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A corked glass bottle on a beach with the message "Out of office" inside
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I work for Automattic, a company with two unique benefits.

First: we are a completely distributed company. Since Automattic’s founding in 2005, we’ve never had an office. Our employees are scattered around 70+ countries and are empowered to work from almost anywhere. It is this nature of Automattic that enables me to be a digital nomad.

Second: for every five years of employment, we are granted a paid, three-month sabbatical… and my five-year anniversary was this past January. That means I can take a quarter of this year off from work to do whatever I want and still get paid, with the guarantee that my old job would be waiting for me when I get back.

Knowing this benefit was on the horizon, I’ve been planning for it ever since I began nomading in October 2019. I intended to spend the intervening three years as a nomad: one year traveling from my home state of Massachusetts to the United States’ West Coast; one year exploring Alaska, Hawaii, Australia, and New Zealand; then another year traveling back to Massachusetts, returning in time for my sabbatical. Tired of nomading, I would then use those three months off to end my journey, buy a house, and settle down.

I was confident everything would go exactly as planned.

Then a pandemic happened. Although I’ve persisted as a nomad, travel has become more complicated and limited; of the places on my original itinerary, I’ve visited only a fraction.

But something else happened, too: I’ve found my tolerance, even my enthusiasm, for nomading has not diminished, but grown. This lifestyle suits me, and a sabbatical seems an artificial deadline for ending this adventure.

But many sabbaticals are spent traveling — an activity that already defines my life. I wanted to do something unique with that time. So what does a nomad do on a sabbatical?


Over a year ago, I asked for suggestions of sabbatical activities on reddit. The resulting ideas were inspiring, but I needed more than advice; I needed structure.

Fortunately, as anyone who knows me can tell you: I live and breathe structure.

Star Trek's Borg Queen saying to Data: "I bring order to chaos."

I started using Trello, a project management tool, to record every potential sabbatical activity: go on an African safari! Learn a foreign language! Register for Space Camp for Adults!

Then I grouped my proposals into four categories:

  • Experiences: Vacations, destinations, and memories that would last a lifetime.
  • Self-improvement: Activities that would improve who I am or what I can do.
  • Environment: Not global, but my own personal environment — such as sorting through all my photos, or cleaning my stuff out of my parents’ basement. These are tasks that need to get done some day, and recognizing that without acting on it is a mental burden; completing them while on sabbatical would allow me to come back to work with less clutter, both physically and mentally.
  • Products. Developing new inventory for my WooCommerce store — or expanding to a whole new store (such as online workshops, something I already teach in real-time).

Some of those categories would need to be adapted for a nomad. For example, if self-improvement means taking a three-month intensive course, then that would likely require I not travel for three months — something unprecedented in my nomadic experience.

Tina Fey saying "That just sounds hard"

And if I’m going to travel, where to? The answer: somewhere I can’t go when I’m working. My division of Automattic is especially synchronous, and there are certain timezones that don’t overlap with our customers, making remote work from those destinations nonviable. The only time I can go there is when I’m not working.


I ultimately settled on this itinerary, which spans March 18 – June 18, 2023:

  • Two weeks in Massachusetts. (Experience) Not only will I be attending Boston’s annual game convention PAX East (I haven’t missed one since its founding in 2010!), but Massachusetts is where I keep all my stuff. Having been nomading in Europe for the past six weeks, I’ll need this opportunity to change my loadout in preparation for my sabbatical’s next phase:
  • APAC! (Experience) In my goal to visit all 50 states in my lifetime, I’ve so far been to all the continental ones; Hawaii will bring my tally to 49. Next I’ll visit Sydney, Melbourne, and Tasmania, Australia, which I haven’t been to since a semester of undergrad last millennium. Then I’ll make my first trip to New Zealand.
  • Massachusetts again. (Environment & self-improvement) Last year, I cleaned just one corner of my parents’ basement, resulting in four boxes of donations to museums; I’m eager to discover what else I have hiding down there. I’ll also use this month to train for cycling a hundred miles in one day. I rode my first and only century in 2018, and I’m unsatisfied with it having been an anomalous experience; I want to prove to myself that I can do it again. (Coincidentally, the new Zelda game, Tears of the Kingdom, releases during this time.)
  • Yellowstone. (Experience) I spent a week in Yosemite National Park in 2021 and had an amazing time. Now I’m looking forward to a week of exploring another national park on foot! This region also dovetails with me spending the rest of the summer in Missoula, Montana, one of my favorite fair-weather destinations.
Two astonishingly handsome young men leaning on an outdoor sign that says "Old Faithful Geyser"
My first and only other time at Yellowstone, on a day trip with my brother in June 1998

If, somewhere in there, I have time to work on other tasks on my Trello board — developing new store products, achieving inbox zero — I will. But those are the kinds of things I don’t need a sabbatical to accomplish.


When I share this itinerary, I’ve been met with one of two reactions. First is “OMG, that’s the best sabbatical ever, it is so epic!”

The other reaction consists of frowns of disappointment as people exclaim, “You’re spending only a week each in Hawaii, Australia, and New Zealand?! You’ll never be able to see everything. You need at least two weeks, if not two MONTHS, for New Zealand alone!!”

That latter response is stressful for two reasons. First, there’s a lot of pressure to make something of a sabbatical: write a book, build a shed, learn an art. But those with imposter syndrome work hard to prove themselves and justify their value every day; that same expectation shouldn’t be put upon us during our time off, too. If I want to disconnect for three months and do nothing but play video games and go for long walks without my phone, then I’ll be better for it, and that’s nobody else’s place to judge.

The other reason that reaction is disappointing is because, wow, really? I’m being chastised for seeing more of New Zealand than most Americans ever will? There’s a lot I want to do in my three months, and I can’t spend more time in New Zealand without taking time away from my other sabbatical goals; the alternative isn’t to spend more time in New Zealand, but to not go at all. I’m confident that nine days is better than none.

(I suppose there is a third reaction I’ve received to my itinerary — a mix of confusion, admiration, and astonishment: “Wow… you’re really going to spend your sabbatical cleaning your parents’ basement?!”)

Making space

It’s odd to tie up all my loose ends at work, knowing I’ll be back in three months — but it’s also liberating. While it’s nice to be wanted, I hate being needed, which can create unhealthy dependencies for both parties. Fortunately, Automattic’s sabbaticals ensure no one person is indispensible. Knowing that my team will be fine without me is what empowers me to enjoy my sabbatical without concern.

The last time I disconnected from work to travel internationally for this long was on an October 2012 trip to Machu Picchu. Just that one week of new experiences and environments provided clarity that I brought home with me. The next four months saw the rapid accomplishment of many long-time goals: I got a new job, launched a YouTube channel, became a freelance writer, and started speaking at conventions. I don’t know that my goals for this sabbatical are as far-reaching — but that’s okay. While some of my three months are highly regimented (ask me about the joys of booking seven separate one-way flights), I’ve also created space to be slow, calm, and spontaneous (what am I doing with the entire month of May? Whatever I feel like).

I’m eager for the experiences my sabbatical will offer me — and for the tales I’ll bring back to this blog.

What would you do with three months off from work? Leave a comment with your ideas and inspirations!

Ken Gagne

Digital nomad, Apple II geek, vegetarian, teacher, cyclist, feminist, Automattician.

6 Replies to “Preparing for a nomadic sabbatical”

  1. I wish you the best on your sabbatical. I couldn’t tell exactly when you plan to be in Yellowstone, but if you haven’t set the dates in stone (pun intended) yet, I would highly recommend going in mid-May. I did this in 2008, and it was incredible. There was still some snow on the ground, which was really interesting, mixed with all the thermal pools steaming. Also, there were hardly any people, and tons of animals everywhere.

  2. Love this post! As someone who has a sabbatical coming this year as well, am astonished to all the planning and thought you put into it! Really like the separation of goals in different categories, to make sure that you get a bit of all the things you want!
    I also really admire adding the cleaning of the basement as an activity – carving the time to do it right makes a lot of sense to me personally!

    Thanks for sharing these, definitely loads of food for thought!

  3. Enjoy! And touch base if you get through Colorado. If I had a three-month sabbatical and money was no object, I’d spend two months in Europe (next month I’ll be there for the seventh time, but I can’t get enough), and the other month driving from the Pacific to the Atlantic in Canada.

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Ken's Itinerary

Easthampton, MA

Sep 19, 2023 - Oct 20, 2023

TAP Air Portugal

Oct 21, 2023

Málaga, Spain

Oct 22, 2023 - Oct 26, 2023