Episode #50: Why We All Need a Bad Plan and How to Make It Work with Jennifer Stapleton

Sometimes, the biggest obstacle to success isn’t failure—it’s waiting for the “perfect” plan. In this milestone 50th episode, Chuck welcomes back Jennifer Stapleton to explore why having a bad plan is often far better than no plan at all.

Jennifer shares her insights from the FasTrak program, including how creating a simple “bad plan for success” helped her break through analysis paralysis, build consistency, and drive real results. Together, they unpack practical ways to design a plan you can actually execute, how accountability tools (like giant paperclips!) can keep you on track, and why movement—not endless planning—creates clarity.

Jennifer Stapleton is the founding partner of Fire & Bliss, a communications and marketing firm serving philanthropies and nonprofits. With decades of experience as a strategist, advocate, and senior communications executive, Jennifer has helped organizations achieve major legislative wins, secure funding, and land coverage in top publications. Her unique mix of creativity and strategy continues to empower mission-driven businesses and nonprofits to thrive.

If you’ve ever found yourself overthinking, stuck in planning mode, or waiting for the perfect conditions to start, this episode will help you take action—because even a bad plan can lead to great outcomes.

🔗 Learn more about Jennifer’s work at fireandbliss.com 

🔗 Connect with Jennifer on LinkedIn

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For more from Jennifer, go back and listen to her first guest episode:
Episode #26: Serve, Don’t Sell: The Path to Sustainable Success Listen here