My journey from Software Engineer to Entrepreneur and back again

Date: 2024-01-06 | create | business | career | entrepreneurship | startups | software-engineering |

Alt title: There and back again, a Technomancer's tale.

My Entrepreneurship Journey

Over the years I've had lots of side projects.

  • Primary school - Made school newspapers, planned a TCG game
  • High school - Started websites (and the first version of this blog!), a video-game-walkthrough YouTube channel, tried to code games, resold things online
  • College - Got into creative coding, art, and explored little tech projects
  • Professional - Continued building projects from creative coding to productivity apps to mobile games to clothing collections

Since 2016 I've worked professionally as a Software Engineer. This allowed me to learn about software in the real world, beyond the ancient practices of academia (I have a running hypothesis that academia is always 10ish years behind the industry / "real world"). On the side, I continued to build my side projects with the idea that I would eventually do this full time as part of my Endless Game (kind of like my Retirement hobby).

But I've come to the conclusion that waiting on artificial reasons to do the things you want is rarely an optimal strategy. In the best case you've robbed yourself of years of higher quality of life with that thing and in the worst you realize that the thing you want is not actually what you want and again have robbed yourself of years doing something you actually want by blindly chasing a false dream.

So in late 2022 I quit my job as a Software Engineer at Instagram to pursue entrepreneurship full time. This was a good time in my life to make this change as I was feeling bored / uninspired / stagnant at work (having been in the same / similar role for ~3 years), morale was low due to layoffs, and stocks were low / I was nearing the end of my optimal 4 year vest schedule.

Aside: The stocks then proceeded to sky rocket but timing the market is hard / impossible so I always caution people to not equate their market outcomes with their evaluation of themselves. You can only really judge yourself on the decisions you made based on the information available to you at the time, timing the market is basically never a good decision so just do index funds, and for the purposes of this story money was not the point.

I ended up joining Reddit as a Software Engineer. I felt this was a good fit because it balanced my want to explore entrepreneurship with my utter inexperience actually doing that. I felt experience at a startup would give me first-hand experience about how things actually work while giving me a safety net (via regular job / paycheck) and allowing me to leverage my strengths (working as a SWE).

But I quickly realized that this was also not the right fit for me for my current life phase. What I wanted was to experience a startup but what I got was a scale up trying to refactor itself out of a decade of technical debt using "industry enterprise best practices" (read: academic best practices) with a very corporate (hierarchical) leadership structure (Reddit was purchased by Conde Nast in 2006, while independent there seem to be some influences). This is not to rag on Reddit - I love the product and my team was full of wonderful people - but this was simply a bad personal fit for me. They were doing what they felt was right for Reddit and its goals but that structure didn't allow me to do my best work and wouldn't grow me in the areas I wanted.

So in 2023 I quit my job as a Software Engineer at Reddit.

Trying Entrepreneurship Full-time

Now this was not a very good time to be jobless as a Software Engineer. The SWE market was quite cold. Money was not free anymore - for companies big and small - cause interest rates on loans increased so hiring was down and layoffs were up.

This wasn't much of an issue for me - my goal was not to get a job but to explore entrepreneurship. Plus I'd already tried the join-a-startup-and-get-experience route and it didn't work out.

So I put in a few applications to small startups I thought were promising and tried something else in the meantime - building my own companies.

I attempted this for several months.

  • I started building several projects.
  • I launched a few small things.
  • None of those really made money / got much interest.
  • I felt I wasn't really into building things so stopped
  • I felt a bit burnt out / uninterested
  • I had a nagging feeling my efforts weren't aligned with my values

I'll caveat that I don't really know how to build companies / startups. I've still never done it "successfully" though I've taken many stabs at it. If I had to point out what likely led me to failure during this time it's probably:

  • I didn't build things people want
  • I didn't have an idea I was excited to work on
  • I didn't do enough iterations

After stopping building I was mostly idle but did manage to read / watch / consume many books, videos, and courses around solopreneurship / indiehacking. I also started participating in communities a lot more on Twitter / Reddit / Indiehackers.

Over time I built up a mental model of what it would take to be successful as a solopreneur and also what success actually looked like in this domain. Ultimately comparing the ideal / happy path of an Entrepreneur with where I wanted to go led me to decide this wasn't the path for me.

Here's what I learned:

Entrepreneurship isn't for me

This section is an excerpt from my 2023.H1 Review. I've edited it to make more sense as part of this standalone post.

What I found was that most entrepreneurial successes required lots of work over lots of years with relatively low ROI (most successes come out to ~$200k / year) and often lots of ongoing costs before breaking even. Now $200k / year is a lot of money, but perhaps less so when you consider that the company likely has costs not reflected there (employees, compute costs, etc), a long period of no income (still have to pay personal expenses and lose out on opportunity cost / time value of money), and that the chances of success are quite low.

Now I'm not bashing entrepreneurship or those who do it full-time. If anything I'm more impressed with those who have succeeded.

But what I am saying is that it's not the holy grail of careers any more than any other career is. It comes with its own rules, meta, and risks / costs for participating.

It warrants saying because I think it's too often placed on a pedestal without warning labels - along with its wall of heroes Elon, Zuck, and Levels.

For some this is the way. For me, it's not - at least not fulltime.

  • Risk - I'm a very risk averse person. I like time to be on my side. Entrepreneurship oft has a low median outcome. There are ways to fight against this (Small Bets) but the median is the median and I have better median options.
  • Work I like - I like Creation and Ownership and Autonomy. In theory Entrepreneurship allows you to do a lot of these things. But in practice you're often forced to wear many hats that maybe you don't want to - marketing, sales, customer support, etc. Now I think these are all great skills to have and things I would like to improve on over time - but prob not at the levels often required to run a full biz successfully. The running joke on solopreneurship is that you quit your job so that you're your own boss but end up trading your one boss for dozens / hundreds of demanding bosses each threatening to chargeback their $20.
  • Freedom - What is freedom? Doing what you like when you'd like to? Being able to take a full day off w no worries? I see how some entrepreneurs give themselves room to be free - to take a Wednesday off and do nothing. But I also see a large swath who constantly worry about the next thing and even when they could take off decide to pour more time into their business. I have an obsessive personality - I'm not totally sure I could stop myself from overworking / being on all the time if I'm the thing in the way of "more".

Not all of these apply to everyone and I know there are entrepreneurs who have found good balances for themselves. For me, personally, right now I don't think this is the best hand I have to play so I'm choosing something else.

Twitter - Indiehacker red pill, blue pill

So what's next?

My hypothesis is that the best hand for me is: Backend Software Engineering at a company I like with tiny projects on the side.

I came to this conclusion by rethinking a few things:

  • What's the point of Business? - At the end of the day it's to make money to support your life. Previously I was trying to make my Career (the thing I did for money) also be the impact / purpose of my life. This is unhealthy and destined to fail as incentives are not aligned. If I no longer need to get fulfillment out of my job / projects - I can focus on doing things that actually fit the way I want to work and find balance / purpose in the rest of my life. This seems like a more sustainable and attainable strategy.
  • What do I like doing? - At the end of the day I like to build systems. Systems for myself, systems of accomplishing things, systems that are interesting. Software was never really the end goal - it was / is just the best way I've found to build most systems.
  • What leads to a fulfilling life? Knowing that, what can I do in Business to promote it? I've done a lot of research into this externally and internally (via Reflection). The best resource on this I've found is 80000 Hours. They basically found that most job satisfaction comes from three things: 1) Work you're good at, 2) Work that helps others, and 3) Supportive conditions (lack of pressing negatives).

When we put these together, we basically back ourselves into the Hedgehog principle:

  • Work you can get paid for (and that has supportive conditions)
  • Work you're good at
  • Work you're interested in

Looking at this, the answer for me was pretty obvious - Software Engineering better fulfills these buckets for me than anything else I can think of.

  • Work you can get paid for (and that has supportive conditions) - Software Engineering is currently one of the highest paid professions on the planet and until recently has been considered one of the cushiest (we'll see w all the recent job market turmoil). Fulfilled.
  • Work you're good at - I'm often told I'm a bit of a narcissist and that is probably true. But I also like to think I'm very honest, especially about things that I'm bad at. Software Engineering is not one of them. I am pretty good at systems and that means I'm pretty good at building software. Fulfilled.
  • Work you're interested in - If I pick a company that has a product / impact that helps others, has problems I like solving (building systems), and solves a problem I have some direct experience with, this is fulfilled.

Thus I think Software Engineering provides a pretty good balance for me. It's not perfect but it's the best play I've found.

Entrepreneurship going forward

Fast forward several months and I'm now working as a Software Engineer at Rippling - an HR scaleup. I'm pretty happy and the work has been pretty fulfilling.

Looking back on my journey so far, there are glaring issues with my approach to entrepreneurship - both part-time and full-time. But that's hindsight - you often don't see the mistakes until after you've done them, I certainly didn't.

What I did ultimately learn is that for me it's very important "how" the work gets done, not just "what" we're doing and "why". If we do the work in a way that is not supportive / conducive to me doing my best work in a way that interests me then it won't be very fulfilling and I'll eventually quit / do something else.

The Simplest Scalable System I've found to model work / projects I will be into and fulfilled by short and long-term is really just Hedgehog:

  • Something the world wants (and will pay for)
  • Something I'm good at
  • Something I'm interested in

If it fulfills those things - I'll probably have a decent time doing the thing and be pretty good at it. If it doesn't, it's probably not the right project for me. If it's not for me, I should figure out a way to avoid it so I can instead work on something better.

Some nay-sayers will probably be like "grow up", the "real world" doesn't work that way. Sometimes you need to do things you don't enjoy. To which I'd respond to these imaginary detractors that you're probably right but there are infinite things to do and finite time / energy with which to do them so you might as well do things you enjoy.

Now this is just a hypothesis so ofc I'm experimenting with putting these learnings into practice. So far it's worked out pretty well but I've been running this experiment for less than a year and have small n data so we'll see.

Overall I've been happier / more energized with the projects I've chosen that check these boxes. Anecdotally this has led to better work on my end and I think better outcomes overall. These projects definitely aren't global maxima for impact - I could probably have way more impact focusing on different projects that max for those - but since I wouldn't actually follow through on those long-term, I think this approach more reliably maximizes for my impact over time - and my enjoyment of the journey which is kinda all that matters at the end of the day.


  • Action: 3 business milestones a week, 1 TECH milestone (investigation / project / idea I'm interested in)
  • Outcome: Exceeding grades and pushing the company / software forward while enjoying the work


  • Action: 1 exploration a week, focused on whatever I'm interested in at the time
  • Outcome: Lul I've built so many projects and it's been quite fun - 7 in the last 2 months for my HAMY LABS project repo (available to HAMINIONs) and a lot more just me playing around and never published


  • Action: 1 Share a week, focused on whatever I want to talk about. If nothing that's okay too but I like to talk (really write) so rarely is nothing.
  • Outcome: I've got posts scheduled for the next month or so and it feels fun to make so that's a win.

All this to say that I haven't exactly stopped entrepreneurship in the sense that I'm still discovering problems / opportunities and solving for the ones with highest opportunity for me. In fact you could largely argue that I'm doing this more and better than I was before. But what I did stop doing is chasing the false dream of Entrepreneurship - the rags to riches story of if you work super hard for long enough you will eventually make it.

That story is not true. I think it's even dangerous. Most entrepreneurial ventures fail so if you wreck yourself pursuing one then you've essentially wrecked yourself across all future opportunities.

There are better approaches that optimize for median outcomes, allowing you to both live a good life and make small bets for outsized returns / impact without wrecking yourself.

We should not glorify unnecessary, self-imposed hardship. Time / Effort is not what matters - 80 hours a week is meaningless if all you were doing is staring at your screen sending emails.

We should instead focus on impact and support each other to make better decisions in pursuit of our goals for life.

Real artists don't starve. Real entrepreneurs don't starve either. And real businesses are profitable.


That's it - a long-winded summary of my entrepreneurial journey. Nowadays I'm but a simple Technomancer building things I find interesting. You can explore a mostly-complete list of my projects on my projects page.

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