You got to know when to hold ‘em, know when to fold ‘em. – Kenny Rogers, The Gambler
“Never give up.” It’s one of the most repeated pieces of advice in business, sports, and life. Winston Churchill is famously quoted as saying, “Never, never, never give in.” What people often forget is that he added an important qualifier: “except to convictions of honour and good sense.” In other words, grit without wisdom can do more harm than good.
In business, grit is often praised as the ultimate trait of successful leaders. Perseverance keeps you moving forward when others give up. It helps you push through long nights, setbacks, and skeptics. Without grit, many of the world’s greatest companies wouldn’t exist.
But like any strength, grit has a shadow side. Sometimes, the very determination that propels you forward can blind you to reality. It can keep you pouring time, money, and energy into a venture that no longer makes sense.
The Sunk Cost Trap
One of the most common ways grit backfires is through the sunk cost fallacy. You’ve already invested so much—whether it’s dollars, years, or personal pride—that you feel you must keep going.
Think Blockbuster Video. In the early 2000s, they had over 9,000 stores worldwide. Even as streaming technology emerged, leadership doubled down on the brick-and-mortar model, convinced that late fees and foot traffic would sustain them. Netflix even offered to partner with Blockbuster in 2000, but Blockbuster dismissed them. Their grit in holding to the old model led straight to bankruptcy in 2010.
The lesson: staying the course isn’t always noble. Sometimes it’s reckless.
The Danger of Tunnel Vision
Another risk of unchecked grit is tunnel vision. When you’re determined to make a specific idea succeed, you may ignore market signals telling you the world has moved on.
Think Kodak. Despite inventing the digital camera in 1975, Kodak clung to film because that was their cash cow. Leadership had the grit to keep fighting for film’s dominance, but it blinded them to the future. In 2012, Kodak filed for bankruptcy.
Similarly, BlackBerry had incredible perseverance in the smartphone market. Their engineers and executives believed so strongly in physical keyboards that they dismissed the touchscreen revolution sparked by Apple. Their grit in protecting the keyboard—a product once beloved—became the reason they lost relevance.
The Myth of the Lone Hero
Unchecked grit can also lead to stubbornness—believing you alone see the truth and must push forward no matter what.
Think Elizabeth Holmes and Theranos. Her relentless grit and determination were often praised early on. But as evidence mounted that the blood-testing technology didn’t work, she refused to quit. Instead, grit morphed into deception. The result wasn’t victory—it was fraud convictions and the collapse of a multibillion-dollar company.
Contrast that with leaders like Howard Schultz of Starbucks, who had the grit to expand aggressively but also the humility to pull back when overexpansion hurt profitability in 2008. He closed 600 stores, re-centered on quality, and revitalized the brand. Schultz showed that quitting strategically can be as valuable as persevering.
Knowing When to Quit
So, how do you know when grit is working for you and when it’s working against you? Here are three checkpoints:
- Data over emotion. Are you continuing a project because it’s performing, or because you’ve already invested so much?
- Opportunity cost. By staying committed to this path, what opportunities are you missing elsewhere?
- Energy audit. Does this effort energize you or drain you? Sustainable businesses are built on projects that align with both market demand and personal motivation.
Quitting Isn’t Failure
Reframing is key. Quitting doesn’t mean you’ve failed—it means you’re reallocating your most precious resources: time, energy, and capital.
Think Google. They’ve killed dozens of projects over the years—Google Glass, Google+, Google Wave—sometimes within just a few years of launch. Did those quits make Google a failure? Hardly. They freed resources to double down on what worked: Search, Maps, YouTube, Android. Strategic quitting built one of the most profitable companies in history.
The Superpower of Strategic Surrender
In business, grit matters. But grit without wisdom is like driving with your eyes closed—lots of motion, no direction. The real superpower is knowing when to apply grit and when to let go.
Be gritty. Push through challenges. Work harder than the competition. But also develop the courage to stop, pivot, or quit when perseverance turns into self-destruction. Sometimes the smartest play isn’t fighting harder—it’s walking away.