"It's kind of an unfortunate fact of life that high rewards require high risk, and high risk requires frequent failure. There's basically a continuum between doing what you're told, never taking on any risk, and collecting a steady paycheck, or shooting for the moon at every chance and falling on your face each time. FWIW, I had the same sort of existential crisis when I was about 13, and it was so depressing I almost wanted to kill myself. However, the real working world is not (always) that bad. I found it helpful to think of every job as a learning experience. When you've milked it for everything it's worth, move on and find a new job. If you don't have any possible new jobs, quit and found a company, take it as far as you can possibly go, and if that's not far enough, go and get another job that'll let you work on the reasons you failed as an entrepreneur. This, BTW, is false: "It's eight hours a day, almost completely absolutely and rigidly, five days a week, for forty-sixty years..." - Jonathan Tang