The don't-sweat-it-you'll-be-able-to-connect-the-dots-in-hindsight approach to life is both forgiving and encouraging in an almost avuncular way, especially when you're going through a period of intense personal turmoil that accompanies rejection. But then again, it suffers from a heady dose of survivorship bias.
And so the question begs, how do you know that you're on the periphery of a cul de sac, and all you need do is retrace your steps and begin with a clean slate? (This would definitely not have augured well for, say, an Airbnb. Then again, languishing in mediocrity or persisting in a stagnating job is like a slow death.)
It does feel a bit trite, but it lines up just fine with the classics:
Military tactics are like unto water; for water in its natural course runs away from high places and hastens downwards.
So in war, the way is to avoid what is strong and to strike at what is weak.
Water shapes its course according to the nature of the ground over which it flows; the soldier works out his victory in relation to the foe whom he is facing.
Therefore, just as water retains no constant shape, so in warfare there are no constant conditions.
He who can modify his tactics in relation to his opponent and thereby succeed in winning, may be called a heaven-born captain.
The lost concept in anecdotes like this is opportunity cost; he was rejected from all those art schools and found success -- by some definition -- in going to NYC. The implication in the story is that success is binary, that you achieve it or you don't.
But he may've switched to advertising at any of those other schools. Or he may have stayed in fine arts and enjoyed even greater success that he can't even dream of now. But those opportunities were lost in favor of the path he took instead (whether by choice or not).
Arguably, if you end up happy and without regrets, you DID succeed. But not everyone has that same metric, and depending on your dreams there's a wide spectrum of possibilities. Being happy doesn't mean you couldn't have been even happier otherwise.
I think there's a few underlying themes in this story:
1. Don't let others get in the way of what you want to do.
2. Rejection isn't the end, it's just a wall to climb over.
3. (This message was definately between the lines) Success takes hard work.
I know a lot of people I applied to school with and eventually graduated with felt entitled to a position to the program or to a job after graduation. But these same people bumbled through school, never really caring or putting in the work to complete the project the way it needed to be completed.
I'm right there with the author in saying never give up, but not giving up takes a lot of hard work and you can't forget that.
In the famous Last Lecture by Randy Pautsch, he said something to the effect that life puts obstacles between you and your goals to make sure you want it badly enough.
I think he actually said that the walls were to separate those who want it badly enough from those who don't. The point is not just that obstacles test you, but that they give you opportunity because others who want it less will give up and you will be the only one left.
I originally saw "fail upwards" in alpinist Mark Twight's writings[1] ten years before that: his sense is to keep going up and over the summit even when things have gone terribly wrong: you may no longer have the option to descend the way you came up.
[1] "Extreme alpinism" (passage can be found on google books)
Probably the best thing I ever quit was my 4 months into my 12 month Honours year at university, I decided to change subjects. (Out of FPGA/HDL programming.. that just wasnt working for me)
Everyone I talked to told me I was crazy as they continued with subjects they didnt enjoy, but it allowed me to choose a subject I really loved and produce something way better than I could have on the original subject. Definitely worth it
Push until you fail - that last, highest place you got to is where you are best; to go one step farther is to enter Peter Principle territory, and you DON'T want to be there (at least not then). Then make the best of that position, and leap from there. The top rung of the ladder may be higher, but it's very hard to stay there - the next rung or two down is far more productive.
And so the question begs, how do you know that you're on the periphery of a cul de sac, and all you need do is retrace your steps and begin with a clean slate? (This would definitely not have augured well for, say, an Airbnb. Then again, languishing in mediocrity or persisting in a stagnating job is like a slow death.)