I Spent Two Years Trying to Make Money on the Side. Here's How Badly I Failed.
It's 11pm on a Tuesday. I have Binance open in one tab, a half-finished pull request in another, and a Slack notification I've been ignoring for forty minutes. My portfolio is down six percent. I have standup in eight hours.
This was my life for most of 2021.
I make decent money as a software engineer. Not "quit your job and move to Bali" money, but good money. The kind where you're not stressed about rent but you're also not building any real wealth, because San Francisco has a way of consuming paychecks that would feel enormous anywhere else. I was maxing my 401k and throwing whatever was left into a Vanguard index fund because that's what the Bogleheads subreddit told me to do.
That was fine. Responsible, even. But fine wasn't what I was after.
I wanted something that scaled. Something where I put in the work once and it kept paying. The engineer brain does this thing where it looks at every problem as a system to be optimized, and I kept looking at my income and thinking: there's only one input here. Me. That's a single point of failure. What if I get sick? What if the job market tanks? I needed another stream.
So I started trying things.
The Forex Phase
A guy in my company's random Slack channel posted about how he was making an extra two grand a month trading forex. I asked him about it, he sent me some YouTube links, and three weeks later I had a demo account on MetaTrader 4 and I was convinced I was about to become a currency trader.
I learned what pips were. I learned about the spread. I watched probably fifteen hours of content about support and resistance levels and I drew lines on charts with complete confidence that I understood what they meant.
Then I opened a real account with five hundred dollars.
I lost a hundred and forty bucks in the first week. Not because the market was crazy. Because I had a full-time job and I was trying to day trade currencies, which is insane. The yen moves when Tokyo opens. The dollar moves during the US session. The euro has its own thing happening in the morning before I'm even out of bed. Forex doesn't care about your sprint planning meeting. It just keeps moving, and if you're not watching it, you're losing.
I closed the account after about six weeks.
The Crypto Phase
This one hurts more to write about because I actually believed in it, not just as a trade but as a technology. I still kind of do. But there's a difference between believing in a technology and being a competent trader of that technology, and I confused those two things badly.
2021 was a wild time to get into crypto. Everything was going up and then everything was going down and then things I'd never heard of were going up a thousand percent and I was reading about Solana at three in the morning like that was a normal thing to do.
I bought ETH, some SOL, a little MATIC. I had a rough thesis about layer-two scaling being the future. The thesis wasn't even wrong, honestly. But I had no position sizing, no exit strategy, no risk management at all. I was just... holding things and hoping. When stuff dropped forty percent in May of that year I panic-sold half my position at the worst possible time, which is the most human thing you can do and the most expensive.
The part that really got me was the opportunity cost. I spent probably four hours a week reading crypto Twitter, which is four hours I'll never get back, and I made essentially nothing for it.
The Affiliate Marketing Detour
I'm not going to spend much time here because it's embarrassing. I built a personal finance blog. I wrote maybe eight articles. I spent two weekends getting the SEO setup right because that's the kind of thing engineers do: we perfect the infrastructure and never ship the content. The site got eleven organic visitors in its entire existence, ten of which were probably me checking if Google had indexed it yet.
The fundamental problem with affiliate marketing as a side project is that it takes eighteen months to see results, minimum, and that's if you're putting in real hours. I was putting in like three hours a week while exhausted. Content marketing rewards consistency and volume. I am consistent and high-volume at my job. I have almost nothing left after that.
So by late 2022 I'm batting zero on the side income thing. And I'm tired. Not just sleep-tired, though I was that too. Tired of starting things and not finishing them. Tired of the mental overhead. Tired of feeling like I was hustling and going nowhere.
I almost just gave up and accepted that index funds were enough. Maybe they are, for some definition of enough.
But I kept coming back to this one thought. All of my failed attempts had the same failure mode. They required my active attention during market hours, or they required consistent creative output, or they required me to be present in a way that competed directly with my job. The moment I got slammed at work, the side thing died. Every time.
What if that constraint was the actual problem to solve?
I'm an engineer. I build systems that run without me. I've written cron jobs that have been running without a single human touch for four years. I've built data pipelines that process millions of events while I'm asleep. The thing I'm actually good at, professionally, is making things that run automatically.
Why was I trying to do a job that required me to be awake and alert and watching a screen? That's not a system. That's just a second job. A worse job, with no salary and no benefits.
Investing, though. Investing has this property that most things don't: the underlying action, buying and selling financial instruments, is fully automatable. A broker with an API doesn't care if the order came from a human clicking buttons or a Python script running on a VPS at 4am. The execution is the same.
I'd vaguely heard about algorithmic trading. Quant funds, HFT, all that. I'd always assumed it was out of reach for a regular person. You needed Bloomberg terminals and PhDs and co-location servers next to the NYSE. That whole world seemed sealed off.
Then I started actually looking into it, and I realized that landscape had changed a lot. (Last time I use that word, I promise.) Brokers like Interactive Brokers and Alpaca had opened up real API access to retail traders. There were Python libraries. There were backtesting frameworks. There was an entire ecosystem of people building exactly the kind of automated systems I was imagining.
It wasn't easy. I want to be clear about that upfront because this is where a lot of these stories turn into hype. I'm not going to tell you I found a magic indicator or figured out some trick the institutions don't know. The stuff I eventually built took months to work, failed in ways I didn't expect, and still has problems I'm actively dealing with.
But the basic idea held up. If I built something solid, it could run while I was in meetings. It could place orders while I was asleep. My attention wasn't the limiting input anymore.
That realization was enough to make me actually focus for once.
I remember the specific night I decided to take it seriously. It was a Saturday in November, I think. I had a coffee that had gone cold, I was reading the Alpaca docs at my kitchen table, and I got this feeling I sometimes get at work when I'm looking at a gnarly problem and I can suddenly see the shape of the solution. Not the whole thing. Just the shape.
That's enough. That's all you need to start.
My roommate walked through and asked what I was working on. I told him I was maybe going to try automated trading. He said "isn't that what caused the 2010 flash crash" and went to bed.
He wasn't wrong, technically. But I wasn't building anything that was going to move markets. I was trying to build something that would let me not check my phone at 2pm during a code review.
Small ambitions. Good enough.
Next: I'll get into what automated trading actually is for someone without a quant background. Not the theory. The practical stuff. What a strategy even looks like when you write it in Python, why backtesting is both essential and deeply misleading, and the first mistake I made that cost me real money.
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