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 We can easily fall prey to outdated stories about ourselves or coping mechanisms that keep us stuck: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