> 2x the pain when you’re also on call at your day job
I know this is a side point, but I imagine people might be interested in the challenges of being able to work a second job while not annoying your employer. How did you manage it?
I ran my company (https://buttondown.email/) as a side project for ~three or so years before taking it full time and it was _similarly_ in a position where I could get paged for downtime or plumbing-related issues. My suggestions:
1. Honestly, choose a project where downtime or operational issues are less prevalent. This is a cop-out answer, but when you're evaluating potential projects it should be top of mind.
2. Be very up-front and honest with yourself and your employer about your commitments and your priorities. My personal rule was to only ever look at Buttondown-related stuff outside of what I considered my "core" working hours unless I was getting paged, and even then responding to pages would wait until my meetings or time-sensitive work was finished.
3. Set a schedule and rely on the schedule. For me this ended up being "side project hours are from 7-9pm M-F and 3-8pm Sat"; at times I wanted to do more and at times I wanted to do less, but the former path leads to burnout and the latter path leads to languishing.
Avoid doing any work on my side project while at my regular job (unless it was needed by my regular job, e.g. on the open source front), and never let my responsibilities of my regular job slip or become a lesser priority.
The real challenge here: running an infrastructure service as a side project is what nightmares are made of.
It will be close to impossible in a mega corp with strict rules. For instance doing this at Apple is from what I have heard effectively impossible. On the other hand I know folks who left to a smaller startup and they took that job under the precondition that they can bootstrap their side hustle alongside.
I love side projects so much and hate the grind of day-in-day-out repetition, I just became a contractor.
One thing you can do is try and find AOR clients. For example, I have a very strong relationship with several other agencies and one even keeps a desk for me. Which at times feels like Im just working for them.
Then I can bail or chose to work on whatever. 2 years ago I joined a start up for some time. etc.
I wanted to go deeper on so many things, but I also didn't want this post to be 5,000 words long :s
My cofounder was in a similar but different position at the time. He was at GitHub and also had two young kids. I'm happy the outcomes are looking good for us, because damn was that period of life painful for all.