I'm 40 and I currently live with my mother. I've moved out a few times, but always found my way back. She's rather needy, and I've found it's just easier to live with her than drive over to her place 5x a week to change a light bulb or swap batteries in a remote control. I also don't mind the cheap rent, so it helps me, too.

Oddly, I feel more content now than I ever did when I was younger. I'm not sure if I'm deluded in some way, but in my own mind, I've accomplished plenty. I've been a university professor, I've written three books, I've obtained several IT certs and pseudo-successfully switched careers, I've learned to play guitar, and I've accomplished several other small things.

Above, when I said "pseudo", it's because I tend not to keep my jobs longer than 6 months to a year. I save a little money, quit, take some time off, then rinse-repeat. It drives at least one friend of mine crazy. He thinks I should just stay in the cube farm, move up the financial ladder, and happiness will be there waiting for me. I don't agree with him at all, and I don't think we'll ever see eye-to-eye on it.

I've determined that despite what friends and family say, my real sin in their eyes is I haven't made enough money, or prioritized money. If I won a million bucks tomorrow, I know every issue they have with my life would melt away. I think it's that way for a lot of people struggling in society. It isn't that you didn't accomplish or achieve anything in your life, it's just that you didn't make enough money to make everyone happy.

The nice thing about getting older is, if you work at things, you'll become confident enough to not worry about the naysayers.