Let me tell you what the greatest heartbreak in the world is.

It’s not being good enough. And I don’t mean for someone else. It’s not being good enough for yourself. It’s knowing that you’re brilliant at one thing, but nothing else lining up the way it should.

You know what I’ve always wanted? To be a great musician. I started playing piano when I was three years old. My grandfather had an old blondewood upright in his basement. I would pound on the keys while he chain smoked Camel’s and drank thin black coffee. I’ve never felt so loved, or so safe as I do when I’m sitting on a piano bench.

Here’s the real heart-smasher: Doesn’t matter how long I practice or how much I focus, I just don’t have rhythm. My hands are small, but they feel giant and awkward when I play. Same goes for guitar and every fucking instrument I’ve ever tried. I got into Berklee in 2002 and I couldn’t cut it. I couldn’t keep up with the virtuosos who weren’t faking it. I’d spend hours in cramped practice rooms trying desperately to translate sheet music. I felt like Jordan Catalano trying to read Of Mice and Men. It was humiliating. I could hear the 17 year old in the adjacent room NAILING Rachmaninoff (he was probably blindfolded for all I knew) while I couldn’t even get through a basic music theory class.  It almost goes without saying, but I flunked out of Berklee. I was barely able to gain admittance to the state university I eventually landed at, and the only reason I did is because I won a prestigious writing award my senior year of high school. But I didn’t want to be a writer. I wanted to be a rock star.

The worst thing in the world is admitting defeat and letting go. There are just some things that hard work and persistence will never get you. Every few years I take a stab at the RPM Challenge. Ostensibly it is a great refresher – a great working out of song writing muscles that have perhaps gone slack from lack of use. What I can tell you is that I’ve written some excellent lyrics and my voice sounds great…. but hoo boy, the rest is straight up humiliation.

There is danger in surrounding oneself with brilliant people while maybe not being as brilliant. Sure, it’s inspiring, but it can be kind of a letdown. There’s a specific face that everyone who has tried and failed in front of an audience of friends will recognize. This face is the “Oh no, Honey” face. It’s a sort of pained half-smile that says “I support you, and I’m so proud of you for trying, but please oh GOD don’t ask how you did because I hate lying”. I am a connoisseur of this face. The friends I respect the most are the people who have the stones to say “it needs work”.

At a certain point a question needs to be asked, and the question is “but seriously, how much more work do I need to put into this before I say ‘fuck it’ and accept the long khaki-clad walk into obscurity”? I’m in my 30s, and I’m not entirely certain that duct-taping a metronome to my forehead is going to make any difference. I never expected any of this to be easy, I just always kind of figured I’d get… better. Maybe even good.

The 30s are a funny time. There’s all this pressure to finally figure out what we want. What the future is. Where we’re going. To make some kind of plan. I’ve known for a while now that my plan is that I don’t have a plan – really just to go where the work is, to follow the tide and try to survive (man).

The worst thing in life is knowing that you have to grow up some time. For a lot of people that means having kids and getting married and I guess having the ability to pay bills on time. I’m still trying to figure out what that means to me… but maybe part of me knows that no matter what “it” is… “it” needs work.