Sabbatical #1: Adjacent Dreams

Plus: The reasons this newsletter exists

Welcome to the first issue of Sabbatical — an exploration of the future of work, modern life, and travel. You likely signed up for this in the past two months when I posted about this on Threads or LinkedIn.

This newsletter was born from dozens of conversations with ambitious people in my life who were reconsidering the roles work, family, and place have in their lives. These periods of reflection are often punctuated by a sabbatical, an extended break from normal routine to reflect on one’s life. In many (but not all) cases, what comes after the sabbatical looks nothing like what came before.

The mission of this newsletter (and whatever sprouts from it) is to create a guidebook for the modern sabbatical. To use the experience of those who came before to come out on the other side with a life and career that aligns with you, whoever you are. Consider these newsletters never-ending chapters to a book. 

Each monthly-ish issue will start with a note and end with a story of someone who stopped everything to figure out what’s next. 

Today’s itinerary: The beliefs underpinning this project + Tam Pham’s sabbatical and “Adjacent dreams”. 

Today’s Note: What’s going on?

Calling our lives before 2020 the “before times” went from clever joke to cliche. But like most cliches, there’s some truth there. Careers, travel, community, and work are all in a state of change.

These trends are difficult to quantify, as one can find research, surveys, and coverage that both supports and counters them. Instead, after conducting roughly 15 interviews (and counting!) with people who have taken sabbaticals, I’ve noticed several common reasons people are slamming the pause button. 

Reason #1: Remote workers are feeling disconnected

When many white-collar jobs went fully remote in 2020, the general response was positive. Workers loved no longer having a commute, having more time with family, and gaining a more flexible work schedule.

Three years later, the cons are starting to catch up with the pros, especially for those who prioritized their careers as a source of fulfillment (“live to work” rather than “work to live”). A sort of existential panic sets in when one realizes they hustled for years only to spend all day talking to talking heads in boxes on a screen. It’s 2024’s version of the Office Space cubicle. In many industries, you never meet your customers, coworkers, or managers. Is the flexible working style worth the isolation?

Reason #2: Tech and startups are less appealing to the ambitious

If you worked in tech startups in the aughts or earlier, you sacrificed salary and prestige for massive upside if your company was successful or exited. To work for a startup was to toil for 12+ hour days for years. But something changed in the 2010s. Tech startups offered upside and best-in-market salaries. Young people prioritizing money exchanged finance jobs for tech jobs.

After an unprecedented bull run, growth tech companies are getting hammered with layoffs and sinking valuations. If you never really cared about technology or the problems they solved and were in it for the money, you may have a bit of a career crisis on your hands right now. 

Reason #3: The nature of “place” and “home” are changing

Prior to COVID, ambitious college grads often moved away from family to a handful of cities (as profiled in books like The Big Sort and The Rise of the Creative Class). When work was decoupled from location, that naturally left many folks wondering why they were living where they were — to say nothing of the ever-increasing price of buying a home and putting down roots.

Reason #4: The increasing focus on mental health

The reasons vary from “I watched my parents burn the candle at both ends for their career” to “I’ve been going to therapy for years and know how to navigate this” but if you’re under the age of 40, you’ve probably been well-versed in the treatments and culture around protecting your mental health. “Burnout”, “quiet quitting”, “emotional labor”, and “work/life balance” are common phrases I’ve heard when discussing this. When it’s time to reconsider our options, we’re all much better equipped to talk candidly about how we’re feeling and what we need.

Reason #5: Traveling arbitrage is still possible (for now)

Someone once told me that the best plan is to earn your money in America but spend it in Europe. Consider this reddit thread asking what do Americans even do with all of that money. Or that the money that Americans spend shopping for the holidays would rank 19th largest in GDP. Despite decades of globalization, those with high-earning jobs in advanced economies can still derive great value by taking their money elsewhere. One month of a tech/finance/law salary can pay for a three-month sabbatical. 


Sabbatical Story Time: Tam Pham and Adjacent Dreams

Tam Pham has taken two sabbaticls, one ended up being about getting better at chess and the other to learn (and eventually teach) Bachata. He’s about to start his own business teaching the latin dance style — something he attributed to his sabbaticals.

Tam Pham takes on a challenger

You’ve taken two sabbaticals. Why did you take your first break?

After trying for a long time, I landed what I thought was my dream job in marketing. And I thought, “This is amazing! I’m working with one of my role models!” And then, guess what? I'm still the same old person. Nothing in my life changed in a dramatic fashion.

Second, I was living the remote work digital nomad life. And after I was done work, I had a lot of time on my hands working in an off-timezone from North America. I had to figure out how not to get bored when my coworkers were sleeping and I was in a new place by myself.

What did you do?

One of the things I started doing was playing chess. I fully immersed myself in playing and experimenting, not expecting that I was going to have a sabbatical just for chess. I leaned into it and, holy crap, I'm addicted. I got really passionate about it, and it felt like I was a kid again back in high school when I was competing in my chess club and stuff. I took a break to focus just on that.

How did this change your approach to your career after? 

That sabbatical reminded me that I've always been a great learner. But I've always thought I should learn things within the realm of work. I had to learn digital marketing or I have to learn coding, etc. And I realized, “Oh, wow, there are actually a lot of things I can learn outside of work that can challenge me.” 

So a few years after your first chess sabbatical, you took another break.

It was a bit of an accident because I got sick. I had long COVID, and I didn't have any energy to do anything. My work visa in Canada also expired. And I knew I needed a vacation. As I was resting, I wanted to rest in Mexico. And it just so happened that as got better, I started to lean into the things that were available around me, which was learning Spanish and dancing.

And now you’re starting your own business based on dancing?

Yes. I took a “one-week retreat” in Oaxaca. I spent a week there by myself to see what thoughts come up. And the biggest realization I had was that, deep inside, I've always wanted to start my own business. But instead, I've been taking adjacent jobs as, like, a chief of staff role an operations role or marketing lead role. Because those jobs felt safe. They were all very adjacent to the entrepreneurship goal without taking my own risks.

My setup is great. But if I'm thinking about it long term, that'll be my life for 30 more years. And if I'm going to do that for 30 more years, I might as well tackle the dream I know I have sooner rather than later.

Right. It can be easy to do the safe version of our ambitious goals, so if it doesn’t work out, no one faults you.

Yes, and it’s seen as a good thing by your peers too. They’ll say “Wow you have a job working working with your role model!” or “You know this entrepreneur that I’ve heard of!”

So how did you create that blank space in Oxaca to allow that revelation to come in?

I was burnt out. But I knew with enough space, things would naturally come up. My mind is always running. And so just journaling and not having any distractions I can dive deeper into what's actually under the surface in my own mind. 

I didn't do any drugs, but some people might recommend shrooms or something similar. For me, it was just yoga twice a day, walking on the beach for an hour or so, and then watching the sunset by myself and just seeing how that was. My life was quite overstimulated before that and it was really helpful.

So what’s next?

In February, I’m going to go full-time on my own business teaching Bachata. I haven’t felt this aligned in a while. All of my other jobs were adjacent to my dream. But I’m putting myself on the line for this. I already gave my notice to my full-time job.

Tell me about the finances of these breaks you’ve taken for chess and bachata.

I would have done things very differently for my first sabbatical knowing what I know now. I went broke after my chess one. I had to borrow money from friends to move to my next job. I remember Keith Ferrazzi writing, “Learn in your 20s, earn in your 30s.” I was totally investing in learning. 

With my Bachata one, I moved to Mexico where I could extend my runway. I was also very confident I could get a job whenever I wanted. That speaks to some privilege of having marketable skills. My friends tell me it was risky but I don’t think that at all.


I could find another job. I could live on my parents’ couch. I could live in a cheap city if I needed to. I could borrow money from friends. I have options. Not everyone is as fortunate as I am, I know.

How do you deal with the lack of community that can come from being a nomad and moving often?

This year I tried something new that I call “slow living”, I was like, “You know what? Let me just have a few home bases around the world and go to those places the most often.  So for this year, I spent six months in Mexico City, three months in Toronto, where I used to live, and then a month in California with my family, and then with the other two months I went where I wanted.

The difference between a digital nomad and slow living is community. When I go back to Mexico City, I feel like I have made more friends here in the last two years than anywhere in the world.

Of course, there are trade-offs. But for now, at least in this stage of my life, I think it's quite cool. I learn new things through people. 

What’s your advice to people considering a sabbatical or designing their life in the way you have?

I hope anyone considering a sabbatical truly does things for themselves and not for clout or accomplishment. Just doing it for the love of doing something, learning a skill, and having an experience you’ll remember forever.

My hope for people is that they take sabbaticals and they aren't outcome-driven. Sabbaticals are personal and special to each of us.