8 Tips For A Successful Holiday As A Small Business Owner

8 tips for a successful holiday as a small business owner

Prince Harry is a victim of a burnout.

In an interview in 2021, he opened up about how he found himself in a situation where it seemed like everything was working against him.

As a father, husband, and amongst others; Chief Impact Officer at BetterUp (a mental health company), he got to a point where he felt like he was ‘getting to the end of everything that he had.’

The Prince emphasised the need to take a break, and the reality that self-care often becomes the first thing to drop. 

His story is not an isolated one, burnout is real, and statistically someone in your circle is suffering with it as you read this.

Did you know that 9% of small business owners have not taken a holiday in 5 years, and 70% of small business owners do not see a holiday as a break from work? The self employed often continue to squeeze in work even when they’re supposed to be on holiday.

Taking a break from work is necessary for everyone, and not just business owners. It results in less stress, clearer thinking, and greater productivity.

As we celebrate the Jubilee weekend, here are 8 things you can do to make sure that you have a successful break from work.

1. Accept that there’s probably not a perfect time to go on holiday

We’ve all been in a situation where we plan a holiday at the ‘perfect time,’ only to realise that it wasn’t actually good timing.

Because if we’re REALLY being honest, there is no perfect time to take that break. There will almost always be work to be done,  a problem to be solved or a critical task to be completed.

Going on holiday as a small business owner requires INTENTIONALITY.

You can, to a certain extent, predict when things will be a bit slow for your business, but you can’t predict if and when important things will come up.

The best you can do is prepare adequately for the break, foresee any problems that arise, and think up solutions for when they do. 

Which leads me to the next point…

2. Define what is REALLY an emergency

Suppose you’re on holiday and one of your valuable clients calls you to ask you to do something for them…

What’s your first instinct? Do you stop everything you’re doing, turn on your laptop, and get to work? 

Or do you politely ask them for some time and explain that you’re on holiday?

An emergency, to me, would be something that would cost you an opportunity that you’re counting on.

Even so, you need to define what an emergency is to you. Discuss and write down under what circumstances you want your second-in-commands to contact you while you’re on holiday. 

Perhaps you want to be contacted if a particular client calls or it could be that unless there’s a natural disaster like a fire, flood or earthquake, you don’t want to know about it. Put those structures in place.

3. Cover your bases

If you’ve been in business for a while, you’re able to pre-determine some of the things that could possibly go wrong.

I mean, it’s nearly impossible to do this for every possible disaster, but you can try.. 

Have a set structure to fix or solve anything that could come up. You can do this by making a list of everything you do and continually looking for things you’re spending time on. Turn these into processes that you can put your employees in charge of.

If you do this efficiently, it will be hard to drop the ball since everyone will know what they need to do to keep things moving.

4. Don’t hide your holiday

Everyone deserves a break from work.

It’s why leave days were invented in the first place.

Even though this seems rather obvious, many of us are in the habit of hiding our holiday from our clients and our colleagues.

Why? It feels like a sin to take a break from working, and that’s rather sad.

If you communicate with your clients and customers in good time, they most likely won’t want to bother you while you’re taking time off. Assure them that they’re in good hands with your team, and prepare your staff by having a meeting before you leave to ensure that they are on the same page.

You will get to enjoy the time off without any secrets. This will give you the peace of mind that you need to unplug and get some rest. 

Plus, it’s highly unlikely that a client will walk away from your services because you’re on holiday.

5. Contact your customers early

Don’t wait until the eleventh hour to let your customers know that you’re going on holiday.

In fact, it’s best to let them know as soon as you’ve confirmed it. Then, you can send a reminder two weeks in advance.

By doing this, you will help to set expectations, build your relationships, and show you have their best interests at heart.

It will also help you to know how much work needs to be done before you take the break. In case they foresee anything urgent coming up, they can let you know in good time so that you find a way to work around it.

It will reduce the chance of a last minute request delaying your departure. 

Contacting them at the last minute may make them perceive you as disorganised or indifferent towards their needs. And you definitely don’t want that.

6. Delegate what you can

Let’s be honest…

Delegating your work to other people can be one of the hardest things. Why? Because your expectations may not always be met, and so you’d rather just do it yourself to save time.

However, what you need to remind yourself is that you can’t do everything. You must communicate clearly to the people you delegate to what you expect of and from them.

In fact, taking a holiday as a business owner may just be the perfect time to upskill any staff and expand their responsibilities.

When you get back to work, you may find that they’ve done the job so well that you can focus on other tasks and completely hand over the responsibility to them.

7. Pre-schedule what you can

Technology has been and continues to be one of the greatest things that ever happened to us.

With social media for example, you don’t have to do things in real time. You can create your content and schedule it ahead of your break from work.

Your audience will receive your content in real time, and it will be hard for them to tell whether it was scheduled or not.

Some social media scheduling sites that you can look into are Hootsuite, Social Pilot, Planable, Buffer, and Preview.

8. Give yourself permission to do absolutely nothing

I know of someone who found it terribly hard to take a holiday as a business owner. She would work over lunch hour, and if she wasn’t working, work was the only thing on her mind.

When you’re on holiday, you need to unplug from work. Be fully present in what you’re doing.

Remind yourself that it’s okay to do absolutely nothing. 

In fact, boredom can lead to brilliant ideas, even for the business. If you allow your mind to wander, you connect incredible ideas, create goals, and figure out how to make things happen.

In the long run, that break from work may do more for you and your business than you’d ever imagined.


Contrary to what most of us think, taking a holiday as a business owner is not a luxury but a necessity. Every so often, you need to put everything aside and take a breather.

For business owners, it’s much harder to do so because there’s a lot of responsibility on you. Even so, and in summary, here are the 8 things you can do to ensure that you take that break:

  1. Accept that there may be no perfect time to go on holiday
  2. Define what is REALLY an emergency
  3. Cover up your bases in good time
  4. Don’t hide your holiday
  5. Contact your customers early
  6. Delegate what you can
  7. Pre-schedule what you can
  8. Give yourself permission to do absolutely nothing

Now go forth and enjoy the jubilee weekend!

And if you need any help putting any of these structures in place, get in touch with us or check out our resources page.


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