This strikes me as a teenager attitude - trying to look cool. If your stories are great because you go out of your way to try make those stories.. it's not that interesting to other people.
Being boring is seen as bad to teenagers but really, it's not that bad.
What's important is that your criteria is based on what you think is interesting or worthwhile (or by your paraphrase, "cool"), so that you personally are happy with your own story. The mistake teenagers make is trying to optimize for the definitions that others have for those things.
(I say "mistake", but really it's just the natural consequence of not yet having a clear sense of self, which is perfectly normal at that age)
As a teenager myself I experience a lot of external pressure from my peers, adults, and even the education system to not be boring.
My friends don’t want to hang out with someone who is boring. Adults don’t want to talk to a kid who can’t show that they are mature and can’t provide experiences to back that up. Colleges aren’t going to admit a potential student who can’t an tell an interesting story.
There is too much incentive to not be boring in my current environment.
That's why it's a teenager attitude. Teenagers are building themselves, everything is about them mostly. (nothing wrong with that, it's the perfect time and place for that attitude).
But once you're older, you want a companion, kids, strong ties to family and friends, and then you realize it doesn't really super matter that you're boring or not to the people who hold the keys to your future (admissions officers, teachers, professors, etc.), just that 5-10 people close to you aren't bored by you.
> If your stories are great because you go out of your way to try make those stories.. it's not that interesting to other people.
It reminded me of something I've read about the attitude among Math students at Oxford some decades ago - you were only cool if you we've shown effortless brilliance. If, on the other hard, you were working very hard to bring your math skills to a remarkable level, you were basically a rube.
I'm an adult, and I think the story is a reward of its own. I don't share many of my stories, but still cherish them, and love when they resurface in my thoughts.
The adult version of this advice would be "if you do what you've always done, you'll get what you've always got". I rarely regret taking the more adventurous route.
For me, this isn't about being interesting to others, but about making life interesting to myself.
I don’t build my life around it, but I try to sometimes do things that would have tickled my teenage self. I did sell the loud, blue-with-green-flames 1988 Fiero that all the kids in the neighborhood waved at. I still try to do cool stuff and scare myself from time to time.
I agree it’s not bad to be boring... but it’s not the only thing that /I/ want to be.
Being boring is seen as bad to teenagers but really, it's not that bad.