"Trying too hard" is a phrase that gets tossed around, usually with the cruelest intentions. " You're trying too hard" or "So and so celebrity is just trying too hard". It implies that the speaker has a superior sense of confidence or outright coolness that the subject of the phrase, "you're trying too hard" can never attain and should be admonished for striving for in the first place.
It's a mean thing to say, yet I say it all the time.
I guess I overlook the "try" part. There should never be any shame in "trying" to do anything. The shame should be in not trying, not trying hard for anything. We don't roll our eyes at superheroes, dusting themselves off from a spectacular defeat and refusing to give up. We don't accuse them of "trying too hard". We don't sigh in disappointment at our US Olympic Teams, in any sport, for "trying too hard". We are Americans, we want to win, we want to do what is right, and we like to think we would never give up. There is no "trying too hard" in sports
What I refer to as "trying too hard" is pretending to be someone you are not. When it's so obvious it's painful for others to witness. Women who pretend to enjoy being promiscuous when I can see the loneliness in their eyes and hear it in their voices. I'm not condemning promiscuity, it should be you own choice for yourself, your body and your own well-being. Not because you want to attract men, to solve underlying issues that no can resolve but you. Men that act dumber and meaner than they truly are, to be accepted as "one of the guys". Teens that deny the differences within them, that make them unique and wonderful, to fit in with other kids that don't appreciate or recognize their true potential. This is "trying too hard".
This abandoning everything that is truly "you" in a frivolous pursuit of fitting in or standing out. Not standing out on your own terms, but on someone else's terms, and doing it poorly. When the seams show, your thoughts, words, manner of appearance comes across totally artificial, like a weird batch of Starbursts or Skittles, when they just taste wrong. Making a Herculean effort in an ignoble task.
This is not the same as "fake it 'til you make it", which operates best when a small kernel of your true self DOES reside in the position or title you are after. No, "trying too hard" is when your actions, your attitude, your motivation is completely alien to you, yet you operate through a cloud of delusion, thinking you need to be someone else. Putting forth admirable energy into an exercise that ultimately diminishes your true self. A lamentable waste.
I think "trying too hard" happens after adolescence, usually. Beyond the normal time period of finding yourself, though I suppose that goal is more of a moving target, shifting and evolving throughout life. However that first step in a gradual evolution of your true self should have occurred by now, yes? After we have survived high school? Pure mathematics dictates the majority of us did not "fit in" in some way in high school. We faced a little ostracism in some way for being too smart, too quiet, too loud, too tall, too fat, too skinny, too nerdy, too ugly, too new, too short, too poor, too dark skinned, too light skinned etc. This made us introspective, made us come to terms with who we are. Some try to change their spots, and that is perfectly normal, early on, in our adolescence. Some decide they are just too unique, too brave, too special and they make their own way. There will never be another person like me and I need to own this. This is who I am.
Too see someone bypass this process in their formative years is practically a giant mystery to me. Even the popular kids have their own crisis in confidence, if not in high school then in college, surely. If not then, I don't really see them doubting themselves later on. They surely have cracked the magic formula of fitting in and need not to try so hard. I try to ascertain the motivations of those that do "try hard", but it is still a rune I cannot decipher. Perhaps they didn't suffer in high school, perhaps they did. Don't fight who you naturally are. You shouldn't have to try so hard.