The Dip: A Little Book That Teaches You When to Quit (and When to Stick)

Imagine standing at a crossroads where one path is smooth and endless, offering comfort but no real progress, while the other is steep and rugged — this is the essence of the Dip. The Dip is that challenging phase after the initial excitement of starting something new fades away, and the hard work begins. Almost everyone encounters it, whether they’re climbing the ladder of a career, learning a new skill, or building a business. It’s the moment many decide to quit, overwhelmed by the difficulty and frustration. But here lies the secret: those who push through the Dip gain access to extraordinary rewards because scarcity makes success valuable.

Think about the hundreds of people who start law school each year, but only a handful make it to the top clerkships. Or the countless entrepreneurs who launch startups, but only a few survive the grueling early years to dominate their markets. The Dip acts as a natural filter, ensuring that only the most committed and focused succeed.

But quitting isn’t always a sign of failure. In fact, strategic quitting is a powerful tool to avoid wasting precious time and resources on pursuits that won’t pay off. Imagine a woodpecker tapping twenty times on a thousand trees, never getting food, versus tapping twenty thousand times on one tree and finally getting dinner. The lesson is clear: focus your efforts where they matter most and quit the rest. This is not about giving up on your dreams but about choosing the right dreams to pursue.

Many people grow up with the belief that quitting is shameful, a moral failing. Yet, clinging stubbornly to a dead-end job, a failing project, or an unproductive relationship often wastes years of potential. Quitting the wrong things frees you to devote yourself to the right challenges — the ones that offer a real chance to be the best in the world.

Understanding the Dip is the first step to mastering your journey. It’s a call to embrace the hard parts that lead to mastery and to have the courage to quit the parts that don’t. This balance between persistence and quitting is the art that separates winners from everyone else.

As we continue, we will explore why being the best matters so much, and how the marketplace rewards those who overcome the Dip with outsized success. Let’s move forward to understand what it truly means to be the best in your world.