A friend asked me recently what I think tends to make life and a career go well. With the caveat that I've only lived a fraction of one life and am still trying to figure things out, here's the advice I'd give past me.
Fail fast. The way to grow and accomplish anything in life is to fail fast. You are going to make mistakes no matter how smart you think you are. The speed with which you find the mistakes matters too. You don’t want to spend five years building the wrong product. Or realizing at 50 that you are in the wrong career.
Think backward. Instead of asking how to succeed at something, ask what would guarantee failure. Then avoid those things. There are many ways to succeed at things but the ways to fail are usually more obvious and easy to learn.
Be a hyperrealist. You need to understand how the world works and accept it as it truly is. Distorting reality to fit your worldview leads to really bad decisions.
Make it easy to take risks. The biggest risk in your life is not taking enough risks. We are surprisingly good at seeing the downside of a risk and surprisingly bad at seeing the upside. The opportunities you never pursue will ABSOLUTELY shape your life just as much as the ones you do.
Make lots of asymmetric bets. Look for small winnable bets in your life where the upside is much bigger than the downside. Eg. Spend a little time working on multiple side projects you find interesting, then gradually focus on the ones gaining traction.
Make yourself a big target for luck. When you study people who’ve done great things, you notice that a lot of it comes down to luck. Larry Mullen was 14 and wanted to start a band so he wrote it on a piece of paper and pinned it to a school bulletin board. A bunch of kids showed up at his house, including Bono and The Edge. That became U2. You need to make yourself a big target for luck. Try lots of things, meet lots of people, do weird things, ask for what you want!
Don’t spend too much time contemplating your big goals. Even if they motivate you. Seeing how far you still have to go will make you want to quit. What works for me is cutting a really big goal into micro goals I can finish in under an hour. That keeps me from wanting to quit because I literally get to forget about the big monster goal.
Get a coach. You can't do this alone. You might believe you can, but you can't. Keeping every idea to yourself is as close as you can get to guaranteeing failure. You want your bad ideas to be challenged.
Learn to love the process. If you are driven and ambitious, chances are you'll keep setting bigger and bigger goals. So learn to enjoy the process. The people who do this well are the ones who enjoy the process.