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Never Normal Newsletter

Never Normal Newsletter

Every week I send a Never Normal newsletter to share what I’m learning and new ideas to help you find freedom, success, adventure, and more:

You can find the most recent issues here.

You can find the most recent issues below.

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Never Normal Newsletter

The Accommodation is the Destination

Last week I wrote about Airbnb’s new nomad policy and the accommodation affordability crisis affecting digital nomads.

As expected, this past week Airbnb unveiled their Summer 2022 Release, which they describe as “the biggest change to Airbnb in a decade”.

In short, there are three main changes:

  • new search and browse options based on “Airbnb Categories”
  • the ability to book “split stays” (one trip split across two homes) and
  • an improved support program for guests (AirCover)

Watching CEO Brian Chesky’s announcement video, it’s clear that the company sees the new Categories feature as the most groundbreaking of the three.

Instead of simply searching for “a place to stay”, Airbnb now emphasizes (and allows users to browse and search) all of the different categories of homes available on the platform — from houseboats to vineyards to urban lofts.

With this new feature and announcement, Airbnb isn’t simply allowing customers to search for different types of homes, they’re actually making two bold statements about travel and their business:

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Airbnb’s New Nomad Policy

Howdy 🤠 This issue of Never Normal is all about Airbnb — the company at the center of the ongoing transformation in work, life, and (especially) travel.

Full Disclosure: I’m a (small) investor.

Airbnb’s New Nomad Policy

CEO Brian Chesky announced on Twitter that Airbnb has adopted a new remote work policy.

We’re already over two years into the mainstream adoption of remote work, but Airbnb’s new policy is notable, because the company now explicitly condones employees working from other countries and they pledge not to adjust compensation based on the employee’s location.

In other words, now you can get a job working for Airbnb, making Silicon Valley money, while hopping between Mexico, Bali, Budapest, and Lisbon (or wherever you want).

Plenty of remote workers are already traveling while working, but this is the first time I’ve seen a company the size and stature of Airbnb make such a flexible policy. I suspect that more tech companies will follow suit.

Spend It Where You Earn It

Of course, Airbnb stands to benefit the most from such policies.

After all, where are all these workers going to sleep if they move out of their homes to travel and live all over the world?

Its already happening.

Airbnb released their latest earnings statement this week. The numbers are up. Big time:

Revenue of $1.5 billion increased by 80% from Q1 2019, and by 70% from Q1 2021—demonstrating the strength of the travel rebound.

The comparison with 2019 is especially interesting, because it shows how the company has grown relative to where they were before the pandemic. The included letter to shareholders explains:

Two years since the pandemic began, a new world of travel has emerged. Millions of people are now more flexible about where they live and work. As a result, they’re spreading out to thousands of towns and cities, staying for weeks, months, or even entire seasons at a time.

Where have you heard this before? 🤔🙃

Perhaps most interesting of all, the shareholder letter also teased “the biggest change to Airbnb in a decade” to be announced on May 11.

But there’s a downside…

As I’ve written about over the past few weeks, it’s become significantly easier and much less of an extreme lifestyle choice to travel and live all over the world these days.

And as more and more well-paid workers become digital nomads, competition and prices for Airbnbs in desirable locations is heating up:

ADR [average daily rate] averaged $168 in Q1 2022, representing a 37% increase compared to the same period in 2019…

As a result, seasoned digital nomads have started talking about Airbnb prices the way Brits talk about the weather. It’s the single biggest threat to our lifestyle. Especially for the many (most) nomads who don’t have a cushy Silicon Valley salary.

The accommodation affordability crisis is most acute in Europe at the moment, thanks to a perfect storm of the summer high season, pent up demand from American travelers, and constraints on vacation rental supply (imposed by local governments whose residents complain they can’t afford to live in their own cities anymore).

All of this has prompted some nomads to abandon Airbnb in favor of alternative platforms and strategies for finding cheaper places to stay.

More on that next week…

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The Never Normal Schoolhouse

Howdy regular readers and new subscribers just joining us!

Over the last couple of weeks I’ve written about how being a nomad is becoming less of an extreme lifestyle choice and about nomad families traveling with kids.

A common response to the idea of nomad families is “you can only keep it up for the first few years until the kids reach school age.”

Presumably because not putting your kids in a normal school would be detrimental to their future 😱, right?

Not so fast…

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Raising a Never Normal Family

As I wrote last week, many of the sacrifices one used to make to travel the world have been eliminated.

Now you can work as an employee of a big company, live in comfortable apartments, and have an active social life, all while hopping from country to country.

But what if you want to have kids?

As a long-time digital nomad and now a dad, this is something that I think about quite a bit.

In my particular case, Covid hit the world just before our baby arrived, so settling down and staying put for a while was the only choice.

Now, as we start to emerge from the pandemic, there are a lot of hard questions, like:

  • How often can you move around once you have a kid? Is it even worth all the hassle? Or should you just hang up your backpack for good?
  • How much does traveling and seeing different places and cultures firsthand enhance childhood and learning?
  • Does not being “rooted” in one particular place harm children? What about having friends?

Of course, I’m not the first one to wrestle with these questions…

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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…

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The emerging nomad economy

I wrote last week about what we should call ourselves (and leaving America). Whether you like the term or not, one thing is clear…

The number of people who are digital nomads or interested in becoming digital nomads is growing.

In 2015, Pieter Levels famously predicted that there would be 1 billion nomads by 2035. We’re not there yet, but the MBO Partners® 2021 State of Independence research study found that “15.5 million American workers currently describe themselves as digital nomads, increasing 42% from 2020 and 112% from the pre-pandemic year 2019.”

This rise in the number of digital nomads is an opportunity for businesses and entrepreneurs — a new market that’s often not well served by existing products and services.

That’s why I got excited when I heard about Genki a few months ago from one of their investors (who also happens to be married to my cousin. It’s a small world. Also #familymafia).

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What should we call ourselves? (and leaving America)

I’ve noticed over the last few years that, as the term “digital nomad” has become more common, so has the resistance to being labeled as a digital nomad.

I still use the term, because I don’t think there’s a better, more succinct way to describe the same idea. But I do worry that it can give the wrong impression.

People hear “digital nomad” and they imagine a 22 year old strapping on a backpack and hopping to a new country every few weeks.

But you don’t have to be 22 years old to travel the world or move to a new country. And although traveling constantly can be fun for a while, most digital nomads I know tend to slow down at some point and spend more time in each place.

Slowmad Life

Steve Tsentserensky is a perfect example. He was recently profiled by CNBC’s Make It:

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Pablo Picasso and Ben Franklin did it too

In my last email (learning like Mr. Beast), I wrote about how Jimmy Donaldson went from being a socially awkward teenager with “terrible acne” whose YouTube videos made less than $1 / day to earning an estimated $54 million dollars last year at just 23 years old.

The lessons from Jimmy’s story don’t just apply to becoming a rich and famous YouTuber…

You can use the same principles to achieve your big goals too:

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Never Normal Newsletter

Learning Like Mr. Beast


In my last email, I wrote about why it took me five years after quitting my job to actually start my journey as a digital nomad. In short:

Making a big change is extremely difficult if you are trying to change your life in a way that makes you different from the people around you.

In case you haven’t noticed, this is something I think about often…

If you want to become a doctor, the path will look something like this:

  • Study hard and get good grades in school
  • Go to university and study biology or pre-med
  • Take the entrance exam and apply to medical schools
  • Go to medical school
  • Work as a resident
  • Get your medical license
  • Congratulations you’re a doctor! 🎉

Becoming a doctor is not quick or easy, but at least there is a proven path to follow.

And perhaps even more important — while you’re on that path, if you tell people what you’re doing, they will cheer you on and encourage you.

“Wow, a doctor! That’s great! Your parents must be so proud…”

But what if you don’t want to be a doctor?
(or a lawyer, or an engineer, or an investment banker…)

I’ll never forget Justin Gary telling me the story of how his mom cried when he dropped out of law school to pursue his dream of becoming a game designer (spoiler alert – he’s now one the most sought after, successful game designers in the industry).

I was reminded of that story again yesterday, listening to Joe Rogan interviewing Mr. Beast. There are a bunch fantastic life lessons in this 15-minute clip from the interview:

In case you’re not familiar, Jimmy (aka Mr. Beast) is one of the most successful YouTubers on the planet. Across his network of YouTube channels, he has nearly 200 million subscribers and his videos have been viewed about 24 billion times. 🤯

Forbes estimates that he earned $54,000,000 from YouTube in 2021. Not bad for a 23 year old who never studied or even brought his books home from school.

Naturally, these days Jimmy’s mom is supportive and proud of her son (how could she not be?), but there was a time when they fought constantly about his poor performance at school and his obsession with YouTube.

Jimmy started uploading videos when he was just 11 years old. But with “terrible acne” and general awkwardness, he was an unlikely social media star. Especially since, “professional YouTuber” wasn’t even a thing back then.

He spent years making videos that earned nothing. So how did he stick with it for so long when it seemed so unlikely that he would succeed?

Joe credits Jimmy’s success to his having a ‘hyper obsession’ and being willing to put in the hours to become the best at his craft.

But there was another important ingredient too…

Early in his rise to YouTube stardom, Jimmy formed a mastermind group with a few other aspiring YouTube “lunatics” who shared the same vision. They spent hours each day talking, experimenting, and analyzing popular videos.

They all went on to become successful YouTubers, including of course, Mr. Beast himself.

That’s the power of learning together in a group — you get to accelerate the learning process by effectively increasing the number of iterations / experiments you’re exposed to.

Having a group of supportive peers also provides accountability (you show up because you don’t want to let the group down) and best of all, it provides a counter to all the naysayers and people nudging you to abandon your dreams.

That’s why I decided to create a cohort-based, live course (taught by me) for people who want to become digital nomads.

The first cohort kicks off in May. I’ll share the syllabus next week.

In the meantime, if you think you might be interested, and you haven’t done this already, then please click the button below and fill out the two-minute survey.

​There’s no commitment required, it’s just a couple of questions.

Your feedback will help me make the course extra awesome, and in return, you’ll get a $100 discount if you decide to enroll later.

Again, there’s no payment or commitment yet! This is just letting me know that you’re interested in the course when the time comes.

That’s all for this week. More soon!

Not a subscriber?

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.

Want to learn along with me? Join my Never Normal Newsletter:

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Never Normal Newsletter

It took me 5 years…


In my last email, I shared my Digital Nomad Getting Started Guide.

I created the guide as part of my mission to help more people escape from the boring “default life plan” and live life on their own terms instead.

There was no guide back when I got started on my journey.

I had to figure it out all by myself.

I spent years stuck in a corporate job — sitting in a cubicle and daydreaming about traveling the world instead.

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Never Normal Newsletter

Digital Nomad Getting Started Guide

In my last email, I shared five reasons to become a digital nomad in 2022.

This week I want to share my Digital Nomad Getting Started Guide with you, plus a nice surprise I just received on Twitter (at the end of the email).

The digital nomad guide is available on my website now (totally free). Here are a few of the most popular sections: