I screwed up, big time

So, what's next?

Activation Energy

A newsletter to provoke thought, to inspire, and to catalyze action.


Getting Started…

I know it’s been a while since I’ve sent out the last edition of this newsletter. To be honest, the last few months haven’t been the best for me. I completely stopped doing the things that I enjoy. Writing this newsletter is a part of me getting back to it.

Why else am I continuing to write it?

  • This newsletter allows me to reflect on the thoughts sparked by things I’ve read.

  • It’s a great way for the people close to me to stay updated on my state of mind.

  • Standalone, each newsletter serves as a resource for people early in the process.

Recently I’ve been reading a lot on early career decision making by people I admire, see links in the lighting a match section…

While reading Paul Graham’s essay in particular, I realized the source of a lot of my angst over the past few months. I’ll get back to this later.

First, a quick recap for those who aren’t that close to me. At the end of last spring I was in a committed relationship with someone I cared deeply about, I was working close to full-time at a well regarded startup in NYC, and I had an internship offer to work in a supply chain operations role at Amazon for the summer.

At the time, I made the decision to take some time off from “checking boxes.” Leaving all those opportunities on the table, I moved to an unknown city, Seattle, to work on side projects and build a relationship with a friend I respected.

During my hiatus, I spent some time traveling across the west coast, India, and London. Had I stayed back and took a summer course, I was on track to graduate a semester early with a degree in supply chain management. Instead, I decided to take the fall semester off with plans to not return to college.

Fast forward a few months, my trip had caused a significant amount of friction in my relationship. This prompted me to come back in an attempt to fix it. Unfortunately, the damage had already been done.

Parental pressure made me re-enroll in college to finish my degree. Rightfully so, they wish the best for me and believe a college degree increases my options. However, they don’t understand why I’m not interested in finishing my degree.

While I do the bare minimum to finish school, I’ve had a lot of time to reflect.

I recount these experiences as a note to myself and to offer context to you. Writing this is definitely not easy for me, but that’s what tells me it’s important to.

Back to Graham’s essay, he notes, “Instead of working back from a goal, work forward from promising situations. This is what most successful people actually do anyway.” He defines working forward from promising situations as going ‘upwind.’

One of the reasons I don’t find an undergraduate business education valuable is because it’s not going upwind. Instead of learning first principles most business students are taught how to perform operations for jobs in the corporate world.

Graham describes studying math as being upwind, it opens more doors than it closes.

“Suppose you're a college freshman deciding whether to major in math or economics. Well, math will give you more options: you can go into almost any field from math. If you major in math it will be easy to get into grad school in economics, but if you major in economics it will be hard to get into grad school in math.”

I believe most business majors are limiting. The unfortunate part about it is that once you’ve completed enough coursework you’re locked in and can’t switch to something more upstream. Especially if you don’t have the financial resources to do so.

I mention the rest of the reasons for my distaste of school in this tweet storm…

The source of a lot of my angst over the past few months is not being ‘upwind.’

With that said, where does that leave me now?

Above all, grateful for all the opportunities I’ve had.

I like to spend my time reading, writing, learning design, meeting new people, and launching experiments. If you have any ideas for projects, let me know!


Providing a Catalyst

Every week I’ll share key insights from a conversation I had learned a lot from in a series called, Providing a Catalyst.

I spent last Friday night with Mike Policastro. He’s one of the best criminal defense attorneys in the state of New Jersey, and a close friend of mine. Before becoming a lawyer at the age of 42, he launched a 8 franchises of Bagel Bazaar.

Our conversation centered around discovery and how to find one’s passion.

A few points stood out:

  • When you’re young, invest in as many experiences as possible.

  • Don’t listen to anyone or me, learn from your own experiences. Take into account what others have to say but in the end it’s your decision.

  • Once you determine the direction you want to go in, work as hard as you can.

  • Find and work with people you enjoy being around.

  • Stay as lean as possible for as long as possible.

  • Avoid debt, as much as you can.


Lighting a Match

I hope something here inspires you to do something or learn something new.

Guide To Choosing Your First Job In Tech - Naval Ravikant

If you're just coming out of school, Naval guides, prioritize your career trajectory above all else and choose an environment where you can both build a strong network and rise through the ranks quickly. Evaluating whether a job offers both requires a framework, and Naval's is extremely simple—and effective.

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If you had to sum up Naval's philosophy in one quote (or perhaps, more appropriately, one Tweet), his advice for finding your first job in tech would come down to a single concept:

“All returns in life, including in relationships, are from compound interest.”

You want to rise, early in your career, to a senior position because that position will accrue more compound interest over the 30+ years of your life than if you take your time getting there.

“Some of the most successful people that I've seen in Silicon Valley had breakouts very early in their careers,” Naval says. 

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What You’ll Wish You’d Known - Paul Graham

In practice, "stay upwind" reduces to "work on hard problems." And you can start today. I wish I'd grasped that in high school.

Most people like to be good at what they do. In the so-called real world this need is a powerful force. But high school students rarely benefit from it, because they're given a fake thing to do. When I was in high school, I let myself believe that my job was to be a high school student. And so I let my need to be good at what I did be satisfied by merely doing well in school.

If you'd asked me in high school what the difference was between high school kids and adults, I'd have said it was that adults had to earn a living. Wrong. It's that adults take responsibility for themselves. Making a living is only a small part of it. Far more important is to take intellectual responsibility for oneself.

If I had to go through high school again, I'd treat it like a day job. I don't mean that I'd slack in school. Working at something as a day job doesn't mean doing it badly. It means not being defined by it. I mean I wouldn't think of myself as a high school student, just as a musician with a day job as a waiter doesn't think of himself as a waiter. [3] And when I wasn't working at my day job I'd start trying to do real work.

When I ask people what they regret most about high school, they nearly all say the same thing: that they wasted so much time. If you're wondering what you're doing now that you'll regret most later, that's probably it. [4]

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Other interesting links…


Thank you for reading this edition of Activation Energy.

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