The first (and only) job I quit, I went to both of my bosses (I had two) and told them The Time Had Come.
I had no other job offer, and didn’t know what I’d do next, and had little savings and a mortgage to pay — but I’d done what I’d set out to do in that job and did not want to grow further in that career. The next phase there, at that job in that industry, was not for me.
Both asked me to stay, but when I explained in terms of being grateful and needing to do the next thing, they didn’t push too hard. One offered to pay me a significant bonus ($60k) to stay for the rest of the year. I declined, but agreed to stay on 60 days for no bonus.
It turned out staying those 60 days (instead of 2 weeks) ended up costing me $400,000, for slightly complex reasons around stock option pricing when joining a pre-unicorn.
I don’t know if it was worth it — boy it ended up costing me a lot of money to stay — but by doing the right thing, and treating folks the way I’d like to be treated, and going the extra yard … I felt better about quitting.
And in the end, that boss I stayed those extra 60 days for much later (a few years down the road) got me a job that was critical to my career growth.
No true regrets.