In the nineties I made good money — but not rich-guy money — selling pickaxes to the gold miners. It was a good time. I was my own boss, selling an imagemap editor (remember those? You might not, if you came in after image slicing) and web analytics software (before it was called web analytics). Among other things.

I’m proud of that because I spent my time creating something useful. And I also created a few jobs.

But it’s hard not to get sidetracked sometimes, thinking of the random ways I could have become rich. And the not-so-random ways.

I could have hung in longer at RealAudio. I could have paid attention to my spam folder the day VA Linux Systems invited everyone who contributed to Linux to buy stock at the pre-IPO price. I could have tried harder to sell off my little company before the first dot-com crunch put an end to that possibility.

But all of these conversations eventually end in confronting the absurd: I could’ve registered cats.com!

But I didn’t, because it’s in my nature to try to do useful things. I want to be productive and create necessary tools.

I was also resistant to working for companies that didn’t reflect my personal values, which is something you can more easily say when you’re in your twenties and don’t have any dependents, yet.

Eventually, as my little company wound down, it all led me to a great job with a design firm that works for clients I believe in. That firm also supports my work on an open source nodejs CMS, Apostrophe. And I live in Philadelphia, a city that is not ludicrously expensive. We’re not building the next Instagram, but if you love what you do, it’s not necessary to “escape” from your work by getting rich.

So I have few real regrets. But I do keep my eyes open for opportunities to make early, pivotal contributions. And like everyone else, I sure wouldn’t mind finding a way to make financial security a permanent non-concern for my family.