Knowing When to Quit is Mental Toughness Too

We idolize perseverance. Stick it out. Grit your teeth. Never quit.

But mental toughness isn’t about endless suffering. It’s about knowing which battles deserve your grit and which ones demand a strategic retreat.

The Double-Edged Sword of Grit

Most of the “battle stories” from my personal and professional life involve grit and perseverance.

The time I emailed seven times to a prospective employer without receiving a single response, yet I continued, ultimately leading to an offer that turned into my first job in finance.

Or when I spent three months on my friend’s couch after my employer went bankrupt, my relationship fell apart, I had less than $100 in my bank account, and my visa was about to expire if I didn’t find a job.

Reflecting on the past, I realize that my perseverance was driven by meaningful goals, and my resilience and stamina ultimately led me to where I needed to be.

But when applied without judgment, perseverance can become self-inflicted damage.

In George Orwell’s 1945 classic Animal Farm, the animals spend years building a windmill that is repeatedly destroyed. Each time, they double down, confident that grit and persistence will lead to freedom.

But it never does. Instead, it becomes a symbol of manipulation and blind endurance. In the end, their grit becomes their downfall.

We don’t need to go to the allegorical Soviet Union to understand the lesson. Here are a few examples of how this can manifest in our lives:

• Staying too long in a toxic job or relationship because "I'm not a quitter."

• Continuing a doomed project out of ego.

• Pursuing goals that no longer align just because of sunk time.

The Power of Course Correction

In air navigation, there is a rule of thumb that states if the plane is 1 degree off-course, it will be 1 mile off target for every 60 miles traveled ¹. So, traveling from San Francisco towards New York, a one-degree error in heading could lead you to Connecticut or New Jersey.

Just like a plane, seemingly small misalignments add up over time and distance, in work, relationships, and goals. Blindly pushing forward without evaluating and adjusting course isn’t a strength; it’s a recipe for burnout and regret.

Like countless others who started their career on Wall Street, I blindly followed “the path” for many years, ignoring signs of burnout and dissatisfaction, while developing bad spending habits and becoming a slave to the infamous bonus cycle of investment banking.

Only after I realized the damage I’d done to my relationships and the personal goals I’d put on hold, did I ask myself: Does this still serve me? Do I still want to go where this road is taking me?

The lesson for me was that mental toughness isn’t just about endurance, it’s about agility. The goal isn’t to “stick it out”; it’s to stay on target.

What’s Keeping You from Quitting

In order to correct the course, you need to be aware of your current path and biases.

Sunk Cost Fallacy: "I’ve put in too much time to back out now."

As introduced in 5 Cognitive Biases That Are Holding You Back, sunk cost fallacy is sticking with something just because you’ve already invested time, money, or energy.

We want to recover our investment, so we double down on choices that may no longer serve us.

Loss Aversion: "Quitting would mean I failed."

Loss aversion is our tendency to fear losses more than we value equivalent gains. According to Prospect Theory, developed by Nobel laureate Daniel Kahneman and Amos Tversky, the emotional pain of losing $100 is about twice as strong as the joy of gaining $100.

We want to avoid the pain of failing, so we stick it out.

Illusion of Control: "If I just push harder, maybe it'll turn around."

Illusion of control is our tendency to overestimate how much impact our effort has on outcomes.

We think we have control, so we push harder into situations we should be walking away from, convincing ourselves that effort alone will change the outcome.

Direction > Endurance: How to Train Mental Agility

Awareness is the first step. Now it’s time to strengthen the mental muscles through reps.

• Value adaptability over sunk costs. Ask: "Would I choose this again today if I hadn't already done so?"

• Set external checkpoints. Give yourself objective stop-loss points (like investors do).

• Respect effort, but prioritize outcome. Not all effort is virtuous if it leads nowhere.

• Reconnect to your "why." Are you fighting for a meaningful goal, or your ego?

I’ve quit jobs, deals, and even relationships, and every time, quitting what no longer served me freed up energy for the right thing.

Bottom Line

Toughness isn't about gritting your teeth through everything.

It's about being sharp enough to know what’s worth fighting for and brave enough to walk away when it’s not.

What’s one thing you know you should quit, but haven’t yet?

Sometimes the strongest move is letting go.

1  https://en.wikipedia.org/wiki/1_in_60_rule