I have a similar day job, and would love to start consulting on the side. Legal and worries that it could be seen as “conflict of interest” prevent me from starting however. How do you manage that?
i have an extremely unusual position as a contractor bc of covid so i am actually not technically a fulltime employee for the day job as well. so it works out there at least on the employment terms level. as for conflict of interest, it's a product they dont (yet) offer, its open source, and i'm performing a different role to the day job. i've been public about it and nobody's raised an issue on either side. ofc if you want to get nasty you could, in which case my downside is having to give up either gig. not terrible. its amazing what you can do with job opps when you dont need the money.
There actually is a second chance pool, but you usually would get an e-mail about it.
in any case fwiw I am not the author but I listen to his podcast. I also have some kind of weird hyphenate career - by day working at AWS, by night consulting for Temporal, and on weekends working on my book/indie making. Its a busy life but I'm finding I always have something to apply myself to and I have options galore. contrasts vs my mid twenties when I was just playing games outside of my day job.