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Small to Medium Businesses

How To Plan For A Holiday When You’re Your Own Boss

By June 14, 2019July 29th, 2021No Comments

The mental health benefits of holidays go without saying, but if you’re a small business owner you could be avoiding booking that well-earned break. As many as 76% of small business owners and entrepreneurs sacrifice holidays to keep their business running smoothly, but with some planning and preparation there’s really no reason why you can’t get some R&R this summer.seashells on the beach


1. Communicate your planned holiday dates as far in advance as possible

Whether its clients (if your business offers services) or suppliers, contractors or otherwise, it’s always a good idea to flag upcoming holidays well in advance to those you’re working with. So send those dates around as soon as you’ve got them, or share your holiday dates as a meeting invite (mark it as ‘free’) with key people so you know they won’t forget. People will appreciate the early heads-up, and you never know, it might encourage them to do the same in return.

2. Identify potential problems and get a plan of action together

It may sound counterintuitive to splurge and write down all the possible problems that could arise if you went on that holiday, but you can only truly prepare for them and mitigate the risks if you’ve identified those worst-case scenarios. So bear with us!

  • Map out 6 columns on a whiteboard, paper or spreadsheet
  • In the first column, jot down all the potential problems that might arise if you go on holiday, however big or small
  • In the second column, rate the likelihood of that problem happening from 1-5 where 1 is very unlikely and 5 is very likely
  • In the third column, rate the impact on your business if the problem happens from 1-5 where 1 is very low impact and 5 is very high impact
  • In the fourth column, calculate the overall risk by multiplying the likelihood by the impact
  • In the fifth column, write down what you could do to prevent that problem from arising BEFORE you go on holiday
  • In the sixth column, write down the ways in which you could mitigate the impact of the problem once it’s happened (some things you may not be able to prevent, but you can at least have a plan for managing the situation when you get back)

Your overall risk rating can act as a priority order, so you know where best to spend your time in the run up to your holiday.

3. Take advantage of automation

There’s a lot that you can schedule in advance, from newsletters and social media posts to any other communications that may need to happen at that particular time. If you’re using cloud accounting software, you can also set up automatic invoice reminders to go while you’re away. Talk to your accountant if you have more specific worries about business finances while you’re away, they may be able to help with particular payments or other concerns.

One particularly useful tip for your inbox is to set up filters that file incoming emails automatically to specific folders, so that your inbox isn’t such a blur of unread emails when you return – you’ll be able to deal with them in a sensible priority order.

You could even add a filter for urgent messages so that they are forwarded to your phone if “URGENT” is in the subject line (and you can add instructions in your out-of-office message for people to resent urgent emails with “URGENT” in the subject line). Speaking of which…

4. Spend good time on your out-of-office

That automated out-of-office reply is the easiest thing to forget when left to the last minute. And even if you do remember, the chances are that your message will be pretty basic and perfunctory. So we have two suggestions for you:

  • Think about why people could be emailing you, what they might need, and how you can help point them in the right direction or give them clarity on when you’ll respond. There are some great examples here of out-of-office messages that show loads of personality and even act as a lead generation tool in some cases, doing some work for you while you’re away.
  • Get it sorted early! As long as you’ve provided the correct date range and turned it on, it will only activate on the days specified, so there’s really no reason to leave it until the last minute.

5. Decide in advance what will and won’t be done

Be realistic with yourself and your clients/suppliers. There is only so much you’ll be able to get done before your holiday, so decide in advance what you’re going to prioritise and what will have to wait. Then stick to the plan. As long as you’ve clearly communicated any amended timelines or impacts, you’re unlikely to upset anyone. The worst thing you could do is take on an unrealistic amount, fail to meet pre-holiday deadlines, and then spend your time away working or worrying over it.

6. Be ready to switch off

If you’ve followed the above steps, you should have no problem relaxing and recuperating while you’re on holiday. You’ll have a plan in place for emergency situations or urgent requests, so there should be no more “what ifs” rolling around in your head. All that’s left to do is enjoy it and, if you’re in the UK this summer, cross your fingers for sunshine!

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