One area where guys flounder a bit is "the pursuit of happyness", like it's an achievement, but really it's just a fleeting moment of self-awareness that you're in control of the universe right now.
Long-term self-esteem and contentment is through moving forward in waves, increasing what you control (mentally/physically/financially/emotionally) in a surge forward, then pulling back to enjoy the benefits until you feel the need to level up and increase your control again.
Think of it this way, when mum first took you out for driving lessons, you're on top of the world, acutely aware that you are in control of a powerful machine, capable of many great or evil things - your power is in the options. After a while you're no longer focussing on controlling this thing, you have a good handle on how it works, you're enjoying it, but kinda over it.
Then comes the day you get your full license, you hit the road unsupervised, WHOOSH this is awesome! You're not thinking about how cool it is to control the car, that's something you long ago internalised, right now you're in complete control of your fucking destiny! Every road is an adventure you can take and there's nobody else to be concerned about, you're pretty damn awesome.
Of course after a while things ebb, you're enjoying the freedom, but mostly you're not exercising it. You need another challenge. You need to increase your control over the universe or your feeling of contentment will dissipate.
So yeah, this is where a bloke really needs to find balance, push forward constantly trying to improve yourself and your position in life and you'll develop hubris and burn out, sit around not trying to achieve anything new and you'll wither into a husk, your contentment and self-esteem will erode slowly like boiling a frog.
The movie American Beauty is a great example of this.
Go forth and conquer, but leave plenty of time to survey your universe.