by Louise Brace

Our colleague and friend, Lisette Sutherland of Collaboration Superpowers is an expert on the subject of working from anywhere. She demonstrates through her podcasts and workshops, just how easy it is to work outside of the traditional office environment with all of today’s super tools we have at our fingertips.

As it becomes easier for us to work from anywhere, the working holiday, workcation or ‘work-whilst-on-holiday’ concept, becomes an enticing and totally justifiable possibility.

And it’s especially appealing if you run your own business and have a family at home. For those of us living this scenario, it’s a constant juggle. Always striving to give a balanced commitment to work and children is something that many of us struggle with.

It can be a constant daily battle to perfect the work-life balance.

When I gave up my full-time job at the beginning of this year to set up my own vacation rentals project. One of the biggest motivations to make the leap from full-time to self-employed was the flexibility to enjoy more time with my daughter during school holidays.

What do you do with your children during holiday time when you are a full-time working parent, who only gets four weeks paid holiday per year?

If you’re like me you have to do some serious precision planning. You pay for your children to go to various summer camps, make an agenda with other parents to do shared child duty, and take separate holidays from your partner to break up the summer. My partner and I haven’t been on a holiday together in eight years! That is definitely NOT the ideal work-life balance scenario we strive for.

Enter the Working Holiday

Even if you are not self-employed, the working holiday is fast becoming a possibility for many, with the trend in organizations offering employees Unlimited Vacation Time. The concept was first introduced in Silicon Valley by tech companies who knew how easy it was to reach burn-out in such an intense environment and who wanted to attract and keep talent through offering a more attractive work-life scenario. Netflix and Hubspot were two of the first companies to introduce the concept. And other global brands are following suit: Richard Branson has just introduced it at Virgin; as have Pocket, Prezi and LinkedIn.

The Unlimited Vacation Time policy is about giving trust to employees. Actually most policies don’t offer completely unlimited time off. The idea is pass on trust and in turn responsibility to the employee. The unwritten rule is as long as you get the job done, then what does it matter how many hours you spend in the office? Most employees who have the option, don’t take more time out than they would normally, but to know it’s there if you need it, counts for a great deal.

Aside from technology and unlimited vacation time, one of the biggest influencers in the working holiday concept is the rise of the holiday rental or Airbnb market. The business travel space is a huge market, and today more and more business travellers are choosing Airbnb style accommodation over hotels.

Why? It’s cheaper, you have more space, comfort, flexibility and privacy. And the same applies to working holidays. No longer do you have to feel cooped up in a hotel room, you can find your own home-away-from-home in which to work and enjoy a holiday at the same time. I should know, I work in the Vacation Rental space!

So how does it work and what are some of the pros and cons? I spoke to two business owners who have been taking working holidays with their family for a few years now, to find out why this scenario works for them.

Case Story One: Lisa Sadleir, Family Life In Spain

Lisa is a huge advocate for enjoying life with the family. Through her Family Life In Spain business she addresses the subject of a better work-life balance through moving to Spain. Lisa spends every summer with her family on a working holiday.

How do you combine two kids, 11 weeks of summer holidays and work?

I spend all year telling new clients that I do not work in July and August. I schedule work in advance and ensure nobody visits during this time. This may seem crazy but I am helping them to create a better lifestyle by moving to Spain, aren’t I ? I practice what I preach. I schedule posts and social media as much as I can over this period too.

How do you allocate your time when you are on a working holiday?

I tend to set a time each morning and often in the evening to check emails and clear my inbox i.e. before and after going to the beach and if we have a day at the house, when we just play in the pool, barbecue meals – we call them “lazy days”, I will grab an extra hour or two to get some planning or writing done.

Hotel or holiday home?

We usually take a private holiday rental. We tried the all-inclusive resort option last year and did not enjoy it at all. Often we go back to the same place, as we know and love it. It takes the stress element out of the trip.

What are three most important things you need to enjoy a workcation?

• Peace and quiet
• Internet connection / Wifi
• Great natural light and space

How do you set up your work space in your holiday accommodation?

Any surface with a view – usually the outside terrace, where I can enjoy a view of the pool and the natural surroundings is good enough for me.

All I need to work is my MacBook Pro, mobile phone, a pencil and paper!

Case Story 2: Hannu Heljala of Happy Melly and Muuks

My Happy Melly colleague and founder of Muuks Creative is based in Finland, but every year Hannu and his family shoot off for a spot of surfing in Bali.

How long have you been combining Finland and Bali as your work-life locations?

This is the third year running that we have taken two months out in Bali as a family on a working holiday.

What gave you the idea to give it a go?

We had been travelling for 14 months in Asia during 2011-2012. When we got back we established Muuks. We knew it was going to be impossible taking indefinite leave from our new business, but by the end of the first year we were slightly frazzled and decided to give a two month working holiday a try. After all we are our own bosses and we wanted to see how it would work out.

How do you combine a baby, surfing and work whilst you are away in Bali?

I go surfing very early every morning, waking up at 5am to go out. When I get back there is still plenty of time for work and children. We don’t have a nanny, so we divide our days: when one works the other takes care of our daughter Aava and vice versa.

How do you allocate your time during the working holiday?

Exactly as at home, we work on week days and take the weekends off, just in a different country! We know Bali well, so we don’t need a lot of time to do stuff like sightseeing.

Hotel or holiday home?

In Bali we stay in a guesthouse, because it’s cheaper than both hotel and Airbnb accommodation. Maybe in the future, if we chose a different destination, we’d go for a private holiday rental.

What are three most important things you need to enjoy a productive and enjoyable working holiday?

Reliable internet is essential, as is air conditioning if, like us, you happen to be in the tropics with a small child. You also need to pick accommodation with good working ergonomics and a quiet place where you don’t find constant interruptions and noise.

How do you set up your work space in your holiday accommodation?

This can sometimes be tricky, especially in guesthouses. You need to find a place with a decent table and chair, or in easy reach of a wifi-enabled coffee shop, or co-working space (these are also available in Bali).

Is there anything you can’t do easily when away?

The time difference can be a problem, especially when you’re trying to have remote team meetings. Plus there is no tap drinking water in Bali, which can be a pain when you’re away for such a long time and travelling with a baby.

There are some comforts that make it nice to get back home.

The Pros and Cons of a Working Holiday

A better work-life balance, get to see the world… hey these are just two great reasons for a working holiday. There are so many reasons why this is the best way to live your life.

You get to take a holiday!

For many entrepreneurs and business owners, especially those of us starting out on the journey, being able to take a holiday is akin to pure fantasy.

It’s easy to get into the mindset that working 24/7 is the only way from here on, but we have to shed that belief straight away. Working without pause is counter-productive and does nothing for your well being or state of mind. You won’t get more done, in fact you’ll get a lot less. Taking a holiday – whether a short break or two-month working holiday, will do your creative self the world of good.

You don’t feel guilty about taking time off

Yes stop it! You don’t need to feel guilty about taking time off, but if, like me, you do have trouble taking time off without questioning it, then a working holiday could be just for you.

Longer Holidays

Yep, no longer do you have to restrict your holiday time. In fact, you can take short, medium or long holidays, as long as you put aside time to check in with your team and plan a work schedule during your vacation.

Quality time with children

Summer holidays just got more fun – for you and the kids. Book an Airbnb or private holiday home and you can spend the whole summer on holiday, working and having fun.

And why restrict it to one place? If you plan in advance, you could spread the vacation across several destinations. You’ll have time and a place to work, and your children will benefit greatly from the travelling experience and spending time with you.

On the flip side…

What about the downsides? Some of the reasons that work in favour of taking a working holiday, can also work against it.

Do we really switch off?

A big part of going on holiday is switching off from work. But how can we completely recharge our batteries if we are working during our holiday? The answer is you won’t completely switch off, but with some careful planning you’ll be able to organize your days so you have time to recharge and time to work.

Quality time with the children

Will your children feel that they have spent quality time with you, when you are working during your holiday? You’re children will always expect your undivided attention, especially when they know you’re not at work. So it’s important to sit down with them beforehand and explain how this holiday is going to work. And make sure you stick to your family-time schedule. Believe me they will be happier to be with you on a working holiday, then stuck in a summer camp on their own.

Three essential factors to enjoy a working holiday

Plan & prepare: Plan your destination and accommodation based around your needs for connectivity and comfort. Make sure you have a space to work, table/desk space and a comfortable chair.

Budget: If you are taking a longer working holiday, remember you need to budget accordingly. Eating at home most of the time and planning activities around the weekend only.

Scheduling is key: If you want to satisfy your work and family, it’s essential to create a daily schedule and stick to it. Decide the days/hours that are for work and those for play. As Lisa suggests, schedule the mornings for email catch-up and save an hour or two in the late afternoon for work catch-up.

The rest of the time be in proper holiday mode and enjoy it!

I didn’t manage the working holiday scenario this year. But I am definitely going to make it happen next year. I’ll share my experiences as they happen.

Do you take working holidays? How do you plan and manage your time? And what are the best and worst experiences? Comment below and help others make the leap to a more flexible work-life balance!