EP 269 - Let’s Retire Retirement: Derek Coburn’s Bold Blueprint for a Fulfilling Life at Every Stage

In this powerful return to Paper Napkin Wisdom, the bestselling author of Networking Is Not Working and the new book Let’s Retire Retirement dives into a game-changing mindset shift: what if retirement was never the goal? 

Derek is a financial advisor, entrepreneur, community builder, and father. With decades of experience advising high-performing individuals and leading powerful networking communities like Cadre, he’s seen firsthand how many people are grinding through their best years waiting for a someday that may never come. That’s why his napkin—“Let’s Retire Retirement”—is both a provocation and a plan. 

“The subtitle of the book is: How to enjoy life to the fullest now and later,” Derek explains. “Because what’s the point of waiting?” 

This episode is not about abandoning discipline or long-term planning—it’s about shifting your paradigm. Derek offers a compelling argument that if we keep chasing a future reward at the expense of the present, we may never get the life we actually want. 

From Deferred Living to Designed Living 

Derek shares how the “retirement” model came from industrial-age thinking—a system that assumed people would be worn out by 65 and needed time to rest. But with rising life expectancy, improved health, and the flexibility of modern work, many high-performers are capable of thriving well into their later years. 

“It’s not that I’m anti-retirement,” Derek clarifies, “I’m anti-deferring joy.” 

He urges leaders to rethink the way they structure their lives. Instead of slogging through decades to reach a mythical endgame, he encourages micro-retirements, intentional sabbaticals, and rebalancing life now to ensure you’re not just accumulating money—but accumulating moments. 

The Mindset Shift That Changes Everything 

Derek’s take is deeply personal. As a dad and husband, he’s recalibrated how he spends his time. Rather than front-loading his career and back-loading family, he’s building a life that blends both. He believes this is not only possible—but essential—for entrepreneurs and leaders. 

“Why are we so okay with this cultural lie,” he asks, “that the best years of our lives should be sacrificed for the unknown promise of leisure later?” 

In his experience coaching and advising leaders, the ones who thrive the longest are those who remain curious, active, and engaged—not those who drop everything at 65. 

This episode invites listeners to question deeply held assumptions about success, productivity, and legacy. And Derek doesn’t just share theory—he offers practical ideas you can act on today. 

 

5 Key Takeaways from Derek Coburn – Episode 269 

1. Retirement is an outdated concept—design your life instead 

"Why are we deferring the good stuff? Let’s build it into our now." 

• Take Action: Audit your calendar—where are you deferring joy? Schedule one thing this week that brings long-term joy now. 

2. Micro-retirements and intentional breaks are powerful 

"You don’t need to stop working to rest. You need to be intentional." 

• Take Action: Plan a 2-3 day “mini-retreat” in the next 90 days where you focus on rest, reflection, and connection. 

3. Enjoy now and later—it’s not either/or 

"You can be responsible and present. It’s a false tradeoff to think otherwise." 

• Take Action: List 3 experiences you’ve been putting off. Choose one and create a plan to do it this quarter. 

4. Curiosity and contribution are key to lifelong fulfillment 

"Most of the happiest older folks I know are still contributing in some way." 

• Take Action: Identify a way to use your skills to serve a cause or mentor someone—even in a small way this month. 

5. Relationships and community matter more than wealth 

"No one retires well alone. The people around you are your legacy." 

• Take Action: Reconnect with one person this week who energizes you. Reach out and invite a deeper conversation. 

 

Derek’s message is timely, practical, and deeply human. If you’ve ever wondered if there’s more to life than the next milestone, this episode is a must-listen. 

📌 What’s your version of retiring retirement? 

Write it on a napkin. Share it. Start living it. 

👉 Tag your takeaway with #PaperNapkinWisdom and let’s spread the message that fulfillment isn’t a destination—it’s a design choice. 

Connect with Derek:  

www.derekcoburn.com