What Does it Mean to “Live Your Life in Seasons”?

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

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”

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

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

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.