[Falkon1313]

If you're young, healthy, and streetsmart enough, and the risk is acceptable, go for it. Take a summer and be homeless (or maybe even a year if you're in a survivable climate). You'll have some exciting adventures in amongst all the boredom and misery. And if you survive it, you'll learn a lot. Like why you don't want to live like that and what you actually want out of life. (Also maybe how to explain that gap in your employment at a job interview.) Plus you'll have some cool stories to tell your kids once you get old.

If you're older or wiser, you might want to consider a more positive-oriented way to address a midlife crisis - focusing more on what you want instead of what you don't want, and considering how to get the most value out of your time instead of how to get more time that's not as valuable as you'd like for it to be.