Show Notes
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:
Instagram: https://www.instagram.com/lindsaycrouse/
Book: The Case for Quitting — available wherever you buy books.
A Word from Our Sponsors:
- The most successful business owners don't do it all themselves — they delegate. Upwork lets you build a team of highly skilled specialists for every function your business needs, so you can focus on what you do best and let experts handle the rest. Visit Upwork.com right now and post your job for free!
- Scribe captures workflows as work happens and automatically generates step-by-step guides with screenshots and instructions, so no one has to sit down and write documentation from scratch. Learn more at scribe.how/tmm and mention Travis Makes Money for your first month of Scribe Capture free on select plans.
- When you need a legal hand, visit LegalZoom. Go to LegalZoom.com to get started! Learn more about your ad choices. Visit megaphone.fm/adchoices
More from Travis Makes Money
In this clip from the Shane Sams Podcast, Travis Chappell shares how he used podcasting, conferences, and intentional networking to rebuild his circle of friends and create meaningful relationships with successful entrepreneurs. Travis explains why adult male friendships are essential, how a podcast can open doors to people you never thought you could reach, and why showing up in the right rooms is only the beginning of building real connections. He also shares the vision behind Travis Makes Money and Travis Makes Friends, along with an exciting new content project called Dinner Party.
In this snippet from his conversation on the Shane Sams Podcast, Travis Chappell opens up about how interviewing more than 1,000 people has shaped his perspective on success, ambition, and what it really takes to reach the top. Travis discusses why some high achievers sacrifice more than others, how becoming a father changed the way he evaluates business goals, and why chasing someone else's version of success can leave you feeling unfulfilled. He also shares his journey away from a fundamentalist religious upbringing, exploring the challenges of questioning deeply ingrained beliefs and learning to define his own values and direction in life.
Calum Marsh is a writer, reporter, and editor covering arts, culture, and sports, with work featured in The New York Times, The New Yorker, The Atlantic, GQ, and other leading publications. He is the author of The Glass Box, a narrative nonfiction book exploring the rise and fall of CrossFit and its controversial founder, Greg Glassman. Drawing on years of research and his own experience as a CrossFit athlete, Calum unpacks how a grassroots fitness movement grew into a global business empire—and how the very culture that fueled its success ultimately contributed to its downfall.
In this special episode, Travis Chappell joins the Closers Network Podcast to break down the skills that separate good salespeople from great closers. Drawing from his experience in door-to-door sales, entrepreneurship, and building relationships with influential people, Travis explains why trust is the foundation of every transaction. He shares practical strategies for using empathy, asking better questions, improving discovery calls, and handling objections without turning every conversation into a battle. Whether you're a sales rep, business owner, or entrepreneur, this conversation offers actionable insights into building stronger relationships and closing deals that leave customers confident in their decisions.
Mercer Carlin and Christen Bavero are leadership development experts who help businesses achieve better results by investing in their people. Mercer was a founding partner of Transact, which grew from five employees into a billion-dollar business, where she oversaw more than 1,100 insurance salespeople across four sites and helped build a strong company culture. Christen brings 25 years of experience across public education, public health, and business, including leadership training for fast-growing companies. Together, they founded a leadership development and executive coaching business focused on helping leaders build thriving businesses without sacrificing the people who make them successful.