After I quit my job in 2017 I spent 5 weeks in Europe. It was the longest break from the “real world” I had ever taken and in the second week, I started to feel extremely guilty. I became hyper-aware of the script in my head that said I should be working or that at minimum, I should be trying to make money. By the fourth week, I started to relax in a way that enabled me to look at my life in a way that I hadn’t in nearly ten years. What was happening? I sensed that I had just embarked on a path that had something worth finding.

Instead of sharing more about my story, I want to share the stories of the many people I’ve talked to over the last few years. This includes millionaires and people that are broke and the unique Americans who are in massive amounts of debt before they start their careers. People spanning from the US to Malaysia to India to Nigeria and Pakistan. Across all these people I’ve discovered one consistent intervention that consistently enables people to improve their relationship with work and has a 100% approval rating.

That thing? Taking an extended break from work.

A Quick History: Sabbaticals In Universities

Harvard University was one of the first universities in the world to offer a sabbatical to professors in 1880. In predictable fashion, other universities followed suit and by the early 1900s, many universities had their own program.

Here is a statement from Columbia University in 1907 describing the thinking behind their own policy (bolding mine):

The practice now prevalent in Colleges and Universities of this country of granting periodical leaves of absence to their professors was established not in the interests of the professors themselves but for the good of university education. University teaching must be progressive; it requires on the part of the teaching body, as it were, a periodical refurbishing of its equipment. It is not merely national, it is international; contact with other institutions, with specialists of other countries, with methods of acquiring and imparting knowledge in vogue elsewhere, which cannot be obtained during the summer vacation, as this is a period of rest practically everywhere, is for the real University teacher an intellectual and practical necessity.

Here is a similar statement from Dartmouth University in 1922:

The purpose of the sabbatical leave is to render the recipient more useful to the college as a teacher, as an investigator, or as an administrator. Leaves of absence are in nowise to be regarded as increased vacation periods, as primarily opportunities for increased financial advantage to the instructor, or as due him upon the ground solely of the length of service. They are an investment of college funds designed to increase the efficiency of the teaching force

While Dartmouth framed the sabbatical in the interests of the university, they are acknowledging that they are also attached to the idea of a teacher as someone that should have a broader range of knowledge and wisdom. The mindset of both of these schools was that there was something valuable in existing outside of the domain of their primary work that was of value to both the University and professor as well as the society at large (schools were not seen primarily as job-training at this time).

In the early 1900s, the kind of “knowledge work” that professors engaged in was the exception rather than the rule but now almost all readers of this newsletter are engaged in a similar sort of intellectual, knowledge-based work.

Why then, do we still accept a factory schedule for our lives?

Taking A Break Is Scary & Not Broadly Accepted

One of the hurdles that stop people from taking a break is the idea that life transitions are all-or-nothing leaps. Work is either something you do indefinitely until retirement or something you quit and then go live on a beach.

David Vaucher wrote a viral post on LinkedIn a few years ago about “ending his career” a few years ago. He decided to take a break from work to spend time at his father’s home in France, one he didn’t get to enjoy because he passed away before he retired from work. David felt that he needed to shake things up but admitted at the time “Who knows how this really all turns out.” I reached out to him last year to see where he was on his journey and was surprised to learn that not only had he returned to work full-time he was also really happy with his choice:

I now see the foolishness in feeling life is only about work, and that more hours lead to more and better output. I have near- complete professional autonomy, as well as the time to pursue things outside the office and it’s been fantastic. I’m in the most creative period of my life, my clients are happy, the product line I manage has improved by leaps and bounds and the team I helped build is phenomenal.

Finally, the bigger shift is I don’t feel the need to chase the next promotion or raise. I am grateful for all the things I do have right now, and I trust that if I do my best when I am in the office, things will work out.

For many people, like David, a sabbatical is not the start of a crazy adventure but a pause to ask questions that might add to the wisdom needed to live the life we want to live. This kind of break is not for the “what about…” people but for the people who have the fear of“living a life that was not true to themselves” as Bronnie Ware wrote in her book Five Regrets of the Dying.

And when people take these breaks they tend to experience many of the same things:

#1 People Are Surprised At How Burned Out They Were

The day after I quit my job I woke up and started to write. I wrote about being burned out, something I would have denied a day earlier. I felt broken and it shocked me that I had spent the previous six months in a numbed state, going through the motions, and pretending everything was okay. A German report on burnout described my state:

They may start being cynical about their working conditions and their colleagues. At the same time, they may increasingly distance themselves emotionally, and start feeling numb about their work.

One of the weird benefits of self-employment is you become hyper-aware when you are becoming cynical, exhausted, or burned out. Without managers and the other sort of emotional pressures to do your work, you have to face the fact that you created the conditions you claimed you didn’t want. In full-time work, you can go years doing work you don’t really like all because it’s the normal thing to do in today’s world.

A friend who recently took a sabbatical shared his surprise at how things had gotten out of alignment without him noticing:

#2 Curiosity Re-Emerges

One thing that seems to consistently happen is that people re-discover hobbies, relationships, and ideas they were once drawn to.

Here is Edward, who took a break from medicine:

I’ve been lucky enough to take a few extended vacations, of one month or more, but even after a couple of weeks, I notice that my brain starts to change, starts to alight upon new topics or rediscover old subjects of interest. I find myself writing a lot of notes on a whole host of different topics and wanting to explore them further. This is my creative process, liberated by the neocortex now that my mind isn’t wholly occupied by the strain of everyday sustenance, the rat race, and the grind.

For some people, it’s curiosity about a different way of life. Gabe, writing about an unexpected sabbatical after getting laid off shares: “A month ago, I was newly unemployed and unchained in the panhandle of Florida. Now I live in an eco-village on a volcano, in the middle of a lake in Nicaragua.”

#3 It’s Uncomfortable But Often The First Step In A Longer Journey

Jacqueline Jensen planned a “structured sabbatical” for herself centered around a question: “What if I took work…working for a paycheck, what if I took that out of the center of my life, what would my life look like?

She found it much harder than expected, “It was hard. It was not a four-month vacation. It was a lot of work to untangle myself from all the things I get from work – the validation, the excitement.” However. at the end of the sabbatical, she found a new spark for life, ended up deciding to write a book, and reprioritizing what she was willing to compromise for success in her career and has found a stable remote job that has enabled her to live in Portugal while still doing work she enjoys.

Diania Merriam had worked up the courage for months to ask her boss for unpaid leave to walk the Camino de Santiago. She walked in and to her surprise, her boss said “sure” instantly. What she didn’t expect was how scared she would feel before she took her trip:

I planned as much as I could on the material side and the physical side but what I could never plan for was the emotional side of being without work for two months, completely disconnecting, and dealing with the uncertainty of where I would be every night, where would I get food? I just had to trust that I was going to walk and find it. Battling the uncertainty of all of it on the way there and while I was in it.

She went back to work for a couple years, but her curiosity led her to a number of side projects, including launching her own conference to explore a “new American dream” and a part-time podcast host gig on personal finance. Eventually, she decided to take the full leap to self-employment.

Another friend shared how she took multiple sabbaticals with her partner and kids as part of a larger transition to become self-employed.

So for some it may be a one-off thing but for others, it is the first step of many.

#4 Lots of People Start Writing

I’m not sure which direction the causality goes here, but many people who take an extended break end up finding writing as something that they want to keep doing. Like Jacqueline, Lenny comments on how his sabbatical led directly to him deciding to launch a paid newsletter and to continue writing

After leaving, I planned to take 6 months to explore and tinker. That turned into a year, and that turned into the newsletter that you’re now reading. There is a 0% chance this newsletter would have emerged if not for the space that this time off created—the space to tinker, to research, and to write.

Alex Pang’s own sabbatical inspired led him to live what he described as a “leisurely” life and while on his, reading a book by Virginia Woolf inspired him to go down a rabbit hole which has led him to write several books about our relationship with work7.

I had been reading Virginia Woolf’s book A Room Of One’s Own that makes the argument that for in order for women to be creative, but really for anyone to be creative, they needed a certain kind of space and independence that had long been denied to women. That got me thinking about all these issues and their interconnection.

I had been writing before I took a break from work but it definitely exploded when I moved to Taiwan and had no paid work to do. I think the reason writing is such a draw for people is that to take a sabbatical in today’s world is to split away from the default reality of today’s world. This can be disorienting and writing is a way of figuring out what you actually think.

#5 Forces You To Look At Your Life From A Distance

Sean Blanda has written one of the best posts on sabbaticals. If you follow any of the links I mention, it should be Sean’s. He offers eight insights that people typically have from taking a sabbatical. Here are the eight:

  1. You are creating a new map.
  2. Be ready for “the thrash”
  3. Release your “curiosity constipation”
  4. You may have the instinct to plan this like a vacation. Don’t do that.
  5. You won’t do this alone. Much of your progress will come through people.
  6. The distance from your “normal life” will make you realize what you miss and what you don’t.
  7. When you come back, you’ll need a narrative.
  8. Lastly, every single person I spoke to would do it again:

A lot of them resonate with what I’m sharing here but I thought the most interesting was his idea of the “thrash” which is the moment when you “peel away layers of your identity” and start to realize that you are more than what you do:

The fact that you are able to take a sabbatical means you have enough money and are good enough at something to give you a bit of an ego. But for this trip, that person who is “good at something” is no longer you. It’s just part of you. And you’ll have to let that part go (for now). And it will feel like starting from scratch. And it will feel like you’re giving up all the “progress” you’ve made.

One day you are going through the motions of your life and the next month you are suddenly disconnected from that former identity and seeing everything you were doing much more clearly. A friend, James, noticed how a break helped him get back on track with what he really wanted:

I started to realize how, on a personal level, my job was excluding me from so many opportunities. It offered some opportunities as well, but they could be taken away by office politics, the election cycle, or the company deciding I was more valuable to them in a role I didn’t enjoy.

The sabbatical let me think more objectively about my career because it removed me from that environment long enough for me to figure how to pay attention to myself, rather than all the external demands that came with the job.

#6 Travel Often Amplifies The Effects Of A Sabbatical

Our modern conception is limited to vacations. Josef Pieper was writing in the 1940s that people had started to lose connection with a definition of leisure that prioritized contemplation and active engagement with the world before work became so central. He noted that the vacation was “part and parcel of daily working life” and that it is “there for the sake of work. It is supposed to provide ”new strength” for ”new work.”

Contrast this with how travel writer Pico Iyer talks about travel, “We travel, initially, to lose ourselves; and we travel, next, to find ourselves.” Iyer came to realize that the real power of travel was that it enables one to “become young fools again—to slow time down and get taken in, and fall in love once more.”

In the last four years, I think one of the interesting things to see that my body language has softened. You can kind of see it in this how it started, how it’s going comparison from a month after my leap to another from last month:

The biggest shift happened when I moved to Taiwan and didn’t have any sort of script to guide me for how I was supposed to feel:

Walking around in Taipei was the first time I experienced this feeling. When I was living in New York or Boston in the previous ten years I might be wandering around the city doing very little but it was always in tension with the predominant culture that I should be doing something, that I might have forgotten something, or I might not have done enough.

In Taipei, that feeling evaporated. I didn’t yet know the cultural scripts or expectations around me. I was both in a state of not-knowing and non-doing. 

Edward, from above, feels that “You don’t have to necessarily travel during these times but I believe it is optimal” There is something about travel that enables you to get distance and to start to ask the questions that matter.

Sabbaticals Are Essential For The Way We Work

Sabbaticals are shifting from a rare thing to something that a much broader range of people will consider. A big part of this is the changing nature of work. As I covered last week, the types of jobs that people often need breaks from demand much more lifelong learning, decision making, and “management” work than before. In addition, its also creating much more gig work driven by the explosion of technology, platforms, and disappearing middle-class jobs. Gig workers will likely be the ones that pave the way in taking sabbaticals and normalizing them in our culture and corporations and full-time employees will eventually fall in line.

The idea that one should have a straight, linear path of work throughout their life is still alive in many people’s minds but not a great strategy for a career. The industrial labor economy leaned on people’s ability to do repeatable tasks while also aiming for incremental improvement. The digital economy is oriented much more around creative work, complex decision-making, and information abundance.

This new economy will favor those who work as Naval Ravikant described:

We are moving from what Seth Godin has argued is a competition of “being more ordinary, more standard, and cheaper” to “being faster, more remarkable, and more human.” Many jobs operate like this but we are stuck with the 40-hour workweek mostly because all the people that used to argue for shorter workweeks have already passed away.

I’ve noticed increasing numbers of people taking breaks from work earlier in their lives, like Maria who decided to cash out $4,500 from her retirement account to explore for four months. Here was her reflection and call to action:

After 4 months and 4500 spent, I feel more self-aware, confident, and energized than ever. I feel more mellow, grounded, and more in control of my future. I grew so much that I had now made it a rule to have a big break in between gigs fully devoted on play.

I keep highly highly recommending to any and every of my friends to do this. Put some money aside and just live your life. The money will be plentiful in your 30s but your time and independence will be scarce – at least that is my belief; take it or leave it-.

Another model might look like what Sean McCabe embraced in his life after realizing he literally had no life beyond work. He was simply working all day every day including weekends. He decided to try an experiment where he would “work six weeks and take off every seventh week” and has said that it changed his life9. After six years of doing this, he decided he would take it to the next level and take every seventh year off.

Taking a break is scary but from what I’ve seen it’s probably one of the simplest ways to grapple with one of people’s biggest fears: that they didn’t live a life that they were capable of. Taking a break is a way to take a different perspective of your life, remember the things that mattered to you, and sometimes simply rest and be with the ones that matter to you.

As Alex Pang concluded in his book: “If you want rest, you have to take it. You have to resist the lure of busyness, make time for rest, take it seriously, and protect it from a world that is intent on stealing it.”



    Want To Join 5300+ People For A Weekly Reflection On Work, Life & Philosophy?