Whatever you do, you don’t want to look like a “Try-Hard.” 
I get the idea. Masculinity is fearless and expansive. If you want to “alpha” a situation, you want to exude effortless competence. A supernormal aura of ease and certainty conveys mastery—the third tactical virtue . You want to be The Fonz to every Ralph and Potsy. You hit the jukebox and it plays. You snap your fingers and chicks pay attention.
But who was Arthur Fonzarelli anyway? He was a big fish in a small pond. Yeah, he really ruled that local family restaurant scene. He taught high school kids how to be a big douchebag…albeit a douchebag with a heart of gold. (I guess he did famously jump a shark , which is something.)
I understand the reason why men want to avoid looking like a “try-hard”—no one wants to be Ralph or Potsy—but I hate the message it sends. It puts appearances before substance. It’s hollow, hipsterish and sophomoric. It’s an easy excuse for never stepping out of your comfort zone and looking awkward.
It’s easy to be “cool” if you stick to what you know and do what you’ve always been good at.
But you’ll never really be great at the things you’re good at, or good at the things you suck at, if you worry too much about looking like a try-hard.
In fact, the easiest way to avoid looking like a try-hard is to be a troll. What could be easier than sitting back and poking fun at the guys who are faking it, but not quite making it? It’s easy to hide in the crowd and mock the man in the arena .
Effortless cool is something you earn. Mastery is on the other side of the learning curve. People seem to accept this—or at least say they do—with activities like “playing an instrument” or “learning a sport.” But when it comes to something that reflects on a man’s reputation as a man, guys seem to worry even more about being try-hards.
Well, my name is Jack Donovan, and I’m a fucking try-hard.
In fact, I recommend that you try to be the man you want to be really, really hard, and make a complete ass of yourself until you finally get it right.
(And then immediately erase all of the evidence from Facebook.)
I’m a try-hard at every new thing I do. Every new habit is like a new pair of boots. It’s uncomfortable until you break it in, and then eventually it becomes so comfortable you forget it’s there.
I don’t have time in life to get butt-hurt about the idea that someone, somewhere is better at something than I am now.
The try-hards who really suck are the ones who lack humility. It’s not the try-hard part that blows, it’s the pushy know-it-all novice who deserves five across the eyes. Find someone who knows what he’s talking about because he has a track record of success. Ask that person what you’re doing wrong and how to fix it. Then take his advice. At least try it. Sometimes it will work for you and sometimes it won’t, but do not assume that you are so special that every problem you have is brand new. Internet access is not a substitute for firsthand experience when it comes to anything but regurgitating raw data. Do you really think that the guy who has been five levels above you for five years has never seen the information you found in five minutes? Doing your own research is helpful, but it’s not everything.
And bragging . . . bragging is for boys.
Real accomplishments speak for themselves. People are always trying to sell themselves before they have a product. Humility is an underrated virtue. There’s nothing wrong with telling your friends you got from point A to point B, but don’t throw it around like it’s a big deal. It just makes you look like an idiot to people who are at points D, G, and X. There is always more to learn, and the guys who seem most willing to recognize that are the guys who have learned the most.
So, stop worrying about being cool and be a try-hard.
Let the stupid hipsters nerd themselves out with ugly sunglasses and ironic moustaches and intentionally unflattering clothes so they won’t look like they are trying too hard to be anything worth being. Let them live life like a joke. Let them be trolls and half-assed hecklers. Let them worry about looking too cool to care. I’m sure they’ll have a great time down at Big Al’s, ruling the local restaurant scene. Like, ironically.
Try hard, make an ass of yourself, and be humble about your progress.
If you don’t take yourself seriously, no one else should, either.