Finding interests seems to be the common issue. Some people "retire" with a ton of interests and wonder where they ever found the time for their previous job. O

Finding interests seems to be the common issue. Some people "retire" with a ton of interests and wonder where they ever found the time for their previous job. Others not so much. But you do mention a few interests: - scale-up - coffee shop or maker space [etc] hanging out with my customers - more freedom and more ability to make a difference [for a little while at a time] - rewarding purpose You could dig in that direction: identify what's underdone or missing in your field or city or tribe and put some energy into that. Don't worry about "buying yourself a job": as part of the scale-up, install an on-the-ground manager there - since after all it won't matter too much if you are paying yourself or making a profit. There is one thing you don't mention and that's paying attention to your investments. This is where your living and retirement and (now expensive) hobby money all come from - and so that should actually occupy a decent fraction of your time...