This thread has been a fun read. Like the OP, I'm self employed and work daily with people. I will say this, compared to 5 years ago, what people expect will sometimes make our head spin. I've done my occupation since 1987 and have to regrets as it's provided a good lifestyle. I work about 4 days a week on average and can take any amount of time off when I want. Like many I had that thought of retirement at 55, but when I hit that mark, my thoughts was what was I thinking. This fall I turn 60 and will retire from my business when I hit 62. That doesn't mean I will quit working, just make a change, take some time off from the daily grind and then reevaluate things. My wife retired 4 years ago from an advertising career and even though she enjoyed and kept busy, she wasn't ready to no longer work and has worked part time. When I retire, we both will, then plan to have many trips in the RV to see more things we enjoy.