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As a contractor or freelancer, you are not a direct employee of a company or organisation, therefore you are not entitled to holiday pay as a company benefit. However, that doesn’t mean there aren’t things you can do to have a stress free holiday… In this article, we will give you all the information you should need to feel confident taking time off as a contractor or freelancer, highlighting what to do before, during and after your holiday.

Why Taking Time Off Is Important

Taking time off can be difficult for any freelancer, with feeling guilty about taking time off and simply not being able to afford any time off being cited as two of the main reasons for not taking a holiday. While there are plenty of excuses for not taking a break, it’s essential that you do, as taking some personal time is vital for a number of reasons.

Before even thinking about planning your holiday, it’s important to consider why taking time off is so vital. Many freelancers fall into the “I’m too busy for a holiday” trap, and whilst it’s true that you will be extremely busy, you simply must make time to take a well earned holiday.

There are several physical and mental benefits to taking a holiday, with the chances of you burning out from fatigue significantly lowering when you take regular time off work throughout the year. Constantly working can pose a risk to your health and can eventually result in a drop in motivation and work quality, so it’s essential that you take the time off that you deserve.

Taking time off regularly shouldn’t be seen as a problem, as it gives you something to look forward to throughout the year, whilst reducing the chances of you having a burnout. It’s extremely important that you remember that your business won’t fall apart in the week or two that you take off – so be sure to give yourself a break!

In this article, we will give you some tips on how you can minimise the impact on your workload when you do want to take a holiday, how you can enjoy your holiday by putting contingencies in place and some steps you can take to ease you back into freelancing when you return from your break.

How The Self Employed Should Plan Holidays

When it comes to taking holidays as a freelancer, planning is the key to ensuring that you make the most of your break away from work. In this section, we will give you some of our top tips when it comes to planning holidays for a contractor.

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Plan As Far In Advance As Possible

Giving yourself and your clients as much time as possible to plan for your break is the first, and probably most important step to take when planning a holiday as a freelancer or contractor. Giving your clients plenty of warning gives them time to prepare for when you won’t be around, whilst also giving you the peace of mind that they are fully aware of your break well in advance.

When planning your break, be sure to make the most of the time you are planning to have off – keep yourself busy during your travels and take advantage of your well-earned break. Holidaying as a freelancer or contractor can be difficult as your mind can often be fixated on work, even when you are supposed to be relaxing, so keeping yourself busy during your break is a great way to ensure you really do make the most of your time off.

When you have your holiday planned in, be sure to stick to it. There can be a tendency for self-employed individuals to cancel holidays close to their due date simply because they are too busy, but don’t fall into this trap – you have earned the break.

Plan Holidays For Quieter Periods

No matter what industry you work within, there will be quiet and busy periods throughout the year – so, where possible, plan your holidays into those quieter parts of the year. Obviously, this won’t always be possible, but it can take some of the pressure off you if you are a serial worrier when it comes to work. Taking holidays in quieter periods of the year can put your mind at rest and can result in a nice period of time you can fully enjoy.

Prepare Your Finances

As a freelancer or contractor, you will obviously not be paid for the time you take off, so it’s important that you put plans into place to ensure that your financial situation remains stable while you are away. This might mean that you work extra hours in the weeks leading up to your break to boost your income, accounting for the well earned time off you will be taking.

It’s also worth ensuring that your contractor accountants are aware of your time off as they may be able to give you some guidance in terms of the best ways to ensure you have a consistent flow of income.

Get Ahead With Your Work

Where possible, you should consider getting ahead with your work before heading off on holiday. If you find yourself worrying about work while away, we definitely suggest putting in some extra work before jetting off so you can rest assured that your clients won’t be affected by your absence.

Planning is essential to getting ahead with work, so be sure to spend a significant amount of time planning your day-to-day tasks in the most efficient way possible.

Block Out The Day Before You Go Away

At first glance, this may sound counterproductive; however, we would strongly suggest that you block out the day before you go away in your calendar as far in advance as possible. The main reason for this is to ensure that you have some time set aside to tie up any loose ends with no distractions.

Taking this time to ensure that everything is taken care of before you go away can help to genuinely put your mind at ease and allows you to properly relax from the start of your holiday.

Put A Plan In Place For While You’re Away

Now that you are satisfied that you are fully prepared ahead of your holiday, it’s time to consider how you will plan for when you are actually away. It’s absolutely vital that you put a few contingencies in place for when you are on holiday, so you don’t worry about your phone ringing or your emails being clogged with client messages whilst you are away.

Here are just a few of the plans you should put in place ahead of your trip:

Prepare For Emergency Situations

It’s inevitable that your clients will come to you with emergency situations while you are away – but don’t fear, there are ways to combat this. If there is a genuinely pressing issue that comes up, that needs to be dealt with immediately; for example, if you are a PR professional and there is a brand crisis, you should have a plan in place to remedy this before going away.

This might mean that you have given someone else in the company a detailed plan of action for certain situations, or you could have another trusted freelancer on hand ready to step in and manage the situation. Remember that it’s important that you do have the opportunity to genuinely switch off when you are on holiday, so having someone on hand to pick up the pieces in your absence is essential.

Managing Client Expectations

Before going away, be sure to set out the type of break you are going to be on to all of your clients – this will help to ensure they are fully aware of whether you will be free to take calls and answer emails. If you are going on a complete digital detox break, be sure to let your clients know this as it will minimise the risk of them getting in touch with you during your break. If you will be monitoring your emails but won’t be carrying out any actual work, be sure to let them know this too.

A simple email to all of your clients will suffice, but it will immediately set out exactly what you will and won’t do whilst away.

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Set An Auto Respond On Your Email

This could be considered a pretty obvious suggestion, but you’d be surprised just how many contractors forget to set an out of office message. If you do forget to let anyone know that you are away, your out of office message will save you an awful lot of problems, such as clients wondering where you may have gone.

Out of office auto responses are the ideal place to put a short message that gives your clients an idea of how often (or little) you will be working during your holiday, so don’t be afraid to put all the information you feel is necessary in your auto response. For example, the dates you are away and when you are likely to start picking up your emails again.

Make Arrangements For When You Are Back

Whilst you probably don’t want to start thinking about being back from your break, it’s essential that you do plan this into your next break as it will make life much easier for you once you are back.

Here are a few suggestions for arrangements you will want to make ahead of your return from holiday:

Give Yourself An Extra Day

When you get back from your holiday, there can be a tendency for freelancers or contractors to simply dive straight back into the day-to-day work grind. However, we would advise against this. Consider giving yourself an extra day off when you return from your holiday, since it really can make a huge difference on your mental health.

Let’s face it, no one wants to get straight back to work after a relaxing break, so taking an extra day can allow you to catch up on sleep after a long trip, gives you time to unpack and get the laundry done and even provides you with some time to get through your emails, allowing you to prioritise work for the coming week.

We can’t emphasise enough just how useful this extra day off can be for you, so be sure to consider taking it, even if you don’t feel it may be useful for you.

Plan Your Workload Before Going Away

There is a good chance that you will already have an idea of the work you will want to prioritise when you get back before you even go away. Simply writing a list of work that needs to be prioritised when you return – including adding a due date – can give you some clarity when you return from your break.

Providing nothing pressing has come up during your travels, you will have a detailed plan of action ready to go as soon as you return, allowing you to hit the ground running straight away. There really is nothing worse than coming back from a break and being faced by a daunting list of tasks that you weren’t expecting, so forward planning really can be a saviour.


Hopefully, you found this guide to taking a holiday as a freelancer or contractor helpful. Whilst taking a holiday can be daunting for any self-employed individual, it really need not be, provided you have taken the time to properly plan. Be sure to take some time to properly recharge your batteries during your holiday, switch off and enjoy your time off to the fullest. When you return from your break, you will feel completely refreshed and ready to get back to work.

At Gorilla Accounting, we provide expert accounting for contractors so, if you are interested in learning more about how you can maximise your take home pay, why not take a look at our contractor tax calculator?