“Whenever you have a choice of what to do, choose the more interesting path."

In honor of our upcoming Free Time x Long Game IRL event in Miami on February 1 and 2 (it’s not too late to join!), today I’m bringing you a favorite episode from the earliest days of the Free Time pod. In this conversation with Dorie Clark—aka “DC”—one of my closest friendtors, we discuss how she "optimizes for interesting," says no to good opportunities, builds relationships by following her "no asks for a year" rule, and when to call on trusted advisors to ensure you don't quit something too soon.

We're discussing her bestselling fourth book, The Long Game: How to Be a Long-Term Thinker in a Short-Term World—be sure to grab your copy for even more insights on how to apply strategic thinking to your biggest vision.

This episode originally aired on September 28, 2021.

More About Dorie: Dorie Clark helps individuals and companies get their best ideas heard in a crowded, noisy world. She has been named one of the Top 50 business thinkers in the world by Thinkers50, and was honored as the #1 Communication Coach in the world by the Marshall Goldsmith Leading Global Coaches Awards. She is a keynote speaker and teaches executive education for Duke University’s Fuqua School of Business and Columbia Business School. Dorie is the author of The Long Game: How to Be a Long-Term Thinker in a Short-Term World, Reinventing You, Stand Out, Entrepreneurial You.

🌟 3 Key Takeaways

• Building and Maintaining Relationships: Dorie doesn’t make any significant asks from new connections for at least a year. This strategy is aimed at building genuine, agenda-free relationships, nurturing them over time, rather than using them for immediate benefits.
• Optimizing for Interesting Opportunities: Pursue what genuinely interests you rather than feeling pressured to follow a predetermined passion or path.
• Balancing Opportunities and Saying: It’s a skill to decline opportunities, especially alluring seemingly “free” ones. Evaluate opportunities based on alignment with your long-term goals and the true cost of saying yes, including opportunity cost, time, and energy.

📝 Permission

“You don’t have to do this,” for types of events that you hate attending! Decline joyfully.

✅ Do (or Delegate) This Next

What decision would you make about a current or future project if you were optimizing for interesting?

🔗 Resources Mentioned

• Dorie on the web, Instagram: @dorieclark, LinkedIn
• Articles: Dorie on HBR
• Video: TEDx—How to Future-Proof Your Career
• Free Time Miami on Feb 1 and 2: Learn more and register here »

📚 Books Mentioned

• Dorie’s Books: The Long Game, Reinventing You, Stand Out, Entrepreneurial You
• Decoding Greatness by Ron Friedman
• Free Time: Lose the Busywork, Love Your Business
• Pivot: The Only Move That Matters Is Your Next One
• Life After College

🎧 Related Episodes

• Russel Brunson's The Marketing Secrets Show
• Pivot: 298: Building a New Network and Becoming Broadway Investors with Dorie Clark and Alisa Cohn
• 268: Decoding Greatness with Ron Friedman
• 58: Monetize Your Ideas with Dorie Clark
• 66: Create Multiple Streams of Income with Dorie Clark
• 33: Find Your Breakthrough Idea and Build a Following with Dorie Clark

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✍️ Check out Jenny’s personal business essays on Substack, Rolling in D🤦🏻‍♀️h

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