When to Break the Glass

Picture this: You are standing in a stairwell. On the wall, behind a small pane of glass, is a red box with a hammer inside. There is a sign above it that reads: “Break only in emergency.”

You have been standing there for a while. You know what needs to happen. But breaking the glass means something changes permanently. Once you do it, you cannot undo it.

Five years ago, we broke the glass.

The pandemic had devastated the entire travel industry. We had already cut everywhere there was to cut. Made every difficult call a leadership team makes to save a company. But the pot kept boiling. And we knew what was coming. 

And to add salt to the wound, we were not in this position because we made bad business decisions. We were in this situation because of world events we had no control over.

How do you tell the founder, the person whose name is the company, whose identity is the company, that is time to find a buyer?

We broke the glass in my mother’s apartment.

The four of us, sitting together, finally saying out loud what no one wanted to say. After more than forty years, Valerie Wilson Travel was not savable without outside capital. My mother had been willing to bet everything to save it. That is the instinct of a founder. The second generation had to lead the conversation she could not lead herself.

And we had to do it while keeping it completely confidential.

Telling the team was the hardest day of my professional life. We gathered in the conference room and on video. First there was silence. Then tears. The sadness in the room felt like a funeral for a family member, because in the most fundamental sense, it was. Valerie Wilson Travel was something we had all built together.

Here is what we did next that I am still proud of: we sat in the fear with everyone. We held a joint fireside chat with the company that was acquiring us. We answered every question.

We sold the family business on April 30, 2022.

The Wider Lens

My mother saw a gap in the luxury travel industry and built a company to fill it. That is what a founder is. The same instinct that built it would have held on until there was nothing left to hold. 

The instinct that creates the company is rarely the instinct that knows when to change it.

And so, the hardest conversations, the “it is time to change” conversation, sit just outside everyone’s job description. So, the conversation never happens. People are not failing in their roles. They are refusing the harder part of the role. Until something forces the conversation.

Every company has two leadership systems. The one that built it. And the one it needs now.

In a family business, in a legacy brand, in any organization where identity and institution are intertwined, the next generation carries a particular responsibility: to see clearly what the people who built the thing cannot see from where they are standing.

That is not disloyalty. That is the deepest form of stewardship.

Breaking the glass is not a betrayal of the person whose name is on the wall. It is honoring everything they built by caring enough to protect it, even when protecting it means admitting that what got you here will not get you to what comes next. And the “magic” you built will not be the same in the next chapter.

The Wondering

Take a moment with these questions. You do not have to answer them all. Just notice which one stops you.

For those in the next generation:

• Is there a conversation you already know needs to happen? The one you have been circling but not starting. What are you waiting for?
• What is the difference between protecting someone and enabling them to avoid a truth they need to hear?
• If you could have the glass-break conversation today, with full honesty and complete empathy, what would you say?

For those who built the business:

• Are the people closest to you free to tell you the hard truth? Have you actually made space for that?
• What would it feel like to be the one who led the change, rather than the one who had to be led through it?

Try This — 5 Minutes

Find a quiet place and a blank page. Set a timer for five minutes.

Write down the conversation you have been postponing. Not the version you would deliver out loud, the honest version. The one where you say what you actually see.

You do not have to send it. You do not have to share it. You just have to let yourself write it.

When the timer goes off, read it back. Then ask yourself two questions:

What am I protecting by staying silent? Is it actually worth protecting?

My Intention

I share this story because I know I am not the only one who has stood in that stairwell. The glass is always harder to break than it looks. The aftermath is always more tender than you planned for. And the pride, the quiet, complicated pride of having done the hard thing with care, is something no one can take from you.

My intention is to keep naming the conversations that do not have a job description. To keep making space for the next generation to lead with both courage and love.

Because that is what it looks like to keep wondering why.

About Kimberly

I spent thirty years inside one of the most relationship-driven industries in the world: luxury travel. I was part of a family business, watched it being built from scratch, was the next generation of leadership, and was part of the difficult decision to sell. I now help financial advisors, family offices, and luxury hospitality businesses prepare for the next generation of client and employee.

Curious about your next transformation? Let KWW Inc. help. Contact Kimberly at kimberly@kwwinc.com

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