Why Your Holiday Plan Needs a CEO-Level Upgrade

Stop Planning Just Vacations. Start Planning Your CEO Role

You’ve mastered planning flights, hotels, and itineraries. But have you ever planned your freedom?

Let’s get straight to it: school holidays are coming.

My son finishes the term on 26th September—two weeks off then one more term and he is off for seven weeks over summer. 

Even if you don’t have kids, your team or clients might. And even if no one in your orbit does, the final quarter of the year always brings project slowdowns, inbox chaos, and end-of-year fatigue.

If the thought of stepping away from your business gives you heart palpitations, you’re not alone:

• Only 57% of small business owners took a holiday last year—and nearly half checked in every single day. (Xero Small Business Trends Report 2024)
• 1 in 5 business owners haven’t taken a full week off in over a year. (Startups.co.uk)
• 81% of entrepreneurs work while they’re on holiday. (SmallBusiness.co.uk)
• Over half spend more than an hour each day working during vacations. (GorillaHub)
• 97% admit they still work on holiday, with around a third working 4 hours daily. (AbsolutelyBusiness.com)

That’s not freedom. That’s just working somewhere else.

How I Took a Four-Week CEO Holiday and Grew My Business

What if your business could earn more while you’re sipping coffee in another country?

Over Aussie winter, I took my kids to the UK for a month.

This trip wasn’t a whim—it was four years in the making. Between passport drama, ex-husband logistics, and the emotional pull of seeing my entire family in one place for the first time in years… when the plane finally took off, I cried.

And here’s the kicker: my business didn’t just survive. It grew.

While I was away:

• 100+ people registered for a free masterclass
• Event tickets sold for my Leadership Essentials in person Event
• Clarity calls booked for my return
• Every ongoing client fully supported

And I worked fewer than 15 hours over the entire month.

Why Visionary Founders Must Design Their Role Before They Burn Out

If you don’t design your CEO role, your business will design it for you — and you probably won’t like the result.

When I work with visionary founders, I don’t just talk about revenue growth. I talk about role design.

Your CEO role should be built around the life you want—not the leftover hours once client delivery is done.

We decide:

• How many holidays you want each year
• Whether you take all school holidays off
• Your working hours and boundaries

If you don’t, you’ll fill every gap with work and become the operational bottleneck.

As Gino Wickman puts it in Rocket Fuel:

“Visionaries need Integrators to bring their ideas to life and run the day-to-day.”

Without that, your big ideas stay stuck while you drown in Slack messages and admin.

The Business Operations Systems That Made a Four-Week Break Possible

Freedom isn’t an accident, it’s built into your systems months before you pack your suitcase.

Here’s exactly how I made a four-week break work without sacrificing growth:

• Block personal time first – All family trips, events, and days out locked in before any work touched my diary.
  
• Optional work windows – Early mornings only, so the rest of the day was mine.
  
• Holiday Asana board – Included content scheduling, client handovers, payroll, and internal comms.
  
• Clear comms plan – Clients knew when I was available; my VA was the gatekeeper.
  
• Revenue shift – Sales-heavy June so July could be light on delivery.
  

Here’s the best part: I barely used my work windows. My team handled it all.

The Untapped CEO Advantage of Stepping Away Completely

The best ideas for your business don’t happen at your desk, they happen when you’re far, far away from it.

Psychologists say a proper break shifts your brain into “default mode” the part responsible for creativity, problem-solving, and strategic thinking. (Harvard Business Review)

When I returned, I had more clarity, sharper ideas, and a refined list of small operational tweaks to make my next holiday even smoother.

One of my clients, Eva, experienced the same. Thirty days after we built her process hub and clarified team ownership, she took a guilt-free holiday and her business kept running without her.

3 Red Flags That Your Service Business Can’t Survive Without You

If even one of these is true for you, taking a real holiday could be risky until you fix it.

• You’re still the answer to every team question.
• Revenue stops if you’re not selling or delivering.
• You can’t remember your last full switch-off.

Your CEO Role Deserves a Holiday. Here’s How to Make It Happen

Scaling isn’t just about making more, it’s about living more.

Freedom in business doesn’t come from doing less, it comes from planning better.

When your team structure, systems, and leadership model are built for scale, you can step away knowing your business will still grow.

This is exactly what we do inside Grow Advantage.

Book a Free 30-Minute Clarity Call

We’ll pinpoint the 2–3 biggest blockers keeping you from taking time off, and map the systems and team structure to fix them—fast.

Chrissy Elle
Founder | Grow Advantage

Helping visionary founders become strategic CEOs without the burnout, the bottlenecks, or the “always-on” habits holding them back.