Why Successful Leaders Are Trading Boardroom Time for Family Adventures

Family time is not what remains after work. It is the fuel that makes the work worth doing.

This September Melissa and I celebrated two major milestones. Her 60th birthday and our 36 years of marriage. We chose Italy and the Mediterranean because this kind of celebration deserves a great setting, plus it's been on Melissa's bucket list for a while. I'm deeply thankful we're in a position to make these moments happen, and even more grateful that I get to share them with someone who's been by my side for 36 years.

Celebration is not a quick dinner or a post on social. It is a choice to create memories on purpose. For us that often looks like a family vacation. For you it may look different, but the principle is the same. You have to plan it or it will not happen.

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Why leaders make this trade

Great decisions come from rested minds and connected relationships. You cannot brute force clarity. The executives who scale well protect three assets that family adventures strengthen.

1. Perspective. New places change how you see old problems. A trip to the island, a ski in Chamonix or ramen in Tokyo has a strange way of shrinking yesterday’s drama and revealing the next smart step.
2. Trust at home. When your home life is strong, leaders show up stronger. Shared experiences create stories your family retells for years. That stability shows up in your patience, your risk tolerance, and the way you lead under pressure.
3. Energy that lasts. Burnout does not announce itself. It creeps up on you. Planned time away interrupts the creep. You return ready to play the long game.

The Power of Family Connection in the Mediterranean 

Just last month, we spent an unforgettable week together as a whole family at a villa on the east coast of Sicily. Melissa and I had put a lot of effort into finding the perfect spot, we looked at places on the beach, looked at all the different hotspots. We eventually decided to settle for a comfortable house with plenty of space, a pool, a yard, and a big kitchen for everyone to enjoy, and plenty of room to just relax together.

It turns out we didn't need the beach or the fancy hotspots, we spent so much time in that pool. We rigged a makeshift volleyball net, ran diving-board contests, and took afternoon siestas on blankets spread across the lawn. No Wi-Fi at the villa, so phones stayed away. Outside of using maps for driving, and checking emails once a week, we unplugged. More conversation. More laughter. Better sleep. I'm grateful for how naturally everyone settled into the rhythm of just being together.

Looking back, some of the best moments were the simple ones, just being present and letting the days unfold with the family. I don't take for granted that all our kids still choose to spend this time together.

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We did a few adventures together. A day hiking on the slopes of Mount Etna, ducking into lava tubes with helmets and headlamps, then a long lunch at a local winery. We tasted grapes straight off the vines, picked prickly pears, and the staff surprised Melissa with a birthday plate of miniature ricotta cannoli. Watching her face light up in that moment—surrounded by family, celebrated by strangers who became friends—reminded me how blessed we are to create these experiences together. One morning I ducked out for a solo summit of Etna. Rumbling underfoot, steam rising, a quick personal checkmark that still fit inside a family-first week.

It's hard to capture just how special these days felt. When life is moving fast for everyone, pausing together as a family always brings it back to what's really important: connection, presence, and memories. I'm thankful for every single one of these moments, knowing how rare and precious they become as life gets busier. These aren't just nice-to-haves. They're the stuff that matters, and I'm grateful we prioritized them.

We renewed our family pact to take an international trip together every couple of years as the crew grows.

At the end of the day, what do we really have other than our memories.

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Family vacations are not a luxury

Every year or every other year our extended family meets somewhere in the world. Two years ago we skied Chamonix with my brother and his family. Earlier this year I skied Japan with my sons. Last month our kids meet us in Italy. None of it happened by accident. We put dates on a calendar and built the plan around them.

Melissa and I both grew up in families that traveled. They chose to make it a priority for us. That choice gave us a wider view of the world. Street food at a night market teaches you about the different flavours of another culture. Listening to a bus driver in another language teaches patience and humility. Sitting at a table with people from somewhere else reminds you that there are many right ways to live a good life.

This kind of family adventure is not a distraction from leadership responsibilities; it is a powerful tool that refuels leaders' minds, spirits, and connections, enabling them to return to work refreshed and more effective.

The playbook busy CEOs actually use

If you do not schedule family, work will take the space. 

If we do not book the flights, a year will pass and we will promise to do it next year. 

If we do not choose a place, we will end up with “sometime soon,” which never comes. 

Sound familiar?

Here is the simple system I give my clients and use myself.

• Name the why. Celebration, reconnection, or rest. Write it at the top of the plan.
  
  
• Set dates first. Put it on the calendar before the agenda exists. Protect it like a board meeting.
   
• Keep one anchor per day. A hike. A museum. A beach afternoon. Leave room for serendipity and naps.
   
• Create one ritual. First day gelato. Sunset walk. No phones. Nightly round table where everyone shares a best and a funniest moment. Rituals turn trips into traditions.
   
• Capture and retell. A few photos. A short journal. A dinner at home where you tell the story again. Retelling locks in the value.

Do this every year and you will create a chain of shared memories that compounds. Your kids will expect it. They grow into it. It’ll become a habit that protects what you value. One day they will plan the same for their own families. That is legacy.

The honest part about cost and convenience

Travel costs money, time, and energy. It always seems to collide with something urgent. School schedules. Quarter end. I understand all of it. It is tempting to say we will go when business is calmer or when the budget feels better.

My view is simple. If we do not set a priority, life will set one for us. We try to plan within our means and still stretch for the memory we want to create. The goal is not luxury. The goal is together. A rented cabin a few hours from home can deliver the same connection as a flight across the ocean. Pick a version that fits your season and commit to it.

Celebration is fuel, not a finish line

In my leadership work we talk about risk and reward. We ask teams to take smart swings. What smart risk will you take? If it works, how will you celebrate it? Celebration is how teams encode wins and give themselves permission to swing again. 

Your family deserves the same thought. Marriages. Birthdays. Anniversaries. Graduations. Hard seasons overcome. Mark them on purpose.

That is why Italy mattered to us last month. We were marking Melissa’s 60th and our 36 years together. We are not posting and moving on. We are slowing down and taking it in. Because the people we love deserve more than a quick dinner when the calendar allows it.

A challenge for leaders

If your summer memories feel thin, schedule a one-day adventure in the next sixty days. Phones away. One shared activity. One story you will retell. 

If your summer felt full, awesome, put your next family trip on the calendar now. Dates first. Details second.

Successful CEOs and leaders are trading a little boardroom time for family adventures because it pays them back in perspective, stability, and energy. The work will be there when you return. The window to make memories will not always be there.

Life does not hand out space. 

We make it.

Three takeaways for leaders

1. Family adventures are essential mental health resets that restore clarity, reduce burnout, and increase resilience for making high-stakes decisions.
2. Deep connection at home builds emotional strength and trust that strengthens leadership presence and enhances team dynamics.
3. Intentional shared experiences create lasting family legacies that fuel wellbeing, creating a foundation for sustainable success both at home and at work.

Struggling to make space for your own family adventure?

Contact me if you need a little accountability to actually put it on the calendar.