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How to take a meaningful holiday when you own a business

By June 26, 2015May 24th, 2021verve

I’ve put off taking a holiday while running a business… well… since I’ve owned a business.

Sure, I’ve taken small, weekly trips here and there but I’ve never carved out a block of time – four weeks to be exact – away from my baby.

The truth is, you don’t think anyone can operate your business as well as you.

…or so I thought.

Up until 12 months ago, I was afraid that if I ever took a decent holiday, that things would quickly turn pear-shaped and that I would come back to a mountain of problems, unhappy customers and debt.

Living by this ‘myth’ meant I constantly put my dream of taking an overseas trip on the back burner; and I dare say many business owners reading this can wholeheartedly relate to this so-called ‘sacrifice’.

So what changed?

How was I able to take four weeks off, travel to Europe, disconnect my phone, reset my creative brain and recharge my soul while completely (well, almost completely) forgetting about my business at home?

The truth is, you don't think anyone can operate your business as well as you.

Let me share with you four insights into how I found it possible to take a meaningful holiday while running a successful business.

Create a team that’s on the same page as you

I have an amazingly awesome team whom I trust 100%.  But having a trustworthy team is only half of it.

When it comes to confidently leaving your baby in the capable hands of your team, you not only need to have a trustworthy team – but a team who is totally on the same page as you.

When I hire people to be on our team, I hire based on talent but also on values.  My team and I are people who are so similar in our daily lives both inside and outside of work. We value family and friendships.  We place a high level of importance on the way we treat each other – and this extends to the way we treat our clients and the projects we work on.

The passion, commitment and energy is there – it doesn’t need to be manufactured – because we all believe in each other and the work we’re doing as a team.

When I left to go away I knew that my team would make decisions as I would because we have the same views on what’s right and wrong. If there was ever a problem, I knew they would be able to solve it using the same strong set of values that I would use to solve problems that arise.

Most business owners hire people based purely on talent, only to find out later that they clash because their vision and values are completely different.  It’s a pretty simple business concept, but one that needs to be reiterated constantly: hire people who have similar values to you!

Hire people who have similar values to you!

Dissect your role

Twelve months ago I booked my trip. That meant I had a whole year to plan my trip and ‘dissect’ the various components of my role, so that by the time my departure date was imminent, I was effectively redundant in my own business!  On a side note, 12 months is pretty excessive.  I think you could do the necessary planning in three months (my flights were just on sale, thats all!)

Dissecting your role means figuring out how you operate within your business. It’s not easy when so much of what you do is second nature. But you can break it down!

Ask yourself what the things are that you do on a daily basis?  For me it was everything from solving customer service issues, to booking meetings, to brainstorming ideas for new branding projects.  Once you’ve done this, delegate those tasks, paying particular attention to each team member’s individual strengths and then go about training that team member in that role.

As part of this ‘role dissecting’ procedure, I also started streamlining our business processes so the tasks that I didn’t need to be doing (even prior to my trip) seemed second nature to my team by the time I was on the other side of the world.

Things ramped up one month before I left when I released all of my personal roles onto the team member I thought was best suited to carry that responsibility.  This meant I was pretty redundant for the month leading up to my departure, but it also meant I could take a step back to watch and correct anything that didn’t sit well. My team was essentially being ‘me’ one month before I left!

If you don’t have a team, ask yourself how you can create one or a few team members by dissecting your role. Perhaps you could hire a virtual assistant for admin tasks, or a friend who’s great with people and writing to manage your email enquiries. Obviously, you need to engage people who you trust and who share your vision and values as I mentioned in the first tip.

Interestingly, I found that breaking my role down prior to me leaving has also meant that some of these processes can and will continue to operate now that I’m back because they also help with productivity, confidence and growth in my team in an ongoing way.


Get weekly updates

An ambitious entrepreneur’s mind never switches off – but one way you can make sure you still feel ‘connected’ to your business is by getting one weekly update from your team.

In my months leading up to the trip I developed a list of things I reported on as part of my day and workweek. Things like financials, upcoming projects, customer service enquiries, overdue accounts – the things I saw as making my business ‘healthy’.

I asked myself, what was important to know and what was not so necessary to know right then and there? (This is hard to do if you’re used to knowing everything – but you don’t need to know everything on your holiday – just where the next great coffee shop is!)  I also asked what key items would sum up how the business was doing in a snapshot and what were the key indicators that I know make my business healthy.

From here, I created a report template that was simple and straight to the point. Further, that it was able to be filled out in 15 minutes and read by me in five (while sipping away at a glass of wine, of course).

A couple of hints to make this report effective: keep it to just a page or two with simple ‘yes’ and ‘no’ answers and only very small comment areas.  All you want is to be able to get a quick snapshot of the health of your business from the week gone.  Everything else can wait for your return!


See the holiday as a serious investment into your business

You are a strong, savvy entrepreneur who is invincible. But you are also a strong, savvy human – and humans need time out. (Think of the financial cost to your business if you burn out because you’ve neglected to take a holiday!)

Not giving yourself a break can create a stressful environment for your team because their leader is out of whack.

The financial risk is that there is loss of staff or loss of motivation which then impedes on the quality of work and output – and ultimately a loss of work and reputation in your industry.  This then creates even more stress and frustration for you, which means the hope of ever taking a break will seem utterly impossible.

There’s a domino effect to you not taking a holiday, you see?

On the flip side – there’s also a magical domino effect to you taking a break. A BIG break.

There's a domino effect to you taking a big break.

Your world is bigger, so your ideas are bigger.

You come back inspired, energised and hungry for fresher processes, systems and ideas for your business.

You project positivity, a worldly outlook, inspiration and vibrance onto your team, your community, your family and your friends.

I’ve realised that a one week trip is nice, but the energy, ideas and fire that’s in my belly post a four week trip is the most magnificent feeling and I know that it’s going to do wonders in my business moving forward – so watch this space!


Are you a business owner and feeling apprehensive about taking a well-earned holiday? Maybe you’ve taken a break and can relate to what I’ve shared. Share your experiences below!