The Holiday Test: Why You Can’t Take Two Weeks Off (And How to Fix It)

So, let's talk about the ‘holiday test’. Because if as a business owner you tell me that you can't take two weeks holiday... Then I’m guessing that there is a very good chance it’s because your business has been built around you.

You might protest at this and tell me that you have a great team, or your clients just prefer dealing with you But honestly? If you stepping away means the business slows down, you haven't built a fully functioning business. You've built a very complicated job for yourself!

A lot of founders may think this is normal. They assume being indispensable is just what entrepreneurship looks like.

But I promise you it really isn't. It's a structural issue in the way your business has evolved.

Let's look at what actually happens when a founder or business owner tries to take a week off.

Day one is usually fine. You might check your emails in the evening from the hotel balcony with a glass of something nice in your hand. You might reply to one or two emails, thinking that you are helping the team and your keeping the business moving. It’s not big deal your just doing what any good founder would do.

But STOP, that single action has just told your team that even though you are on holiday you remain available.

By day three, they start sending emails expecting an answer. Then it moves to WhatsApp. Things that could have waited until you got back suddenly become urgent decisions that only you can make. And if you don't respond? Well, then the business doesn't move forward.

By the end of the week, you haven't really switched off at all. You feel drained. You're trying to run a company with one arm tied behind your back from a sun lounger. And if you're with family, it's probably causing friction. You're there, but you're not really there. Sound familiar?

So why does this happen? Why do capable teams suddenly lack the decision to make decisions when the business owner heads off to France for a week?

It’s almost certainly because of one thing…they lack authority.

They're used to you making the decisions. When you aren't there, they might know exactly what needs to be done, but they just don't have the confidence that their decision will be the right one. They've never really been given true ownership.

And as founders, we're often to blame for this.

We've all been there. You delegate a task. The team member takes a little longer than you would (which is completely normal when they're taking on something new and it’s not their business). But because you're used to working at pace and can make decisions on the spot because after all it’s your business, you step in to ‘help’.

You say, "Well, I think what we should do is this…" and you genuinely think you're being a good boss and are helping.

What you're actually doing though is rescuing them.

As a leader, it's incredibly easy to rescue people. It feels good. But it stops the team from learning. It reinforces the dependency. It dents their confidence and ensures that next time, they'll just wait for you to decide. Defaulting to you becomes the norm it becomes a habit.

So, how do you fix this?

The most important thing is structure. And by structure, I don't mean an organisational chart. I mean having the right roles, with the right people in those roles who actually understand what they're accountable for and what decisions sit with them.

If you are struggling to take time away from your business but really need that holiday, here are three things you need to put in place to make that happen:

1. Set clear boundaries

Define when it's okay to contact you, and how while you are away. I always recommend WhatsApp for absolute emergencies. You do not want to be going into your inbox and then getting caught up in tasks that someone else can complete or that can wait. Ideally nominate one trusted person who is your point of contact. The person who can make the judgement call on if a task really does need you or if it can wait.

2. Stop last-minute handovers

As founders we love a quick-fire conversation and moving at speed, but a 5-minute handover as you're walking out the door. "Do this, don't do that, call them, priorities this." It's unstructured and completely overwhelming. Instead, put a diarised hour in the calendar. Sit down with the key people in your team who have authority while you're away. Talk through the week ahead, clarify what should and shouldn't be escalated, and document what is agreed.

3. Tell your clients

If your clients are used to dealing with you, they'll default to you. Let them know you'll be away and exactly who they should contact. Don’t be afraid to put your out-of-office is on and provide an alternative number or email. Saying your away from the business for a week does not mean you care any less about their business it means you are human and need time out to enjoy the freedom and flexibility you built your business for.

I worked with a client recently who hadn't been on holiday for nearly two years.

He'd bought a business, but the team was full of conflict. He didn't trust them to run the business without him. If he stepped away, he genuinely believed it would be detrimental to his clients and the business. He had three young kids, he was exhausted, and he was ready to pack it all in because the business wasn't giving him the life he built it for. He was at the end of his exhausted, at the end of his tether and seriously considering closing the business.

So, we started by looking at everything that was sitting on his plate using my DASH framework:

And together we made some big decisions. It took six months of restructuring, including changing some roles, removing others, streamlining the product offering and bringing in new talent to the team.

But after those six months, he took his family to Spain for a proper holiday. He sent me photos of them making memories and enjoying the life he bought the business for.

That's what this is all about. We grow businesses to create a certain life for ourselves and those we care about. If your business requires you to be the only answer in it, you'll never have the freedom you set out to achieve.

Ask yourself this: What needs to happen in your business for you to be able to take a proper break without feeling the constant pressure of being pulled back in?

Fix the structure. Stop rescuing your team. And take the holiday.

And remember… Freedom doesn’t come from being the only answer in your business.

If you want a quick starting point, you can run my 3-minute diagnostic here:
Diagnose Founder Dependency in 3 minutes: (Score App link)

If you’d rather get fast clarity with me, the next step is the Founder Dependency Review.
It’s a focused 90-minute session where we pinpoint exactly where dependency is being created in your business, and what to fix first to give you back time, headspace, and control.

Founder Dependency Review (£500 + VAT): (booking/payment link)

And if you’re not sure which route is best, book a discovery call and we’ll talk it through:
Discovery call: (link)