Two people in deckchairs on the beach, facing the sea, having a work free holiday.

How to enjoy the Ultimate Work Free Holiday

June 2020.    Photo by Simon Matzinger from Pexels
Have you ever got back from holiday, seen 2,000 unread emails and wondered if it was worth it? After just a few hours at your desk, the mojitos feel like last year not last week And your desk feels out of control? Yes?
It needn’t be like this. With a new mindset and some savvy management, you can feel in control of your inbox when you get back.

Here’s what to do…

Before you go

Reboot your mindset

Decide to believe that you & your holiday are more important than work. Ditch the belief that you can’t say ‘no’ when a client says she wants the advice before you go. Ditch the belief that you ought to be available in case something urgent comes up. Instead, choose to believe (yes, it’s a choice) that you deserve a complete break; you can leave things half done; you’re not indispensable; and it’s okay to ask others for help.

This may feel uncomfortable.

If it does, that’s your critical inner voice talking. Perhaps it says things like: people won’t like it; they’ll think I’m lazy; or they won’t rate me? Thoughts like these are not facts. They are your guesses at what other people may think = your mind has made them up. Choose to believe something more empowering instead.

If you find this bit difficult, which it is (let’s be honest), a coach can help you break free from your inner critic’s grip.


Decide if you want to disconnect completely from the office, or whether you will do a short, bounded amount of work while you’re away. Ask yourself, what will enable you to enjoy your holiday the most?

Jim, a partner, spends 30 mins before breakfast each morning of his holiday to deal with urgent emails & voicemails that ONLY HE can deal with e.g. no one else in the firm knows about them. In this 30 mins, he forwards urgent items to colleagues. For the rest of his holiday, he leaves his phone in the villa.

Sarah turns off her work phone and emails as she goes through security at LHR and only switches them on again when back at LHR.

‘Yes’, I hear you thinking, ‘but my work emails are on my personal phone’. Okay, turn off all email notifications while you’re on holiday and don’t look in your work inbox, or temporarily delete your work email account from your phone (you can reinstate it later).

If you have colleagues, decide if they can catch you up on your return, or whether you’re going to catch yourself up. If colleagues, clearly tell them you want them to do this and that you won’t be reading emails on said projects/ clients because you’re relying on them. Then schedule a 20-30 min meeting with them on your first day back.


Block-out your first two days back to give yourself time to get on top of your in-tray and to prevent others from hijacking your time.


Communicate your absence clearly in advance to colleagues and clients. Say that until you go, your focus will be on existing urgent and important matters and you’d like them to support you with this. I recommend you tell them 10-14 days in advance. Start earlier and people have time to put in extra requests. Start later and people may complain you’ve not given them enough notice.

Enlist the help of others

If any new requests come in during this pre-holiday period, delegate. If there’s no one to delegate to, coach the person to take action without you. Say something like, “I’m sorry, I’d like to help but I don’t have any spare capacity before my holiday. How could you progress things/ what could you do to move this forward/ what alternatives are there to handle this?” Your sole aim here is to leave THEM with the monkey (the action), not end up with the monkey on your back.

If you work solo, you may not want to take this approach with clients. What do to? Have you considered setting up a reciprocal arrangement with another entrepreneur to progress urgent client work in your absence (and you do the same for them)?

Also, if it’s just you, you may worry about a client being unable to reach you on a truly urgent matter, or that you’ll miss a new business lead. If so, get yourself a Virtual Assistant (VA) to handle your urgent calls – you divert your phone to them. Your VA will contact you in the way you’ve agreed if something urgent comes up. In my experience, VAs provide a very professional and affordable telephone answering service which they usually charge on a per-call-answered basis.

Be smart with your out of office message

I bet your current out of office reads something like this:

“Hi, Thanks for your email. I’m on holiday from [XXX date] to [YYY date] inclusive and will not be checking emails. If your request is urgent, please contact [Name] at [Email] or [Phone]. Otherwise, I will respond to your mail on my return. Thanks, [Your Name].”

This approach is boring (sorry!) and leaves you with the time-consuming job of sifting through your inbox on your return to fathom what’s important and what’s not.

‘Yes’, I hear you thinking, ‘that’s the job’.

And it’s also your job to train people to work effectively with you. And to model a healthy work life balance. How about this instead…?

“Hi, Thanks for your email. I’m currently on holiday [in the land that invented the stapler/ enjoying German efficiency/ something amusing] until [XXX date]. I’m sorry, you’re stuck in the office.

If your request is urgent, please contact [Name] at [Email] or [Phone].

If it’s not urgent, I fear your mail may become swamped in the [2,000] new emails I expect to receive while away! To help me get back to you as quickly as possible, please resend your email again on [XXX date], with ‘For Info’ or ‘For Action by [date]’ in the subject line. Thank you for help. I appreciate it very much, [Your Name].”

‘I can’t do this’, I hear you thinking. ‘Why not?’ Put yourself in your client’s shoes – you’ve been amusing and friendly up front; and you’ve asked them to do one small thing to help you get back to them more quickly. What’s not to like? Go on, try it. I call it the ‘Resend Tactic’.

If you work solo, give your VA as your alternative contact. And instead of the Resend Tactic, you may want to use the following approach:

“Hi, Thanks for your email… stuck in the office. [As above.]

I’ll not be checking emails while away but will reply to you by [YYY date – commit to a realistic deadline, NOT your first day back].

In the meantime, did you know I have a [regular newsletter? The current issue covers ABC.] Click this link to get your copy.

I look forward to connecting with you soon, [Your name].”

While you’re away

Enjoy your holiday!

Stick to the boundaries you’ve set yourself. If you find yourself wanting to check your work phone, pause. Notice what you’re feeling and thinking. There will likely be an uncomfortable emotion and some unnoticed, habitual thoughts. It’s these thoughts you need to grab hold of and change because they’re driving your habit. Just like Ann and Matthew (not their real names) did:

Ann realised she had FOMO (a Fear of Missing Out). This originated from when she was young and felt left out by her older brother. She told her boyfriend over a bottle of Malbec and asked for his help. By the end of the holiday, she’d kicked her phone habit.

Matthew realised he felt bored sitting by the pool with his family; checking his phone was an excuse to get away. He decided this was sad so suggested they all visit the local market - a trip that led to a pic-nic of cheese and chorizo on the sea wall - one of the best meals of the holiday.

When you’re back

1. Have meetings with the people who are catching you up.

2. De-brief with your VA.

3. If you used the Resend Tactic, don’t read ANY of the emails that arrived during your leave. Move them all into a new sub-folder called ‘Holiday’. Instead read those received on [XXX date]. Read what’s in the ‘Holiday’ folder if the business need arises, plus schedule some time to read newsletters etc. After (say) a month, delete or archive the sub-folder.

4. Celebrate.


Are your post-holiday blues a sign of something else? Do you feel fed-up, or even worse, trapped? Do you want more but don’t know where to start? Click on the image or button below to get your free copy of my Rethink Your Life Toolkit.

This Toolkit will get you unstuck! Inside you get my 7 step Rethink Your Life system, within which to rethink your career and life (the very same system I use with my clients), and I give you the 7 questions to ask yourself to work out what would make you feel happier and more fulfilled. Click on the button or image below to get your free Toolkit today.
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About Jo Maughan
Jo Maughan is the founder of YourThinkingPartner. Her first career was as a FTSE 100 Tax Director. After suffering a fall and a significant brain injury, she overcame her fears to follow her calling as a coach and artist. She is now living the life she was meant to live, inspiring successful mid-life professionals at or near the top of their careers to rethink their careers & lives for more balance, fulfillment, purpose & joy. She and her clients use her 7 step Rethink Your Life system. Jo is a sought after speaker and is currently writing her first book.
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