I also thought about titling this post "Putting Money into your Career" but the one I went with seemed a bit more universal. Not everyone had supplemental income to throw towards their passion and I don't want to discourage anyone who can't afford to use money to make moves. There are lessons here for all socioeconomic classes.
The real theme is you need to make investments. If you are in a line of work that doesn't have a concrete ladder to climb - usually means you're in the arts or self-employed - then you know how difficult it is to navigate the maze. You always want to make the next step but you don't even know what direction to walk it. It doesn't just get easy (especially in the arts) but it won't be any easier if you're not willing to invest in yourself. Maybe it's time to lose a little more sleep, maybe you need to stop drinking for a bit (for the money not for your sanity) or maybe you need to cut some relationships out of your life if they aren't getting you where you need to be.
You can't always be afraid. You can't fear failure or be scared of making the wrong move - making any move is going to give you learning experiences and help you make better choices the next time. Just keep doing and stop finding ways to stop yourself from doing.