The One Thing Money Can’t Buy: Planning Your Meaningful Finish
- Harry T. Jones
- 9 hours ago
- 3 min read
“Commit your work to the Lord, and your plans will be established.” — Proverbs 16:3
Robert sold his business for hundreds of millions of dollars.
Having lost the desire to compete, he simply cashed out. With his money, he played with his big toys and tried to be generous.
I hadn’t seen Robert for a few years when he came to town. The first words out of his mouth weren’t about his wealth.
“I’ve been diagnosed with lung cancer,” he said. “It has metastasized and is rapidly spreading.”
Robert’s time was short. When I asked him what “finishing well” meant for him now, he had one word: Legacy.
“Money means nothing,” he continued. “How my children and grandchildren will remember me is everything. But the one thing I need is the one thing I have so little of… time. I want desperately for my grandchildren to know the values worth living and dying for.”
Robert had filled his life with activity instead of purpose—not realizing that purpose was what mattered most. He had simply sold his business instead of passing it on in a way that would preserve his values.
I talk about Robert in my new book, Succession Planning for Impact (The Workbook). His story leads us to Pitfall #7: Failure to plan for a meaningful finish.
>>> Regrets are the result of neglecting what matters most. <<<
What Does “Finishing Well” Mean?
A meaningful finish is a deliberate, purposeful, values-driven transition where your influence and lessons outlast your ownership. It means both you and the business are in a healthy, thriving place at the end of your succession plan.
When you fail to plan for this finish, you often see a dangerous symptom: “Rushing the Throne.”
Why successors rush the throne:
Emergency Mode: The transition started too late, putting everyone in crisis.
Bottled-Up Leadership Hunger: Competent successors, denied decision-making for too long, erupt with pent-up ideas.
Founder Identity Crisis: The founder views succession as an existential threat to their status and relevance.
A Tale of Two Outcomes
Consider “King Charles”—a domineering bank president who ignored all advice to build a team. He sold his bank at 63, but within two years, the new owners forced him into retirement because they couldn’t tolerate his “kingly” ways.
At 65, he was retired and without purpose, spending his days day-trading stocks and watching television. He lost the relationships that kept him vibrant. In a few short years, he passed away—but he had stopped truly living long before then.
Now contrast that with a different Robert from our Breakthrough Mastermind. He was stuck on his second business because his general manager wouldn’t buy it.
Then came the “hot seat”—when everyone in the group focuses their collective wisdom on your problem. Here’s what they saw that Robert couldn’t: His general manager didn’t just want the business. She wanted his wisdom.
Robert’s breakthrough came when he agreed to stay involved on a per diem basis. His general manager stepped into ownership, and now Robert is finishing well—having his cake and eating it too. Picking only clients he loves. Traveling with his wife. Working when and with whom he wants.
How to Plan Your Meaningful Finish
Start early, before you think you need to. Begin succession conversations decades before retirement. Confront your fears and internal resistance now.
Phase leadership development. Delegate non-critical projects first. Allow controlled failures. Gradually increase authority over five to ten years.
Build a real team, not a figurehead board. Include truth-tellers who ask hard questions. Rotate successors through roles to test competence.
Reframe your role. Shift from operator to encourager-in-chief. Learn to ask questions, let others provide answers, and speak last—if at all.
Your Legacy Awaits
Through Robert and “King Charles,” we see that succession planning always requires a shifting of roles. You may have always been the leader in suggesting solutions. Now you must become the guiding coach—ensuring your values and lessons continue to shape the business long after you leave.
Don’t wait until time runs out to think about your finish.
Ready to Finish Well?
The Succession Planning for Impact (The Workbook) gives you the final tools to cross the finish line with significance:
✅ Discussion Questions
✅ The Pitfall #7 Checklist to audit your transition timing and role transformation
✅ Step-by-step guidance on becoming the encourager-in-chief
Your influence should outlast your ownership.
What do you want your legacy to be? Share in the comments.
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