Breakthrough #1: Moving from Fear to Freedom

“I guess I will find out when he dies...”

The words hang in the humid air of the pickup truck, as heavy as the construction equipment rumbling across the job site outside. 

Rick surveys his father's construction site, wondering if he'll ever know the succession plan before it's too late.

Rick’s knuckles whiten on the steering wheel as he stares straight ahead, the frustration in his voice unmistakable.

I had simply asked what I thought was a straightforward question about succession planning for the family contracting business he runs for his father, Robert. The business that employs dozens of workers whose livelihoods depend on its continuity. The business whose multiplier effect causes them to be a cornerstone in their community.

“Well, dad owns the business and I run it,” Rick explains matter-of-factly. 

“He shows up on Fridays to hand out paychecks.”

The tension thickens as I press gently, “What’s the plan going forward?”

Rick exhales sharply, the sound cutting through the hum of the engine. “I can’t even get him to talk about it. It is so frustrating.”

His voice cracks with emotion. “When I bring it up, he shuts me down. I don’t know what’s going to happen.”

Then come those haunting words that still echo in my mind…

“I guess I will find out when he dies.”

The First Breakthrough: Moving from Fear to Freedom

For decades, I’ve watched leaders like Robert come to this critical crossroads, and instead of stepping forward into maturity and emotional growth, they shrink back into fear. 

It becomes habitual. Over and over, leaders come to these crossroads and make the wrong choices.

Not making a choice is, in fact, a choice. 

And the consequences ripple through families, businesses, and communities.

The first breakthrough in succession planning is confronting these fears head-on. 

The Deafening Silence of Succession Planning

Rick and Robert’s story represents a crisis I witness repeatedly in my work with businesses. 70% of businesses fail to make it to their second generation of leadership. That’s seven out of ten family legacies that collapse during leadership transitions.

Why the Resistance?

This brings me to my question for you, my readers: Why do you think leaders avoid initiating succession planning conversations?

I’ve witnessed founders who built empires from nothing, who fearlessly navigated economic downturns and fierce competition, suddenly become paralyzed at the mere mention of succession planning.

Will You Help Me Understand This?

I’m genuinely perplexed and increasingly desperate for answers about why leaders resist taking this crucial first step from fear to freedom.

Would you reply and help me? I need your insights desperately (and I read EVERY email).

Your perspective might be exactly what someone else needs to hear to take that first step toward securing their legacy.

The clock is ticking. The silence is deafening. But it doesn’t have to stay that way.

One of the greatest legacies you can leave behind is a business that continually makes a profit and blesses its community for generations. 

The first breakthrough—moving from fear to freedom—is where it all begins.

Harry T. Jones

P.S. PLEASE be courageous and give me your observations about why leaders don’t initiate succession planning. Sharing your insight with our Breakthrough mastermind groups could be transformational!