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 We can easily fall prey to outdated stories about ourselves or coping mechanisms that keep us stuck: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.