If you don't think you're doing what you should be, or think you could be doing So Much More, or that you have wasted potential, then maybe you're not successful yet, even if you're doing better on paper than some people who do view themselves as such.
Even a boring thankless job for me is where many of my peers dream they could be.
That said, there is something to having risks be actual risks. A friend of mine who has been much more successful than I have decided to take out a huge second mortgage on his house to start his own business (at the time it was an ISP and he spent nearly all of the money he pulled out on building out his data center and network). I advised him against it, after all if it failed he would lose his house. But his response was sobering, it was "Chuck, I need to know that if I fail I'll lose my house to keep my feet to the fire of not failing." Gutsy? Stupid? He made it work and is "retired" to his own boutique winery. Would I be as impressed if he had failed? I suppose it would depend on what he did after he got through that.
I didn't face any big financial loss, I had no mortgage, debt or capital requirements in the business. Just my own living expenses.
But I really, really, really didn't want to fail. That would mean moving back in with my parents and getting a job.
It really worked. If I had had enough money that I could have been in modest comfort indefinitely, I don't think I would have gotten off the ground.
I see a lot of people who would like to start a business. And they make some efforts here and there. But they have a decently comfy life, and they don't seem to have that drive that motivates you through the tedium, the tiny initial results, the lag between effort and something tangible. I consider it a virtual guarantee of failure.
"Young man, I could probably ask you the same question." The young man looked puzzled. The rich man continued, "Do you feel as though you have enough money?" "Well, sure, I suppose, but it would be great to have more."
"How does it feel--feeling that you have enough money and more would be a luxury? I've never once felt that way, so I can't stop until I feel that way, too."
Devoting your life to getting above some very high percentile in money is not the best use of your only life for most people, in my opinion, but as long as they're not stealing it, it's okay with me if others want that for themselves (and I don't feel entitled to a share of it.) I think we all should take seriously the responsibility to support ourselves and to help others who can't, but beyond that, there are countless forms of success that are as worthy as "owning lots of valuable things".
I've met simple people, with not much money or education, although they are successful to me cause they managed to create a nice family and have a happy life. Something that usually its hard for people working towards their careers 24/7.
Hesiod once wrote 'Moderation in all things'. That personally is my moto. I don't have to have done something that is out of this world to be successful. I can be successful enough by valuing my own time, raising my kids in a proper manner and generally being happy. If I am happy, I am successful.
The topic is more about attributes of people who do large scale endeavors. Success should not be used in this context.
Eventually if you want to scale yourself in the exponentiation formula you become a vc, vs grist for the founder mill.
You only have so many 1% 5 year adventure chances to do a startup before you find your 50 and dont have much to show for your life.
If each have a %1 chance of success, it's very likely that the 6 adventure person wouldn't have much to show at the end of it.
Ending up an equivalent of mr. bullet ball is horrifying: https://www.youtube.com/watch?v=leHwNiXgnh0
Because of survivorship bias, you usually never hear about these people.
Many people also try only 1 or 2 adventures, and if unsuccessful go into normal employment. But you jump off the 'potential exponentiation train' that sama describes by doing that, and you've lost out on 5-10 years of potential compound savings growth, which for many who can work at FANG instead means a million or two.
You also get to learn a lot and do fun stuff at FAANG employers too.
Notorious B.I.G. - may he rest in peace, has a great song which IMHO is pure wisdom when it comes to money - "Mo' money, mo' problems"
So be -content- with what you have. And being content is an art form - easier said than done.