I had to hustle when I was getting started in my career. I don't think it should be a requirement, but I never saw another path in for myself. I now consider my entry to tech as "the founders way in" tho I don't currently claim the role of Founder.

A couple years ago I tried to write a blog post about taking risks in your career, out of an instinct to share what I'd learned about tech jobs, startups, and getting the most out of a career. It made me really introspect on my path and why I had taken the risks that I had, which were pretty substantial: I quit a full-time job to work 60 hours a week without a paycheck; I slept at the office; I got hit by a car while distracted by a work dispute. While writing, I kept stalling out on the fact that I had an enormous safety cushion to rely on, and no responsibilities. It didn't feel right to try and tell people how to make decisions when I had such a relatively clear playing field.

The grind worked for me, but I very intentionally set myself aside in order to pursue startups. I told myself in my early twenties that my twenties were for work, and my thirties would be for all the things that I wasn't going to do then. All said and done, I realized that I had probably been running from parts of myself that were too scary to accept at the time.

The problem with the hustle and grind is that it pressures you to couple your identity to your work. The grind tells you that it's not enough to clock in and out, you have to be putting in extra hours to develop yourself. I both accept that as a truism (if you put more in, you should get more out) and believe that a stable career with growth opportunities should be achievable without making it your hobby and social circle, too. But I did that; I made it my job, my hobby, and my social circle. Who am I to tell people to do otherwise?

I'm sharing this, rather than keeping it as a private journal entry, out of the hopes that it might be valuable to someone in some way (and also because I compulsively introspect and am trying to be less precious about what I publish).

I joined a school of entrepreneurship project being built by some U of M students while finishing my associate's degree, because of a chance meeting while I worked a retail job. I sold a laptop to an old acquaintance who remembered that I was learning to program when we were teenagers, and he asked for my help with a project he was doing for school. I worked 10 hrs/wk for a few months, gradually increasing over time until he asked me to join full-time. By that time, I'd left retail and gotten a full-time tech support job, which I quit to go all-in on this startup.

I worked unpaid for 2 years, and even covered some company expenses. I did so learning CakePHP on the job, and following the cutting edge — CoffeeScript, Grunt (no wait; Gulp), Backbone (no wait; React) — with some background in Bash, MySQL, and PHP from my associate's and my tech support job. I owned 7% of the company, with 4 year vesting.

I was able to spend 2 years learning on the job because of a comfortable safety net: a brokerage account with over $100,000 in it. Combined with savings from my full-time job, money wasn't a problem for the foreseeable future. The flip side is, this was life insurance money from my dad dying. It feels weird to call it a privilege, because it came with such a big cost. How much money would you trade your dad for? Would you trade him for a successful career in tech? I didn't get to choose, so I made the best of it.

I consider that startup to be "college by experience", and it kicked off my career. I got my next 2 jobs through people I had previously worked with. I even got most of the money I spent covering company expenses back out, so for 2 years grind with a good squad, I felt I came out pretty okay. I still see them now and again.

It disquiets me to think that I found my way in by attaching myself to a charismatic founder who needed my skills and found me easy to work with. How many smart, driven, talented people stumble at that starting gate? To what extent was "being part of the in-group" a factor in my success? I don't like to think that it might have been a big influence.

At the time, 2012 and 13, I felt like I was in the first chapters of a startup wunderkind saga. I was 21, I had dropped out of college after almost dropping out of high school, and now here I was CTO of a startup that had a contract with a local government to do bike share service. Now we just needed to build it. It was essentially an episode of season 1 Silicon Valley: SoLoMo was definitely on a slide deck somewhere. At my next job, I watched from a YC startup office as Richard entered wearing the same sweatshirt I had on (a Trunk Club buy). It's comical how badly I fit the stereotype, minus the success.

Turns out hardware is hard, and five new grads with $150,000 doesn't cut it. We actually did get some bikes up and operational, but we spent all of our money on them and they did not last very long. When the founder and CEO fired me, I was given a check for $0.42 to buy back my shares. The rest of the company left within 2 months, and he rebooted under a new LLC a year or so later.

I took a 6-month contract job, and by the time that expired, an coworker from this startup referred me to a job at a YC startup that really kicked off my career. I went from unpaid in 2014 to a $90k offer in 2015 with an associate's degree and some experience (I took $70k and more equity — it was a bad call).

So far, at 32, my early-20s plan of switching from work to hobbies is holding up pretty okay. Just around the decade mark of my professional life, I finally pulled enough startup lottery tickets to get a payout — it's not retirement money, but I own an apartment and it have been self-employed for 2 years. I want to believe that I have enough skills in a wide enough range of domains that I can scrape together durable sources of income that make me happy. We'll see.

Now, semi-retired, I'm working on seeing if I can turn one of the places I hustled in into something sustainable, turn a portion of the effort invested into money. It's not working yet, but it feels good and lets me set my own pace. It's a different type of hustle. Build new skills and put them to use as I see fit, take the long view, invest my time. My days now are full of cafes, books, walks, and a todo list that I'm final arbiter of. It feels good, so I guess I'm a winner of the grind.