Meet the Nomads

Kaitlyn Reed and Taylor McKnight travel the world for a living. They have spent so much time in so many places that they now count the number of countries they’ve called “home” in dozens. And while on the road, they run two successful businesses.

Taylor founded Sched, a scheduling app which has been used by festivals like Comic-Con and Lollapalooza, and Kaitlyn founded Workcation Club, a truly nomadic business that creates custom nomad-like retreats for teams. Kaitlyn and Taylor are living the dream. Kaitlyn and Taylor are Digital Nomads. Don’t be jealous.

As part of a rare but growing breed, they don’t work like most people. They earn their money and choose to live where they want, out of a carry-on bag, and flit regularly around the world. Their Instagram feeds are amazing. They fill their life with experiences, not things.

It sounds too good to be true. Spoiler: it isn’t. But the Digital Nomadic lifestyle is not without complications. Welcome to a way of working where money, time and work all break step with each other.


The dream

Maybe you’ve felt a deep, tart pang - a feeling that couples confusion, frustration, bewilderment and helplessness. A feeling of having slipped in time. A feeling that the world has moved forward, but you, and most of the people you know, are trapped in the tar of the past.

And it all boils down to this: deep down, the idea of millions of people trudging into an office five days a week simply feels wrong in 2017.

You don’t need me to explain why, but here goes anyway: it’s the technology, stupid. We don’t need to work 40 hours a week, but we do. We don’t need to sit in an office for that same 40 hours, but most do. It’s madness. We just want a compromise. We can make our money and take our choice.

But plenty of people now also go for the extreme approach. They step out of the system, often for good. These are the digital nomads, and they’re richer than you. But not necessarily how you think.


The fever dream

The Digital Nomadic life is part lifestyle choice, and part adventure. For Kaitlyn and Taylor, it began by happy accident, five years ago:

“Starting this trip was on purpose: one summer away in Paris. Keeping it going for over five years was a happy accident of momentum. We get pulled to the next place because there's a new culture we want to experience or event to attend or friends to visit -- and I am lucky enough to have a successful business that enables it all.”

Taylor and Kaitlyn are happily riding a wave they boarded by happenstance, and making the most of it: Kaitlyn’s company organises Workcations - which are exactly what they sound like, but more fun - and are also an opportunity for people to try out the Digital Nomad life for a week or so.

For others, part of the lifestyle is breathless advocation of itself. Online, the word “cult” regularly crops up in fascinating proximity to the phrase “digital nomad”, and it can sometimes feel like a fair comparison when you read the writings of some digital nomads. For the ultra-devoted, their belief system is a cross between the clear-eyed enthusiasm of a Transcendental Meditation devotee, and a member of Opus Dei, self-flagellating to get closer to their God, the ideal work-life balance.

(One devotee calls it the “Riskiest Thing You Can Do,” which may come as a surprise to firefighters, underwater-welders, lion-tamers, and astronauts.)

But really, calling Digital Nomadism a "cult" is not only unfair, it's to miss the point.

Digital Nomadism emerged for a thousand reasons, many of them deeply personal and individual, but looming large near to the whole concept is the book The Four Hour Work Week”, which divides opinion among the Nomad community.

The book’s author Tim Ferris has been described as both, "a god to bros who dream of fashioning themselves into blisteringly efficient Web 2.0 business robots just like him” and someone who “just may have saved my life.”

The truth, as always, is somewhere in the middle. If you boil Tim’s teachings down to a couple of broad ideas, they are reasonable-sounding recalibrations for people wondering whether there’s more to life than the late-capitalist-grind pattern of schooling-grafting-retiring-dying.

Tim’s big idea is essentially a call-to-action for digital nomads: if you were a millionaire, how would you live? Most people would respond, “to see the world” - and Tim’s answer is: do it - by rejecting the old time=money equation, figuring out what you want, and regaining time by automating various work processes.

Then you, one of whom Ferris terms “the new rich,” can spend that time living your dream life.

It sounds great. One digital nomad says that it is, indeed, great: it’s just that “the price of overwhelming freedom is often my isolation,” which sounds kind of… bad.


The challenge

Digital Nomadism is enabled by, and relies hard upon, technology and the ease of connectivity and communication that comes with it. You just need your laptop, your brain, and a ton of apps that allow you to IM and collaborate with other people who are also working on whatever you are working on.

It gives the impression of ultra-connectedness: I can chat to my team, my investors, or my mum any time I like. It’s almost better than if I was physically there!

Or is it? Stories charting Nomads’ creeping loneliness appear on /r/digitalnomad, some expressing surprise that while they feel more connected than ever, the lack of physical proximity to loved ones, or close friends, or just people with the same niche interests, is an emotional gut-punch they did not expect.

Taylor agrees that the compromise is real:

“You give up some sense of community, certain career options that only lend themselves to office-life, most of your belongings and creature-comforts of home. And all the stuff you don't think about from day-to-day life - like where to get groceries, do laundry, send mail - becomes more of a challenge.

Disconnecting from a steady but slightly stagnant social world (the same old friendship circle that frequents the same old bars, shops and plazas) in exchange for an exciting, ever-changing one is, it turns out, a case of exchanging one set of fears for another: swapping the fear of tedium for that of isolation. It’s how you deal with them that matters.

After travelling while working for so long, Kaitlyn has a deep understanding of the importance of real contact and made this a key part of her business: “Finally meet your workmates… jokes are funnier IRL than in Slack!”


Be careful what you wish for

The digital nomad life is appealing when viewed from afar: you work less, achieve the same, and money becomes a less important part of life - meanwhile, you get to start to live the life you really want. Of course, it doesn’t always work like that.

One digital nomad, Clayton Cornell, describes the “The 4-hour Workweek letdown: a feeling of unhappiness and discomfort, especially following the realization that getting what you want in life will require hard work.”

Digital Nomads generally share one big thing in common: at some point, they all made the huge decision to zig while everyone else was zagging, quit what they were doing to travel the world, and try and make money doing it.

Huge decisions carry risk. And they’re not always the risks you think. The unintended consequences of burning a bridge are also, with the fulness of time, the intended consequence: you only know how you feel about burning the bridge to your old life after you’ve burnt it.

That’s not a reason to not burn the bridge. But there’s only one way to find out. This too is part of the allure, and maybe it’s the same reason many nomads also want to start their own business: do something else that’s characterised by huge risk and chance of failure.

The ability to become a nomad raises some moral considerations. Documentary maker Do You-jin, who spoke to many nomads in South-East Asia, made a pointed observation: “Maybe this location-independent lifestyle is only for privileged people from well-developed countries who have amazing passports.”

Hopefully, being a Digital Nomad fosters humility and awareness of privilege among its participants too.


The sweet spot

Kaitlyn and Taylor dodge the loneliness part by being a happy couple, relying on the strength of their relationship wherever they happen to be at that point in time.

For them, how they accept and address the challenges of constantly starting anew defines their experience - and their life. For them, the trade-off works - but it is real:

“My biggest learning is that this life is not for everybody. There are a lot of things that have to align for it to work. It's made even more difficult if you have kids or are looking after a loved-one. We enjoy turning the mundane activities like groceries or laundry into an excuse to explore the city we are living in.”

But it’s not for everyone. Taylor and Kaitlyn are exceptions, insomuch as they stay on the road and fulfil most of their needs. It helps that they treat nomadic life with the transient mentality it demands:

”My happiest moments are the unplanned adventures -- from deciding at midnight to fly to an island off the coast of Thailand scuba dive the next day to spending 3 days on a Moby Dick Marathon (we were the only two people who survived).”

And they’re able to see non-nomads’ envy for what it really is:

”Many people mention how they wish they could do what we're doing. For the first few years, I'd respond with a list of steps you could take to help. Then I realized that it's really just a day-dream. Most people don't want to make the trade-offs, which is totally understandable.”


The new balance

Digital Nomad life is not the solution for everyone. But it waves a vague finger towards the future of work for the rest of us: one where we call the shots more, recalibrate how we consider wealth, and feel confident enough to simply be us. It’s a powerful, and tantalisingly achievable dream.

Taylor has lived the “daydream” Nomad life long enough to see a realistic glimpse of our work future:

”I don't think remote work marks the end of office life -- just that our options for finding work-styles that fulfill us are expanding. For me, it's the flexibility to work when and where I want.”

If being a Digital Nomad is the extreme on one side of the work equation, then working full-time in an office is the other extreme. And yet most of us do the latter. But just being able to work less - and from home a bit more - would be life-changing for most people: not all of us can or want to set up complex Customer Marketing Funnels whilst bobbing on a lilo in Thailand.

Perhaps the biggest questions that Digital Nomad life poses for the majority is: why are you spending most of your waking time at the extreme? Can you free yourself, just a bit?