I am rich and have no idea what to do with my life

Life has been a haze this last year. After selling my company, I find myself in the totally un-relatable position of never having to work again. Everything feels like a side quest, but not in an inspiring way. I don’t have the same base desires driving me to make money or gain status. I have infinite freedom, yet I don’t know what to do with it, and, honestly, I’m not the most optimistic about life.

I know. This is a completely zeroth-world position to be in. The point of this post isn’t to brag or gain sympathy. To be honest, I don’t exactly know what the point of this post is. I tried to manufacture one, but I just felt like a phony. Then I recognized the irony of creating purpose out of a blog post when I don’t currently have much conviction or purpose in life.

So I’ll just go ahead and explain my current situation for my own selfish purposes. To push myself to be completely (and awkwardly) vulnerable to a blob of nameless strangers over the internet. No expectations of what comes out of it.

Going to the redwoods and giving up $60m

Last March I had no idea what to do with my life. I knew that staying at the acquiring company was not it for me for the big company reasons you might suspect (lots of politics, things moved slowly, NPC coworkers, etc.), but I found it very hard to give up a $60m pay package. I had already made more money than I knew what to do with, but your mind does funny things when you start to consider numbers like this.

So I decided to go to the redwoods and figure it out.

Within 5 minutes of my first hike, the trees smiled at me and whispered their simple wisdom.

What is the point of money if it not for freedom?

What is your most scarce resource if not time?

I would leave to do something. Anything. To be alive again. I had no idea. But I was hell bent on making sure everyone knew I had it all figured out. Out of ego. Out of fear of wading into the unknown. When you work on something that consumes your life for a decade, it’s hard to let go of the certainty and purpose you’ve grown accustomed to.

Robotics, or my cringe “trying to be Elon” phase

The immediate 2 weeks after leaving an intense 10-year journey, I did what any healthy person does and met with over 70 investors and founders in robotics. I had been learning about robotics for quite some time and was positive I wanted to throw myself into giving computers arms and legs. I had come up with all the tag lines to delude myself into thinking this was my “life’s calling”. Everything had been “leading to this exact point”.

“The world is going through a major labor shortage!”

“We must stay competitive against China!”

“The market for highly repetitive labor is multiple trillions of dollars.”

At the end of the 2 weeks, I left feeling deflated and foolish. I didn’t want to start a robotics company. The only thing that seemed interesting to me was humanoids. It started to dawn on me that what I actually wanted was to look like Elon, and that is incredibly cringe. It hurts to even type this out.

Breaking up with my girlfriend and realizing I’m very insecure

After deciding to not start a robotics company, I found myself rudderless. No sense of direction. I traveled to many beautiful places with my loving and supportive (ex) girlfriend. This 6 month stretch could be several essays on its own, but the outcome of this period is that nothing seemed right.

We started getting into regular arguments, and I knew it wasn’t on her. It was me. I was starting to come to terms with all the mounting insecurities I had stuffed down over the past several years. I didn’t feel like I could work on them with her. So I broke things off after almost 2 years of unconditional love. It was extremely painful, but it was the right call. I needed to fully face myself.

I have only started to realize that, when Loom was in its early innings, I felt very secure with my position in life, and lots of this stemmed from an extreme gratitude for the journey I was on. I was happy with everything as it was. The growth trajectory of the company was more than I could ever dream for. I was happy. I felt secure. It could all turn to shit the next day, and that would be ok.

Then, as the company continued to skyrocket to new heights, I started to have growing expectations for myself, and others started to have growing expectations of me. When we went through our first round of layoffs, this company my ego was hitched to had suffered a massive blow, so I lost myself. This whole chapter of Loom has created a complex web of internalized insecurities I must now work hard to disentangle and free myself from.

(If my ex is reading this. Thank you for everything. I am sorry I couldn’t be what you needed me to be.)

Climbing mountains in the Himalayas, remembering to do hard things

After breaking up with my girlfriend, I did what any healthy person would do and decided to externalize my emotions by climbing a 6800m peak in the Himalayas with absolutely no mountaineering experience or training. In the earliest stages of trekking into the valley, before the altitude sickness, cold, and chronic bronchitis started to settle in, this seemed like the best idea in the world. It wasn’t until every person I met along the way asked how long I had been training for, that it started to settle in how insane what I was doing was.

Needless to say, there were some rough patches. I got very hypoxic on one of my summits and had to repel down cliff faces while tripping out of my mind. In the end, I pushed through, completed both my planned summits, and got reacquainted with how important doing hard things is to me. It is the heart beat of my life, and I don’t 100% understand why, but it probably has something to do with me having not the best childhood.

When I got back home and regaled my friends with my mountain stories, one of my friends joked that I should work for Elon and Vivek at DOGE and help America get off its current crash to defaulting on its own debt. So I reached out to some people and got in. After 8 calls with people who all talked fast and sounded very autistic smart, I was added to a number of Signal groups and immediately put to work.

Working for DOGE for 4 weeks, remembering the power of urgency

Within 2 minutes of talking to the final interviewer for DOGE, he asked me if I wanted to join. I said “yes”. Then he said “cool” and I was in multiple Signal groups. I was immediately acquainted with the software, HR, and legal teams and went from 0 to 100 taking meetings and getting shit done. This was the day before Thanksgiving.

The next 4 weeks of my life consisted of 100s of calls recruiting the smartest people I’ve ever talked to, working on various projects I’m definitely not able to talk about, and learning how completely dysfunctional the government was. It was a blast.

I learned about the power of urgency and having an undeniable mission. Not by reading it somewhere. By experiencing it. I came to realize how laughable my robotics stint had been in comparison. And I started to realize that, although the mission of DOGE is extremely important, it wasn’t the most important thing I needed to focus on with urgency for myself. I needed to get back to ambiguity, focus on my insecurities, and be ok with that for a while. DOGE wasn’t going to fix that.

So, after 4 intense and intoxicating weeks, I called off my plans to move to DC and embark on a journey to save our government with some of the smartest people I’ve ever met. And I booked a 1-way ticket to Hawaii.

Studying physics in the jungle, focusing on my insecurities

So now I’m in Hawaii. I’m learning physics. Why? The reason I tell myself is to build up my first principles foundation so I can start a company that manufactures real world things. It seems plausible, but I’m learning to just accept that I am happy learning physics. That’s the goal in and of itself. If it leads to nothing, that’s ok. If this means I’ll never do something as spectacular as Loom, so be it. It’s been too long since I’ve been completely raw and real with myself, so I’m applying a healthy dose of humility to everything I say and do. It’s the only thing that feels authentic.

However, there are some questions left unanswered.

Why did I need to do the absolute most to reach this point?

Why couldn’t I just leave Loom and say “I don’t know what I want to do next”?

Why do I feel the need to only be on a journey if it’s grand?

What is wrong with being insignificant?

Why is letting people down so hard?

I don’t know. But I’m going to find out.