How to Plan a CEO Getaway That Fuels Creativity and Growth| OOO
Most CEOs I know (myself included) used to think of time away from the office as “vacation”—a break, a pause, or even a guilty indulgence. But here’s what I’ve learned: when you approach travel strategically, a getaway becomes so much more. It’s not about escaping your business—it’s about creating the space to sharpen your leadership, spark bold ideas, and restore the energy it takes to make game-changing decisions.
A CEO getaway is about leveling up, not checking out. Here’s how I plan mine—and how you can make your next trip work just as hard for your business as you do. Here’s how to plan one that works for you and your business.
Step 1: Define Your CEO Getaway Intentions
Ask yourself: What do I need most right now as a leader?
Clarity? Choose destinations that are peaceful and distraction-free.
Inspiration? Opt for experiences rich in culture, art, or natural beauty.
Connection? Align your getaway with industry conferences, networking cruises, or mastermind retreats.
When your intention is clear, your destination and activities fall into place.
Step 2: Choose a CEO Getaway Setting That Matches Your Vision
Your environment directly influences your creativity. Don’t default to the same resort you’ve always booked. Instead:
For big-picture thinking: Secluded villas, mountains, or quiet beach towns.
Such as, The Mountains of Salt in Bonaire providing grounding environments for expansive thinking. I felt like I could see my whole business from 30,000 feet.For energy and new ideas: Vibrant cities, cultural hubs, or themed cruises like Virgin Voyages’ Scarlet Night.
The view from a Virgin Voyages ship at Scarlet Night reminded me that fresh horizons often lead to fresh ideas.For balance: Hybrid spaces where you can work in the morning, then explore in the afternoon.
Coconuts for sale: Stopping at a roadside coconut stand once taught me that even simple moments can spark creativity if you let them.
The right setting makes it easy for your brain to shift gears and imagine possibilities.
Step 3: Build in White Space
The biggest mistake CEOs make? Packing their “getaway” with back-to-back activities. Real growth comes from white space—unstructured time where ideas can surface naturally.
Schedule blocks for reading, journaling, or simply watching the ocean.
I Limit calls and email check-ins to a set window (if at all).
Allow yourself the freedom to follow curiosity rather than obligation.
This white space is where breakthroughs happen.
Step 4: Mix Inspiration with Reflection
A powerful CEO getaway balances outward exploration with inward reflection.
Visit museums, markets, or performances that stretch your perspective.
Pair these with intentional reflection sessions: morning meditations, evening journaling, or strategy notes over coffee.
Capture insights in real time—your next big business idea often comes in unexpected places.
Step 5: Make It Tax-Smart
Here’s the bonus: if your getaway includes business activities—client meetings, research, or conferences—it can often be structured as a deductible business trip.
Document your work sessions, meetings, or relevant events.
Save receipts and keep a simple travel log.
Talk with your tax strategist before you go—smart planning ensures you maximize both inspiration and savings.
Step 6: Return with Action, Not Just Memories
The final piece of a CEO getaway is the integration.
Schedule a “CEO Debrief” day before you dive back into daily operations.
Review your notes, highlight key insights, and translate them into clear next steps.
Share your refreshed vision with your team—it not only fuels momentum but models the importance of rest and growth.
Final Thought
A CEO getaway isn’t about checking out—it’s about leveling up. When you plan with intention, the result isn’t just a rested leader. It’s a visionary CEO with the creativity, clarity, and capacity to take the business further than ever before.
Your next getaway could be the strategy session your boardroom could never deliver. Where will you go?
