I feel like if you put in a lot of effort into anything, it is almost always a win- win situation. I remember when I sucked at drawing or running, but I tried my hardest and I made some massive improvements and became really good at it.
Even if you fail, it is always good experience in my opinion.
You're trying too hard when you try to fit in a certain clothing style but fail at it pretty hard, when people with a lot of experience know that you're going to fail regardless (think school or work) or when you're trying to get something that you won't get whatsoever (like a GF/BF). Usually trying too hard involves nuisances for people whatever you're trying to do.
I was failing in my P.E classes and my art classes, but every time I failed I made increments in improvement. Eventually I got good.
I had to fail to improve.
That example doesn't fit the description.
It's not clear what you are on about. Did someone tell you, that you are trying too hard?
You know the word "trying" already has a big emphasis on the chance of failing. It doesn't need the "too hard" part for that. The to hard part is used to not describe somebody who tries and either fails or recovers, but who tries in a wrong way.
For example: You want to be good at soccer. Somebody says "hey you aren't really fast at running, practise before you get good at soccer." So you run and run and run, to the point where you only stop to eat and sleep. For a fact, this way you won't get much better at playing soccer at all. Your coach tells you "First of, get a plan, you are trying to hard at getting faster, when you could put a focus in your regular soccer training on speed and still become a great player." This can be contracted towards "you are trying too hard". As in this case and often in real life, the contraction makes only real sense in situations where the phrase is customary and the "goal" is so obvious to be possibly left out. An example: You are trying too hard to get her attention. Now for example, it's a medical fact, that if you want to train your physique, you need to follow the proper order of rest and training phases, to get the best result. Everything you do over a threshold is worse than a waste. Injury recovery is a prime example, where people are often neglecting proper pacing, which hurts them in the long term. So, if you where really trying to hard, you where not achieving your goals thanks to that. You where in spite of that. Also you are not most likely worse at what you do than you could have been. There is lastly no way to point that anything but negatively.
Finally, just trying and trying and trying is no way to solve a problem. It's a way to gain a shot at solving a problem you don't understand and you don't have the facilities to gain an understanding of, but other than that, it's a bad approach at things in life. You made it through once, because the problem you faced was trivial. Try "brute forcing" your way to getting money, friends, love, wisdom and fame (or creating real, artful art) and if you get even one of those things, it was an elaborate series of accidents that got you there, not your approach of "trying too hard".
The negative stigma of trying too hard usually comes about when an individual focuses more on being impressive than improvement or reaching some kind of mutual understanding/recognition. For example, no one is going to fault the person who is trying to lose weight and get in shape by keeping a log, eating healthy and discussing it casually among friends/family/coworkers when asked about it. However, everyone hates that person who's always on about the newest diet, the crossfit olympics, how they are the most fit and can do 100 pull ups (incorrectly) and manages to be knowledgeably ignorant about fitness and health in general.
There are people who try way to hard to be recognized for things that most others just don't care about. Know your niche.
Be careful of what you say, tomorrow or today, for the words you now speak, may become the poison your enemies later seek; truth. "Rules do not exist to bind you, they exist so you may know your freedoms"
Hmm. I'm not really sure how to phrase this...
Trying too hard and doing your best are not the same.
Doing your best is doing everything within your power to accomplish something. It's usually associated with positive action.
Trying too hard is similar but involves forcing yourself to attempt something that is not possible or involves a negative trade off that outweighs the positive.
If you were bad at drawing and became better through practice that would be an example of "doing your best."
If you are bad at running and decided to do a 10k without proper training and conditioning and your heart explodes that's an example of "trying too hard."