Every now and then, a friend asks me 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 will make mistakes however smart you think you are. And the speed with which you find the mistakes matters too. You don't want to find out in your 40s that you’re 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 but the ways to fail are usually more obvious.
Be a hyperrealist. You need to understand how the world works and accept it fully. Distorting reality to fit your worldview leads to terrible decisions.
Make it easy to take risks. Most people overestimate risk and underestimate reward. You have to take risks because you can’t know in advance what will work. An easy way to take more risks is to think about the opportunity cost of not taking them.
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 that are gaining traction.
Find your own luck. We underestimate how much control we have over luck. A lot of it is random, but I would guess that many of the luckiest things in your life started with a small action you took first. Luck tends to increase with the amount of action you take.
Don’t contemplate the outcome of a big goal. Even if it motivates you. At some point, seeing how far you still have to go will make you want to quit. A strategy that works for me is to break big goals into pieces small enough to finish under an hour. Then I only have to work on the next piece. This helps me forget about the big goal because I always have something to tackle in front of me. I also tend to hide the big goal from my checklist (for obvious reasons).
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 will keep setting bigger and bigger goals. So learn to enjoy the process. The people who do this well are the ones who enjoy the journey.