Welcome to the second issue of Sabbatical — an exploration of the future of work, modern life, and travel. Sent every month-ish. We start every issue with a note and end with a story of someone who stopped everything to figure out what’s next.  

See last month’s issue here. Since then, 25 totally chill people have signed up. Today’s itinerary: The emptiness of being a digital nomad and Anna Redmile shows us how families can take sabbaticals too. 

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Today’s Note: Digital Nomad vs Sabbatical

Few books have poisoned the minds of (mostly) millennials than The Four-Hour Work Week. The book, first published in 2009, argued that thanks to the internet, we can work anywhere and lean on new software and outsourcing to run tiny but profitable businesses.  

Long before COVID threw millions into the remote workforce, the book was of a movement that inspired a wave of people to “escape corporate life” and live the “nomadic” lifestyle, traveling from place to place and working on their laptops for as few hours as possible.

The digital nomad lifestyle framed labor as something to be hacked. Your surroundings are something you observe but not something you participate in. To the nomad, optionality is everything. Stay free to chase the next business idea, live in the next town, and make the next set of friends. It’s thrilling, good for social media fodder, and makes for a good story. 

Most nomads call it quits eventually. They stop moving and lay down roots. Or they stop viewing labor as a thing to avoid and instead, as a tool to affect change, however small.

Things worth doing are difficult. They take commitment. They require you to sacrifice optionality. (You know, the kind of things that make one sound like an old crank.)

But as I get older, I realize it’s the stuff life is made of. It’s the homecooked meal from a friend versus the Doordash order. It’s walking down the street and making small talk with one neighbor versus 100 likes on your LinkedIn posts. It’s jumping in and improving your neighborhood versus moving to the next town when things get boring or difficult. 

There’s a hollowness to the digital nomad movement - because it exists largely in opposition to something. When your life design is geared toward running AWAY from something, you’ll come to the crashing realization that you eventually need to run TO something.

A sabbatical is an absence of normal to figure out what your next version of normal should be. It’s removing things that don’t work so you can add things that do. In issue one, Tam Pham talked about his pivot from the nomad life to “slow living” picking three cities to rotate between. That’s running TO something.

The point of all this is to have a day-to-day life that you don’t want to run away from — whatever that means for you.

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Sabbatical Story Time: Anna Redmile’s family sabbatical

In the name of seizing adventure when and where you can, Anna Redmile and her family of four took a 13-month sabbatical that concluded just before COVID. We explore the benefits of taking a Sabbatical with children and the role ego plays in our work.

Why did you take these 13 months?

It's something my husband and I had been thinking about for a while. We had been working hard for a long time and had a hankering for a break and some adventure. Then my husband's brother died unexpectedly at the age of 45. That really put things into perspective and motivated us to go for it. You just don't know what's ‘round the corner. 

Our kids were four and seven and it felt like a great time to do it - they were still at an age where they actually enjoyed spending time with us! And we were keen to bank the experiences and memories with them now.

How did you handle pulling your seven-year-old out of school?

When I went to the school to tell them we were doing this and taking him out, I thought they would shut it down and say “What on earth are you thinking? What a ridiculous idea!” But they actually said, “Wow this is a really amazing opportunity!” 

In Australia, a lot of people don’t know this, but the government supports distance learning. Even before COVID. So they gave me all the resources I needed to homeschool. That was the moment the sabbatical changed from an idea to a reality.

Why did you take the break? Were you burned out or tired? Or was it more personal than that?

My husband was burned out a little bit, bearing in mind what happened to his brother. For me, it was about the adventure and spending time with the kids.

Between our planning and leaving, my husband and I were both offered promotions and it was tempting to put the trip on hold. The promotions would not make a meaningful difference to our lives, so we stayed true to our plan, grabbed the bull by the horns, and went for it.

One of the benefits of staying in the same town and community is the deep roots that your children benefit from. How did you balance showing them the world with the stability and continuity kids often need?

When we were away for the year and came back, we picked right back up where we were. The kids were re-enrolled in their school, picked up their friendships and within a few weeks it was like we'd never even left! 

Whilst we were traveling, the homeschooling gave us structure to our days, which were otherwise very varied. We moved every 3 to 5 days which meant we were constantly doing and seeing new things. We tended to do 3 to 4 hours of homeschooling in the mornings, then would head out to do something cool in the afternoon. The schedule was super flexible, but it gave us a sense of structure and stability.

They weren't concerned about friends or missing out on things whilst we were traveling because we were always doing such cool stuff ourselves, and because they had their support network traveling with them. What's more, they had our undivided attention

To your point about laying down roots, since traveling we relocated from Sydney to London. Now that has been hard. The traveling for the year was not hard at all.

I’d love to talk about finances. Did you work while abroad? Did you save money?

We probably spent about $100k AUD all up over the 13 months. We saved money before we went, and rented our house out whilst we were away. 

We didn't travel on a strict budget, but we stayed in hostels, took public transport, ate at local places, and traveled overland where possible.

We generally tried to book accommodation for $50 a night for the 4 of us - in Central & South America that was ideal, but in Europe it was tricky. It's another benefit of going when the kids are younger: With the kids smaller, it was easier to all fit into smaller rooms or buy three meals for four people.

How did your perspective on work change after you returned?

I came back really revived from the trip. It was important to me that I find a job that I would find fulfilling as we spend so many hours a week working, you might as well make it count. I like a sense of achievement and I like being able to add value in a meaningful way.

My identity was no longer tied to my work or my role, and my sense of ego had also diminished. Work was no longer about me climbing the ladder because it fans my ego, it was about a sense of fulfillment, purpose, and earning money which is an enabler to do cool things.

So I returned pumped and ready to go but with some subtle differences around my key motivators.

How did your perspective on parenting change?

I wanted our kids to see how lucky they were living in Sydney in this bubble where most people look the same and everyone is doing fairly well in life. When they came back, they did appreciate that.

While we were traveling, they gave me a lesson: All of the things that I think make them “lucky”? They didn’t even notice that it was gone. It was superfluous to them. They didn’t care they didn't have those things while traveling. 

I remember we were in Turkey, and there was a guy by the river who had a tarp, a tap for water, and a pallet with some rocks around it so he could sit. That’s it. And my son said. “That’s a nice setup he has.” 

And I said “Is it really?  It's not as good as an actual kitchen.” 

And he said “He’s got running water, he can fish, he has shelter and he even has a table. He has everything that he needs.” 

His learning was that as long as you have your basic needs met, you’re covered. And that made me realize many of the things we showered on our kids were superfluous. 

That’s a proud parenting moment!

It was one of the moments when I knew the trip was the right thing to do. I appreciated how they interacted with people and learned languages. They had no baggage and preconceived notions. They befriended people they couldn't communicate with. They learned and experienced so much.

I want to be real here though, you had to have some moments that were tough with the kids on the road. How did you handle tough moments on the road vs at home?

The most challenging thing was home-schooling. Thankfully it was only one child. My husband and I shared the load and tag-teamed when we needed to. We learned to recognize when to call it a day, or switch it up and not just carry on banging your head against a brick wall!

We had to set some clear boundaries and expectations which was tough at first, but we stuck with it and it got easier. My son actually got incredibly efficient at getting his work done so we could crack on with the fun stuff. 

What do people get wrong when they think about taking a break like this?

People think it’s a high-risk situation for their career. But it isn’t. We quit our jobs and came back into COVID. We resumed our lives. Same friends. We slotted back in and picked up our things. A year sounds like a long time, but people don't forget you in a year. Your network is there when you return. 

Is it fair to say it altered your path but it didn’t “set you back”?

Yes. It saw me move into a partnerships role (which was an exciting new challenge) for an EdTech company which was strategically a strong sector to be in during COVID. Again, relocating from Sydney to the UK has been a lot more disruptive than this trip.

What is your advice to other parents considering a trip like this?

I would strongly advocate doing a trip like this (or something totally different) if it is an option open to you. You have to plan for it, but don't wait forever! We have a gift of time, but we don't know how long it will last or how our circumstances might change. 

It was the most incredible thing I have done, and it was such a gift to spend that much time with our children, having fun and shaping them into responsible, open-minded global citizens. I don't believe you have to choose between doing this and having a career.

We would stay at hostels alongside people in their twenties and thirties. And they were often surprised to see a family there. People would tell me they were traveling to “get it out of their system” before they had to “settle down”. You don’t have to live your life that way.

(Submit your Sabbatical story for a future issue here.)