The Dog on the Nail: Why Most Leaders Wait Until It’s Too Late

You’re the dog on the nail. The question is: when will you move?

I want to tell you about a dog.

Not just any dog - a dog lying on a nail, whimpering in pain. A young man sees this and asks the old owner, “Why doesn’t he just get up?”

The old man shrugs: “It’s not hurting bad enough.”

That dog is you. 

That nail is your succession plan. 

And Robert’s story is what happens when you wait too long to move.

The $100M Lesson Robert Learned Too Late

Robert built his business now worth hundreds of millions. He bought the toys, played at generosity, and thought he’d won.

Then came the diagnosis: “Lung cancer. Metastasized. Not much time left.”

I asked him, “What does finishing well mean to you now?”

His voice broke: “Legacy. How I’ll be remembered.”

What he said next made me sad: “Money means nothing. The one thing I need—time—is the one thing I don’t have. I waited too long to teach my grandchildren what matters.”

Robert’s nail? Ignoring succession until the pain was unbearable. His whimper? “I filled my life with activity, not purpose.”

Now it’s too late.

Why You’re Still Sitting on the Nail

You’re not stupid. You know you need a succession plan. But like the dog, you tolerate the discomfort because:

1. “It’s not that bad yet.” (Spoiler: Ask Robert how “not that bad” feels at 68 with no plan.)

2. “I’ll do it next year.” (Next year becomes never. See: Henry, 77, still running his $100M business alone.)

3. “My business is my identity.” (Then what happens when you’re gone? Poof—no legacy, just liquidation.)

The truth? You’re not avoiding the work of succession planning. You’re avoiding the reckoning—admitting this isn’t your business. It’s a torch you’re meant to pass.

How to Get Off the Nail (Before It’s Too Late)

Robert’s regret wasn’t selling his business. It was wasting his victory lap—the years he could’ve spent mentoring, embedding values, and ensuring his impact outlived him.

Your move:

1. Write your eulogy. (Not morbid—clarifying. What do you want it to say?)

2. Ask the “bus question”: “If I got hit by a bus tomorrow, what would happen to my business?” (No plan? That’s your nail. Get up.)

3. Start with the “3 D’s”:

   • Discover your true purpose (beyond profit).

   • Discern who carries your torch.

   • Devote time now to train them.

The Question That Changes Everything

Robert’s last words to me: “I thought I had time. Then I didn’t.”

So here’s your question: What’s your nail? (And when will the pain be bad enough to finally move?)

Hit reply and tell me—I’ll help you name it. Then let’s get you off the porch.

Talk soon, 

Harry T. Jones

P.S. Know someone sitting on a nail? Forward this. Their future self will thank you.