[jjkaczor]

It's different when you do it to found a company/startup/product.

Me - I quit being a permanent employee decades ago, and only do consulting contract engagements - no regrets. (Admittedly - I am in a country where my basic healthcare needs are provided - and I can purchase reasonable coverage for things that are not)

[apercu]

I sort of did the same. Quit a job and joined a start-up consultancy as a partner. The politics of that were a little tiresome after 6 years (and that was probably due to the post dot com crash year or two).

I then moved to Canada, consulted for a couple years with legacy American companies and then got enticed to take an executive gig at a Canadian "start-up" (that basically turned in to a consultancy). 8.5 years of that and I was pretty unfulfilled and very stressed.

So I went back to consulting. I will say that Canadian health care made that decision easier, but in 2022 I started my move back to the US.

Still consulting, but for sure, that health insurance bill makes me take projects that remind me of why I left the executive gig.

That said, I've never wanted to fully "retire". I like the work, I just don't like the unreasonable parameters most engagements have, and I'm hoping that in a couple years (when mortgage and some other expenses are over) that I can go back to maintaining healthy boundaries with clients and work.

Because, I do like the work. I just don't like the grinding.

-s

[gmuslera]

And one that manage to succeed. History is written by the victors. On hindsight every move was right or at least not so bad if you ended winning, and wrong or plagued with mistakes if losing. Even if they are all mostly the same in both cases.