Oct 25th last year I did....one day shy of my 36 year anniversary. Family business, inherited my Mother and Brother as primary partners after my Father died unexpectedly on Sept 10, 2001 and they eventually became my dependents and biggest critics. As partners they only lacked work ethic, knowledge, and vision.
Our kids are 12 & 15 and thankfully my wife has a decent job and the only loan we have is our home which we owe less than 50% of accessed value. Medical expenses, insurance, and utilities are the biggest future concern, if we can get the house paid off we'd be pretty comfortable for our "modest" lifestyle.
$500K isn't much as one medical event could take that and more. At 55 years old finding a decent job ($50K+) in our area isn't easy. Our son has multiple medical issues and is ASD (Autism Spectrum Disorder) so that pretty much requires an at home parent right now. I will say I had more time to myself when I was working full time (50-60 hour Mon-Sat week) vs. being a full time househusband.
If you're single and have little debt and no young kids it's a different game than mine. Medical is your wild card right now IMO.
The overall stress reduction has been priceless though.