What Twenty Years of Leadership Taught Me About Traveling Well

For more than two decades, much of my work centered on transformation. 

New strategies. New launches. New ways of working. Important decisions with real people on the other side of them. 

I was often invited into those moments because I could see both sides of the equation: what needed to move forward and the human experience that would determine whether it truly could. 

Over time, I learned something that followed me far beyond the boardroom: 

The best strategy doesn’t ask people to carry more. It creates the clarity and confidence to move forward differently. 

I didn’t know then that this idea would eventually help shape the way I think about travel. Looking back, the connection feels almost inevitable. 

The best recommendations begin by listening

Some of the most important conversations of my career began before anyone had the answer. They began by listening. 

Understanding what mattered. Asking better questions. Recognizing what wasn’t being said. Seeing the goal alongside the people who would ultimately experience it. 

I’ve found the same to be true in designing travel. 

There are beautiful hotels everywhere. Extraordinary destinations. Remarkable experiences. Endless lists of places everyone says you should see. 

But abundance isn’t the same as clarity. 

The more important question is whether any of those choices are right for you. 

How does your family actually like to spend time together? What makes everyone light up? Where do you want adventure, and where would a little ease change the experience? What would make you come home thinking, I’m so glad we did it that way? 

The right recommendation begins there.

Preparation creates room for possibility 

My professional life taught me to anticipate. 

What needs to happen first? Where could complexity emerge? Which decisions matter most? What can be simplified now so there is greater freedom later? 

I approach travel much the same way. 

The room. The transfer after an overnight flight. The dinner reservation. The private guide who knows exactly how to bring a place to life. 

None of those details is the reason you travel. 

But each can shape how it feels to be there. 

I don’t believe preparation is the opposite of spontaneity. Done well, it creates room for it. 

When the decisions that deserve attention have already been made, you can stay for another glass of wine. Wander down the street that caught your eye. Go back for the amazing chocolate you sampled earlier. Linger in the museum as the crowds fade and everything feels a little softer. 

The plan has done its job. 

On a shore excursion in Honduras, I remember watching my son ask our guide if we could stay a little longer in a small artisan market we’d stumbled upon. 

It wasn’t because he wanted another souvenir. 

During the drive, he’d learned something about our guide’s childhood that stayed with him. Instead of hurrying back to the ship, he wanted to choose a small gift, something that simply said, You matter. 

We stayed longer than we’d planned. 

Years later, I couldn’t tell you exactly what time we returned. 

I can tell you every detail of that conversation. 

That’s the kind of moment thoughtful preparation quietly protects. 

The experience belongs to the people living it 

Leadership also taught me that something can make perfect sense on paper and still miss the people entirely.

Travel can too. 

The most impressive suite isn’t automatically the right one. The restaurant everyone is talking about may not be where your family has its favorite dinner. An itinerary can include every important sight and somehow leave no room to experience where you actually are. 

Expertise matters. 

But expertise without understanding is simply someone else’s opinion. 

That distinction has become fundamental to the way I design travel. 

I don’t believe the measure of a beautifully designed journey is how impressive it looks on paper. 

It’s how right it feels to the people living it. 

Knowing what matters means knowing what doesn’t

Good judgment isn’t only about knowing what to add. 

Sometimes its greatest value is knowing what to leave out. 

Not every day needs another reservation. Not every upgrade meaningfully changes the experience. Not every highly recommended hotel is right for the way you want to travel. 

More isn’t automatically better. 

The goal is to understand which choices will genuinely change the experience and give those decisions the attention they deserve. 

That leaves more room for the things no itinerary can manufacture: curiosity, connection and the unexpected pleasure of discovering that the best part of the day wasn’t part of the plan at all. 

What I thought were leadership lessons were really lessons about people 

For years, I thought of these as lessons about leadership. 

Now I understand them as something broader.

Listen before recommending. Create clarity before action. Anticipate what others may overlook. Make complexity easier to navigate. Know when expertise should lead and when there should simply be room for something unexpected to unfold. 

Those principles have shaped the way I’ve led, the way my own family travels and, eventually, the company I felt called to build. 

Horizon & Haven is a new chapter, but in many ways it feels like the natural continuation of everything that came before it. Even the name reflects what I have come to believe about traveling well. 

Horizon is the curiosity to see what lies beyond what we already know. 

Haven is the connection, restoration and sense of being cared for that gives us room to experience it. 

I believe the most meaningful travel gives us both. 

And I have the extraordinary privilege of helping others find their own version of each.

For the stories you’ll still be telling years from now 

You don’t need more places added to your list. You need a journey that reflects what matters to you and the people beside you. 

That begins by listening, choosing well and creating enough space for the experience to become your own. 

Looking back, I don’t think I changed careers. 

I think I finally found the place where everything I’ve spent twenty years learning belongs next. 

And if it means more people come home with stories they’ll still be telling years from now, I can’t imagine a better place to spend the years ahead.