INTERVIEW | Make Money by Knowing When to Quit with Lindsay Crouse
Lindsay Crouse is a journalist and 15-year veteran of The New York Times, where her Emmy-nominated work on women’s sports helped change policies across the industry, including bringing maternity protections to athletes at Nike. She also commissioned the Times’ first Academy Award-winning film. Now, with her first book, The Case for Quitting, Lindsay challenges the idea that perseverance is always the key to success. She joins Travis to discuss the difference between healthy persistence and stubbornly sticking with something that no longer serves you, how to recognize when it’s time to move on, and why quitting can be an essential step toward your next chapter.
On this episode we talk about:
How Lindsay went from a small town in Rhode Island to a 15-year career at The New York Times.
Why quitting isn’t necessarily failure—and how letting go can create room for new opportunities.
The role fear, embarrassment, and regret play in keeping people stuck on the wrong path.
How entrepreneurs can recognize the sunk cost fallacy and know when to walk away from a failing venture.
Why successful people need to learn when to say no, set boundaries, and moderate their ambition.
Top 3 Takeaways:
Quitting can be a tool for success. Walking away from a job, project, or goal that no longer serves you can create the space needed to reset, refocus, and pursue something better.
Your strengths can become your weaknesses. Persistence, ambition, and saying yes to opportunities can help you get ahead—but without boundaries, those same traits can lead to burnout, poor performance, and missed priorities.
Don't let past investments dictate your future. Instead of continuing something simply because you've already spent years or money on it, ask yourself whether you would choose it if you were starting today. Sometimes accepting a loss now prevents a much bigger one later.
Notable Quotes:
“Our strengths, in fact, often are our weaknesses if we don't learn to moderate them.”
“Our minds will lie about how much we can take, but our bodies tell the truth.”
“It doesn't get easier to quit with time. We just get older.”
Connect with Lindsay Crouse:
- https://lindsaycrouse.com/
Instagram: https://www.instagram.com/lindsaycrouse/
Book: The Case for Quitting — available wherever you buy books.
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