Came across an old man in a funky bar in Cambridge, Massachusetts on a cold winter night a few years ago. Quite a few years ago.
Funky dude - long white hair, long white beard, battered but functional coat. Holding court in a booth, college kids lined up to ask him questions. When his dimpled beer mug was empty, it was quickly refilled by the next truth-seeker.
I stood back, sipping my whiskey, watching the parade, feeling cynical. An opportunistic old dude and a bunch of idealistic young dudes. But, what the hell - a Cambridge bar on a Friday night - seemed appropriate.
I managed to make myself invisible that night, allowing me to look around and form opinions unobserved. I decided if the old man was just running a scam, well, good for him - free booze is the holy grail in this harsh world. But maybe he actually had wisdom to share. You never know. Wisdom happens, if you hang around long enough. You may not feel it, but it is most likely there. If you are so inclined, share it, but selectively - most people just don't give a shit.
When it got quiet I grabbed two whiskeys and sat across from the barfly philosopher. We shot the shit a little, then I asked if he had any advice for me. He leaned back and took a minute or two to size me up. Kind of felt like all of my weaknesses were on display. Eventually, he looked directly into my eyes and said:
"You will be old before you know it, and you'll have more regrets than victories. You'll become desperate for one last chance at defining yourself honestly, through deeds, not words. Don't let the fear of death paralyze you, and keep you from trying. If you don't try, you will just die, and no one will ever know who you really were."