Part 2: Contribution →

How to live?

I've tried a couple answers to that question. Got it right sometimes, temporarily in each case.

I'm combing through a couple of the guesses I've tested over the last couple years. Guesses about how much freedom to aim for. Guesses about what to do with time and money. Guesses about pursuing meaningful work. Guesses about how much to push myself. Guesses about when to walk away.

What have I tried? What results have I gotten? What was it like living like that along the way? What can I learn from it and take forward? What to let go that isn't serving me? Who am I?

How to live: Freedom

When I got out of college, I didn't want to get a regular job. I'm not really sure why, but I guess a couple things contributed to it.

Dad had his own business, and I like how his way of doing things let him branch out in a bunch of different directions. I learned from my time as a high-school bank teller that being an employee sucks.

Someone at a seminar I went to fed me a line that stuck with me: job stands for "just over broke" Turned out to be a pyramid scheme pitch, but the idea resonated with me.

I wanted to be able to say yes. Yes to invitations, adventures, calls for help. Yes when someone needed me or when something sounded fun.

I wanted freedom.

Having to show up regularly wouldn't be good for any of that.

Somewhere along the line, I saw an episode of Spongebob where he and his friend became entrepreneurs. Not sure how it ended, but I vaguely recall that it didn't work out for them.

An entrepreneur?

I signed up for a master's degree after my BS. The Physics Entrepreneurship Program. A move from Florida to Cleveland for grad school. A few weeks in, I was getting skeptical and cynical about it. A real entrepreneur should be able to figure this all out for himself, right? The prospect of $40k of debt didn't sit well with me either.

My visit to the registrar's office to drop out was quick and easy.

Time to crush it! I can do it all by myself! No time for the relationship I've been building for two years! Potential marriage? No! I need to work!

Public speaking with toastmasters! Programming! Books by Seth Godin and his successful friends! Cold-calling people to talk about patents they'd licensed and cashed out on! Building prototypes of my gold-ticket ideas! All while holding down a slowlane job to keep the burn rate under control.

Gold ticket idea prototype: The Dart Eraser. The eraser you blast your students with will blast me toward freedom.

But, sometimes I wondered. Is this gonna work? A visit to some friends getting their PhDs got me to pay attention to that risk-averse part of myself. They had a path to follow. What did I have?

The high ends after a few months. My resolve broken, I'm walking the streets of Cleveland at 1am. Defeated. I pass a group of people walking the other way on the narrow sidewalk. One says to her friend "did you see the look on that guy's face?"

My aunt and uncle take a little detour on their road trip to visit. They see that something's off. They offer to take me in, and I accept.

Nah, not an entrepreneur

Listless for weeks at my family's house in New Jersey, I wake up one day in a frenzy. I'd been toying with the idea of getting a job in insurance as an actuary. If it's gonna happen you need to start today.

The actuarial exams on probability and financial math are the way in. But they're only offered a few times each year. I need ten weeks to study for the first test. But it's only eight weeks away. By 1pm, I'm in the library brushing up on combinatorics.

Nine months later, I settle into my own cube at Prudential. I made it.

But... this doesn't feel right either

It was a honeymoon for a few months. They paid me a lot. The job was pretty easy. I got along with my coworkers. People complimented me on my executive presence. Life was good.

The word fraud starts showing up in my journal. In theory, I should have been moving out of trainee mode and into autonomous contribution mode. But I was afraid to ask questions when I should have, thinking that I could just figure it out later. That strategy only sort of worked.

I also started questioning our mission. I worked in long term care insurance. The product was pretty new, and LTCI people were realizing about 15 years in that everyone had priced it too low. So my job was to use data analysis to justify price increases.

I felt incompetent at doing a dirty job.


Meanwhile, money was coming in, but I wasn't that interested in spending it. All my time was spoken for anyway by the job and by more actuarial exams. No time left for spending money. Yeah, my fridge was stocked with fancy coconut waters. (It was a promise I made to myself before earning my cube.) One of my new friends asks "Matt, where's your Audi?" He was kidding, kind of. But also kind of not.

How to live: Freedom

What to do with the salary? I got curious about answering that question. Web searches eventually led me to the hot new trend: financial independence & retire early. FIRE. Oooh what's that?

Here was a hybrid approach that I could use to get what I wanted back when I dropped out of grad school. Yes, I'd have to work for a few years at a job. But I wouldn't be just over broke like pyramid scheme man from a few years ago would have me believe. No, following this plan would mean that in a few years, I'd earn get that freedom I wanted. Holding down any job for five years and staying frugal was How to Live. The reward as my favorite FIRE man put it: "anything you want, whenever you want, within reason." I was sold.

I changed jobs to get a fresh start. I moved into a cheaper place. I kept a buzzcut so I could do it myself. I rode my bike to get groceries. I rarely went out or tried to make new friends. I stopped organizing trips to the climbing gym. I saw invitations as ways to waste money on hedonism. I met the requirements at work and didn't make much noise.

I got kicked out of my craigslist sublease when my roommate took my money and didn't pay the bills. No problem -- a perfect opportunity to try vanlife* for a month to take this frugality test to the limit.
* Well, not quite a van. A Honda Element. The most toaster-like car in America.

My net worth net wealth kept creeping higher. People around me were splurging, adapting, splurging harder... But they didn't seem better off for it. The smug satisfaction of outsmarting the system kept me focused.

...For a little while anyway.

Part 2: Contribution →