How to De-Risk Your Sabbatical
The 5 layers of readiness, based on dozens of interviews.
One of the most common questions I receive in my sabbatical coaching (totally free! Schedule a session here) is “What should I do to prepare for a sabbatical?” Which is another way of asking, “How can I feel good about the risk I’m taking?”
Like most adventures, you’ll never be 100% ready, and that’s part of the fun. Sometimes, you must leap and a net will appear.
However, I usually work people through five “layers” of preparedness to help. These are known areas, proven by speaking with dozens of people who have taken sabbaticals, where there is some amount of risk.
You do not need definitive answers for each one. Indeed, some of them you can only make educated guesses. But considering each one and having a strategy or a rough idea can be enough to feel good about taking the leap.
Layer One: Identity.
Are you ready to feel adrift?
This is for all of you overachievers: who are you without your career? Who are you without the doing?
Most people start with the financial considerations (see next layer), but this is more important. What you do for a living is a core part of your identity — it’s one of the reasons “So, what do you do?” is a standard cocktail party opener.
When you are considering taking a break from working, a core part of your identity is now in flux. The space created by temporarily removing your career can be difficult to internalize before you do it.
Be comfortable with the idea that you will not know how to describe yourself or that you will be met with a blank stare when you do. At least, be comfortable with being uncomfortable.
Layer Two: Money.
Do you have the savings for the kind of break you want?
Sabbaticals are sometimes described as “mini retirements.” Much like a retirement, you need to be honest about the lifestyle you’d like to maintain during your break and consider the length of time you expect to take off. Things to consider:
The length of time of your break
Do you have a condition that requires medical insurance or expensive prescriptions?
Do you want to travel? To where? And what is the right balance of price and comfort?
Are there side projects or businesses you want to start that may require investment?
How much of a buffer do you have if you have a sudden unexpected expense such as a large home repair?
Don’t forget to bank in time to enter the next phase of your career, whether that’s finding a new job or starting your own thing.
Consider Melissa’s story, after her break she ended up taking longer than she expected to find her next move. Luckily, she had the savings on hand to weather the delay.
See this video for a breakdown on the four ways people pay for a sabbatical: Savings, flexible work, secondary income, a windfall.
Layer Three: Employment.
How confident are you that you could come full circle?
There’s a truism in investing circles: “Nobody can time the market.” You can’t know what’s coming around the bend like, say, a global pandemic. But using your best judgment, do you believe that, if you had to, you could find a job similar to the one you are leaving? That if none of your exploring and self-discovery yielded anything, you could end up roughly back where you are now?
This mental exercise is a good way to prepare yourself to take the risk of a long-term break. If everything went wrong and you didn’t find some brand new way forward, could you land roughly back where you started? If you are a nurse do you think you could find another nursing job, even if the location and salary weren’t an exact match?
The answer doesn't have to be “yes”, but knowing the answer helps you take the long-term break with eyes wide open and helps you understand how long it would take you to find a job when you return.
For example, if you are a C-suite executive, you may be able to find another job. But given executive hiring cycles can take months, you have to bake that into your “re-entry” plan.
Consider Amanda’s story, where she ended up back in a similar role in a similar industry, but with a few changes to her approach.
Layer Four: Goals.
What does a “successful” sabbatical look like to you?
It’s important to be honest here. Some take the definition of sabbatical that is grounded in academia, where you take a break to produce something. Others have a simple goal of recovering from burnout. Or maybe you want to end your sabbatical knowing your next career step.
Especially if you’re an ambitious person who likes to plan and strategize, you may benefit from seeing what bubbles up during your break.
For example, when considering his sabbatical, Len purposefully focused on rest above all else: “Because if I had a goal and then I didn't achieve it, then I would have failed sabbatical. And can you imagine anything more demoralizing than failing at rest?”
Layer Five: Discovery.
Are you ready for some uncomfortable introspection?
Especially if you travel during your sabbatical, you are taking a very full life and removing your community, your career, and your home. What’s left is what I affectionately call “The Abyss.” When you create an absence, you allow some latent feelings or thoughts to come to the surface.
Sometimes this is good. Maybe after years of working alone, you remember you always loved working with people and perhaps your next career step should focus there. Or maybe you realize your bank pain comes from all the hours at the computer.
For example, with some space to think, Rachel realized that she had been subconsciously rushing things, often for no reason.
Sometimes this can be difficult: Maybe your focus on your career has damaged relationships in your life, and it took taking a break to realize that.
This can be uncomfortable and bracing, but it’s the work that makes taking a sabbatical worthwhile.
The Collapse of Traditional Retirement is a Good Thing.
Mini-retirements, thin-sliced retirements, and the unique opportunity for an unconventional path.
What will you do when you’re done working? Chances are, some image popped into your head about moving to some warm climate. Maybe you also think of all of the hobbies you’ll pick up. How’s that pickleball backhand?
The post-WWII retirement blueprint of working for 30 years and then living off a mix of savings, pensions, and Social Security is so embedded in our culture that you may have never stopped to consider an alternative.
But most of the signals are telling us we need to change our expectations. Consider:
The number of Americans with pensions has been more than halved since 1975, from 27 million to fewer than 13 million.
As of this writing, Social Security is due to run out of money in 2033.
The median years of tenure for private sector workers is 3.5 years.
Early retirement is linked to shorter lifespans.
Our “retirements” are no longer in the hands of institutions—they are now up to us.
If you’re operating with the “work for 30 years and then call it a career” mindset, this can be terrifying. And this is where most of the conversation around this topic usually stops.
Never let a good crisis go to waste. There is an upshot here: the benefits of diligently working at a single job, industry, or company are lessening. This gives us more control over our own journey, and the chance to be more varied (and interesting) humans. The feelings of being “on track” are ours and ours alone to determine.
There are many types of sabbaticals. There are also more than one approaches to retirement.
Three to consider:
Traditional. Front load work, back load retirement.
Mini-retirements. Episodic career with two or three chapters and long “mini-retirements” in between that stretch six months or longer.
Thin-sliced. Borrowed from Richard Banfield, this is interjection adventures and breaks that are a few weeks long as often as you can. Best if you have freelance, remote, or fractional work set up.
A few reasons this is uniquely possible now:
The remote work boom. In 2019, only 8% of workers in “remote capable” jobs were fully remote. In 2023 that number climbed to 29%. Many knowledge worker fields such as computers, media, and finances have remote worker rates greater than 50%. If your mini-retirement involves travel you decouple your work from your location and keep some cash flow.
Fractional and freelance employees (especially in tech). The wave of tech layoffs in recent years have led to the rise of “fractional” leaders and executives. Companies keep a full-time employee off their books, maintain flexibility, and the fractional employee can focus on a highly specialized part-time role. This makes it easy to build your career like a lego set, with pieces of fractional employment across several companies. When you’re ready for a mini-retirement, you can wind down a client.
Careers are long. Many retirement expectations are rooted in a world where most workers do manual labor, die in their late 60s, and retire in their late 50s. The baby boomer generation is one of the first to regularly have careers that stretch into their 80s. That’s 60 years of working at the extremes. You could have three 15-year “chapters” with mini-retirement in between each one. At 54, Richard Banfield called this approach his “second harvest”.
Cultural expectations. The younger you are, the more obvious the above will be to you. It may be youthful naivete or galaxy-brain smart: but Gen Z is planning on retiring early. Via Vanguard “In 2006, 30% of employees ages 18 to 24 participated in their [401k] plan. This rate rose to 62% in 2021.” Movements like FIRE and digital nomading are picking up steam. The episodic career with mini-retirements is becoming the expected.
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“Knowing” that a mini-retirement is possible is different than giving yourself permission to do it. It involves untangling the role work has in your identity. For you over achievers it also means being okay with a chapter in your life where you’re not moving “forward” — at least not by traditional standards.
But these intermissions give you the structure for the next phase of your career to be more aligned with your values. Rather than sleep walking through it all, you can ensure that the path you are on is the best one for you at that moment.
(Consider Greg’s story, and how he overcame this feeling of laziness to reorient his career about autonomy.)
For more resources on planning your own mini-retirement subscribe to the Sabbatical newsletter, and browse interviews with people who have successfully done it.
The 6 Types of Sabbaticals
Sabbatical archetypes to inspire.
There is no one-size-fits-all way to approach a sabbatical. We define a sabbatical as an extended pause from your normal day-to-day in order to change something about yourself or your life.
As a result, a sabbatical is personal and its shape depends on where you are in your life, your personality, your family situation and a bunch of other factors. That kind of open-endedness can be a bit intimidating. So as a means of providing you with some inspiration, below are some loose categories of sabbaticals we’ve seen — informed by the interviews and essays we publish every other week.
Don’t take these too seriously, they are meant to mix, match, and inspire.
1 - The Family Sabbatical
Goal: In most cases, you’ll get 18-20 years with your children before they move away. And, if we’re being honest, most children prefer to spend time with their friends rather than family in their teenage years.
The family sabbatical takes advantage of the golden window where you children are able to travel with you but not so old that they’d rather be somewhere else.
What it looks like: Two approaches:
If you want to travel during your sabbatical, you homeschool your children for a year while on the road.
You step back in your career temporarily to give yourself more free time to spend with your children. This can mean reducing down to part-time hours, becoming a freelancer, or taking a far-less demanding job. You eventually “lean in” again, but only after your children have grown.
2 - The Breather Sabbatical
Goal: To step aside from the day-to-day expectations of your role so you can recharge your batteries and reevaluate your priorities.
What it looks like: An extended time off from your job, usually 4-6 weeks and often paid for by the company. You fully intend to return to your current position, but with a renewed perspective and energy.
3 - The Burnout Sabbatical
Goal: To refresh your relationship with your career and work. You’ve put your career above most things and that hasn’t allowed time for some other things in your life to grow. Should you still do that? Are there other things you’d prefer to focus on?
What it looks like: For the first few weeks or even months, you’re recovering from burnout. This usually means adopting some low-stress hobbies or goals that have nothing to do with your career.
Eventually, as your burnout subsides you may find your attention naturally being pulled into surprising places. The space created by taking a break allows new interests and curiosities to arise. Follow these hunches and see where they land you.
4 - The YOLO Sabbatical
Goal: To have an adventure and scratch some sort of itch.
What it looks like: Knocking off items from your bucket list that a typical career structure made difficult. It could be spending weeks traveling abroad or finally tackling those personal projects you’ve been wanting to get to.
5 - The Creative Sabbatical
Goal: While you are a creative person, your day-to-day career doesn’t quite make use of those talents. A creative sabbatical is about giving you the space to pursue your craft outside of economic and career pressures. This is similar to a traditional academic sabbatical in which some research is conducted or a book is published.
What it looks like: Maybe you’re a writer who wants to publish that novel. Or a musician who would like to tour. A creative sabbatical usually has a deliverable or output that marks the end of the sabbatical.
6 - The Pivot Sabbatical
Goal: David Brooks calls this “The Second Mountain”: you’ve climbed one metaphorical career mountain, and you’re ready for a new challenge. Is it to double down on your career? Pivot to non-profit work? Change industries? A pivot sabbatical is about exploring those options.
What it looks like: Quitting your previous job and exploring the next step via a handful of tiny experiments. For example, if you are considering switching industries, you’ll take up part-time work in that space.
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Did I miss one? Let me know.
What Does it Mean to “Live Your Life in Seasons”?
You can have it all. Just not all at once.
One of my favorite physiology concepts is the “end of history” illusion.
Say you’re 35 years old. When you plan your life 15 years from now, you likely assume you will not be too different than you today. However, you likely strongly believe that you are much different today than you were 15 years ago.
This belief that your future self will be exactly the same as you are today is the “end of history” illusion.
It’s impossible to know what we will care about in the decades to come. So how come we often plan our lives and careers like we do?
That’s why a repeating theme of Sabbatical is “living your life in seasons.” To live your life in seasons is to recognize that you are a different person at different stages in your life and each of those stages serves a different end. Sometimes it is a restful season. Other times, it is a season to work and amass wealth and knowledge. Sometimes you are focusing on family and community. Other times, yourself.
It’s the answer to the “can you have it all?” question.
You can. Just not all at once.
Most interviewees on this site will cite some version of this as the reason they decided to drop everything to figure out what’s next. Sure, they could work 40 or 50 years straight. But what if there were more options?
Why Living in Seasons is Possible
Living in seasons has long been possible — just ask any seasonal worker. But there is a unique confluence of trends that are making it more achievable:
There is little reward for staying at a single company. There are no pensions to speak of and most of us have 401ks that we can port from place to place. There is often a salary bump for those switching jobs, and one of the fastest ways to grow your network is to do stints at several high-growth companies.
The digital transformation of most industries has created unprecedented opportunities for ambitious and talented people to earn high salaries. It’s created a power curve where the top tier of talent can be rewarded equity, land signing bonuses, and be actively recruited by several companies at once. Saving a few months salary is possible when you are one of these people.
However, achieving these high salaries often requires an extreme commitment that requires much of your time and energy, and in some cases requires you to sacrifice your health or personal relationships as you focus on your career.
We can work from anywhere. Thanks to COVID and the rise of remote work, knowledge worker jobs have been decoupled from the office. Organizations have adapted to have at least some of their team members be distributed.
In other words, there is money, status, and benefits to working extremely hard. There is also ample opportunity to optimize around flexibility. You can earn more money than ever and you can experience more of the world than ever before. However, you can’t do it all at the same time. That’s living your life in seasons.
The key is knowing what season you are in and why you are in it. Be purposeful and unapologetic about what season of your life you are in. This means getting FOMO and letting people “pass you” while you are resting. Sabbaticals can be difficult when you see your peers getting promotions or accolades that, deep inside, you think you could have had.
It also means missing out on some things you would find short term fulfilling in service of some larger goal. Most entrepreneurs of massive businesses point to birthdays missed, health sacrificed, and hobbies left unexplored.
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If you’ve lived your life in seasons, I’d love to feature you on Sabbatical. We’ll be covering more on how to do this, backed by interviews with those who have, in upcoming essays. Subscribe to Sabbatical to follow along.
It’s Never Too Late
The more career experience you have, the more fruitful your break will be.
When we are early in our careers, our knowledge of what our working (and non-working) lives can look like is limited. We lack context.
If your mother was a freelance graphic designer, you’ll be more aware of what it is like to work for yourself than, say, the person with two parents who had a “traditional” corporate 9-to-5. If your father was a powerful CEO, you have a better idea of what it takes to climb the ladder (and the costs and benefits of doing so). Steph Curry has natural talent, but surely having the context of his dad playing 16 years in the NBA helped him realize what was possible.
As we advance in our careers, we meet different kinds of people. We cross paths with different sectors of the economy. We gain an awareness of what is possible.
When I talk to people about taking sabbaticals, they sometimes lament that they “missed their window” or that they’re too deep into their careers to press pause. On the contrary, the bigger the contextual gap between when you started your career and where you are now, the more helpful a sabbatical can be.
Taking a sabbatical later in your career means you are more aware of what is possible. Whether you want to change course or hop back into your previous career, your cumulative connections and talents make it possible.
Sure it’s difficult to press pause mid-career with “more to lose” and more to manage. But we’ve seen already that you can take your entire family on sabbatical. You can do it as an entrepreneur (see below). You can leave a promotion on the table.
The more career experience you have, the more fruitful your break will be.
The Benefit of a “Modular Career”
Sure it’s more work to build something brick by brick with no guide. But once it’s complete, it’s uniquely you.
Several factors make sabbaticals more possible than ever. Sure, we have remote work and widespread broadband connections. But there’s also a cultural component — an acceptance of the modular nature of our working lives. Consider:
The rise of “fractional” executives: part-time leaders who often lead multiple teams across multiple companies. The number of people looking for fractional roles far exceeds the opportunities available.1
Work on Zoom? Or Slack? What is the practical difference between working with a freelancer, a full-time colleague, or someone 12 hours away?
45% of millennials have done freelance work in the past year.
The upside of this is a modular career, one where you can assemble a “portfolio” of jobs, freelance gigs, or contracts to assemble the life and workload you want. That leads to control and flexibility — a career that can better bend to your needs and interests.
Of course, there are downsides, which we’ll address in other issues. But the modular career is like Legos in more ways than one.
Sure it’s more work to build something brick by brick with no guide. But once it’s complete, it’s uniquely you — and a little more satisfying than making something according to the instructions.
Digital Nomad vs Sabbatical
The point of all this is to have a day-to-day life that you don’t want to run away from — whatever that means for you.
Few books have poisoned the minds of (mostly) millennials than The Four-Hour Work Week. The book, first published in 2009, argued that thanks to the internet, we can work anywhere and lean on new software and outsourcing to run tiny but profitable businesses.
Long before COVID threw millions into the remote workforce, the book was of a movement that inspired a wave of people to “escape corporate life” and live the “nomadic” lifestyle, traveling from place to place and working on their laptops for as few hours as possible.
The more books you have, the more hours you’re working.
The digital nomad lifestyle framed labor as something to be hacked. Your surroundings are something you observe but not something you participate in. To the nomad, optionality is everything. Stay free to chase the next business idea, live in the next town, and make the next set of friends. It’s thrilling, good for social media fodder, and makes for a good story.
Most nomads call it quits eventually. They stop moving and lay down roots. Or they stop viewing labor as a thing to avoid and instead, as a tool to affect change, however small.
Things worth doing are difficult. They take commitment. They require you to sacrifice optionality. (You know, the kind of things that make one sound like an old crank.)
But as I get older, I realize it’s the stuff life is made of. It’s the homecooked meal from a friend versus the Doordash order. It’s walking down the street and making small talk with one neighbor versus 100 likes on your LinkedIn posts. It’s jumping in and improving your neighborhood versus moving to the next town when things get boring or difficult.
There’s a hollowness to the digital nomad movement - because it exists largely in opposition to something. When your life design is geared toward running AWAY from something, you’ll come to the crashing realization that you eventually need to run TO something.
A sabbatical is an absence of normal to figure out what your next version of normal should be. It’s removing things that don’t work so you can add things that do. Tam Pham talked about his pivot from the nomad life to “slow living” picking three cities to rotate between. That’s running TO something.
The point of all this is to have a day-to-day life that you don’t want to run away from — whatever that means for you.
5 Trends Leading to More Sabbaticals
I’ve noticed several common reasons people are slamming the pause button...
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.