As I mentioned in a previous thread ("How to Make VP in Private Equity"), a couple years ago I said goodbye to the and decided to try my luck in the tech industry. Not as a VC associate. Not as an "entrepreneur". As a programmer. Yep, you read that right. After thinking long and hard about what it is that I actually enjoy doing on a daily basis, I concluded that programming might just be my path to vocational bliss. I'm now a few months shy of two years into this little experiment, so I thought it might be about time to give you guys an update in case there are others out there wondering what "the other road" might look like.
After almost two years in, I feel as though I'm finally starting to hit my stride. I'm working at a pretty cool spot with some awesome people, and I am thoroughly engaged and excited to be doing what I'm doing. In addition, I now have a freelance project under my belt, and have a few side projects I'm working on. Most importantly, I feel like I can see a path towards career autonomy, which is a very exciting prospect for me. Overall I feel like I'm in a decent place -- not to the point where I'm 100% certain that I made the "right" decision, but trending towards it. The next couple years will likely be pivotal in determining whether or not this experiment has been a "success." In the meantime, here are a few of my takeaways from the experience thus far:
(1) Work is certainly a lot more fun when you are "doing what you love."
I had kind of forgotten what it was like to really "lose yourself" in your work or attend a networking event and be genuinely interested in what the other person was talking about. Being actively engaged and excited about what you do casts your work in a whole new light. You pick up things more easily. You are more productive and spend less time procrastinating. You no longer have to pretend you know what you're talking about because you actually do know what you're talking about. All of a sudden, leading a company someday or becoming an industry expert seem like real, attainable possibilities.
(2) There's a reason most people choose not to do what they love.
While the actual work you do when you're "doing what you love" can be great, the overall process has a lot of significant downsides. These are things that people tend to gloss over when they tell their "quit my boring finance job to find my dream gig / start a company / travel the world," stories. Things like going from a prestigious job with comp that would make most senior executives jealous to wondering if you will even be able to get a job at all. Or going from being able to complete most of your work on autopilot to working your ass off just to be worthy of "entry level" positions that pay peanuts. And then there's the doubt. Other people will doubt you: "why would you leave private equity to do programming?" And you'll doubt yourself. I can't count how many times I asked myself "what on earth are you doing?" or seriously wondered whether the transition was really worth it. Working your ass off for an uncertain, nebulous outcome where utter failure is a very real possibility can be pretty draining at times, especially if you come from a background where your path has always been clearly marked out for you and the rewards along the way obvious.
(3) Having and developing real, hard skills is very satisfying.
Being able build stuff from scratch really is awesome. Knowing that I can go out and directly create, directly build a product, or directly sell my labor (freelance work) is freeing. Knowing that I can sit down and sort through difficult technical challenges and get to a solution is confidence inspiring.
(4) Being technically competent does not necessarily guarantee success and/or organizational influence, even in highly technical organizations.
Becoming a master of a technical craft may be deeply satisfying on an existential level, and it will likely secure a baseline level of vocational security, but it's not going to guarantee you a seat at the table with the real decision makers. In fact, most technical people (e.g. programmers) are treated like second class citizens or worse -- like children -- in many organizations, including top tech companies. The fact that most job postings at tech companies advertise "nap rooms" "nerf gun fights" and "free Vitamin Water" as key selling points exemplifies this. The last time I was incentivized with naps and free juice I think I was about 5 years old. Unfortunately, most techies are content to trade real influence and compensation for these frivolities, so it's kind of industry standard at this point, and I don't see it changing anytime soon.
(5) Moving to a lower cost of living city has some benefits but may not be worth it.
People in the large, tier-1 cities often wonder if life would be better in a smaller, cheaper, slower-paced city. I was no different in this regard, and while I loved LA, I found myself frequently complaining about the typical downsides of life in a big city: too much traffic, high cost of living, no sense of community, etc. My wife and I thought it could be time for a change, so as I mentioned previously, we picked up and moved to Boulder and then Denver, fully intending to stay there full time if the fit was right. It wasn't. A year and a half later we were back in LA, with a newfound appreciation for all things SoCal. Not to say that Colorado was bad per se, it just wasn't LA. Yes things were cheaper, but we paid a price in other ways. We now had to deal with things like snow, which is a nightmare if you have any kind of commute, and a culture that we found wasn't an ideal fit for us. Bottom line, we realized how much we had taken things for granted back in LA.
I have other takeaways from my experience, and I could probably write an essay further expounding each one I've already listed, but hopefully this gives you guys a rough idea of my experience so far. Suffice to say, it's been a pretty awesome learning experience if nothing else, and I feel I've grown a lot in the process. Time will tell if it was ultimately the right call.