I feel rich now. Once passive income is greater than monthly fixed expense is when I started to feel comfortable. I still work. I create investments and offer them to accredited investors so that they can have passive income too. In one fund, we distribute $100,000/month in excess cash flow. It goes out on the 15th every month and it's one of the greatest feelings out there. Of course there is stress but working when one doesn't HAVE to changes ones' perspective greatly. I'm not sure what you mean by "enjoy the fruits of your labors". I realized awhile ago that I'm happiest when I am pursuing a worthwhile goal. Money is just money. Helping other people, donating ones time, spending time with friends and family, etc etc. is most important but like anything else, balance is critical. You can't eat a gourmet meal 3x/day 7 days week or you won't appreciate it. Plus you'll be a fat-ass and a burden to society. Anyway, I feel rich in many ways. I'm not sure it should take money to feel this way but it doesn't hurt - money is a source of control, a belief structure. I didn't set the game up and I think many folks take it too seriously but that's the case with any game, right?