My boss just turned 62 and is starting to think about retirement. He's owned the company for 30 years and just recently asked me to enroll him in the 401k. He's never participated. Then complained that he's not sure how he's going to live on his paycheck. (My husband and I have our 401ks maxed out, which is more than he will be contributing.) He does own some real estate, but not enough to retire on with his lifestyle. The company worth is minimal, so he won't get much if he decides to sell. His wife never worked and he helps support his entitled adult daughter. All of them have to have the best of everything. I see his tax returns because they are bundled with the company tax returns. He makes about the same or less than my husband and I do in a year. I could NOT afford to live his lifestyle. But then again I have investments and don't have to take out loans to pay my taxes every year. He sold some real estate almost two years ago and told me he had to reinvest so that he didn't "piss through the money", then proceeded to do that anyway. I know there was a new house and a new car, but not sure what else. Yet, he was scrambling for $10k in April to pay his taxes. (Was so tempted to offer a high interest loan, just to be obnoxious.) I periodically make very stealth comments, but I don't think he gets it. I was recently very blunt and told him he's never going to retire. Listening to him makes me anxious and want to find more ways to cut back. His friend (same age) comes in the office sometimes. Same age, also a highly compensated business owner. He says he can never retire and will work until he drops dead, because he has nothing. I think part of the problem is that they provide services to very wealthy people and want to look like they fit in. I'm sitting over here looking like I'm poor, but I'm not and don't care what they think. Feel bad for me and give me a raise! LOL!