When business owners and leaders finally step away from their work, there’s a moment of deep, exhilarating freedom … followed quickly by a question that lingers uncomfortably in the background: “Now what?”
After years, even decades, of defining themselves through their work, leaders often find that life after the exit can feel disorienting. The calendar, once jammed with meetings and decisions, now sits open. The phone stops ringing and the work texts stop. The adrenaline that once fueled every day begins to fade.
In Second Wave Life™, I write that selling your business doesn’t end your purpose, it reveals your need to find a new one. And one of the most powerful, underappreciated tools to help with that rediscovery is travel.
Why Travel Matters in the Second Wave
Travel, when done intentionally, isn’t escapism – it’s engagement.
For years, many owners have traveled for business: client meetings, conferences, trade shows. Those trips were transactional, purposeful in a commercial sense. But once the business chapter closes, travel can shift from efficiency to enlightenment.
In the Second Wave Life™ framework, the Travel Tool isn’t about destinations, it’s about discovery. It’s designed to help newly retired or post-exit business leaders step out of the familiar rhythms that once defined them and into environments that awaken curiosity, perspective, and meaning.
Because here’s the truth: the same drive that built your company still lives within you. It just needs a new arena in which to move.
Viktor Frankl’s Insight: Movement with Meaning
Dr. Viktor Frankl, the founder of logotherapy, spent his life studying how people find meaning – not through comfort or luxury, but through purpose and perspective.
He wrote, “What man actually needs is not a tensionless state but rather the striving and struggling for a worthwhile goal.”
That principle applies directly to what happens after the exit. Many business owners think that rest equals renewal. But as Frankl would remind us, endless rest often leads to emptiness.
Travel, when approached with intention, reintroduces that worthwhile goal… not in the form of a profit motive, but as a quest for perspective and contribution. It challenges you to navigate new terrain, learn from different cultures, and engage with the world beyond the borders of your old identity.
When we travel not to escape, but to engage, we rediscover the meaning that work once provided.
The Shift from Achievement to Awareness
During your business years, travel probably meant red-eye flights, hotel lobbies, and PowerPoint decks. The goal was efficiency, right?… how quickly could you get in, get it done, and get home?
But in the Second Wave, the question changes.
Now it’s: How can travel expand who I am becoming?
There are three stages to that transformation:
- Disconnection from Routine:Leaving behind your everyday environment forces the mind to loosen its habitual patterns. The roles you used to play: CEO, founder, and leader lose their automatic context. That’s the first step in rediscovering who you are beyond the title.
- Observation and Reflection:Travel invites you to see how others live, work, and define success. You begin to notice that meaning takes many forms: service, family, craftsmanship and community are all reminders that purpose isn’t confined to enterprise.
- Integration:The final step is translating those insights into your own life. Maybe that means mentoring local entrepreneurs, volunteering abroad, or simply reshaping how you use your time at home. Travel becomes not a pause, but a mirror that is reflecting back what still matters most.
The Power of Perspective
One of the biggest risks after an exit is what I call “the shrinking world syndrome.”
When the company is gone, so is the built-in community — the employees, clients, and advisors who gave you a sense of relevance and belonging.
Travel expands that world again.
Standing in a marketplace in Lisbon or walking through a village in Costa Rica, you see life continuing in thousands of different ways. You’re reminded that meaning isn’t something you had and lost; it’s something you can recreate, anywhere, through connection and curiosity.
Frankl believed that meaning could always be found – even in suffering – if we learned to view our circumstances through a lens of purpose. Travel provides that lens. It reframes discomfort as learning, and difference as depth.
Intentional Travel: Moving with Purpose
The Travel Tool in Second Wave Life™ isn’t about collecting passport stamps. It’s about structuring journeys that align with your emerging sense of purpose.
Here are five ways to make travel a genuine part of your post-exit meaning plan:
- Travel with Questions, Not Just Itineraries
Before you go anywhere, ask yourself: What do I hope to understand about myself through this trip? Maybe it’s patience. Maybe it’s how to listen without leading. Maybe it’s rediscovering the joy of learning. Let your journey become a living conversation with those questions.
- Pursue Purposeful Immersion
Instead of staying insulated in luxury resorts, consider experiences that connect you with local culture and community. Volunteer programs, cultural exchanges, or extended stays let you contribute and learn simultaneously. These trips transform curiosity into contribution.
- Bring Curiosity Home
Travel isn’t only about where you go, it’s about how you return. Document your reflections. Ask yourself how your experiences abroad can shape the way you live, give, and lead at home.
- Use Travel as a Mirror for Time
Many former entrepreneurs struggle with open calendars. Travel reintroduces structure via planning, adapting, reflecting – but with freedom rather than obligation. Each trip becomes a rhythm that replaces the cadence of your old business life.
- Find Tribe through Travel
Just as work once gave you a professional tribe, travel can introduce you to a new one: explorers, mentors, thinkers, and givers who share your passion for growth. Surround yourself with people who are also living intentionally in their second wave.
Case Study: Purpose in Motion
When I worked with a former tech founder named Mark, he confessed that after his exit, he was “lost in leisure.” He had the freedom to go anywhere but nowhere felt purposeful.
We reimagined travel as part of his Second Wave Plan. He started taking immersive trips to developing countries, meeting small business owners and funding local entrepreneurship initiatives.
After two years, Mark told me something profound:
“I thought travel would give me rest. It gave me responsibility instead – the kind I actually wanted.”
That’s the essence of meaning through movement. When travel becomes a tool for contribution, it reawakens the same energy that once built a company — but now it builds lives.
The Logotherapy Connection
Logotherapy teaches that human beings can find meaning in three ways: through work, through love, and through the way we face unavoidable suffering.
Travel touches all three.
It reawakens the creative energy once poured into business (work).
It fosters deep connections with new people and cultures (love).
And it requires humility and flexibility … sometimes discomfort … that leads to growth (attitude toward challenge).
Frankl would argue that the purpose of life isn’t comfort, but contribution …to respond to what life is asking of us in each new season.
When we travel intentionally, we engage that calling directly.
The most meaningful journeys aren’t measured in miles – they’re measured in perspective.
For the newly retired business leader, travel is more than a hobby; it’s a form of healing. It restores context, renews curiosity, and rebuilds meaning where the structure of work once stood.
The Travel Tool in Second Wave Life™ exists to help you move from being a tourist of your own freedom to being a traveler in your own becoming.
So as you pack your bags for the next trip, ask yourself:
Am I leaving to escape something, or to discover something new?
Because when travel becomes a mirror for meaning, you’ll find that the journey doesn’t take you away from your purpose.
It brings you right back to it.
