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Reflections on a Sabbatical

For six years sow your fields, and for six years prune your vineyards and gather their crops. But in the seventh year the land is to have a year of sabbath rest.
- Leviticus 25:3-6

I don’t know about you, but it seems like everybody I know is taking a sabbatical these days. Whether because of lingering malaise from the pandemic, a millennial focus on self-actualization, or something else, I know dozens of people who took extended time (3+ months) off full-time work in the past couple of years.

Besides having the desire to take time off, my speculation is that the dramatic run-up of tech stocks in 2021 meant that many people working in software now had the means to think about taking time off as well.

The idea of sabbaticals originated in the Middle Ages in Europe, but was not systematized until 1880, when Harvard University initiated a sabbatical practice under President Charles W. Eliot. These days, some employers have started to offer formal sabbatical programs. You can even highlight a career break in a first-class way on LinkedIn now.

There’s plenty of logistical advice online about how to think about sabbaticals. But I found there was a lack of narratives that tell you what taking a sabbatical might be like.

I took about six months off full-time work in 2023. As we turn the page to the new year, I wanted to reflect and share what that experience was like for me.

Redefining work

Late night, come home
Work sucks, I know
- Blink-182

What is work, anyway? Like many seemingly simple words, the definition becomes increasingly slippery the harder you try to grasp at it.

"I'm headed to work," someone might say. Or, "I'm out of work." Or, "Work sucks."

In American English, the word "work" metonymically refers to the idea of employment—typically a full-time job where one commits to providing ongoing labor or service in exchange for payment and other benefits (most notably in the United States, healthcare).

If you put aside this conflation of "work" with employment, you can start to think of "work" in a deeper sense: the exertion of effort done in order to achieve some result.

Cooking a meal is work. Cleaning out your garage is work. Emotionally supporting someone you care about is work. Volunteering in your community is work. Even playing a video game or commenting on social media could be construed as work—maybe just not the most meaningful or rewarding kind.

For me, disentangling "work" from "employment" was the most crucial benefit I got from taking a sabbatical.

After you spend many years locked into full-time employment, you can lose sight of this distinction, and begin to believe that you just "hate working." But if you give yourself the time and space to get in touch with yourself, you'll probably discover that you—like all people—have an innate need to do some kind of work.


I think some people can dive into the unknown with relish, without any sort of plan for what to do. I'm not one of those people—I need to be able to imagine what the future looks like, at least vaguely, before I can begin something.

So before I began my sabbatical, I did some reading and talking about what I should do. The main advice I heard was to resist the impulse to come up with any grand plans or goals, and instead just let each day unfold, observing what I was drawn towards.

Given my nature, I found this really difficult at first. What do you mean, I can't have any plans? What am I even doing with my time?

It turns out just taking care of yourself—sleeping, cooking, exercising—can easily occupy a huge chunk of each day. I wondered how I used to hold down a full-time job while attempting to take care of myself in the past. The answer, of course, was that I just wasn't fully attending to my physical and mental health back when I was employed.

Still, having no agenda meant that I had hours each day to see where my mind and impulses drifted to. The places they went to were surprising.

Abandoning old dreams

In January of this year, I traveled—alone at first—to Medellín, Colombia. Although I'm a decent Spanish speaker, I'd had a dream for many years of becoming properly fluent in the language and being able to totally blend in in South America.

After I arrived, I found I just really didn't feel motivated to sign up for a Spanish class or go out and talk to people. I wondered what was wrong with me.

Because I was in a reflective mood, I read through old things I'd written, including an essay I wrote when applying to college. At the age of 18, I wrote: "I intend to become fluent in Spanish over the next few years, possibly by studying abroad in a Spanish-speaking country."

I was mystified. Why did my teenage self decide he wanted to become fluent in Spanish? The essay offered no explanation, and I honestly couldn't recall what prompted it. I could only speculate.

Upon reflection, I now suspect I settled on and clung to this goal for a few reasons:

  1. Because I grew up speaking Hindi, I always found it easy to speak Spanish without an accent. I felt like I was good at it, and that made me want to continue learning more.
  2. Whenever I traveled to South America as an adult (I've been 4+ times), I felt like I could blend in there in a way I couldn't really as a minority kid in the American Midwest and South. Being able to speak Spanish made me feel a sense of belonging I found elusive as a teenager.

It turned out I was still holding onto a decade-old ideal without critically evaluating whether I really still wanted it. A childhood sense of not belonging in my surroundings had prompted this dream to emerge, but I'd since found people and places I felt more affinity with. Now, I no longer needed this escapist fantasy.

Over my weeks in Colombia, I let this Spanish-speaking dream dissipate.

This pattern is one I've heard from many friends who've taken time off full-time work: diving headlong into things you've fantasized about only to discover that they won't actually solve your problems or bring you happiness.

Although abandoning old, irrelevant dreams can be painful at times, I think it’s a critical part of making progress. Like a bird molting feathers, you need to shed the old before the new can start to grow.


What did you find yourself doing the last time you were unencumbered with responsibility?

For many people, their teenage years were the last times they were able to just exist. Summers were spent lazing about, hanging with a few childhood friends and enjoying an unpacked schedule. The trope is that adults get a faraway look in their eyes reminiscing about those years—you don't know how good you have it back then, they say.

What if you could have it again? What would you end up doing? My hypothesis is that given limitless free time, adults end up gravitating to the same things they did when they were young.

As a kid, I traveled with my family to India over the summer every couple of years. The temperatures were fiendishly hot, the power went out regularly, and I didn't have any friends over there.

One of those summers, back when I was eleven or so, all I had to entertain myself was my Dad's laptop and a crappy Internet connection. One of the only pieces of software on the laptop was Adobe Photoshop.

I remember waking up in the mornings and opening up Photoshop tutorials online. I'd let them load during lunch, then follow along with them in the afternoon, learning about all the filters and keyboard shortcuts, one at a time.

My childhood Photoshop creations are lost to time. Good thing, too—I'm sure they weren't very impressive. But what I needed to remember was that even when I was a pre-teen, I naturally gravitated towards getting into a state of creative flow almost every day.

In January this year, after abandoning my dream of acquiring Spanish fluency, I ended up gravitating towards working on my design skills, much like I did when I was young.

I took an online design course, then offered free design help to friends. I crafted logos, overhauled landing pages, and created design systems from scratch. My very first project was designing this blog.

As a software developer, I'd spent my entire career developing and shipping software, but along the way, I ended up taking on managerial duties and getting mired in responsibilities that didn't actually bring me joy or meaning.

All this had led me to question whether I wanted to be in the software industry at all. Should I be doing something completely different instead?

I needed to let myself have total freedom in order to realize that, at my core, I am a person who revels in imagining and creating useful things for people. That's my fundamental nature, and finding work that aligns with that is what brings me the greatest happiness and allows me to contribute to the world.

This insight has already proven useful as I've returned to full-time employment. I've found it much easier to say "no" to roles that are fundamentally misaligned with what actually motivates me. It's now clearer than ever that I need to work in environments where my creative energy is a strength, and where work that I dislike—like having to convince lots of people of my ideas—is minimized.

Sabbatical’s end

When I was first thinking of taking a sabbatical, I tried reading about it to understand what it'd be like. A recent book that many people recommended was The Pathless Path by Paul Millerd.

I wholeheartedly recommend the book. It helped orient me to what the experience of being off work might be like, and provided me with a rough blueprint for the journey.

My one critique is that as you delve into sabbatical-related content, you may find that many people who write about taking sabbaticals end up becoming sort of full-time "sabbatical influencers." It feels like they believe that everyone should quit their jobs and... blog about quitting their jobs, I guess?

In reality, this is just selection bias. The people who are producing the most content about sabbaticals are those who decided to produce lots of content about sabbaticals. This makes sense, but it leads to a distorted view. It made me feel like if I just took a few months off and then ended up going back to full-time employment, I'd done something wrong. Shouldn't I have more radically transformed my life in some way?

Research by HBR suggests that people taking sabbaticals roughly bucket into three types:

  1. Working holidays, in which people work on a passion project and mostly return to their previous jobs.
  2. Free dives, in which people rekindle their desire to work and usually find a different job, but often in the same line of work.
  3. Quests, in which people radically transform themselves and the work they do.

I'm probably part of category 2. And part of why I'm writing this post is to provide a data point for those of us who find that full-time employment—with the right structure, with the right coworkers—isn't actually all that bad.

If you take extended time off work, maybe you should consider what it’d look like if you didn’t return to full-time employment at all. But if you decide that full-time employment is right for you, that’s totally OK too.

Back to work

After I spent a few months traveling the world and tinkering on design projects, I felt an itch to "get back to work"—that is, to more consistently dedicate myself to a particular set of projects.

To sample this, I sought out freelance work. It was pretty easy to find a few paid gigs as a software engineer, so I ended up spending the month of May juggling a few paid projects on a part-time basis.

I found the work rewarding and interesting, but it quickly became evident that to actually scratch my creative itch, I needed to work on something over a longer time horizon and with greater ownership than I'd get through part-time gigs.

That led me back to full-time employment. And for many years, I'd been wanting to work on something related to the climate crisis. After sifting through a lot of opportunities I didn't find substantive enough, I landed at my current job, working on power flow modeling software for the renewable energy sector.

The truth is, it's nearly impossible to make a dent on problems like reforming our energy sector from the position of being a freelance worker or solo developer. Although I do miss the days earlier this year when I would wake up every morning with no agenda or responsibilities, I currently feel more fulfilled spending my days helping customers figure out how to get more renewable energy generation built and interconnected into the U.S. electrical grid.

For me, returning to full-time employment was necessary in order to align my creative energies with working on things I care about.

Subtle changes

Though some of the changes I’ve experienced from my sabbatical are relatively obvious, like improving my design skills, most are far more subtle.

In the past, when I was having an unproductive or unfocused day, I'd often end up just sitting at my desk feeling frustrated. I couldn't get stuff done, but I felt guilty about just leaving my work behind to reset or recharge.

I think that sense of guilt or attachment has loosened a bit. These days, if I find myself feeling unproductive, I'll just leave all my devices at home and go for a walk or head to the gym. Spending time exercising or enjoying nature has a clarifying effect for me, and I feel much more willing to go seek that out when I need it now.

Similarly, I now recognize my need to tap into a creative flow state on a regular basis. A full-time job doesn’t always provide an outlet for this—sometimes, what needs to get done is just drudgery or something I dislike. In those times, I now recognize that I can get into a flow state outside of work, whether that’s through cooking something, writing for this blog, or something else. Having those outlets outside employment helps me keep the momentum going within my job.

The most basic shift I’ve felt is shedding a deep-seated fear of being unemployed. So many people I know are stuck in full-time jobs they find draining simply because they’re deeply afraid of the alternative. What would it be like to just not work at all? How would you get health insurance? What if you run out of money?

During the sabbatical, I had to contend with budgeting when I had no incoming cash, finding my own health insurance through the public marketplace, and lining up occasional paid gigs to feel financially comfortable. Having gone through that set of experiences makes me much more confident about dealing with the logistics of being between jobs in the future. If my work circumstances start feeling wrong for me, I feel much more confident in my ability to just quit and figure out next steps afterwards.

All in all, I'd say taking the sabbatical left me with a lingering feeling of lightness, even as I've returned to full-time employment. I don't feel a need to cling to things as tightly. And, paradoxically, it feels like that allows me to invest my time and energy even more deeply into work that I really care about.

Are you thinking of taking extended time off work? If you have questions, thoughts, or anxieties, feel free to reach out to me—I’d be happy to chat.