Why You Should Quit Even If It Makes You Cringe

Forty of us ran counterclockwise in a giant circle on the field. My helmet squeezed against my cheekbones.

“Sprint!” the coach yelled.

The circle sped up like a carnival ride. I tried to sprint but my legs dragged, exhausted.

It was late summer and I was about to enter my sophomore year of high school. As a freshman, I’d joined the football team but, due to my athletic ability being slightly less impressive than an inflatable tube man with a malfunctioning electrical fan, I hadn’t gotten much playtime. My position was Left Out (get it? I was left out).

A kid breezed by me.

I lowered my head. My helmet flopped forward as I looked beyond its crisscrossing wires to the grass, which jerked around like I was watching The Blair Witch Project Meets Football Practice.

A plastic strap tapped against the body of the helmet, hammering into my brain as the force of my footfalls bounced up, intensifying my nausea. Tap… tap… tap.

Another kid zoomed by.

“Jog!”

The circle slowed to match my sputtering speed.

Soon after that, the coach told us to take a knee and, as we panted, he talked to us. I don’t remember a word he said. I was too busy fighting to stay upright as the world spun around me.

After a miserable season as a freshman, I had returned to play in the Junior Varsity team. Before school started, the players were encouraged to attend a summer of Captain’s Practice.

Five days per week, I met with half a dozen other guys at the public track and, while attempting to keep up with the rest of the guys running through drills, I proceeded to stumble around like a gangly, sleep-deprived giraffe.

At first, the other players gave me shit for lacking stamina even though I was so skinny. But as the late summer turned into early fall and I didn’t get in better shape, I think they switched to regarding me as some kind of deranged team mascot. They might have even felt a morsel of respect for my persistence…but I never befriended any of them, so I’d never know.

The whole summer, I was terrified of how painful and exhausting the official practice would be.

Then it began.

It sucked just as much as I had been dreading. I started to wonder if I were truly cut out for this.

Should I quit? Could I just leave? How would I do it? Maybe it was worth sticking around another day?

On the third or fourth day of practice, I showed up at the high school. The empty basketball court’s fresh floor wax gleamed and the soft thuds of my steps echoed as I walked to the locker room. What was I doing? I didn’t want to face another practice. I sucked at football. Heck I didn’t even like football.

I almost walked by the assistant coach, a mountain of muscle, but he stopped me. “Look, if you’re thinking about quitting, don’t do it.”

Later, I’d wonder how the heck he knew I was thinking about quitting. Maybe it was the defeated set of my shoulders or my hyena-like slinking around. Maybe enough other kids had quit that he spotted a trend. Maybe he just smelled it.

The muscle mountain continued his lecture.

“I remember from high school the two greatest things were meeting a special girl… and football.”

Ouch, that didn’t help too much. Getting a girl to go out with me felt as painful and confusing as the football team’s offensive playbook.

I nodded and thanked him. He kept walking. I kept walking.

Was he right?

His platitude kept repeating in my head as I left the high school and entered the building next door — the library. It was just as quiet as the empty basketball court but without the cave-like echoes. The scent of old book bindings washed over me — as did a giddy relief.

I won’t go back to practice.

I grabbed a copy of Stephen King’s The Long Walk and read maybe the first fifty pages. It was, somewhat fittingly, about a group of kids who march on a long walk, and if any of them slow down for too long, they’re killed.

I didn’t finish the novel (Ha! I quit two things in one day!), but I did enjoy a relaxing afternoon — my first in a few months.

I had an unlocked locker back at the high school with my borrowed uniform and pads and my cleats — which I owned. The idea of returning to the locker room felt like doubling back into a liquor store after robbing it, so I never did. After school started, I heard through the grapevine that the team found someone else with my shoe size and gave him my cleats.

That's what made me cringe the most... the fact that I left my cleats in the locker for someone to just take.

When I remember that moment, the cringiness erupts in my chest and wriggles up to my throat like a spider advancing toward trapped prey.

That was one of my first big experiences “ghosting” someone. Or, in that case, ghosting the coaching staff and entire team. But I knew they’d survive without their deranged mascot — someone else would have to claim the Left Out position.

Nobody bothered trying to talk me into rejoining the team.

I never saw the assistant coach again. The only time I ever interacted with the head coach was several months later when I held a door open as he carried in a box.

“Thank you, sir,” he said. I don’t think he recognized me.

That was twenty years ago. It feels super weird to type that. When I used to say “twenty years ago” it referred to some childhood thing I don’t remember, where I probably sat around drooling and making gurgling noises — which was, fittingly, roughly equivalent to my talents for football as a teenager. Back then, high school years felt as long as little lifetimes. Since then, the years have blurred together as if God yelled, “Sprint!” to the circle of time, and now I can’t help but keep up.

So, do I regret quitting?

No.

In my case, the assistant coach was wrong — on both counts. I never got a date in high school. I have, however, met my special girl. It took another fifteen years, but my wife was worth the wait.

Was I wrong to quit? Meh. I should have told someone, but no disasters were triggered by my sudden absence.

Doesn’t this go against so much self-help advice that permeates our culture? After all, quitters never win and winners never quit, right?

In her bestselling book Grit, Dr. Angela Duckworth cites the ability to stick with one thing as a key factor in success — hence the title of her book. Apparently, without grittiness, you’re a slick, slippery mess that gets nowhere.

Actually, I think grit is damn important. Later in life, I needed grit metaphorically mainlined into my veins via a daily IV, especially after I went bankrupt and rebuilt my career from zero. My greatest success came when I stopped flitting about, started narrowing my focus, and hammered on a select few skillsets that helped me become financially prosperous. No quitting there.

Then what’s the answer?

Strategic quitting.

Look at the stock market. When you own a stock and the numbers stop working, chances are you’ll do better in the long run if you quit. My main stock portfolio is managed by an experienced, obsessed value investor. In the middle of 2020, the value of my Starbucks and Dunkin Brands holdings had plummeted and remained anemic. He cut them. You could say he quit on them. Persevering, or any praise for doing so, wouldn’t help my portfolio.

Neither would caring about what would be deemed "cringeworthy" either.

Perhaps those businesses will survive and eventually prosper, but sometimes they don’t. It’d be wrong to call someone a quitter if they bailed on Blockbuster stock before the company went belly-up. On the other hand, sticking it out is often good. I sure as heck didn’t flee from stocks entirely, even when my portfolio lost over $40,000 in a single day. Anyone who stuck with stocks after the crash of 2008 — assuming their stock picks weren’t restricted to a handful of companies — has seen their grittiness rewarded. Same with many people, including me, who stuck through 2020.

That’s the value of strategic quitting. That's the value of keeping a cool head... and not worrying about regrets or how people will judge you.

The best investors base their decisions on objective analysis and not their transitory emotions. Those who fail in the market, fail mostly because they buy and sell — or refuse to buy and sell — based on impulsive reactions of fear or greed.

So far, I’ve given examples from the stock market. But what about your life? How do you get strategic about your quitting?

How do you avoid the pain of regret?

You need to discern the difference between your transitory feelings — your emotions — and what truly fulfills you. This is tricky because what fulfills you, like exercise that enhances your health and gives you a sense of pride and accomplishment, often doesn’t feel good while you’re doing it. You need to tell whether your discomfort is just discomfort, which is connected to your emotions, or a bad gut feeling, which is connected to your inner knowing. It gets even trickier because your emotions usually blare like the beat in a nightclub, whereas your gut feelings usually whisper.

Here are a few tips to filter through the noise to hear the whisper you need to decipher:

Think about what you’re considering quitting.

Pretend you could quit anonymously. Imagine that somehow, you could magically quit without anyone ever realizing it — now and forever. Pretend you could re-write the past so nobody knew about your commitment, even from the beginning. This way, you wouldn’t get any grief for quitting but you also wouldn’t get any credit for sticking it out. Nobody else’s opinion or gossip matters — only your own.

Would you stay? Or would you still quit?

When I quit the football team, I figured nobody would demand, teary-eyed, that I come back. That cleared the emotional fog and helped me tune into what I wanted without any guilt.

Once you wipe away what other people want, here’s how to tell what you want:

Over a year ago, I started learning from a teacher of Daoist meditation. He’s been training since before I was born.

When we began my first lesson, he looked into my eyes and asked, “Why are you here?”

I answered and, after he was satisfied, we moved on. Later, I thought about the value of the question. It clarified and reinforced my decisions and the direction we would take.

Even if you don’t have someone to ask you that question, you can ask yourself.

If you’re on a date with someone you’ve known for a few weeks and you’re wondering if you’re with the right person, ask yourself, “Why am I here?”

If you’re struggling with a job and you’re wondering if it’s a fit, ask yourself, “Why am I here?”

Your answer might confirm that, even if you’re facing challenges, you’re in a place that fulfills you. Or, your answer might confirm that, despite your fear and uncertainty and need to please practically smothering all your other thoughts, your gut is whispering for you to quit.

This question even helps reinvigorate your grit and keep it nice and sandpaper-y. If you’re scrolling through videos, looking for a workout you can follow and your motivation is draining away, ask yourself, “Why am I here?”

When you answer, you confront what’s important to you. Maybe you’ll find the inner fire to keep going and push yourself harder than you thought possible…

… or maybe you’ll come up with nothing.

Both possibilities are okay because if you ask, “Why am I here?” and all you’ve got is a shrug, then quit.

Find something where your answer is full of meaning. An answer to keep going for.

***

After dropping out of college, Nate Rifkin had dedicated himself to self-help and pursuing his entrepreneurial dreams. Yet he failed to achieve any of his goals. Worse, he spiraled into debt, drank every morning, felt lonely, lost, and hated himself.

A few years later, he went through a brutal bankruptcy and a stint spinning signs on a street corner. He could have wallowed in regret. Instead, Nate Rifkin climbed out of his hole and quadrupled his income, married the woman of his dreams, and found happiness and contentment. He's about to publish a book on how he did it. Read more about his book here.