This post doesn't contain any new ideas that LWers don't already know. It's more of an attempt to organize my thoughts and have a writeup for future reference.
Here's a great quote from Sam Hughes, giving some examples of good and bad advice:
"You and your gaggle of girlfriends had a saying at university," he tells her. "'Drink through it'. Breakups, hangovers, finals. I have never encountered a shorter, worse, more densely bad piece of advice." Next he goes into their bedroom for a moment. He returns with four running shoes. "You did the right thing by waiting for me. Probably the first right thing you've done in the last twenty-four hours. I subscribe, as you know, to a different mantra. So we're going to run."
The typical advice given to young people who want to succeed in highly competitive areas, like sports, writing, music, or making video games, is to "follow your dreams". I think that advice is up there with "drink through it" in terms of sheer destructive potential. If it was replaced with "don't bother following your dreams" every time it was uttered, the world might become a happier place.
The amazing thing about "follow your dreams" is that thinking about it uncovers a sort of perfect storm of biases. It's fractally wrong, like PHP, where the big picture is wrong and every small piece is also wrong in its own unique way.
The big culprit is, of course, optimism bias due to perceived control. I will succeed because I'm me, the special person at the center of my experience. That's the same bias that leads us to overestimate our chances of finishing the thesis on time, or having a successful marriage, or any number of other things. Thankfully, we have a really good debiasing technique for this particular bias, known as reference class forecasting, or inside vs outside view. What if your friend Bob was a slightly better guitar player than you? Would you bet a lot of money on Bob making it big like Jimi Hendrix? The question is laughable, but then so is betting the years of your own life, with a smaller chance of success than Bob.
That still leaves many questions unanswered, though. Why do people offer such advice in the first place, why do other people follow it, and what can be done about it?
Survivorship bias is one big reason we constantly hear successful people telling us to "follow our dreams". Successful people doesn't really know why they are successful, so they attribute it to their hard work and not giving up. The media amplifies that message, while millions of failures go unreported because they're not celebrities, even though they try just as hard. So we hear about successes disproportionately, in comparison to how often they actually happen, and that colors our expectations of our own future success. Sadly, I don't know of any good debiasing techniques for this error, other than just reminding yourself that it's an error.
When someone has invested a lot of time and effort into following their dream, it feels harder to give up due to the sunk cost fallacy. That happens even with very stupid dreams, like the dream of winning at the casino, that were obviously installed by someone else for their own profit. So when you feel convinced that you'll eventually make it big in writing or music, you can remind yourself that compulsive gamblers feel the same way, and that feeling something doesn't make it true.
Of course there are good dreams and bad dreams. Some people have dreams that don't tease them for years with empty promises, but actually start paying off in a predictable time frame. The main difference between the two kinds of dream is the difference between positive-sum games, a.k.a. productive occupations, and zero-sum games, a.k.a. popularity contests. Sebastian Marshall's post Positive Sum Games Don't Require Natural Talent makes the same point, and advises you to choose a game where you can be successful without outcompeting 99% of other players.
The really interesting question to me right now is, what sets someone on the path of investing everything in a hopeless dream? Maybe it's a small success at an early age, followed by some random encouragement from others, and then you're locked in. Is there any hope for thinking back to that moment, or set of moments, and making a little twist to put yourself on a happier path? I usually don't advise people to change their desires, but in this case it seems to be the right thing to do.