If you work in high tech and want to take some significant time off, do it before you’re 50, not after. Tech skills change pretty rapidly, expect to have a difficult time persuading potential employers that you’re a valuable hire when you’re over 50, and haven’t worked recently. Speaking from experience, just saying that you worked directly with [Bob Frankston/Dan Bricklin/Steve Jobs/Jon Sachs/Ray Ozzie] doesn’t mark you as someone they need. It marks you as a historical artifact, a dinosaur. They don’t want to hear about the invention of CSV, even if you had a hand in it. The also don’t want to hear about all the startups you worked for (or founded) that failed in the second round of funding — or got swallowed by a giant corporation that then promptly went bust. (anybody else here get screwed by Northern Telecom?)

All that said, I’m well over 65 and still working — but I’m an ‘IT guy’ now. Doing this scratches an itch for me. After decades of telling people “I know what your problem is and this is the way to fix it — but I don’t have time to help you”, I can just fix the issue.