Recipe #7: The Encore Career (The “Re-Risk” Secret)

At age 65, the world told Dicky DeMott it was time to “de-risk”—to take his chips off the table, head to the golf course, and fade into a quiet retirement.

Recipe #7: The Encore Career (The “Re-Risk” Secret)

Part 7 of the 7-week “Recipe for Executing a Succession Plan” series

Dicky DeMott had every reason to finally slow down. I loved to sit in a swing on his porch and learn from him.

Dicky’s story is a portrait for the Encore Career Recipe. He spent 40 years in education, eventually rising to become the President of Southern Regional Technical College. At age 65, the world told him it was time to “de-risk”—to take his chips off the table, head to the golf course, and fade into a quiet retirement.

But Dicky had a different recipe.

When I asked him for advice as I was starting my own Encore Career, at age 65, he didn’t give me a complex strategy. He just looked at me and said: “You let God know, ‘Here I am.’”

After retirement, for the next 15 years, Dicky entered his Encore Career. Traveling to nine countries on three continents, he built and inspired Gideon camps. He didn’t just retire; he “re-potted” himself. He took all the leadership, wisdom, and energy he had spent 40 years cultivating and applied it to a new mission.

That is the final step in finishing well. It’s not about stopping; it’s about re-risking.

The Key Ingredient: Re-Risk

The world’s playbook says that when you hit it big or reach “the age,” you should de-risk. You protect your resources, your reputation, and your comfort.

But as Dave Blanchard of Praxis teaches, the most impactful founders choose to re-risk. They take the blessings they’ve received—their experience, their relationships, and even their mistakes—and they put them back on the table for a “Redemption Quest.”

As Isaiah 54:2 says: “Enlarge the place of your tent, and let the curtains of your habitations be stretched out; do not hold back; lengthen your cords and strengthen your stakes.”

The Measurements and Timing: Discover, Discern, Devote

You don’t have to know exactly what’s next the moment you hand over the keys. To get the timing right, follow these three phases:

1. Discover (The Dabble Phase): It is okay to dabble for a while. Try new things. Volunteer. Consult. See what brings you joy and where you see a need.

2. Discern: After you’ve dabbled, start to clear the fog. Ask: Where can I have the greatest impact? What is the “one thing” I want to focus on for the rest of my life? What do I want to prune or stop doing?

3. Devote: Once you discern the path, focus your time, energy, and effort. This is where you move from being a “successful” person to a “significant” one.

The Secret Ingredient: Cathedral Thinking

In Barcelona, the Sagrada Familia has been under construction for over 140 years. Antoni Gaudí knew he would never see the finished spire, but he started anyway.

This is Cathedral Thinking. Significant impact often takes longer than a single generation to realize.

Think of the soccer community in Thomasville (TASA). Fifty years ago, it started with just nine players who had to travel 200 miles just to find a game. Today, soccer is the number one youth sport in the community, and five out of six local high school teams recently made the state playoffs.

The people who started those first practices 50 years ago were building a cathedral they couldn’t yet see. Are you building something that outlasts you?

Real Stories: The “Big Toe” Principle

One of our Breakthrough Group members shared a powerful analogy. He reminded us that every member of a team is valuable. “The big toe is just as important as any other body part,” he said. “Try walking without it.”

In ancient times, when an enemy captured a generation of soldiers, they would sometimes cut off their big toes. They didn’t kill them; they just made them unable to fight or stand firm.

Don’t let the “retirement” trap cut off your big toe. You are still a vital part of the body. Choose to re-risk your influence to help others shine.

The Final Test: Finishing Well

Dr. Robert Clinton of Fuller Seminary conducted a famous study on biblical leaders and found a staggering statistic: Less than one-third of them finished well.

Most got distracted, grew proud, or simply gave up in the final miles. Finishing well requires what Nicky Gumbel calls “Prayer and Patience.” It means having a purpose for getting up in the morning and enough money to sleep at night.

When we finally meet our Creator, we want the conversation to be about how we used what we were given to leave the world better than we found it.

Action Steps: Start Cooking Your Encore Career This Week

✅ Audit Your “Mud”: What “mud” or unresolved issues have been created during your transition? Deal with them now so you can start your next chapter with a clean slate.

✅ Identify Your “Dabble”: What is one thing you’ve always wanted to try but were “too busy” for? Schedule a meeting or a volunteer shift this week.

✅ Practice the “Here I Am”: Sit in quiet prayer or reflection. Tell God, “Here I am. I’m available.” Listen. See what doors open.

✅ Tell the Story: Don’t just leave your family money; find ways to tell the story of how that money was earned through hard work and lived out through your values.

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What’s Next?

This concludes our 7-week Recipe series, but the journey of finishing well is just beginning. Starting next week, we are launching a new series: The 7 Steps to Finishing Well. We’ll dive deeper into the “how-to” of this transition, from the first conversation to the final handoff.

P.S. We are on a mission to help 100 founders execute a succession plan and finish well. If you’re ready to move from “Success” to “Significance,” we have two spots available in our Finishing Well Breakthrough Groups. Click here to learn more.