This is basically how I live my life. Throughout high school and freshman year college (I'm 19) I was always so concerned about things that were utterly unimportant in hindsight, like not offending people, making friends, not being a shut-in (I've always been an introvert). I've found that simply not caring about stuff has made the biggest improvement in my life satisfaction.
For example, I tried to make friends in the first week of college by talking to random people. I joined some clubs and went to events. This completely failed, I didn't click with anyone; these kinds of things didn't fit with my personality. All of my current friends I've met serendipitously. And, because I stopped caring so much about it, I think I have much better social skills now.
I think that this passive philosophy is important for finding happiness, but that going against the grain is exactly what it takes to achieve success.
In my mind the hardest part of life is figuring out and prioritizing what I should do. During my freshman year of college (another 19-year-old here) I was very deliberate about taking classes I was interested in, rather than ones that my friends from orientation were taking. As a result I learned a ton of great stuff, I had an awesome schedule, and I met kids I wouldn't have met from just staying within my comfort zone. At the same time, I missed out on valuable chances to get to know other kids that were in the same boat as me: fledgling freshman looking for a friend group. I think if I had gone with the flow in this situation I would have been much happier that first semester. I would've been taking easier classes, getting more sleep and exercise, and hanging out with soon-to-become lifetime friends. That's what I've been trying out this semester, and it's turned out that I'm much happier for it. But is this a road I want to keep going down?
In tasting the happiness of wu wei and satisfaction of focused drive, I've realized the dilemma that I've always been in. As a social yet ambitious individual the hardest part of my life has been finding balance.