5 Tips For A Successful Holiday As A Small Business Owner

5 Tips for a Successful Holiday as a Small Business Owner

As a small business owner, it’s hard to take a successful holiday. One way or another, and without even knowing it, you get roped into a ‘small task’ while you’re away which then turns into a full responsibility. And before you know it, your holiday is over and you haven’t had a proper breath of fresh air.

Let me tell you a story about this…

I once worked with a business owner who was growing much faster than he’d imagined. He was making sales beyond his expectations. He had employed two people within a span of three months.

And the business continued to exceed his expectations.

It was time consuming, but at the same time very rewarding. Plus, he couldn’t complain about the money he was making.


He wasn’t managing his time well, and he had no work-life balance at all. He would spend more than 15 hours behind the screen daily, and the rest of the time sleeping. His wife and kids had to suffer. Because although he was physically present, he wasn’t paying attention to them.

Fed up, his wife decided to surprise him with a holiday. She didn’t tell him any details about it, and hours later they landed in a cabin out in the woods.

But there was a problem.

The internet connection was poor and he couldn’t do much work. This was, of course, only a problem for him. His wife was secretly happy about it.

They were out there for a full week.

And do you know what happened to the business?

Nothing. Nothing happened.

He made a few calls and delegated the work to his assistant.

And when they returned, his business was thriving as always. His employees had handled every little ‘crisis’ perfectly. He had even made more sales than usual. At the end of it all, he had no regrets. 

In fact, he was finally motivated to take up the tasks that he had been putting off for years.

Why Every Business Owner Deserves a Break

70% of small business owners don’t see a holiday as taking a holiday from work. They are afraid to leave their businesses unattended even for just 24 hours.

19% of small business owners admitted to feeling guilty getting away from work.

Do you know what this does to us? We end up suffering from burnouts. We get stressed, and we become less productive. Our creativity diminishes. And we set a bad example for our employees.

Our 8 Tips for a Successful Holiday as a Small Business Owner

At Outside ideas, we help business owners to thrive, and this means establishing a balance between work and personal life. Here are our 8 tips for a successful holiday:

  1. Timing
  2. Crisis management
  3. Preparation
  4. Communication
  5. Delegation

1.  The First Step to a Successful Holiday -Timing

If you want to take a successful holiday, you need to consider timing.

The best time to take a holiday is during slow periods. This means two things:

  • When your Customers are also on Holiday

There are periods of the year like Christmas and Easter when majority of your customers are on holiday.

This is the best time to go on holiday because you probably won’t need to interact with them as you regularly do. 

  • When your Workload is Less

There comes a time of the year when every business slows down slightly, and this is the best time to take a holiday.

When you feel that you have lots of free slots during the day, and that you’re able to tick off your to-do list faster than you usually do, it’s a sign that you can take a break. This will help you to refresh your mind for the busier days ahead.

Even so, it must be said that there’s no perfect time to go on holiday. Slow periods might not coincide with your children’s holiday schedules. Or, it could be that the slow period falls during hurricane season at your destination.

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 on proper preparation.

2. The Second Step to a Successful Holiday – Crisis Management

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?

This is what we define as an emergency:

  • Something Only You Can Solve

If something happens to your business which your employees are unable to solve, then that can be classified as an emergency.

It may be worth putting everything aside and attending to it. Or, if possible, you can take your employees through how to solve that particular problem and go on your holiday.

  • Something That Would Cost You An Opportunity

If you came back to work after holiday and realised that you’ve missed out on some life changing amount of money, you would probably be a little bit annoyed with yourself.

If a potential client reaches out to you while on holiday, the least you could do is inform them that you are away and request more time to get to it.

Or, you could also drop everything and do it at the expected time. It’s all up to you to weigh your options and decide.

  • Something That Cannot Wait

An emergency at work cannot wait for you to return. It needs to be solved immediately. If that’s the case, then you have no choice but to put a pause on your holiday and do it.

You’ll need to go to a quiet place where you can fully focus and do the work to the best of your ability.

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. Don’t be afraid to set those boundaries for yourself and the people that you work with.

3. The Third Step to a Successful Holiday – Preparation

If you’ve been in business for a while, you’re able to pre-determine what’s coming for you. You can predict what the days ahead look like, and this is where preparation comes in.

When you prepare well, it’s harder for things to come up out of the blue. You can then put everything aside and just relax.

Here is what you need to do to prepare well for your holiday:

  • Cover your Bases

After months or even years in business, you can easily tell 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. Explain to your employees exactly how to deal with the crises. When you give them the permission to handle issues that you usually do, you motivate them in their jobs.

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.

  • Contact your Customers Early

As part of preparation, you need to let your customers know that you’re going on holiday.

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.

Communicate your boundaries with them respectfully. If you don’t want to be contacted during that period, find a nice way to put it.

Ask them to send in all their requests beforehand and be sure to attend to everything before you leave.

  • 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.

4. The Fourth Step to a Successful Holiday – Communication

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.

These are the two people you need to communicate with:

  • Communicate with your Clients

Your clients need to know that you’re on holiday, otherwise you won’t get a proper break. 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.

Let them know who they can reach out to in case they need anything. Tell them who you’ve delegated responsibilities to and where they can get any necessary help.

This way, you will get to enjoy the time off without any secrets. You’ll have 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.

If they do, perhaps they’re not the right fit for you.

  • Communicate with your Employees

Your employees will hold down the fort for you while you’re on holiday.

Meanwhile, they have their regular KPIs to achieve. So, you need to let them know in good time so that they know how to organise their time.

You may hold a meeting with them,letting each person know what they’re responsible for while you are gone.

Give timelines, if possible, and explain in depth what you expect from them.

Which brings me to the next point – Delegation.

5. The Fifth Step to a Successful Holiday – Delegation

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.

Here’s what you need to know about delegation:

  • Let go of Perfectionism

Most people that struggle with delegation struggle with perfectionism. We want things to be done to the standard that we do them ourselves, and sometimes, this seems impossible.

To delegate effectively as a business owner, you have to learn to let go and accept a new standard. Not everything will be done exactly the way you usually do it and sometimes that is a good thing.

  • Prioritise Communication and Feedback

As you’re getting ready to delegate and go on holiday, you may have to give the employee(s) some of the tasks that you want them to handle.

And when you do this, be sure to effectively communicate with them on what you need and give them feedback.

Be receptive to hearing their opinions as well. Keep the communication lines open, and you’ll be sure to have a stress-free delegation process.

Five Steps to a Successful Holiday – Our Summary

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. Timing
  2. Crisis management
  3. Preparation
  4. Communication
  5. Delegation

Now go forth and plan your next holiday.

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

Outside ideas firmly believes in a proper work life balance. We can confirm that business owners who take proper time to recharge end up performing a lot better than those who don’t.


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