A big part of becoming less risk adverse, and getting more confident, is having success to build upon as a reminder that while you won't always win, you won't a

A big part of becoming less risk adverse, and getting more confident, is having success to build upon as a reminder that while you won't always win, you won't always lose, and that's ok. Specific to your problems, consider this: 1. Would you pay money to fix your problem? If so, consider taking that money, automating its investment into a 3 fund portfolio (do some Googling on Bogleheads and read 'A Random Walk Down Wallstreet' if you're skeptical), and forgetting about it for a few years. Check back in on it annually and see what you've learned. More importantly, even if you've lost money in an economy that looks like it may start cooling off, be ok with it. You're investing in the experience to prove to yourself the world won't end, not in an expected return. If you get a return, you'll have some success to get excited about and grow your investment. 2. I'm not super tall and started losing my hair in college. If you can get yourself to take the plunge and shave it all off, it can be one of the most empowering things you've ever done. There's a period where people you know get used to it, but then you'll find a lot of people have only ever known you with a shaved head. You'll inevitably get some positive interactions out of it and will stop worrying that people are looking at your hair loss. And if you REALLY want to go all in, take the savings you get from investing in a good pair of electric clippers and never going to a barber again, and use that as your investment capital.