If you've built enough of a nest egg to buy yourself some time off, then why put yourself through the unnecessary stress?Outside of the show someone has already done a deep dive in Steve’s resume and tech projects he’s had a hand in… Dude DOES NOT have to work for a long time. She’s doing too much and it’s not going to stop.
He likely has the skills and connects to pick right up where he left off.....whenever he feels like it.