The Upside of Quitting: Why Quitters Always Win and Losers Never Quit


“Quitters never win and winners never quits.”

These are the infamous words of legendary NFL coach, Vincent Lombardi, considered by many to be one the greatest coaches in American sport history.

Almost half a century after his death, Lombardi’s words are still a good representation of what we believe about success today—that winners never give up and losers always quit.

But, what if our beliefs about success are backwards?

What if quitting could improve the odds of success and grit or perseverance could leave us worse off?

The Art of Not Losing Money

In the business of trading, roughly 90% of day traders lose their money, whilst the remaining 10% make obscene amounts of money. [1]

We’re talking hundreds of millions of dollars a year lost by the losers and gained by the winners.

At some point in the 1980s, Jack Schwager, a renowned expert in futures trading (the buying and selling of an item in the future, based on an agreed price today), began his search for answers to what separates the winning traders from the losing pack.

To solve this mystery, over the next twenty years or so, Schwager researched and interviewed the most successful traders of our time—including traders who had amassed billions of dollars, averaged 30 percent returns on their money each year for up to twenty-one years and grew thirty thousand dollars into eighty million dollars.

After putting together his findings, Schwager discovered a common trait—aside from skill level—shared by the top traders.

A common trait that provides some insight into a habit shared by highly successful people across all fields.

The Cost of “Get-There-Itis”

On one hazy, dark night in July of 1999, John F.Kennedy Jr.—the son of President John F.Kennedy—piloted the take off of a flight, en-route to Martha’s Vineyard for the wedding of his cousin, Rory Kennedy.

As Kennedy navigated the aircraft along the Connecticut coastline and over Rhode Island Sound, a sudden haze and darkness clouded his vision.

Kennedy was disoriented, he could no longer see what direction the plane was flying towards. And then, in a random series of maneuvers, he swiveled the plane to the right and the left, upwards, then downwards—all at varying speeds.

A few miles from his final destination, Kennedy lost control of the plane. Moments later, it crashed into the Atlantic Ocean.

A couple of days afterwards, a rescue team of divers recovered the dead bodies of Kennedy and the passengers—his wife and sister-in-law.

Since the tragic death of John F.Kennedy Jr, there have been several investigations into the possible causes of the plane crash.

Some point the finger at the poor flight visibility caused by the hazy, dark weather condition. Others point to his inexperience of flying a plane in nighttime conditions.

According to Dr. Douglas Lonnstrom, Siena College professor and experienced pilot, there is one standout possible cause—it’s called “get-there-itis.” [2]

“Get-there-itis”—a common word used and sometimes joked about by pilots—is the determination of a pilot to reach a destination, even when flying in conditions that are very dangerous.

Lonnstrom alongside a good handful of experienced pilots suggest that Kennedy had been blinded by “Get-there-itis” on the day of the plane crash.

Prior to takeoff, Kennedy had promised both his sister, Caroline, who was vacationing in Idaho with her family and his wife, Carolyn, that he would arrive at Martha’s Vineyard that night and attend the wedding.

Kennedy was determined to fulfill these promises and fly to the destination, despite two other pilots cancelling their flights due to the bad weather conditions.

In the end, Kennedy’s “Get-there-itis” cost not only his life, but also the lives of his loved ones.

If Kennedy had quit the flight plans, instead of persevering to reach his destination, three lives would have been saved on that day.

Cutting Your Losses to Win Big

Just like Kennedy’s determination to reach his destination, despite bad weather conditions, “get-there-itis” could also blind us in persevering towards achieving a goal, even when the costs outweigh the benefits.

A headstrong determination to persist with a bad business idea, job, relationship, friendship and so on, could cost us much of our money, energy, health and time, which we can never get back.

Once a significant amount of time, money and energy has been invested towards a goal, it becomes more difficult to quit, even though sticking to the goal could cost us as much, if not much more than what we’ve lost already. [3]

Winners avoid “get-there-itis” and pick the right moment to give up on a goal.

In the world of trading, Schwager discovered that the common habit shared by the top traders was the ability to…

“Cut your losses and let your profits run.” (source: Market Wizards: Interviews with Top Traders (Audiobook))

In the world of entrepreneurship, some of the most profitable businesses have been built, after the entrepreneur had quit on another idea and cut their losses.

For example, the social media platform, Twitter, was a pivot idea, built after the founders abandoned their podcasting company, Odeo.

Other examples include YouTube, originally a dating site, eBay, originally a platform for selling PEZ dispensers and Google, which began as library book search engine.

In the world of science, some of the most innovative inventions have been the sequel to a series of abandoned ideas and experiments.

For example, Sir Alexander Fleming abandoned his search for a drug to cure diseases to later discover the powerful antibiotic, penicillin.

What if these people refused to quit on their initial goals? What would the world look like today?

In the book, The Dip: A Little Book That Teaches You When to Quit (and When to Stick) (audiobook), entrepreneur, Seth Godin, makes a strong case that winners quit all the time—they just quit the right stuff at the right time.

Winners quit on different things in their life, to create more time and energy to devote towards something more important and rewarding to them.

Quitting also has health benefits.

According to psychologists Wrosch and Miller, ‘goal disengagement’—that is, giving up on our goals—could also improve overall well-being.

During their one year-long study, which involved tracking the effects of goal setting on 90 teenagers, the psychologists discovered that the participants who refused to quit on unattainable goals experienced higher levels of inflammatory molecule C-reactive protein—a protein linked with heart disease and diabetes. [4]

Winners cut their losses to win big in life.

Quitting Like a Winner

Some goals are worth sticking with and some aren’t.

Sometimes, we have to let go of a business, friendship, relationship, job or idea, to make room for a better one—or in extreme situations, to choose life over death.

Winners quit strategically. They’re not afraid to quit, especially when the costs of sticking with a goal outweigh the benefits of pursuing a different one.

Meanwhile, just like a fighting army that has already been defeated in warfare, losers keep persevering, instead of retreating and waving a white flag of surrender.

In the end, quitters will always win and losers will never quit.

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  1. The actual percentage of traders who lose money varies depending on the source of information. Some sources suggest 95% or more lose money on average.
  2. Dr. Douglas Lonnstrom. JFK Jr. — 10 Years after the Crash, a Pilot’s Perspective.
  3. This is also known as the sunk cost fallacy. The more we emotionally invest into something, the harder it becomes to abandon it.
  4. Miller, Gregory E., and Carsten Wrosch. “You’ve Gotta Know When to Fold ’Em: Goal Disengagement and Systemic Inflammation in Adolescence.” Psychological Science 18, no. 9 (2007): 773–77.
  5. Grit also plays an important role in success. The argument here is that quitting the right goals and the right time, will create more time and energy to pursue better goals.