The challenges of being a digital nomad with a family

For many, it’s the dream. Year-round flip-flops, sand, and a WiFi connection, earning just enough money to get back, while allowing entrepreneurs the chance to pursue their dreams. All a digital nomad needs is somewhere to connect to the internet, and they’re sorted. In addition, flexible working practices mean that in theory, some of these jobs can be extremely lucrative - data scientists, developers, and designers can all work from a laptop, picking up projects when it suits them, and when they need a cash injection.

So far, so idyllic, but what happens when you get a little older, and having children seems like a good idea. Can having a family ever be truly compatible with being a digital nomad?

For Dolly* 32, who travels the world with her two kids aged eight and 11, being a digital nomad and having two mouths to feed can be quite difficult at times. “I’ve been judged for taking my kids around the world. We’re currently in Mexico City, and they’re attending an eight week long Spanish school, which gives me time to work on client demands during the day. I, hand on heart, think I have the richest situation of any mum out there. My children have helped cows to give birth in Tanzania, done lessons on a yacht in Croatia, and seen the Great Barrier Reef. They can both read and write perfectly, and they’re taught by tutors in whatever city we’re in.”

She admits that she had to change her travelling ways after her kids needed to start learning. “I travel because it enriches the soul, and I love being able to run my design company from wherever I am in the world. Plus, to be be blunt, I can afford a much higher quality of life doing this than if I was back in Edinburgh, where I’m from originally.”

She explains that when her kids hit secondary school age, she doesn’t want to deprive them of a future, so they’ll probably head back to Scotland, and call digital nomadism a day – “for now.. But it’s getting harder as my oldest moves towards being a teenager, and she wants to hang out with friends and just do kid things. I get it.”

Other digital nomads can probably empathise with Dolly’s point of view.

Dave Chaplin is CEO and founder of ContractorCalculator, an online portal that has become the expert guide to contracting and freelancing, providing free advice and information to some 150,000 freelancers and contractors who visit the site each month. Chaplin became a digital nomad aged 32, before, he says, the word was even invented.

“I’d had enough of the nine to five and figured that if I could get my web business up and running I could be anywhere in the world and still work. My girlfriend at the time lived in Paris, and my brother was in Seattle with his family and children. I spent five years travelling around the world whenever and wherever I wanted, provided there was an internet connection. This included frequent trips to Seattle, backpacking for two months in China, and spending many weeks in Asia, especially Bali, my favourite place.

When I met my future wife in 2009 we spent many months travelling the world and were out of the country most months. The arrangement was simple – in the morning I would work, and then I’d be free to enjoy the location we were staying in.”

However, things became tougher when he started a family. “We started our family in 2012, so there’s not been much travelling since then. My business now though has grown from being a lifestyle business to one employing staff and having offices. Would I suggest being a digital nomad to anyone else? Of course, it was great.”

One of the best things about being a digital nomad is that you aren’t chained to a location. Chapin adds: “I can’t see how that would affect the family in anything but a positive way – because you aren’t forced to live away from them to do work. In fact, it’s not a like a job where you have to travel to go and visit lots of clients, which takes you away from your family. It’s the exact opposite which gives you geographic freedom.

“In terms of making it work, make sure your business doesn’t require face-to-face meetings too often, if at all, and also don’t let clients think they can just call you ad-hoc. Try and limit correspondence to emails, and/or scheduled phone calls.”

Gavin Mullins, CEO of, has lived and worked in Ireland, Andorra, and Thailand. He is now married, and has two daughters, one of whom was born in Thailand, while he was a “digital nomad”. However, he managed to make the lifestyle work by not moving around too frequently. “There are some really important foundations to have in place to be a successful digital nomad and mobile entrepreneur. First comes a happy and willing family, then it’s good schools if you have children, access to affordable and high quality healthcare and a good internet connection to be able to work reliably.”

Read: Finding the balance between your work family and your real one

He explains: “You share the family responsibilities and workload like you would in any country while you are working, but the benefit of being in Asia is that the cost of labour is much cheaper than the UK and it was very affordable to hire a nanny to help. This factor alone could actually make your financial circumstances more viable than they would be if you were based in the UK, especially when funding a start-up yourself in the early stages.”

He advises that you need to be prepared to work some strange hours, and to put your kids first. “It’s a fantastic experience to travel with family but in my opinion, you need to do it before the kids hit secondary school or their schooling can become very disrupted. That’s not to say it’s impossible – just a bit harder to plan. You also need to be prepared to work odd hours, one day dealing with someone in the USA and next day someone in Australia.”

Digital nomadism can clearly bring many benefits, but alongside those benefits are many challenges too. Those who yearn for travel and a nomadic lifestyle can make family-travel work, whether by hiring tutors, home-schooling, or staying in one location long enough to make it work. 

*Name has been changed

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