In March and April of 2023, I celebrated my fifth anniversary of working for HubSpot with a 30-day, paid sabbatical. The five-year sabbatical is HubSpot’s signature benefit. On our first day, way back in September of 2017, my new hire group talked about what we’d do if we had a month off from work. Finally getting to the five-year mark and scheduling the month off was a great moment.
Since my sabbatical, I’ve been thinking about the experience, what I learned, and how it changed me. It wasn’t quite what we’d envisioned five years ago: a month of not working was unexpectedly tricky and there were some surprising realizations. In the end, I’m better for the rest and a reset of my work. Here's the story of my sabbatical and what I learned from it: thoughts about traveling, working from home, an information diet, and the practice of simplicity.
For five years, I’d been thinking about this sabbatical as a chance for big projects: renovate a room, write a book, or ski tour like a Patagonia catalog hero. I talked about at least three 30-day construction projects. A few of my friends advised me to think of it this way: what could I accomplish in four weeks of 8-hour days? As it turns out, I accomplished just about nothing.
Sure, I skied at a few new places in Vermont for the first time. But I didn’t lift a finger for construction or book writing or any long term projects. My friend Jeff Meyer had a better vision for a month off: be a Dad, be a husband, and take a rest. He was right. Those big, imaginative plans ignored my context. It’s not as if, by getting a few weeks off of work, I’d cease to be a spouse or parent. After five years as a software consultant, I didn’t wake up magically transformed into a house builder or novel writer.
You could put this down as a regret: the unwritten novel or unfinished house project. There’s not a monument to my sabbatical. On the other hand, as a parent and spouse, I used my sabbatical from work to take on those roles more fully. The time I spent “productively,” was mostly thinking back on my career at HubSpot and envisioning what its next chapters could look like. In other words: I lived life, and tackled some big questions, not big projects.
The first week off felt like a normal vacation. That’s because it was: my family typically takes the week around St. Patrick’s day to ski at Sugarloaf. There were a few differences. We opened a nice bottle of champagne to kick it off. As part of my Indy Ski Pass experience, my daughter and I ventured to Rangely for a day of skiing at Saddleback. We didn’t need to arrive home for me to start a new workweek.
It was on that second Monday that the vacation seemed different. It was the first time I had taken consecutive weeks off since my parental leave in 2019. The sixth business day without work is a revelation. The researchers say it’s then that you achieve a state of rest and begin to really enjoy it. I wasn’t quite there: I needed to change one thing to switch into full sabbatical mode.
During the ski week, I stayed on my phone. I used it for ski stuff like arranging ski lessons for the kids, checking conditions, and setting up our day at Saddleback. Any phone use quickly leads to emails, texts, the news, and the full information flow. The stream is always there. Because I didn’t shut off my feeds, my mind didn’t rest. As I began the second sabbatical week, I realized that planning my days and staying caught up on my phone was a thinly veiled substitute for the information flow I get from work. I wasn’t working, but I was pantomiming it.
When I left for Vermont, I decided to take a digital break. I put an out-of-office email on my Gmail account. I didn’t download podcasts or renew my weekly access to the news. I quit my always-on apps, turned off notifications, and removed everything from my phone’s home screen. I still got the twitch: at the first rest stop on the drive up I texted a photo of their plant-based water reclamation system to my wife (what? why?). After that, connectivity and the information feed didn’t seize my attention for the rest of the week. I listened to an audiobook on the drive and actually opened the real books I’d already uselessly lugged to Maine.
While I did some serious skiing (30k vertical feet in a day!), my experience in Vermont was restful. I enjoyed three long days at some of Vermont’s finest ski hills, made friends in the base lodge ski bars, and paid attention to my surroundings. It was a restful beginning to a series of longer, slower days.
Pre-pandemic, if you’d asked me about sabbatical plans, I would’ve said skiing and spending time at home were my aspirations. Prior to working from home, I spent about half my weekdays and most of my waking hours out of the house. Unlike a lot of people, I didn’t feel that early-covid experience of being stuck in the same place. In fact, I enjoyed it! It helped that working from home replaced a frantic 7am scramble to the train with a leisurely 8:45am saunter to my desk.
Since April of 2020, I’ve been working from home. It’s gotten to the point where going to the office feels like a field trip. When Rebekah and I began arranging the sabbatical in detail, it made much more sense to spend the time traveling: we now spend most of our lives at home. Coming home from my Vermont skiing felt like going to work: I spent a few hours in my home office for some reading and writing and it felt like I was back in the HubSpot office. In a sense, I was! I’m glad we planned to spend the second half of the sabbatical on a long journey.
We all set off again, this time to Tennessee and then on to the Dominican Republic. It was just the tonic: when your work is your home, going elsewhere is required to really unplug from work. Travel matters more when you work from home: getting back to the house can feel like going back to the office. This realization will probably take me back to the HubSpot office, at least part of the time, so I can mentally keep my work at work.
The audiobook I listened to during my drives up and down Vermont was the most meaningful of the ten I read during my sabbatical. John Mark Comer’s The Ruthless Elimination of Hurry caught me by surprise. I picked it up from the personal improvement section of HubSpot’s free books library. I thought it would be about doing better work. Instead, it was a new kind of Christian perspective (or an old one) on how to live the good life: following the teachings of Jesus. Comer takes the teachings and life of Jesus seriously: he thinks that Jesus modeled a way to live.
While in Tennessee, I taught my nephew to swing a golf club. Playing golf is something I’ve tried to do since I was probably eight years old. Trying to explain to a newcomer something you intuitively know is hard. He eventually got it: his golf balls were airborne enough to threaten the little cart picking up the balls at the range, which is all you want. Comer’s thoughts about teaching are just like learning to swing a golf club: how to move your hands and feet matters; your opinions on golf pros and golf theories don’t matter. Comer argues, convincingly, that the teachings of Jesus are similar: you need to do what he said and live like he did. The way he lived wasn’t some extraneous part, it was the very thing he asked people to do when he said, “follow me.” The book memorably highlights how Jesus’s life was devoid of speed, efficiency, and wealth–the things we tend to value most.
At the precise midpoint of my sabbatical, I found Southland Books and Cafe, a used bookstore in Maryville, TN. I got a stack of pocket-sized novels (the best book size): Updike, both Amises, Stegner, and more (full list below). Most of my beach reading was the sort of somewhat depressing mid-twentieth century fiction my house is already full of. I like tempering the idyllic vacation scene with some clouds of human darkness. If there’s a theme in the stack, aside from book size, it’s that I read stories of inner lives contrasted with what culture expects. Even the collection of E.B. White’s New Yorker pieces showed his more curmudgeonly side. Such reading surprisingly underlined the importance of reconsidering our values of speed, efficiency, and wealth. They pale in comparison to what actually matters.
My information diet is enormous. I open the day with ten to twenty minutes of reading the news. Then I move to exercise: on the stationary bike, I usually watch a YouTube video, featuring something like a home renovation while listening to a podcast. By the time I hit my information-intensive workday, I’ve already consumed thousands of words. In the breaks during that job, I usually open up a news website or social network or personal email to see what’s new.
This NYT Magazine retrospective on Twitter had this haunting line: “What’s disconcerting is how easy it was to pass all the hours this way. The world just sort of falls away when you’re looking at the feed.” And how much of my non-work and working life is the feed! Slack unreads, the email inbox, the wiki feed: it all comprises a stream of endless updates and chances to engage. You can win the feed and make no real progress. You’ve just passed the hours away.
After the first week, my sabbatical was a decisive break from all of that. My lasting impression from this break was how my work positions me to pass the time in a constant flow of knowledge. Upon my return, I resolved to spend a little less time checking for updates. My email inbox could be a little more like a real mailbox: checked once a day with outgoing messages posted the next morning. The Way of Zen, a book I finished just before the sabbatical started, taught me this. Zen isn’t something you can really study, it’s a way of being in the world and a way of realizing moment-by-moment the thinness of some of our biggest ideas. Whatever your preferred phrase of information diet–whether embracing presence or being in the moment or having a beginner’s mind–this is only worth doing if you do it on weekdays, not just while on vacation.
The sabbatical taught me the difference of a slower everyday life with restricted information flow. After returning, I haven't resumed my daily podcast habit. My relentless email checking has turned into once a day for the personal account and maybe three times a day for work. This attempt to go slower has helped me be a bit more present, a little calmer, and less hurried.
By the middle of the fourth week, we were back in Massachusetts (having listened to the Bee Gees and Guster for the last hour of the drive). And I was ready. Three weeks without work is enough. During the first week off, I calmed down and settled into a mode of rest. I really enjoyed the travels and a calmer brain for the next two weeks. I missed work during the fourth week. Overly calendared days and endless Zoom calls aren’t anyone’s favorite things, but the way work provides consistent challenges makes each day seem more meaningful. Ending the day having spent your energy is good. You can’t spend your whole life in the lazy river.
Upon my return to work, it took a few days to get back up to speed. The time off helped me approach my efforts with fresh eyes. It became clear to me that part of my consulting role really generates value for my customers, but some of it seems more like going through the motions. Without the pause, I don’t think I could’ve seen which was which. My start/stop/keep list is pretty strong, and I’m optimistic about moving forward.
When I got back to work, I told the sabbatical story to my colleagues and customers. I headlined the whole thing “gratitude” because that’s the response I had: to HubSpot, for giving me the time, to my colleagues for working with my customers, and to my customers, who had patience with the interruption of our normal cadence.
Here’s the timeline, with pictures:
Sabbatical places visited:
Sabbatical miles traveled: 5,830
Sabbatical books read:
Our Towns, James Fallows and Deborah Fallows
The Ruthless Elimination of Hurry, John Mark Comer
Everything that Rises Must Converge, Flannery O’Connor
The Information, Martin Amis
Too Far to Go, John Updike
All the Little Live Things, Wallace Stegner
Being There, Jerzy Kosinski
The Second Tree from the Corner, E. B. White
The Same Door, John Updike
Lucky Jim, Kingsley Amis
In sum, here are my resolutions upon my return:
If you've made it this far, thank you for reading. If there’s a sabbatical or a long vacation coming up for you, here are my sabbatical lessons learned:
I’ll keep you posted in 2028, when I qualify for my next HubSpot sabbatical!