It’s Ok To Work On Holiday

It’s Ok To Work On Holiday

1024 635 Caroline Flanagan

It’s Ok To Work On Holiday

work from home


Of course it’s the holiday season so this won’t surprise you at all. But if I tell you I’ve been here since 18th July and I won’t be returning to the UK until 31st August your eyes may widen just a little in disbelief. After all, I have a business to run which has not yet learned how to run itself.

For six weeks of the year my home is a beautiful farm house in the Piemontese countryside in northern Italy. I take two separate weeks of holiday and for the remaining four weeks I work remotely. I do meetings via Skype, phonecalls via whatsapp and pretty much everything else on my laptop and smartphone. If I didn’t tell you, you wouldn’t even know I’d left the office.

That’s the beauty of working in today’s world. All that modern technology has it’s uses. And I am exploiting everyone of them.

There are plenty of challenges. When our wifi doesn’t work, my kids aren’t cooperating or my babysitter doesn’t show up it can be pretty frustrating. When it’s 40 degrees outside (and not much less inside) and there are mosquitoes feasting on my ankles it can be pretty hard to concentrate. But being Babyproof means I’m flexible. I adapt to the circumstances and I find a way to make it work.

The real problem arises when I take holiday. Take last week for example. Me, Pablo and the boys went camping for a week in the Dolomites, the stunning mountain range in north eastern Italy. Our campsite was at the foot of a mountain range so stunning and beautiful we felt we were living in a picture postcard. We went walking everyday, spoke Italian and elementary German to the locals and cooked our evening meal on a tiny little camping gas stove set up beside the tent. It was idyllic, except for one thing:

I needed to work.

I not only needed to work. I wanted to work. The campsite had a patchy wifi connection but it was good enough to give me access to email at certain times in the day. So when I needed to, I got stuff done.

From the outside looking in I know how this looks. Sending emails and doing social media marketing while on a one week camping holiday with the family – that’s pretty bad right? Well, if you’d asked me a year ago I would have agreed with you. But not now. Now when I work on holiday, I don’t feel bad or guilty at all.

If you’re lucky enough to never have had to work on holiday then good for you and long may it continue that way. But if, like me, you find yourself having to check and respond to emails or trouble shoot problems while you’re away, and this makes you feel guilty or resentful I have a new notion for you:

It’s OK to work on holiday.

You can say it out loud if you like: It ‘s OK to work on holiday. I’m not saying it’s good to work on holiday. What I’m saying is that if you have to do it, the worst thing you can do is beat yourself up about it, let it stress you out and ruin your holiday, because it doesn’t have to. When you find yourself forced to work on that long awaited family holiday in Florida, do what I recommend you do in every situation that makes you feel frustrated and powerless: take ownership of the situation and find a way to make it work.

There are convincing reasons for doing so. Taking ownership puts you back in the driving seat again. It stops you feeling like a passenger being driven along by forces beyond your control to a place that is not to your liking. Instead it gets you to look at your situation and find the things you can control, such as your mindset, the time you get up in the morning and what you say yes and no to.

Taking ownership isn’t just a principle I believe in it’s one that runs through my veins and underpins the strategies I teach in my book Babyproof Your Career. I never liked the idea of feeling powerless in any given situation, so I was always looking for a way to wrestle back some control. When I said earlier that I no longer feel guilty or bad for working on holiday, this is the reason why.

It’s easier than you think.

Just ask yourself the right questions about why and how you are working on your holiday. Here are the 3 questions that work for me:

1. Why am I  working?

The way I see it, there are good reasons and bad reasons for working on holiday. If you are working on holiday because you’re afraid something might happen while you’re away or you think your business/workplace/project can’t survive without you then I would consider these bad reasons that speak volumes about your ego, organisation or inner control freak and so need to be ignored. If this is your thinking, why go on holiday at all? But if you are working on holiday because a specific problem has arisen for which you are personally accountable, or because your holiday has come along at a critical juncture in a high value project (a good indicator of this is when the alternative would have been to cancel your holiday), then I’d consider this a good reason and then ask myself the following:

2. When is the best time?

The worst thing you can do is have your blackberry or iphone permanently switched on while you’re on your holiday and take it with you everywhere you go. If you can see it, you’ll keep checking it. If you keep checking it, you’re not fully present and so you’ll miss it all –when a humpback whale breaches right next to your expedition boat delighting all on board, your pulse will barely register. Or when the golden glow of the setting sun flickers across a quietly rippling Mediterranean sea, you won’t even notice the splendour unfolding before your eyes. Certain times of the day lend themselves to email checking, phonecalls and reviewing documents better than others. This depends not only on your holiday routine but your own body clock – whether you’re a morning person or night person for example. For me the early morning always works best. I am writing this article at 6.00 a.m. which is the coolest part of the day, when my children are asleep and when I am at my most alert and focused. By getting my work done in the early part of the day I can ensure I’m free for our day trip to the car museum in Turin later today.

3. Who else is affected?

Most likely you are not on holiday on your own, which means that if you need to dial into a conference call in the middle of the afternoon, other people are affected. If it’s a family holiday, your partner is left in charge of the kids and your kids are one parent down. If there’s just the two of you on a romantic holiday together and you start checking emails at the dinner table, make no mistake about it, you are being disrespectful of their time and company. I’m not saying it’s your fault, I’m saying that it sends a bad message. If you do need to check mail at the dinner table make sure you (a) have an extraordinary reason for doing so and (b) shower your partner with all the reassurances, pleas for forgiveness and promises to make it up to them you can sincerely muster. A little bit of recognition goes along way. By doing this you show that you care, you know it matters and aren’t taking them for granted.

When it comes to working on holiday taking the time to ask these questions is a great place to start. But it won’t work to just mull them over. Questions are most effective when you make the effort to answer them and then act on your conclusions. Doing this allows you to set healthy boundaries between work and life that won’t come crashing down the next time work comes knocking on your hotel door.

About Caroline
Caroline has a BA (Hons) from Cambridge University, England and trained as a lawyer at the College of Law in London. She worked for 8 years as a finance lawyer in two of the world’s leading international law firms, Allen & Overy, LLP and Cleary Gottlieb Steen & Hamilton LLP, before discovering a passion for Coaching. Caroline graduated as an accredited Coach in 2006.

As a mother of four young boys, experienced Coach and passionate advocate of “Having it all”, Caroline is an inspiration to aspiring professional mothers and is uniquely placed to guide and support them on their journey towards a rich and rewarding family and work life.


Caroline Flanagan

Caroline Flanagan

Caroline Flanagan is an Author, Coach and Inspirational speaker on issues relating to women in the workplace. Caroline is the founder of Babyproof Your Life, a niche coaching service for career-focused women who don’t have children yet but know they want to in the future. Her book 'Babyproof Your Career: Prepare to keep your career on track before you start a family' was published in October 2015.

All articles by: Caroline Flanagan

Leave a Reply