Never Normal Newsletter

Sacrifices and opportunities: From the hippie trail to unicorn startups

Last week I wrote about the growing nomad economy and working with Genki.

As the whole digital nomad thing grows and becomes more common, something else is changing too. You don’t have to make the same sacrifices to travel the world anymore.

I consider the hippies and backpackers who traveled the hippie trail in the 60’s and 70’s to be the forefathers of us digital nomads.

Starting in the US and Western Europe, they made their way to Istanbul, and then across Iran, Afghanistan, Pakistan, and India. They went in search of something — a good time, maybe even enlightenment — that you couldn’t get or experience if you stayed in New York or London or Ohio.

Map of the Hippie Trail by NordNordWest

It was a counterculture movement. Those who chose to travel this way were deliberately opting out of “normal life”. This was an ideological choice, but also a practical reality.

There was simply no way you could travel across a place like India in the 1970’s without sacrificing, at least temporarily, your entire life back home.

Fast-forward 40 or 50 years…

By the time I started my journey in 2012, it was possible to get an internet connection in just about any city in the world. It might not have been super fast or 100% reliable, but being connected changed everything.

The hippies and backpackers had to save up at home, then scrimp while they traveled so they could afford to keep going for as long as possible.

But having a laptop and an internet connection meant being able to work while traveling. And being able to keep traveling indefinitely.

Airbnb took off around the same time. Now travelers are no longer limited to living in hotels or youth hostels. Instead, we can reliably rent entire apartments by the day, week, or month.

That’s exactly what I did for years: work online and live in Airbnbs all over the world. It’s been a wonderful adventure, but living this way has still meant making certain sacrifices.

Even with Wi-Fi everywhere, you couldn’t work a “normal” job while traveling the world. Who would hire you?! You had to come up with some way of making money online (typically as a blogger, freelancer, or running your own online business).

Now, that’s all starting to change. Thanks to the pandemic, remote work has become much more mainstream. Some companies are even opting out of offices altogether.

That’s not to say that Karen in HR will be cool with you hopping on the next flight to Herat, but it’s a lot more feasible to work a traditional job while traveling than it was even just a couple of years ago.

From Sacrifice to Opportunity

Startups like Deel, Papaya Global, and Remote (who just raised a $300M funding round at a $3 billion dollar valuation) have sprung up to manage payroll and compliance for companies that want the flexibility to hire employees who live/work all over the world.

Each of the sacrifices that you’ve typically had to make to be able to travel the world represents a lucrative business opportunity, if you can solve it.

Loneliness has long been a common complaint among travelers. Nomads leave their family and friends back home. And maintaining a relationship is practically impossible, unless the other person also has the freedom and desire to travel.

Now coliving and coworking spaces, and programs like RemoteYear, provide nomads with an instant social scene wherever they go.

Selina, the hotel and coworking chain catering to digital nomads, acquired RemoteYear last autumn. Now Selina is rumored to be going public in a $1.2 billion dollar deal.

Another common nomad challenge is staying healthy on the road. For years my approach was to hope nothing bad happens, and then go for the occasional check-up with the doctor every year or two while visiting family back home.

That sort of works if you’re 25 years old with no health issues, but it’s not exactly a sustainable approach for the rest of your life.

The long-term vision for Genki is to expand beyond health insurance for nomads and to cover health more broadly. Like helping nomads stay fit, eat well, find great doctors, and access mental health professionals (therapy and coaching) wherever they are in the world.

There are still plenty of challenges of nomad life waiting to be solved. But as we solve them, being travel and live all over the world becomes less and less of an extreme lifestyle.

That’s all for this week! More soon…

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I write occasional emails to share what I’m thinking, learning, and doing. It’s all related to the idea of breaking free from the “default plan” in life.

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