I Regret to Inform You… You’re Stuck (And Comfort Is Killing You)
- Harry T. Jones
- 7 days ago
- 4 min read
Part 6 of the “I Regret to Inform You” series on succession planning
“King Charles” didn’t finish well.
That’s what his son Robin calls him now—a nickname earned behind his back during his years as President, CEO, andChairman of the Board of a regional bank.
Known for his domineering ways, Charles had no outside voices he listened to.
Even when his board advised him to build a team to eventually buy the bank and continue his legacy, he ignored their advice and sold at 63.
Less than two years later, the new owners couldn’t tolerate his “kingly” ways and forced him into retirement at 65.
He had never taken the time to consider what it meant to “finish well.”
He assumed selling the bank would bring significance and allow him to continue his demanding style.
He was sorely mistaken.
Retired and without purpose, Charles spent his days at home, watching television and trading stocks online. He lost all personal interaction with people. He no longer solved problems with his team. In a few short years, he passed away.
But Charles stopped truly living long before his death.
I regret to inform you… comfort is slow death.
The 30-Day Test
Recently, I was facilitating one of our Finishing Well Breakthrough Groups. We were working through a planning exercise—asking each founder to articulate their one-year, five-year, and ten-year vision.
One member couldn’t come up with anything.
So we simplified it. We asked: “What if you got hit by a bus and were out for 90 days?
What would need to be in place?”
Still nothing.
We tried again: “What if you had to take a three-month vacation with no phone or internet, and you’re leaving in 30 days? What preparation would you need to make?”
His response stopped the room:
“I can’t think as far out as 30 days.”
This wasn’t a young, inexperienced founder. This was a seasoned leader who had built a successful business. But he was stuck. Comfortable in the day-to-day operations. Unable—or unwilling—to imagine a future where the business could run without him.
Just like King Charles, he was stuck in the comfort of what he knew—ignoring the voices around him suggesting he needed a plan.
I regret to inform you… not having a plan is a plan. It’s just a plan for failure.
And the statistics bear this out: 80% of businesses without a succession plan fail to transition successfully.
The Clarity That Comes Before Breakthrough
Another member of our breakthrough group said something profound after we worked through this exercise:
“It helped focus my mind on the right things and discuss actions not yet done well.”
That’s what happens when you shine light into the dark corners of your business.
Clarity comes before breakthrough.
But you have to be willing to ask the hard questions.
You have to be willing to face the uncomfortable truth that you might be stuck.
Robin, King Charles’ son, talks about his father’s early demise and emphasizes the importance of having parallel interests to develop into your next career.
He notes that “entrepreneurs are stimulated by solving problems for others,” and that “continuing to do so is key to staying vibrant and finishing well.”
King Charles lost the relationships that kept him vibrant and the problems that gave him purpose.
Don’t let that be your story.
The Succession Audit: Five Questions to Reveal If You’re Stuck
Here’s a simple audit to help founders identify their succession gaps. Answer these five questions honestly:
1. The Vacation Test
If you were completely unreachable for 30 days, would your business be:
More profitable?
Less profitable?
In total chaos when you return?
2. The Operational Star vs. Strategic Leader
Do you have a person on your team who can make a $100,000 strategic decision without calling you for approval first?
3. The Identity Test
If you retired tomorrow, can you name three non-business activities that would provide you with the same sense of purpose and significance that your company does today?
4. The Soul Test
Is the secret sauce of your brand—your mission, values, and promise—documented in a way that a new owner could replicate it without you in the building?
5. The Baton Test
Do you have a written, step-by-step timeline for your leadership handover? Or is your exit strategy: “I’ll know when it’s time”?
Scoring Yourself
If you answered “no” or hesitated on more than two of these questions, I regret to inform you…
you’re stuck.
But here’s the good news: Recognizing you’re stuck is the first step toward getting unstuck.
The Choice
You have a choice to make:
Stay comfortable and die slowly on the vine—like King Charles did.Or face the discomfort, create a plan, and finish well.
King Charles ignored his board’s advice. He refused to build a team. He sold without a plan for what came next. And he stopped truly living years before he died.
Don’t let comfort become your slow death. Don’t let “someday” become never.
Take the audit. Face the truth. And take the next step.
We have two spots available in our Finishing Well Breakthrough Groups. If you’re ready to get unstuck and create a clear succession plan, reach out today to claim your place.
Because finishing well requires more than good intentions—it requires a plan, a timeline, and the courage to act.
Comments