How long did you keep the day job, and what finally made you quit?

Priya Natarajan· Building a scheduling app for independent physical therapists; still at my product day job· Named it, SaaS & Software·Aug 8

I'm building scheduling software for independent physical therapists, nights and weekends, while working as a product manager. The job pays well, I don't hate it, and it's quietly the reason the thing I care about moves at about a fifth of the speed it should.

I've done the responsible version of the math. Twelve months of expenses saved if I'm careful, more like eight if anything goes wrong, and my partner's income covers rent but not both of us being reckless at once. On paper I could go.

What I actually want to know is how people decided, because the math has said 'you could' for four months and I still haven't.

The specific trap: every time I get close, I ship something at 11pm that works, feel great, and conclude the current arrangement is fine. Then three weeks pass where the job is busy, the product doesn't move at all, and I'm furious about it.

Did you wait for a revenue number, and what was it?
Did anyone go part-time or contract at the old job first, and did that work or just make you worse at both?
Has anyone quit and regretted it? I only ever hear the other version.

4 replies

Dana Kowalski· Open·Aug 8

I left corporate HR with three retainer clients and a spreadsheet that said I had fourteen months. I had eight, because I hadn't counted health insurance properly and I'd been quietly expensing my laptop and software to a budget that no longer existed.

What made me go wasn't a number. It was noticing I was doing my best thinking for the client work at 6am and giving the job the leftovers. That isn't sustainable and it isn't fair to anyone paying you either.

On part-time: I negotiated three days a week for a transition quarter and it was the best decision in the whole thing. Ask. The worst answer is no, and employers say yes to this more often than people expect.

Andre Bellamy· Open·Aug 9

Contrary view, since you asked for the one you don't hear.

I quit too early at my last thing, on the strength of a good month and a feeling, and I spent the following year making decisions from a position of needing money this quarter. That's a bad chair to negotiate from. Every price I set that year was too low, and I took two clients I knew were wrong on day one.

For a software product with no revenue yet, the day job isn't the enemy, it's the funding. What I'd change in your setup isn't your employment status, it's that you're shipping at 11pm and calling it progress. Protect two real daylight blocks a week first and see whether the speed problem is actually the job.

Priya Natarajan· Named it·Aug 10

The 11pm point stung and is correct. My two best weeks this year were when I took Fridays as PTO and worked on this in daylight, and then I went straight back to the 11pm pattern without noticing I'd done it.

I'm going to ask about four days a week before I ask myself about quitting. If they say no, I've learned something about the job that's also useful.

Sam Lindgren· Named it·Aug 10

Three years of weekend weddings before I gave notice last month, so I'm the sunk-cost exhibit.

Mine wasn't a revenue number in the end, it was a calendar problem. I turned down four weddings in one spring because I couldn't get the Fridays off, and those four were worth more than a quarter of what the job paid me. Once turning down work became routine, staying was the expensive option.

Software's different because you aren't turning down bookings. But watch for the equivalent, the thing you're saying no to because of the job. When that list gets embarrassing to look at, you'll know.

Sign in to reply

Replying and upvoting need a free LaunchAdvisor account. Reading is open to everyone.