He compares himself with others and always falls short.

Dear Wayne,
As hard as I have tried over the years, I am still dealing with the same feelings of extreme inadequacy. Whatever I do to improve myself or to be successful, it is never enough. Last week I went to a holiday party. It was hosted by a very successful guy—my age—in his beautiful, enormous house. Having gotten back into exercising and playing music again, I was feeling pretty good about myself. But soon after I walked inside, I began to feel less than. I was comparing myself to this guy, and to the other guests, and feeling like a complete failure. It was overwhelming. I could not get out of there fast enough. What is my problem and can I ever expect to solve it?
Signed,
Lesser Than
Dear Lesser Than,
Many of us kick the crap out of ourselves because we can never measure up. No matter what we do, accomplish or achieve, it’s never quite good enough. It never quite gets us “there.” Well, here’s how one man expressed his similar frustration to the men in his men’s group:
“I don’t want to be messed up, but I am—in my own unique way. And you men have come to this work because you’re messed up, too. And I mean that in the most supportive sense. There has always been a part of me—and I’ve heard this from many of us—that has wanted to NOT be that messed up guy. I’ve wanted to be that other guy over there, the one who is always healthy, balanced, successful, happy, blah, blah, blah”
“Well, I’m not that guy. I’m me, this man. And this man has something to be proud of. In fact, he’s got a lot to be proud of, just as you do. If our expectations are off the chart, we will NEVER measure up and we’ll continue to keep kicking ourselves incessantly.”
“So, join me in embracing yourself and realizing that it is the expectation that is nonsense. You are a good man. And you’re even better because you’re committed to being a better man by doing this work in our men’s group.”
This man’s message hit a nerve with many of his compadres. In fact, each man thought the message was written specifically about him. That’s how much we have in common. That’s how prevalent this feeling of “not measuring up” is amongst us guys.
So, back to you. Your problem is that you’re trying to live up to some expectation that is impossible to meet. Chances are you can’t even articulate the expectation. All you know is that you’re always falling short. And so you keep kicking yourself as if that’ll do you any good. Kicking yourself is just a bad habit, as is holding on to these unrealistic expectations.
The way to kick this bad habit is to start really getting to know who you are as a man. Right now you’re lost in someone else’s very nebulous vision of the man you should be. You need to have your own vision so you can take action to become that man you truly want to be.
Look inside. Ask for help. Find some good men to support you in a journey that is remarkably similar to their own. Together we can bust out of these old expectations, create a clear vision and purpose for ourselves, and start feeling great about the men we are.
So the answer is yes, you can solve this problem. And you can get there from here.