lots of hills. To break down problems and ship as often as possible. Then, if you’re really good, you’ll promote yourself to bigger and better hills over time. Like Warren and Elon.

And it always helps to practice gratitude, especially when feeling feely feels.


Baby-stepping up and down hills is a useful framing for life, business…almost anything.

We all set goals and make to-do lists. Each of these hills is a problem to solve. The more hills, the more problem-solving.

Although problems can take many forms, the skill of shipping solultions is key to achieving success—choosing the right hills and climbing them quickly, while bringing others along for the ride.

The more hills one climbs, the more experience under one’s belt, the more one realizes what’s in her self-control and what isn’t. The more one lives harmoniously.

Motivation is a flywheel turned by habit. Feeling good about our actions provides feedback that enables confidence, ultimately leading to competence, which engenders feelings of control and empowerment…

…hopefully this all gets poured back into doing things that make us even happier to wake up tomorrow.

It’s well-known how Roger Bannister breaking the 4-minute mile led to a bunch of other people doing the same shortly thereafter. What if we all behaved as if we knew our impossible hill was actually surmountable?

After perusing much self-help and reading up on good judgment and goal-setting, it’s amusing how frequently I turn around and addictively play lots of online chess and poker.

More often than not, I’m not very proud of climbing these self-indulgent little hills. They’re all too possible. They don’t move me in the direction of becoming my authentic self. They take me in the opposite direction, away from the awesomeness of friends I’m inspired by.

To reduce thrashing (listen in around hour 2.5) and focus on climbing the right hills, I’ve been adhering to principles from Rework and my friend Brett

Dump the backlogs and to-do wishlists into the trash. Choose one or two top-of-mind things to ship. Then ship them. Repeat.

Sometimes in order to make progress on a hill-climbing project, you’ll need to first dive into it, process things, talk to someone, think about it, read/listen/watch, and be inspired. But processing is ultimately about elimination and achieving harmony and progress.

So you want to start getting it all out as soon as possible. Moving fast and breaking things is about having bad ideas and doing dumb stuff in order to get to the diamonds.

Even if it seems like you’re making negative progress on surmounting the hill, what you’re actually doing is freeing yourself of mental clutter and doing the hard emotional labor of learning.

It’s OK to discard things when the end product is simply the experience of having climbed a hill. The enduring, impactful problems stick around. It’s not necessary to map them all out right this instant. Better to just start climbing!

I’m fortunate to have climbed disproportionately many hills for someone who is 24 years old, and I’m excited to summit many more in the future.

April 2020 is going to be one hell of a hill for us all.

An Aside on Religion

It’s your preferred source of life education.

True believers can’t help but share theirs.

So I’d like to append the following imperative to my tombstone inscription:

Read and listen to and watch and read some more Seth Godin.”

What About Bob?


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