I got my first software job while I was still in high school and when I started my career I mostly worked jobs that I really enjoyed for a lot less than I could potentially make otherwise. I didn't have a family yet, I didn't have a lot of expenses, I didn't care. Later down the road I joined a "real" startup and started getting paid much better (coincidentally or not around the time I had my first child) and since then I've sort of been in the rat race so to speak. Can't complain though but most of my later jobs were not as fun as my earlier ones.