Leadership Lesson: How to Quit Like a Winner

Have you ever wanted to call it quits on a goal for your team—or yourself?

How do you know when the time is right?

How do you know if an opportunity is keeping you tethered securely, or if it’s choking the life out of you?

Quitting is nothing more than weighing two variables and finding that one of them has stopped being worth it. These two variables are something that every human deals with on a daily basis: suffering and sacrifice.

Humans have a knack for understanding the amount of suffering and sacrifice they must endure to reach their goals. The trick is that you need to start doing this consciously and channeling what you find into a decision that leads to a “why,” which leads to a team, which leads to an impossible victory.

As an example, let’s look at two different corporate histories.

Airbnb’s Perseverance

Airbnb is a company that enables people to open their homes to paying guests. That’s a wild idea even today when, as of this writing, the company is currently poised for a massive initial public offering (IPO). But it was absolute insanity back in 2008 when its founders, Brian Chesky and Joe Gebbia, started trying to raise millions for a company most people were sure would be used exclusively by serial killers.

The duo persevered, however, and held on to their idea. The hook, they believed, was the ease and intimacy of people sharing their homes with other people, giving guests the experience of really living in the city they’re visiting. That idea was too powerful to give up, and today the insane company is projected to receive a post-IPO valuation of $190 billion.

That’s one path. But let’s consider another.

The Game That Quit—to Win

Very few people have heard of Game Neverending, an innovative little internet-only video game from a company called Ludicorp. The creators of Game Neverending dreamed of creating a fully immersive digital world, complete with fluid social interactions and a real, dynamic economy. The game had trouble getting funding—and players—and soon Ludicorp was on the verge of collapse.

In the final days of the game’s life, one enterprising programmer launched some simple photo-sharing functionality into Game Neverending’s social system. Photo sharing quickly became the number one activity among the game’s band of diehard players. This put Stewart Butterfield, Ludicorp’s cofounder and chief executive, in a tough position.

Butterfield could ignore the success of photo sharing and leverage the company’s remaining funds into a last-ditch effort to make the game a success—a direction that was championed by most of his employees. Or he could abandon his dream of running a gaming company and start building a photo app.

The decision was difficult, but eventually Butterfield decided to scrap the game and launch a photo company instead. He gave his new start-up an era-appropriate, vowel-discarding name: Flickr.

Flickr became, in a pre-Facebook world, the number one photo-sharing website on earth and was eventually acquired by Yahoo! in 2005 for an estimated $22 to $25 million.

Respecting Your Threshold

These men aren’t special or unique. For every one of them, there are thousands more who refused to pivot, or did pivot and ended up with nothing. The lesson here is not that they were successful. It’s that they became successful by finding and respecting their own thresholds for suffering and sacrifice.

Every human has an undefined threshold that they’re unwilling to go past. We don’t talk about it. We can’t measure it on any objective standard. But it’s there, and it’s there for everyone.

My adventures have taught me that while we all have a threshold for suffering and sacrifice, it’s usually much higher than we think. A person who would be capable of leading a high-performance team takes the time to learn exactly where their line is. Because once you know it, you can tiptoe right up to the edge and actually go further than all the other people who flamed out a mile back because they couldn’t imagine they could make it that far.

A noble quitter is someone who understands this line and learns to respect it. Ask these three questions to judge if it’s time to back off your line:

What’s my ‘why’? Before attempting any goal, you must answer one question: “Why?” Why should you give all your time, energy, and talent to this particular goal or set of goals? Why should your team? If you’re pursuing a goal and there’s no “why” to be found, it’s time to reexamine your end goal.

What’s my capacity for suffering and sacrifice? Every commitment you make requires you to weigh your capacity for suffering and sacrifice. To stay committed to a goal means that you are willing to exchange the amount of suffering and sacrifice this goal demands of you. People who say they cannot do something are actually saying they’re unwilling to endure the suffering or the sacrifice, or both, that are required of them to complete the task.

Where could I refocus? Quitting can be a very productive thing and is often done by those we credit the most with winning. Quitting allows you to focus on a new goal rather than paying the opportunity cost of stubbornly committing to a goal you don’t really find worthy of your time.

The path to doing difficult things is not mindless enthusiasm. It’s about learning about yourself. Learning about yourself is the only way to block out negativity, endure past adversity, and meet the goal you’ve set—or decide it’s time to set another one.

Quitting is not failure. Quitting is realizing that this one goal isn’t right for you and your team, and that you are wise enough to know that it’s time to move on.

Have you read?

The World’s Safest Cities Ranking, 2019.
The Best Hotels In New Delhi For Business Travelers, 2019.
Best CEOs In The World 2019: Most Influential Chief Executives.
Countries With The Best Quality of Life, 2019.