Self-help and cheerleading is an enormous business, but it's also something a great many people commit to as a means of self-improvement. That makes a lot of sense, because at the end of the day, only you can really improve you. However, I think we view it in a way that seems kind of silly once you get a little older.
If I look at 20- and 30-something me, I often looked up to people who seemed "brave" and willing to take risks to do stuff and better their situations. I'm sure I encouraged myself to engage in this sort of bravery, too. I'm sure I can find instances of myself opening up with the greatest vulnerability about my perceived weaknesses, and boldly declaring that I was going to be brave and take a chance to make myself better. (For real, this was Live Journal and MySpace in the early aughts!)
What I really didn't get back then is that the stakes weren't really that high. I think that there are slightly embarrassing elements of narcissism, hyperbole and self-righteousness there to believe that you're really being brave for that big change or that bold move you were going to take. (I mean, unless you're actually doing something that puts your life at risk.) I'm not trivializing the act of making important decisions, or overcoming the discomfort often required for such acts, I'm just saying there wasn't that much at stake.
Now, over 40, you would think that I would take things even more seriously, with a wife and a (sometimes challenging) child, but no, there's still not a lot at stake. In the last 12 years or so, I've made all kinds of "brave" moves, but as I'm often fond of saying, nothing is permanent. The big thing we seem to ignore is that few doors are one-way. We can reverse most decisions. Sure, there are consequences, but that's part of the calculus of any decision.
I remember how I felt when I decided to pursue a technology career and abandon the broadcast world. It was a big deal, and it worked out for me, but there was nothing really at stake there. Moving all over the damn place in a span of a few years wasn't really the big risk it may have felt like. I mean, I did get fired once, which didn't matter.
So to my younger self, or all the people who are younger now, you may feel like you're taking great risks, but honestly, they're probably not. All of that stress and anxiety that you're feeling over the big decisions is probably not serving you. What doesn't work out will probably lead to something else.