http://artofmanliness.com/2011/01/24/dont-should-all-over-yourself/Should-ing on one’s self comes in two forms. First, it could mean doing what you think others expect you to do, doing the “right” thing despite what your hopes, your conscience, and your gut are telling you. This first type of should-ing is rooted in a sense of guilt or in a hope of gaining approval from others. The second form of should-ing on yourself involves re-living past mistakes over and over again, saying, “I should have done this” or “I should have done that.”
I know lots of men who struggle with the first kind of should-ing (me included! more on that in a bit) and today I’ll be focusing on this part of the equation, sharing my personal story in the hopes that others can learn from my mistakes.
We’re conditioned since grade school to follow a certain pattern in order to become a mature man. You know the drill. You’re probably living it right now:
Take out massive loans and go to college —> Get a 9-5 job with a decent salary and benefits —> Get married —> Have kids —> Take on a mortgage —> Work 30 years in something you’re not terribly passionate about —>Retire, buy jogging suit, play golf, and hold up lines at the post office —> Die.