How to Design a Sabbatical

Last November, I resigned from my software engineering job and booked a one-way ticket to Barcelona. Once I dropped my laptop off with couriers, I was unemployed. Going without work may seem like a weird thing to celebrate, especially in the midst of an economic hurricane—startups capsizing, stocks going underwater, and jobs being thrown overboard. 

What possesses someone to make such a decision? Why pursue a path riddled with uncertainty when the desire for stability is so high?

As The Great Resignation showed, many of us feel like cogs in the wheel of work. We sweat through the Sunday Scaries, a perpetual longing for the weekend and desire to escape the perceived dullness of our job. We face the existential chasm: How much longer can we sit in this dull, gray, muted state? 

It’s hard to know what to do when we get stuck; there are no cookie-cutter solutions to break out of stasis. In tech, many people try changing roles to combat malaise (the engineer → product manager pipeline is a common antidote). Others jump industries or companies to find purpose (big tech → startup or SaaS → health tech). 

I considered all these options but ultimately took a different route: I went on sabbatical. By pausing my life and giving myself time to wander, I hoped to recalibrate my relationship with work. In this article, I share how I designed my own sabbatical, and pen broad strokes for what you might expect from the emotional journey of such a path.  

Sabbatical step #1: The morass of messy feelings

On the outside, sabbaticals might seem like one long vacation. But in my experience, sabbatical takers must wade through a morass of messy emotions. We can easily fall prey to outdated stories about ourselves or coping mechanisms that keep us stuck:

• Anxiety (what if I can’t find another job?)
• Shame (am I weak for needing this time?)
• Guilt (I don’t deserve to do this) 
• More anxiety (what if freedom seduces me and ruins me for all future employers?)
• Boredom: (what would I do all day?!)

The list goes on. These feelings can be scary, but they raise important questions for you to explore. To figure out what’s a valid deterrent to taking a sabbatical versus a limiting belief, interrogate the stories you have about your emotions. I recommend journaling on questions like these:

• Why do you think or feel that way?
• What evidence do you have?
• What is conjecture or speculation versus fact?
• If your fear became true, what’s the worst case scenario?
• What can/can’t be controlled? 

Finances: What’s the real price of your job? 

There’s no getting around the fact that sabbaticals are acts of privilege. They presume you aren’t living month-to-month on your paycheck, you don’t support extended family financially, and you aren’t saddled with crushing debt, medical or otherwise. No matter how cheaply sabbaticals can be taken, for some people it’s just not an option.

For others, however, sabbaticals are more feasible than they believe. They require a leap of faith — bucking conventional financial wisdom by spending money we’ve saved for rainy days. In my case, even though I had enough money to support a year without income, the idea of using it terrified me. How could I justify using my savings on this?

I recommend naming your fears and confronting them openly. Comb through the pieces of your life to figure out what matters most:

• Are you reasonably assured you can get another job to pay bills when your sabbatical is over?
• What’s a plausible worst-case scenario for you if you struggle finding work? Could you stay with someone for free if it came to that? 
• Do you have other priorities that need to take precedence, like buying a house?

I’d encourage you not to dismiss the investment of a sabbatical as something inherently frivolous. We often stay in unfulfilling jobs because the opportunity costs (salary, stocks, bonuses — if we’re lucky) seem too large to give up. But what about the opportunity cost of not taking the leap? What price are you paying if you stay in a job that drains you and hurts your mental health? 

In my case, I decided my savings were there to protect me and give me options. And I was deeply in need of new paths to pursue. Buying a house could wait — solving my work disillusionment was my most pressing need. Ultimately, I gained confidence that my future self could take care of himself. 

I realized I'm the same person who saved up money in the first place. And I could do it again if I needed to.

Identity: Rejecting the productivity prophets 

Besides finances, the biggest roadblock to taking a sabbatical is the anxiety it triggers about who you are and what your future will hold. 

Most people who take career breaks agonize over this decision for months, or even years beforehand. Resistance makes sense, because the leap into the unknown tests your inner resolve and raises a crucial question: Who are you without your job? (Cocktail parties are riddled with its pesky small talk cousin—“What do you do?”) 

The unfortunate reality is that we won’t know the answers without taking the plunge. By its very nature, a sabbatical is a leap of faith. It requires rejecting the idea that you are what you do, a lie peddled by productivity prophets. We procrastinate by telling ourselves the next quarter or promotion will fix things. 

In a world where many of us self-actualize through work, it’s disorienting to walk away. But this step is crucial to untangling your identity so you have the freedom to explore other possibilities. For me, there ultimately came a tipping point where I couldn’t ignore the “costs” of my job on my mental health anymore. 

When you finally decide to take the plunge, I recommend celebrating. Rituals are important, especially for moments where you’re carving out your own path. I threw a small “retirement” party when I resigned, even though I'm not a crypto millionnaire who will never work again. Much like certain cultures celebrate death, I wanted to close the door on this phase of my life with aplomb. We toasted to new beginnings. 

Sabbatical step #2: Rest and recover

So, you’ve taken the plunge and it’s day one of your sabbatical. What can you expect?

For many of us, sabbaticals tend to begin with a whimper instead of a roar. If your relationship with work was fractured or you burned out, you need to heal. All that stress and anxiety must find their way out of your body. Tears and fears might visit you in this phase. This is normal. Rejuvenation is on the other side if you give yourself the space for healing to happen. 

You may need a lot more rest in the early stages of sabbatical, as your body decompresses from years of operating in stress mode. Apathy and exhaustion are normal at the start — your nervous system finally believes it’s safe to take a break. You’ll find your way back to a more normal baseline when you’re ready.

To recalibrate your life, you initially need to reject your urges to “be productive.” The desire to fill your calendar to the brim with activities is a trap. It’s a relic from your work brain, trying to keep you away from the restoration and introspection you need. (Perhaps it’s scared of what you’ll learn about yourself when your world quiets down?) The doers among you will ignore me and stuff your calendar with projects, online classes, and impressive-sounding plans. 

Ask yourself a few uncomfortable questions along the way: Why are you so busy? Do you need to accomplish things to feel valuable and worthy? 

Sabbatical step #3: Explore

You need the down time, but as your nervous system starts to recover you should aim to strike a balance between outward exploration and internal reflection. You don’t want to get stuck in a rut, ruminating or doomscrolling. Healing requires movement and new experiences. The key is to be gentle in your pursuits by listening to your body and observing how things feel. 

There’s a lot you can explore. Do any of the below ideas spark excitement for you? (To the doers among you, this list is for inspiration…not an aspirational checklist.)

• Try to experience both solo and group activities—the latter to help you get out of your head. 
• Go for a long walk or plan a road trip. 
• Rediscover your forgotten hobbies. 
• Host a dinner party or two
• Teach yourself a new language through Duolingo or a local language group. 
• Join a board games club, learn to bake bread, or take a photography class. 
• While you're at it, reconnect with family or long-lost friends.

The goal is to spark creativity, excitement, and your sense of possibility in life. This is a time for play, so the more decadent or frivolous an activity feels, the better. Your inner child loves frivolity, so ignore your adult side tut-tutting it. If you only feel compelled to do the “hard stuff,” your real growth edge might be the fun things that bring you joy. (Editor’s note: Read The Artist’s Way to cultivate your sense of child-like wonder in the world.)

As your energy returns, slowly introduce things that push your comfort zone or feel a little scary. I joined Foster's writing class, where I've expanded my writing practice and found fellow wanderers. I took the Portfolio of Small Bets course that teaches people how to work for themselves by taming their uncertainty and reorienting their mind to the world of solopreneurship. 

If you feel lonely, find the others on sabbatical! There are a number of us online writing (like Michelle, Matt, Cécile, and Paul) about our sabbatical journeys. All flavors exist: some have done this for years, while others have returned to work or ventured into solopreneurship. 

Sabbatical step #4: Adventure

If the means are available to you, travel can be another way to expand your sense of possibility in the world. But I recommend approaching it from a different mindset than you do when you take vacations.

Avoid the urge to jam-pack your trips with a dizzying agenda of tourist attractions. Your goal on sabbatical is to expose yourself to new ideas and new ways of living, so opt for longer stays in fewer places so you can marinate in new cultures. 

Choose a mix of popular travel locations with cheaper ones to soothe your wallet:

• Balance an expensive month in Rome with one in Vietnam where you can rent a comfortable apartment for less than $1000 a month and eat filling meals for $2. 
• Seek towns flush with diverse topography like rushing waterfalls, curvy hills, and lush greens. Hello, Mexico City. 
• Abandon the frigid frost of Canada for a sunny escape in Valencia. 
• Or go rogue, and pitch your tent somewhere you get to milk your own cows. 

If you rent out your home and get creative, travel is one of the cheapest ways to take a sabbatical. There are many options for free room and board via volunteering (check out sites like Worldpackers). You can get TEFL certified to teach English abroad. If you're flexible on dates and destinations, you can even house sit for people who are on vacation.

Of course, it's easier to travel this way if you're single and untethered. But if you have a family, you can take them with you. A family gap year might sound like a pipe dream, but people (like Ben and Kate) have managed to make them work. In the latter case, three years of planning and $35,000 sustained her family for 18 months in Mexico. If you're planning to stay in one place, your kids can join a local school, learn the language and be fully immersed in a new culture. 

If you don’t have the runway for bigger journeys, try to incorporate travel in your home life. Take shorter day trips to nearby towns you’ve never seen. Mix in solo experiences with trips where friends meet you on the way.

Alternatively, kids can be homeschooled, tutored via classroom apps like Outschool and access libraries through digital subscriptions. It's best to do this at an age where the children haven't become very attached to their friends and classmates back home. In any case, this option is not for everyone, because of the cost or concerns about the quality of education, but it could be a viable option for you. 

Sabbatical step #5: Examine and course correct

At this point, the sabbatical shine has well and truly washed away and doubts may have arrived. You might yearn to go back to work—not necessarily for what it entailed, but for its stability and structure. So experiment with routines that you want to wake up for while keeping active hours for serendipity. I like to have at least four "free" active hours a day. I also plan a few non-negotiables into my life, like regular check-ins with myself. Every Friday at 11 a.m., I make coffee and ask myself what I miss about my old life, what I don't miss, and what has unearthed itself recently. 

If you have money anxiety, schedule financial reviews into your weeks. Be pessimistic in your planning and honest about what costs you must incur. Since you've cut off the umbilical cord of regular paychecks, you need to stay within your means.

I also recommend examining your media diet in this phase of sabbatical. (Check out this resource as a guide.) The stories we consume unconsciously shape our perspectives. Is your diet nutritious for your current journey? Maybe you feast on hustle-culture podcasts, or you drip-feed on political hot takes all day. Are these aligned with your current headspace? If you find harmful, visceral fat, be sure to cut it out. Consider reading more novels and watching more documentaries: wholler, fuller-fiber stuff that keeps you satiated longer and broadens your worldview.

Sabbatical step #6: Experiment with jobs

You now have the flexibility and time to probe alternative approaches to work, so try making money in different ways. Depending on your background, here’s a few things you could explore: 

• freelance gigs 
• part-time startup consulting: copywriting, engineering, marketing for startups etc
• creating an online course
• podcasting or making YouTube videos
• writing: paid newsletter subscriptions, guest essays, copywriting, e-books etc

Sure, everyone and their dog has a podcast or a Substack newsletter, but the goal isn't superstardom—it's finding space for you to explore your creativity. 

If you're writing about your journey, consider charging for your newsletter or pitching ideas to outlets. There's a huge mindset shift that comes when you see your writing as valuable. The opportunities are vast: UX writing for startups, copywriting, ghostwriting, paid essays. You could write a book and sell zines.

The point isn't the dollars you'll make. If you were maximizing purely for money, you’d have stayed in the old job. The sabbatical is a time for learning from different experiences. You never know where those teachings might take you down the line. (Editor’s note: When you’re ready for it, Wishcraft is a great guide for figuring out new career goals and bringing them to life.)  

Sabbatical step #7: Stick the landing

At some point, you’ll have to decide where to land your plane. Your experiments and reflections will have informed the kind of work you enjoy, what sort of lifestyle you like, and how much money you actually need. A lot of us in tech think we need six figures to survive. We cling to our dollars like life vests that will keep us safe. But maybe the problem is boarding the Titanic in the first place.

After the sabbatical, you might decide to return to work, maybe even to the same company and role you left. But it's unlikely you'd regret having taken time off. Your perspective and values will be broadened, and you will now know your non-negotiables. It's possible you come back as a part-freelancer, part-time tech worker. Or you contract for some months, then go back to creative work during the winter. The options are endless. 

Try to release expectations about making a “perfect” choice. The sabbatical may have granted you more insight into your needs, but there will be a learning curve in how to apply that knowledge practically. Life will continue to deliver you forks in the road, and you’ll have future opportunities to course correct. 

Whatever you choose, you will have a breadth of life experiences you can weave into narratives to  make yourself attractive to future recruiters. Or you will have the courage to pursue another story of work that is authentically aligned with your interests. And that feeling pays dividends above and beyond a 401k. 

Tobi Ogunnaike is a writer and (recovering?) engineer on a sabbatical. In his Substack "Wandering the Grey,” he vulnerably unpacks stories on life, work, and play while collecting passport stamps.