Stop Planning Holidays That Leave You More Exhausted Than When You Left

As business owners, we're incredibly good at being productive.

We solve problems. We meet deadlines. We juggle clients, staff, finances and family. We spend our days making decisions for everyone around us.

Then eventually, usually after months (or years) of telling ourselves we'll "take a break soon", we book a holiday.

But, does your holiday actually give you what you need? Or does it simply become another project to manage?

I love travelling, and have prioritised it since I was in my teens. How I travel has changed though. It used to be a Bucket List type of approach, but as I've grown older (and perhaps a little wiser), my priorities have changed. Now I enjoy taking a slower pace, even if it's only for part of the trip. Seeing out of the way places and going off the beaten track is what I enjoy.

So, when I met and spoke with Kerstin Rheinlander, a bespoke travel planner, recently, I really connected with what she had to say.

When travel becomes another to-do list

It's surprisingly easy to fall into the same habits while travelling that we have in everyday life - which is being busy.

First, we research the destinations we have in mind. Maybe ask AI to suggest an itinerary (at least these days. In the past we just used Google). Research some of the main attractions and book in for those that need to be booked in ahead of time.

Once on holiday, we race from one place to the next, trying to "maximise" the time we have, and squeeze in every sight and experience.

We take hundreds of photos on our phones (including our food), so we can post on social media (and then be sent reminders of our trip by Facebook every 12 months).

Each of the "must-see" landmarks get ticked off the list, and before long, the holiday looks remarkably similar to normal life. Busy, scheduled and productive.

And when you arrive home, instead of feeling refreshed, you find yourself saying something we've almost normalised: "I need a holiday to recover from my holiday."

What if travel was designed to restore you instead?

Kerstin has spent decades helping busy professionals travel differently.

She explained that she doesn't start by asking people where they want to go. She starts by asking who they are.

What's happening in their life? What do they actually need right now?

Because someone who's been leading a team through rapid business growth probably doesn't need the same holiday as someone recovering from burnout, caring for ageing parents, or navigating a difficult season of life.

The destination matters. But the outcome matters even more.

The most valuable souvenir isn't something you buy

For many business owners, travel has quietly become another achievement. But perhaps we've forgotten what travel has always been about.

For centuries, people travelled to experience different cultures, learn new ways of living, exchange ideas and return home changed by the experience.

Not simply to see more places, but to see themselves differently. That shift in perspective can be incredibly powerful.

Sometimes stepping away from your normal environment is exactly what allows you to hear yourself think again, without notifications and the constant buzzing that goes with them. Without the abundance of tightly scheduled meetings, and without everyone needing something from you.

Just enough space to breathe.

Why we struggle to invest in ourselves

This conversation also highlighted something I see often when talking to women about money. Many of us will happily spend money on:

• Our business

• Our children's education

• Our homes

• Professional development

• Courses we'll never quite get around to finishing.

Yet we hesitate to spend money on experiences that genuinely restore us. There's often guilt.

"Shouldn't I be spending this somewhere more sensible?"

"What if the business needs that money?"

"Can I really justify taking time away?"

But here's another question worth asking - what if taking care of yourself isn't a luxury?

What if it's one of the smartest investments you could make?

Because an exhausted business owner doesn't make better decisions. A depleted leader doesn't become more creative by pushing harder.

Sometimes the greatest return on investment comes from creating enough space for clarity to return.

This is why I always suggest that travel form part of the money system that I help my clients set up. If travelling for the business is important, then your business finances need a Money Pie slice for this. If travelling for personal enjoyment is something you want to do, then your personal finances need a Money Pie slide for travel.

That's why the money system includes Money Pies for business and for personal.

Slow travel might be exactly what your nervous system needs

As I mentioned, the older I get, the less interested I become in seeing everything. I'm much more interested in experiencing something. Finding the quiet beach instead of the crowded tourist attraction.

Wandering through a village instead of rushing through five cities. Having conversations with locals instead of collecting another photo.

Staying in one place and exploring it, and getting to know some of the locals while I'm there.

Coming home with new ideas instead of simply another passport stamp (which we don't actually physically get anymore anyway).

That's a very different kind of wealth - a wealth of experience.

Give yourself permission

If you've been telling yourself you'll travel "one day"...

After the business grows, or after the children are older, or after everything settles down.

You might be waiting forever. Life rarely becomes less busy on its own. We have to deliberately create the pause. Not because we've earned it, but because we need it.

The right trip won't just help you escape your life for a week, it can help you return to it with fresh perspective, renewed energy and a clearer sense of what really matters.

And perhaps that's the kind of investment every overworked business owner deserves.