I'm technically a Boomer although I have little that I identify with them. I am born on the last official year of the "boom" so I find little in common with people born in 1946 the first year of the baby boom.

I had my first work crisis when I was about 40 when I realized I didn't want to do the office thing anymore. My wife and I had two kids in quick succession and they were very young when I walked away from my job at Microsoft 20 years ago. In hindsight, if I had just ground it out, I'd be retired by now with time to enjoy myself while I still have a strong body and mind. I foolishly decided to turn one of my hobbies into a job and raise the kids while my wife worked. Then we ran into the great recession which absolutely tanked my new hobby/job. I ended up having to go back to doing software engineering work nine years later because our financial situation was dire. 12 years later I am still working and probably can't retire for another five years.

I am not sure what I would do different. I probably shouldn't have quit that government job I had out of college because it had a pension and I could've retired several years ago.

Part of me says I should've just moved to Hawaii and been a beach bum, but our slave work country has made it impossible to survive old age unless you slave away for forty years and scrimp and save so you can spend it all on healthcare when you are old. My kids, only in their early 20s, still haven't made enough money to help out if I needed it. Fortunately, we won the real estate lottery and will likely make a literal million dollars from a house we bought 25 years ago. But my kids are very skeptical about working 40 years to barely afford an apartment and healthcare. The only saving grace for me is working remotely. It takes a huge amount of anxiety off me from having to go to the office. Maybe my kids can get remote jobs and move to a LCOL location and actually have a family and a house and all that because living in an apartment raising kids sucks. My family did that for three years when I was in high school and I hated it.