Win By Not Quitting

The most startling insights are simple observations, but one must sometimes go to extraordinary lengths to deprogram false assumptions before one can really understand. Truth is easy...if, and only if, you can chop away the dense underbrush of ignorant assumptions.

The following is like that. The epiphany is so gut simple that there's almost nothing there. I've carried it with me for years but only recently did it reach full fruition. If it strikes you as banal, consider removing some underbrush while you reconsider!


The key to winning is persistence.

Unfortunately, that observation jibes easily with preconceptions, so most people wouldn't give it much thought. Sure! You fight and fight and bash and bash and then, voila, you triumph!

But no. That's not it. Let's back up 30 years and meet a hero.

The great trombonist Al Grey from the Count Basie Orchestra had invited me to sit in with him. Al was an old-timey hard-swinging player without any fancy airs or intense harmonic innovations or slick advanced technique. Al was all about joy and soul. He was one of the last of the Mohicans.


By the early '90s, that sort of playing had nearly died out, except in a few pockets in rough neighborhoods where, by coincidence, I hung out on my free nights, sitting in with the only people who ever really "got" me: octogenarian black guys. Family and friends had little idea what to do with me. My only places of comfort were black bars where men wore expensive hats and the sidemen from my record collection took refuge to ply their art. And, despite my age and complexion, I enjoyed tribal bona fides as well. I, too, was of the Mohican persuasion.

But Al didn't know any of this, so when he invited me to sit in, he - and everybody else in the club that night - expected to see a 70-year-old swinging elderly black dude dismantle a slick, glib white upstart from Planet Music School.

It was impossible to predict that I, too, was a swinging soulful elderly black dude. Not in a Walter Mitty fantasy life way, but in reality. That's how I genuinely felt and played. That was my truth. And I earned it, risking my life for years getting from street parking into those venues amid a crack epidemic, not to mention the one hour+ drives out to the boonies of Harlem or Newark or Jamaica or Roosevelt or Hempstead. Nobody knew how far I traveled. They all figured I was local, and that suited me fine. I was family. Comfortable and kindred for the only time in my life.

But on this night, I found myself in shiny Manhattan at a shmancy jazz club where no one, including Al, knew my backstory. So when he graciously invited me to take the first solo on the first song, I had a decision to make. My impulse was to swing the lights out, but I knew Al wanted a foil; a Washington General he could foxily dribble the basketball around. He was hoping I'd play some glib bullshit so he could blow me up with a warm folksy grin (the guy had no maliciousness in him whatsoever).

So I did. I played the role, spitting out tricky bebop lines to deliberately enstooge myself. Why? Because playing straight man to the great Al Grey seemed like a worthy pursuit. I was showing respect, and I knew I'd treasure the memory of his slaughtering me with swinging soul more than one where I'd made it all about me by matching his game. I led myself to slaughter, but it was joyous, like the privilege of being insulted by Don Rickles.

At the time, Al was enjoying a late-in-life renaissance, releasing records as a leader, headlining at festivals...the whole shebang. After six decades as that cool dude back in the trombone section, he was a grand old man of jazz. During intermission, another musician asked him his secret. How had he orchestrated this rebirth?

Al chuckled the weighty chuckle of long experience and shrugged at the simplicity of his reply: "Don't quit! I just never quit!"

That's all you have to do. Don't quit. Keep showing up.

I've chewed on it for four decades, and, to really get it, I've had to chisel away a great many things Al wasn't saying.

Most of us project a heroic cast on our "trajectory". An American confessing unlofty aspirations seems like a stoic monk at best, and a loser at worst. But Al was never a loser. He always played his heart out. He was trying hard; just not to be That Guy. In terms of career and stature, he merely showed up. The big arc of it wasn't aspirational.

Let me try a different angle. You might have noticed that the world goes in cycles. Up and down. No matter how hard you try and no matter how good you are, it will all sink to failure multiple times! And no matter how feckless and stupid other people seem, they all get their moments. That's because it's all in play. Things get better, and then worse, and then better, and then worse. That's the gig here on planet Earth. And as we build out stories about these apparent "trajectories", invested with meaning, we secretly fear that those stories are false, and that nothing (gulp) has any meaning.

The stories are false and nothing has any meaning. It's true. So, take it from Al: you just need to keep going. Wait it out! And the next time your stock rises, take a quick selfie atop the rollercoaster and pin that peak moment just before the grueling drop, while you're still brimming with buoyant exuberance. But you need to stay on the ride long enough to get there. Don't quit! Keep showing up!

I don't know much about Al's endgame, but few humans besides Alexander the Great die gloriously, so I assume he petered out in a bed somewhere with a wince of exertion followed by a sigh of surrender. Sweet dreams, Al. But that wasn't his pinned moment. It always goes south after you imagine you've arrived - because, yet again, it's all a dynamic churn. But Al, having never quit, could say he'd been the cool guy in the trombone section who became a jazz great.

At some point we all reach some semblance of a win. Not because the arc of the moral universe bends toward justice. Not because victory is what you truly deserve. And not because your outstanding attributes can't be ignored. That's all story-telling. No, it's just this: if you wait long enough your number eventually comes up (though seldom in the way you expected).

In truth, there are no wins; just flow. But if you must pretend to keep score, do so while the boat momentarily rises. Which requires staying on the damn boat! Heed the immortal Al Grey, and don't quit! Keep showing up!


“Wait by the river long enough and the bodies of your enemies will float by."
-- falsely attributed to Sun Tzu