How To Quit Like A Winner

While persistence and perseverance are feted as qualities essential for leaders, knowing when to move on is equally important.

- Jason Caldwell

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 is 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 us look at two different corporate histories.

Airbnb’s perseverance

Airbnb is a company that enables people to open their homes to paying guests. That is a wild idea even today when, as of this writing, the company is currently poised for a massive initial public offering. 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 are 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 is one path. But let us consider another.

The game that quit—to win