Generally, they begin with an end in mind. It’s a lot easier to get where you’re going if you know where that is.
Or, as the Cheshire Cat says to Alice, “Which way should I go?” “Where do you want to go?” “I don’t much care.” “Then it doesn’t really matter.” (Abridged)
1. Estimate $X: how much $$$ investment do I need in order for my family to live off interest for Y years so I never work again? For me right now, $X is 5M and Y is 40 years.
2. What do I need to do right now in order to get closer to $X? Maybe it's "study computer engineering". Maybe it's "get a job in tech". Maybe it's "apply for a FAANG company". Maybe it's "Go for promo". Maybe it's "Add more to my retirement savings". Maybe it's even "Change my entire fucking career, I'm at a dead end." Whatever it is will be different for whatever stage of life I'm at.
3. If not at $X, GOTO 1.
4. Retire and do whatever I really want to do with my life.
That's pretty much it for my state machine. I wish I figured this out in my 20s--if I did, I'd be much closer to step 4 than I am now in my 40s.
At some level I think everyone is pushing some part of ‘what I really want to do’ to the future. I know I do. At the same time I think it’s important to remember to enjoy the years leading up to step 4, even if that makes the overall path less efficient.
1: the monk and the riddle
You don’t have to live off interest to retire. 4% withdrawal is good enough [1]. You might be lot closer to retirement than you think.
Do you know what that is? I suspect most people don't, especially after spending 20+ years in various jobs.
Probably. What about the rest of us who aren't really looking to those people for any kind of framework? Part of the whole "thinking there's a grand narrative" that caused me anxiety was trying to model after all of these "successful" people, what they were doing, and realizing I wasn't any happier for it.
Lately, what's brought me a lot of calm wasn't the chase of an "end state" (so to speak) but more optimizing my path. That, personally, and only speaking personally has been INFINITELY more rewarding.
If that's the "it" factor, then so be it ;)
Sergey and Larry tried to sell Google for 1 million dollars, and failed. Zuck thought Facebook would never be profitable. The idea that "successful people" have plan all along is fiction.
They might have a vision and are pursuing said vision, but things rarely turn out anywhere near the way they are intended.