It’s a classic tale, and it rings more true now than ever: Play it “safe” or go for it? In the Instagram generation, it’s more true than ever. All we see are the successes of people who have followed their dreams, so to speak. People standing in front of tremendous crowds on a nightly basis, and so on. And then there’s the flip side: There’s the ever-increasing rent, bills to pay, insurance, taking care of a family, and the belief that if you don’t start SAVING FOR RETIREMENT RIGHT NOW you’ll end up working at Walmart until you’re 90!! The Bearded Man himself was a classic example. Believe it or not, he once had himself a fine corporate job working at a Wall Street hedge fund (that he landed in spite of his disheveled appearance). He was making bank, his life was stable, and his parents were proud. But then, in the middle of the year he was set to receive his biggest bonus ever, he up and quit. He wanted to backpack across Asia. His parents were furious, and no one understood his decision. But that’s just the problem with practicality: We’ll all be Knockin’ on Heaven’s Door soon enough, and in the end, playing it safe just has a hard time beating out the memory amazing life experiences. Ask him today? No regrets.