Anyone who knows me knows that I love my holidays. And that I regularly talk to clients about what holidays they’re planning. Whilst I do that because it’s a great subject to talk about, I’m also a massive believer in taking regular breaks to recharge your batteries, reward you for a job well done and help you refine your business plan.

That’s right, I honestly believe that holidays help you to refine your business plan.

By taking yourself out of the daily grind you give yourself the time and head-space to think, which can bring a level of clarity that’s very hard to find when you’re embedded in the job every day. Without fail my clients come back from a holiday feeling energised, focused, determined and far more productive than when they left.

But I know that many people still really struggle to take time out of their businesses. It can be much easier to talk about than to actually do, so I thought I’d share some tips on how to make this more manageable, and in some cases less terrifying!

  • Plan Ahead

One of the biggest reasons that breaks either don’t happen or that they end up being much shorter than you would like is that they’re just not booked in. It’s very easy to work on the ‘I’ll fit it in when I get chance’ basis but that will almost certainly lead to less holidays. So plan your holidays now. Which days or weeks will you take off this year? Does your holiday buddy / husband / wife / partner need to book those dates off work? Block the dates out in your calendar right now.

Of course this doesn’t guarantee these holidays will definitely happen and if something you feel is desperately urgent gets in the way then you still have the chance to change things. But marking these dates in your calendar right now costs you nothing and probably increases the likelihood of you taking a break by at least 50%. So … what have you got to lose?

  • Give Your Customers Plenty Of Notice

Another stumbling block is having a date in mind but then just finding yourself too busy when the time comes to be able to get away. By giving your customers plenty of notice both they and you can plan your workload better and make the chances of sticking to your plans much better.

I should warn you though that when you let your customers know about your holidays they’re likely to bombard you with work they’d like done in advance, so be sure to give them plenty of notice!

  • Define The Processes and Support That Your Business Needs To Run Smoothly Without You

This is probably the biggest single thing you can do to improve your chances of taking more breaks. Take a step back from your day to day role and make a list of everything that’s likely to happen during a holiday that nobody else could currently handle. Obviously if you’re the only person in your business that will be quite a long list! But don’t panic.

Next, mark the list with things that could wait until you returned and things that would absolutely need dealing with straight away. This is where is gets trickiest because when it’s your own business you may well think everything is urgent and couldn’t possibly wait, when in fact your customers (if given plenty of notice) would happily wait as long as they understood the timescales involved.

Next, look at what processes, systems or support you can create that will allow somebody else to handle these things in your absence or create a holding process so that everything is still under control and you’re not having to deal with 87 bazillion emails every day of your holiday! Because let’s be honest, that’s really not a holiday is it?

Do you need to run some training with your team so that they can deal with more while you’re away? Or do you need somebody like a Virtual Assistant to be your buffer? They can do that for you but only if you plan ahead and get to understand each other’s working practices and preferences in advance. It’s no good contacting a VA you’ve never used before to ask them to hold the fort for you next week!

  • Plant The Seed

This is where the fun starts! Go and spend some time surfing the internet and looking at places that you might like to go on holiday. It doesn’t matter whether that’s Bridlington or Bali, the action of looking things up makes everything more real and will make you more determined to make it happen. And just to give you a little challenge – if your gut instinct is saying this point is rubbish that’s because you still don’t believe this holiday will happen so you don’t want to set yourself up for disappointment!

Knowing exactly where you want to go on your break will undoubtedly make it more likely to happen.

  • See It Every Day

Finally, create a visual reminder of your holiday plans that you’ll see every day to keep the desire strong and embed the belief that it will absolutely happen. You could do that by putting a picture up in your office or in your wallet, or on your bathroom mirror or your laptop screensaver. It really doesn’t matter how you do it, but again this will continually plant the seed and make it far more likely to happen.


I actually wrote this blog as a result of a bit of a throwaway post I wrote on LinkedIn a few days ago about the challenge of taking regular holidays when you run your own business.  It’s fair to say it caused quite a debate with over 100 likes & comments and more than 15,000 views!

If you’d like to join in the discussion you can do that here:

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