Unemployed is Underrated

Unemployed is underrated.

At least that is what I've told myself the last 3 months. Votem died on February 15, 2019; for anyone interested in that story, I put my thoughts to paper here.

Unemployment though is awesome. I wake up to the sun. I read. The weather in Cleveland is nice enough now to run outside. I ride my motorcycle. I've never had a period in my life with so little responsibility and so much autonomy.

I realized I should have taken more vacation.

For the first two months, I spent my afternoons talking with people - I met with over 45 entrepreneurs and business leaders in Cleveland from March to May.

I was looking for reasons to stay in Cleveland. I was looking for work that excited me in the way Votem did. I was looking for something that married my interests - technology for good, financial literacy, increased individual autonomy, exponential technologies (blockchain, AI, all things Elon Musk, etc). I was looking for a startup.

I did not find what I was looking for.

But I did think a lot.

In my life, the best decisions I've made have come from doing things that confuse other people. They were not intuitive, nor conventional; they caused people to ask me "why?"

In first grade, I read Robert Frosts' "The Road Less Traveled" - it strongly resonates:

Two roads diverged in a yellow wood,

And sorry I could not travel both

And be one traveler, long I stood

And looked down one as far as I could

To where it bent in the undergrowth;

Then took the other, as just as fair,

And having perhaps the better claim,

Because it was grassy and wanted wear;

Though as for that the passing there

Had worn them really about the same,

And both that morning equally lay

In leaves no step had trodden black.

Oh, I kept the first for another day!

Yet knowing how way leads on to way,

I doubted if I should ever come back.

I shall be telling this with a sigh

Somewhere ages and ages hence:

Two roads diverged in a wood, and I—

I took the one less traveled by,

And that has made all the difference.

The decision-making heuristic follows: between options, choose the most difficult.

I've come to believe far too many people (and not just people our age) push pursuing what they want today to tomorrow without ever recognizing tomorrow when it comes or weighing the sacrifices made. It's easier to push to tomorrow; it is the societal more to do so. No one is going to question a respectable, stable, high-paying job vs. an unknown, risky, future-paying venture. It's not a novel insight - particularly within our entrepreneurial-minded bubble - but I'm doubling down on it.

Unemployment made me think about retirement. Retirement is normally the explicit marker of that coming of tomorrow - when you stop sacrificing today for tomorrow (h/t Naval Ravikant). I realize the privilege inherent in the ability to make that comparison, but in unemployment, I've just been doing things I enjoy that I would have pushed off in employment.

With that - I'm looking to "retire" - a sabbatical if you will.

If I’ve learned anything since moving to Cleveland from NYC, it’s that travel is fatal to bias and narrow-mindedness (h/t Mark Twain). I've lived in a bubble. To be humbled, you cannot stay in the same place, you have to go. You have to see new things.

Being young and stupid and making high-risk career decisions isn't stupid. It's experimentation. It's investing in learning who you are. It puts you in a high information signal environment where lots of feedback is received quickly and early. People suck at predicting the future...why would we be any better at predictions for ourselves?

People cannot introspect pre-mature career optimization. We learn who we are in practice, not in theory. Rushing to specialize a career track forces people to choose a match for a future them who they do not yet know in a world they cannot yet perceive (h/t David Epstein - Range).

I want to be old and stupid - a regret minimization framework (h/t Jeff Bezos). Time is a strictly waning resource. While Warren Buffet is a billionaire, I'd wager most of us would not trade places with an 88-year-old - our time is far more valuable.

In summary, I have no idea what I'm doing, but that is OK :)

There is no courage without risk - it is trite, but true.