How To Take A Proper Holiday

How To Take A Proper Holiday

I’m sitting on the front porch of an old Sicilian farmhouse in a faded wicker armchair.

My view is of a hammock suspended from the trees, the dappled early morning sunlight is casting gentle shadows on the terracotta tiles. I’m surrounded by butterflies and the scent of jasmine, rosemary, lavender and mint. Soon I’m going to eat a citrus-scented brioche filled with pistachio gelato for breakfast because apparently that’s totally normal in Sicily.

This is as close to heaven as I can imagine being and I can hardly believe I'm here. Or it would be close to heaven, if I weren't on my laptop.

Sicily famrhouse.jpg

The plan on this holiday was to carry on my daily writing practice, and as soon as we arrived I realised three things:

  1. This was a ludicrous plan

  2. The whole point of a holiday is to do things differently to your daily life

  3. I couldn’t write about the importance of holidays if I didn’t practice what I preach

For a long time I was like most creatives I know: a ‘holiday’ was a couple of days tacked on to the end of a work trip in a nice location.

It involved managing most of the usual workload remotely, answering the phone and email as usual, and choosing a cafe for lunch based on the strength of their wifi connection. I’d get back to London a bit browner with a few nice photos, feeling ever so slightly recharged and resentful I hadn't made the most of it.

I’ve been learning how to go on holiday properly for a few years. How to go on holiday mentally even when you can’t afford to go anywhere physically. How to convince yourself it’s OK to spend what feels like a lot of time or money on simply having a good time. How to choose a location based on where you want to go rather than where someone will pay you to go. How to put an out of office responder on your email and then not check them until you get back.

That last point is really important. If you check your messages and don’t respond you’ll likely spend your holiday writing responses in your head. If you check your messages and respond to just one urgent message it’s a very slippery slope. If you work with a team, responding to messages when you’re on holiday tells them:

a) You’re not really on holiday and there’s no need to respect it

b) When they take a holiday you probably won’t respect theirs

Once you’re actually on holiday, you have the sometimes uncomfortable task of rediscovering who you are outside of your work.


It’s easy to think that being on holiday is simply the opposite of normal life. No more organising, driving things forwards, planning or negotiating for a week. That it’s just about being passive and lazy, which is often a way of avoiding the task of finding out who you are and what you want outside of your career.

Until I started taking time off I had never really thought about what I enjoy outside of work. Music, art and culture were my passions, I had made working in and around them my job, and that seemed like enough. All of my friends had similar interests, so it seemed totally normal. For a long time this question terrified me, so I’m asking it of you:

What do you enjoy doing that has nothing to do with your career?

Can you write a list of more than 10 activities that bring you joy or pleasure, not including food? For many of us, that’s not as easy as it sounds.

The point of a holiday is to remind you to squeeze every drop of pleasure and adventure out of life you can. To remember that you are not your work, and that your work is not your whole life. It’s to remind us that the world is more vast and exciting than our little corner of it, and never to stay there too long.


10 Holiday Tips and Challenges

  1. Do something that gets you in the holiday mood before you start. My friend Emma goes for a massage or spa day the day before.

  2. The best out of office response I’ve ever read was “I’m currently on holiday and my emails are being automatically deleted whilst I’m away. If your message is important, please re-send it or give me a call when I return on the [insert date here]”. I'm working up the courage to try it next time, let me know if you do.

  3. If you’re staying close to home, try to set yourself the task of going to the places you’ve never been before, trying something new, changing up your usual schedule, eating different food and meeting new people.

  4. Ask yourself what you would like to do or experience that day every morning, and remember you have at least five senses.

  5. Let the people you’re with know what you want to do and be prepared to do it by yourself if they don’t want to join you. Don’t just hope it will happen if there’s time.

  6. Plan your own solo adventures even when you’re in a group, no matter how small. For some reason I like snooping around pharmacies in every country I visit. French pharmacies are the best by far.

  7. Try to leave part of the trip or time unplanned so that you can respond to tips from people you come across.

  8. Take some time to think about what about how you could incorporate the pleasurable or inspiring activities you do on holiday in to your everyday life.

  9. Use some of your time to get your diary out and add dream future holidays and activities to it, even if you have no idea if you’ll be able to take the time off yet or be able to afford it. You’ll be much more likely to plan them if you do.

  10. Keep some kind of a journal, it could be written, audio, photographic or video, of what inspired you and revisit it every so often when you get back to revisit those feelings.

Bonus challenge:
Don't work. The entire holiday. You can make notes for later or capture ideas, but don't do any work.

How do you make sure you take a real break? Let me know in the comments below.