Ask HN: Advice on quitting job to work on side projects?

4 pointsravroid2y ago2 comments

Hey there, HN - I'm at a bit of a crossroads and am seeking some no-nonsense advice. Here's my dilemma:

I've been a full-stack dev for 9 years. No CS background. It started as a hobby when I was a teenager, and somehow turned into a career. Along the way, I've hopped through 7 different jobs, but only managed to stick around for more than 2 years in a couple of them (plus a couple of layoffs). I'm a bit of a wanderer.

I just can't seem to sit still and tend to inevitably become completely disengaged with the work and team. Most of the gigs I've had were startups and, more recently, corporate teams grinding out APIs and internal tools. Frankly, I've lost the spark and passion for coding and building cool stuff and have settled for a paycheck. I'm desperate to get it back, but I think the only way that's going to happen is if I work on something of my own creation.

Currently I'm stuck in a job that I despise with every fiber of my being. After a layoff at a previous company, I settled for the first halfway decent-paying gig I could find. But I couldn't care less about the work I do. It's fintech, it's soul-sucking, it's passionless work, and I'm starting to fall behind. This seems to be a pattern in my career.

So, I've got this potentially very stupid idea: I want to quit my job (again) and dive headfirst into my own side projects for the next year. The catch is that none of my ideas have been validated yet, so the chances of making any income from them are slim to none. I don't anticipate making money, but I want to put myself up to the challenge.

Sure, I've dabbled with these projects during my nights and weekends, but by the end of the day, I'm drained. There's no sense of urgency to finish them. So, I'm thinking, what if I quit my job? Maybe that will light a fire under my ass and force me out of my comfort zone. I've got about a year's worth of savings to float me through this experiment.

Now, if I fail to make a single buck on my own, at least I'll have sharpened my skills and built up a portfolio. That way, when I'm back in the job market, I'll have something to show for the gap on my resume. But what if I struggle to find a job after this sabbatical? Long gap plus a history of bouncing around? Would this be career suicide?

So, here's where I'm seeking your advice. Has anyone out there ever been in a situation like mine? Have you taken the leap and gone all-in on your own projects? Did it pay off, or did you end up kicking yourself for being so foolish? And if you're like me, on the edge of making the leap, what advice would you give yourself before taking that leap of faith?

Honestly, I'm kind of hoping some of you will talk some sense into me and convince me this is a terrible idea. But if any of you have inspiring success stories or words of encouragement, I would love to hear it all. I need your honest opinions.

Thanks a million in advance for lending your wisdom.

2 comments

PaulHoule2y ago

I worked at a place that was really toxic, bad enough that I talked about the coming storm w/ my doc and got a SSRI prescription proactively. When the product shipped (because I whipped it into shape) I got verbal abuse from a coworker in a meeting, I quit. Six months later they called me up and told me they were having a hard time finding my replacement, I told them if they wanted to retain anybody they'd better fire my boss, I saw on LinkedIn that he was fired the next week.

I worked on side projects for about 3 years including a vision for what could have become a big business, occasionally did some consulting work, partnered up with salespeople who couldn't sell, partnered up with "idea people" who had brought some of the best possible subject matter experts in and pretended to listen to them but didn't really, had LinkedIn bring a huge number of bullshit artists into my life, etc. Worked out at the gym a lot.

Ran up a lot of debt on my home equity line, got my wife pretty mad at me, rolled my car (it didn't even hurt!), got a real job (for a startup doing something similar to what I had envisioned), got fired (I might have been the only non-C level who thought he understood what the company was doing and that was trouble because being more experienced I could easily upstage management in all hands meetings), got another job, paid off my debt, did some work for a standards committee that realized the quest I had been on when I was unemployed, got some new side projects.

So it was not easy and did not work out the way I had hoped but I made it through and I like where I work now.

verdverm2y ago

If you are not worried about the financial impact, then definitely do it!

It will be hard, as anything that is worth it is.

The experience and learning will pay itself back for whatever comes after should it not pan out. This will be more true if you spend more time learning how to "sell" the project (sell as in promote, gain users, and/or make money). The non-technical upskilling will teach you more.

I've been working on my side project for many years, trying to make it the primary project. I consult and contract to pay the bills. It can be difficult, but if you believe in the idea, you will push through. One thing to be wary of is that it is easy to get distracted and work on the wrong things. Motivation and focus will be a struggle, which in itself is a growing experience.

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