Dream, plan, plunge: How to start thinking about taking a sabbatical

What would time away from work look like for you?

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The crazy thing about your life is that you can change it, by choice, completely, any time. Our history is only formed in retrospect, while our future is a persistent blank slate.

This can be difficult to come to terms with, especially in America, where cultural norms around work and family are so steeped in a neoliberal capitalist ideology and the rest of the planet is viewed warily. Do as your parents say, go to school, get a job, work hard, get married, have a family, buy a house…we all know the story. And we know how misleading that story can be. Perhaps there was a brief time in post-war America where this path was more obviously achievable, but I’m not sure it’s ever been in concert with the human animal’s natural instincts and motivations.

Taking a break from (full time, paid) work, for any reason, is considered a huge risk in our society. Work provides financial security, personal growth, and identity— elements of life most people crave. So it’s easy for fear short-circuit exploration of alternative paths: What if I can’t find another job? What if everyone I know judges me? What if AI replaces all our jobs? Thinking about change is stressful! I may as well just keep doing what I’m doing. Besides, it would be foolish to put my paycheck at risk. That thing I want to learn / person I want to see / place I want to visit isn’t going anywhere—I’ll make it eventually.

It’s notably harder to flip the line of questioning: What growth am I missing out on? Who won’t I meet? What ideas won’t I have? Is time running out in the face of global climate change? What if I get in a car accident tomorrow?

Big questions, right? Impossible to answer. But the same goes for the first set.

Most people will never not work unless they are forced by life circumstances, and it is undoubtably a privilege to be able to take a break. One of our goals with Sabbatique is to help our readers who are in the position to consider a career break work through these questions, whether travel-focused or not. Because, for us, the results have been inarguable.

“Life-changing” is sort of an empty phrase because life changes every moment. But putting that aside, a career break focused on goals that are impossible to achieve if working full time will have a dramatic impact on your life and sense of self. We have returned from our break better people—kinder, more patient, healthier, more resilient, with a fuller understanding of our planetary society and our place in it. Are these professional hard skills? No, though we developed those too (running our own ecommerce company, teaching Maven courses, researching and using AI products to stay up to date).

But, in our opinion, over the span of a lifetime, kindness, patience, resilience, understanding, and health are the forces more likely to lead us to contentment, awareness, and [insert your ideal outcome here]. This isn’t a newsletter to read if your goal is to get rich or die trying—but rather if you aim to live a richly-textured life.

Start by dreaming

When considering a career break, the only place to start is in your own mind. What do you want from life? What do you want from tomorrow? What dreams have been bubbling in there for a loooong time, maybe since childhood? Write down what you find. Make a list. Talk about your list with friends and family. Mix big—these can be ideas that seem totally unrealistic and impossible—with small—ideas you know you can act on and achieve today if you put your effort and time to it.

For us, visiting far away places and cultures emerged as a dream that combined a sense of urgency with an emerging sense of reality. Much of Earth’s natural beauty is under grave threat, including the rainforests and coral reefs that power the planet. Whether the impacts are driven by climate change or direct human interference (logging, fishing, etc.), and regardless of whether we wish it were untrue (or want to argue the root cause), even the most resilient ecosystems are breaking under the strain. Back of the napkin math says: go now. With news of mass coral bleaching and rapid deforestation worldwide, the urgency rose to a level we couldn’t ignore.

What feels urgent to you? Perhaps it’s writing the book you’ve been working on in your head for a decade. Maybe it’s spending time with older relatives before they’re gone, or with your kids as they grow up. For one friend of ours, it was getting physically healthy—something they were really struggling with working at a fast-paced tech company.

If you find your dreams aren’t readily apparent, it’s worth spending some time investigating why. Plenty of people are focused on the day to day, living moment to moment, and there’s nothing wrong with that. We have found, however, that recognizing our deepest instincts and desires and using them as inputs into life decision making is the only way to achieve our dreams.

Draft a plan

You’ve narrowed down your list and decided which goal to work towards. What will it take to make it happen? What changes, large and small, will you have to make? Who are you nervous to tell? What are you worried about?

Getting some semblance of a plan on paper is a huge step! For us, it was “we know we want to dive the planet’s healthiest coral reefs.” There are many possible paths to get there, and we started by sketching the shortest possible trip to dive one specific reef area. Then we imagined a bigger vision, and expanded the plan to see what it would look like if we had more time. We didn’t expect this exercise to snowball into many months of travel—that came as we asked ourselves all of these questions and did the planning required to fully envision the experience.

Over time, your plan will get more concrete. You’ll decide what matters most and what qualifies as a maybe. You’ll figure out what needs to be done to open the door to this new chapter. And you’ll keep putting it down on paper. I can’t emphasize this enough—when you write it down, it becomes that much more real.

Prepare mentally and materially

Taking time away from formal corporate work (or whatever model you spend all day in) is not a decision to be taken lightly. There are pressing realities. Like money. Like ego.

Your time off will be challenging if you’re constantly dogged by fear of what you’ve left behind. Frankly, those thoughts will definitely come no matter what, but that’s the nature of the mind and can be mitigated with preparation. Talk to a professional. Journal. Look around the corners as much as you can to figure out how you’ll handle challenging scenarios—a missed flight, an illness or injury, a death in the family. We discussed all of these scenarios during our planning phase, and when they all ended up happening, we felt as ready as we could be.

Now for the brass tacks: make sure you understand your financial situation and are comfortable with the possible impacts of time without a steady income. There are always ways you can make money, but assume zero earnings for your prep. How long can you afford to not work? What happens if you can’t find a job at the same pay level when you come back? These question is highly variable, of course. We decided we could, mentally and materially, afford a year off. Other people we met on the road had shorter and longer timeframes, with varying financial buffers. Lots of folks we met (usually those from countries with universal health care and free education) spend a few years earning some money, then take a long break and spend most of it down. Others have strict budgets, and when they hit that number, they return to work.

There will always be opportunity cost, but as we’re discussing, you take the step because you believe the costs are worth the outcomes.

We’re not going to dive too deep into money details in Sabbatique’s free tier, but obviously its a huge part of the story. We set a daily budget, used that to estimate a maximum spend cap, and tracked it closely, which gave some peace of mind. We played credit card points games (not as hardcore as some travelers, but welcome bonuses go a long way). We spent very little time in the most expensive locales (looking at you, Paris). We traveled below our means, often cooking in our lodging and, during some stretches, camping for days on end.

But look, for us, money isn’t the most important part of life. It’s easy to say that, and much harder to believe it and practice it. There are definitely times where we aren’t so sure of our own stance, and it’s much easier to take this position when you’ve saved up and feel relatively secure. If you are someone who is fixated on earning money and measuring your self worth by your salary or account balances, it will be very hard to take time off of work. If you’re someone who has saved up for a while, but doesn’t “feel rich” and are thinking you need to reach that vague threshold before taking any breaks…this newsletter is for you.

You never know the details of the fellow travelers you meet on the road, but most of those we met were making median salaries (in the US, that’s between $50-60k, lower in most of the world) and simply choosing to prioritize other parts of life. Let me be very clear: You do not need to be wealthy to take a career break or to engage in long-term travel. Sure, you won’t be staying at fancy hotels and indulging in tasting menus every night, but who wants to do that? Our favorite meals were usually the cheapest, and my favorite nights were spent in a tent (not sure Kira feels the same way on that point!)

Take the plunge

You’ve examined your own dreams, figured out what motivates you to want to change, planned how to make the change…there’s only one step left.

It’s the easiest one.

Have the conversation with your family and friends. Have the conversation with your employer. You don’t need to give any more detail than you want to, to either group. We both were very frank—that we felt urgency to explore other parts of life and the world, were sad to leave jobs and teams we loved, and would love to come back even though we understood the company couldn’t hold a role for us (though in Europe, that’s quite common!) We received overwhelmingly positive support, which was a huge boost during a confusing and stressful time. The confusion and stress faded fast though, once we packed our bags and boarded the plane.

Life can be mercilessly short. We chose our path, embraced it fully, and are reaping the dividends a full year later. And those dividends will continue to compound... forever.

That’s the thing about taking risks to pursue your dreams. You never know who you’ll inspire, and what they’ll achieve from the risk they take. I’ll end where I started, by offering an eternal reminder: You can change your life, by choice, completely, any time. No one else gets to decide your path. My advice, no matter where you are in life: embrace this incredible existential freedom, and do the work to empower yourself to make informed choices about what comes next.

— Nicky

We’ll be diving into the specifics in each stage described in this post in the future, but wanted to offer this framing for our readers before returning to our flagship series next week—52 Places to Go On Your Sabbatical.

Thoughts? Questions? Let’s engage in the comments. We’re here to help you think through big decisions and figure out how to make your dreams a reality. Welcome to Sabbatique.

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