Here are two conflicting sets of perspectives.
On the one hand, there's an argument to be made for self actualization.
On the other hand, there's an argument to be made that the "bugger it all, I'm swinging for the fences" is dangerously unrealistic.
Believe it or not, these two extremes are not mutually exclusive. How do you reconcile them? I take inspiration from one of my teachers, Ken Savage, who says frequently to us in the martial arts: don't reach for what isn't there.
When I was testing for my brown belt long ago, I thought I was a lot better than I actually was. That overconfidence got me injured fairly badly, and it took me two more tries to pass that test, once to overcome fear of re-injury, and one last time to break my beliefs about my abilities in order for me to clearly see what I could and could not do. In order to train for that final (passing) test, one of the senior black belts, Jon Merz, spent 6 weeks applying percussive education to me until those delusions were broken and I could see myself for what I was, not what I wanted to be.
When one of your teachers is barreling towards you, slinging knockout punches and kicks, it's foolhardy to do anything except rely on what you actually know and can do to protect yourself until you find a moment of advantage. You don't get cute or try to be clever, you just focus on not getting your head taken off. Eventually, you know what you are actually capable of, and you make improvements.
That's the danger of a lot of the "self-actualization" advice being given. It's conceptually reasonable advice - shoot for your dreams - but the uncomfortable truth is that many of us, myself included, don't always have a realistic perception of where we actually are with our skills, with our capabilities, with our resources. We can believe we have abilities or resources we don't actually have, and when we try to make our leap, we fall far short of where we believe we should be.
The higher the risk, the more sure you need to be when you make a jump. If you can jump three feet, you can confidently do a one foot jump under adverse conditions. If you can jump three feet, you can reach for three feet, one inch under safe conditions to see what you can and can't reach. The danger is when you reach for something that isn't there under adverse conditions and it forces you to lose focus on the things that you have a solid foundation in - and the "quit it all and do it" is the most adverse of conditions imaginable.
So how do you benchmark yourself? You put yourself in adverse conditions that are reasonably safe and you work on breaking your delusions until you know where you are. The easiest way to do that is to try with a reasonably low risk project that forces you to put all your skills to the test. Volunteer for something, or promote your own stuff if you've got a regular job, but set a goal for yourself and force yourself to hit it until you know what you can and can't do. When you're 6 weeks into a 90 day project and you're not at all on track for your numbers, you'll know what areas you still need to skill up on. You'll know what is and isn't there, and when you face a higher pressure, higher risk situation, you'll know what you can and can't reach for in order for you to achieve what you want to achieve.
Once you hit that point, the idealist self-actualization perspective won't seem like a moonshot. "Quit your day job and break through" will seem like a natural, logical next step and not a pie in the sky dream. It will take time - perhaps years or even decades - to reach that point, but when you do, it won't surprise you. In fact, it may even happen without your notice.
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