Dear CEOs: Here’s How a 2-Week Sabbatical Will Make You a Better Leader

A two-week sabbatical isn’t indulgent—it’s strategic. This post explores how intentional time away can reset your mindset, recharge your leadership, and spark fresh vision for CEOs and entrepreneurs.

If you’re a CEO or entrepreneur, chances are your calendar is always full, your phone never stops buzzing, and true time off feels impossible. But here’s the truth: the best leaders aren’t the ones who grind the hardest. They’re the ones who know when to step away.

A two-week sabbatical might sound impossible, but it can change how you lead, how you think, and how you live.

Perspective You Can’t Get in the Office
When you’re in the thick of daily decisions, it’s hard to see the bigger picture. Time away gives you the distance to evaluate what’s working, what’s not, and where you want to go next. I’ve worked with executives who came back from a sabbatical with new clarity about their business direction—and with the courage to make changes they’d been avoiding.

A few years ago, I realized I was doing the same thing: designing transformational trips for clients but never giving myself permission to step away. My so-called vacations looked like this:

• Hotel inspections squeezed between sightseeing

• Client calls from the pool deck

• Measuring “rest” in hours, not days

So I made a change. I started taking one intentional, two-week sabbatical-style trip each year—and it transformed how I approached both life and business.

Space for Real Rest
Let’s be honest: a long weekend doesn’t cut it. It takes days just to unwind from the adrenaline of work mode. A true sabbatical gives your body and mind time to reset. One client told me that by day six of her trip, she finally stopped checking her email. By day ten, she felt more rested than she had in years.

I know the feeling. By the end of the first week, I stop reaching for my phone out of habit. By the second week, my nervous system has reset. That’s when I’m able to show up with fresh energy and better ideas.

Stronger Teams Back Home
Stepping away forces you to delegate and trust your team. It shows them you believe in their ability to run things without you. The ripple effect is powerful: teams often return more confident, more capable, and more engaged when their leader models balance.

Ideas That Need Breathing Room
Creative breakthroughs rarely happen at your desk. They come on long hikes, in quiet moments, or over a glass of wine in a place that inspires you. Sabbaticals create the breathing room for those ideas to surface. Some of my most impactful business decisions weren’t made in front of my laptop—they were made mid-journey, when I was fully present somewhere new.

It’s Not Just a Trip, It’s a Strategy
Taking two weeks away isn’t indulgent—it’s intentional. It’s a leadership strategy that prioritizes long-term vision over short-term busywork. The CEOs who embrace this are the ones building businesses that thrive without burning out the people at the top.

Ready to Lead Differently?
If you’ve been waiting for the “right time” to take a real break, consider this your sign. A two-week sabbatical might just be the most productive thing you do this year—for yourself, your team, and your business.

FAQ

1. Why should a CEO take a sabbatical?
A sabbatical allows leaders to gain clarity, reset mentally, and return with fresh perspective. It’s a strategic break, not a luxury indulgence.

2. What does a sabbatical-style trip look like?
These journeys often blend rest and reflection—think two-week getaways with immersive stays, light structure, and no pressure to perform or decide.

3. How can a sabbatical improve leadership?
Time away often leads to better delegation, creative breakthroughs, and renewed energy. CEOs report improved team trust and stronger strategic thinking post-trip.

4. Can Milk + Honey design sabbatical trips?
Yes. We specialize in tailor-made, high-touch itineraries for executives, ensuring the right pace, environment, and support for true restoration.