Knowing When to Quit and When to Stick

“Should I stay or should I go now? If I go there will be trouble. If I stay, it will be double.”

– The Clash

I suck at quitting. Seriously, it’s a flaw. Since 2013, I’ve read 759 books while only abandoning three. Why did I trudge through all those 1- and 2-star books? Because I often hang on when I should let go. In college, I watched Sister Act II: Back in the Habit until the credits rolled. I’m pretty sure this qualifies as a form of self-abuse. I justified staying because my date picked the movie. When the lights came up, I discovered she’d been asleep for who knows how long. This haunts me.

If you want to know where this foolish level of commitment comes from, I’ll share. When I was in fifth or sixth grade, I fell hard in a mile race. I was in the lead going into the second turn of the final lap. The runner behind me clipped my heel and down I went. I bloodied both knees, an elbow, and my chin. Everything hurt— especially my pride. By the time I found my footing and resumed the race, the pack was approaching the finish line. I didn’t see the point of running the final 200 meters and limped across the infield to the bench. 

On the way home, I could tell my dad was upset. “I’m really sorry you fell and I’m glad you’re not seriously hurt,” he said. “But I’m really disappointed you didn’t finish.” I started to protest about getting tripped and being hurt but he cut me off. “Everyone knew you were probably going to win. But if you had walked to the finish line, they would have given you a standing ovation.” 

I don’t remember anything else he said, but I remember the message: Don’t give up. For the most part, this was an A+ parenting moment. If you list the biggest successes of my personal and professional life, most would be the product of dogged persistence and doggish loyalty. I rarely give up. The downside has been sticking with things and people I should have quit. 

Thanks for the therapy session. How much do I owe you? 

I’ve gotten better at distinguishing between “giving up” and “quitting.” For me, giving up is abandoning a strategy, a person, or a situation prematurely. Either you haven’t given it your all or you haven’t given it a fair chance. Quitting is stepping away when you have given the strategy, the person, or the situation a fair shot and it’s clear that it is not serving you anymore. Giving up is a shade of surrender. Quitting is a form of agency. You’re removing yourself from a bad situation.

It’s incredibly hard to know which decision is correct in the moment, or even after. We all have a cognitive bias toward the choices we make. If we choose to stick it out, we naturally elevate evidence that supports our choice. When we judge in retrospect, we are biased by the outcomes. Author and professional gambler Annie Duke calls this “resulting.” If you bet on an offsuited 2-7 (widely regarded as the worst starting hand in poker) and somehow win, you still made a horrible decision. Yet some poker players will interpret the outcome to mean their gut is superior to the odds. 

So, how do you decide? 

A friend recently asked me for advice on whether to give up on an employee. I replied with a question: “Have you given them a chance to be who you need them to be?” This has become an important question for my relationships. If I’m unhappy with someone, I must first assess whether they know how their behavior is impacting me and give them a chance to be who I need them to be. Hanlon’s Razor is one of the mental models I try to live by. It states: “Never prescribe to malice what could also be attributed to ignorance.” This is often true of that driver that cut you off on the freeway and of that coworker that seems to have it in for you. Yes, some people are jerks. Much of the time, people just aren’t aware of how they come across. Sometimes we discover our own DNA in a bad relationship. 

The same is true of strategies and goals. I ask myself if I’ve truly done what it takes to make it work. Scott McNealy, co-founder and former CEO of Sun Microsystems, was once asked how he made decisions. He shared that he spent “much less time and energy worrying about ‘making the right decision’ and much more time and energy ensuring that any decision I make turns out right.” I love that philosophy within reasonable limits. You can make the right decision or make your decision right. Both require the correct approach and effort. If you invest in both and it’s still not working, maybe it is time to quit. I find I have far fewer regrets when I quit after putting in the proper effort. 

The common thread here is accountability. The return you get is often proportionate to your investment. Are you approaching the situation correctly? Have you given it your all? If yes, it may be time to move on. If no, lean in. 

Extraordinary success requires extraordinary effort and time. When we give up, we cheat ourselves. Starting over is seductive, but we lose momentum and the benefit of previous experience. The most successful people I’ve studied play the long game. They change their approach and redouble their efforts. They identify what matters and make it stick. Strategic quitting plays a part. By shedding things that no longer serve them, they free up energy and effort for what does. 

One question to ponder in your thinking time: What is one thing you can quit today to free up more time and energy for a higher priority?

Make an impact!
Jay Papasan

Co-author of The One Thing & The Millionaire Real Estate Agent ​