#243 | How To Take A Sabbatical With DJ DiDonna

Have you ever come back from vacation and thought, “Well…that was nice. I’m still exhausted”? Same. There’s a big difference between getting away from your inbox for a week and actually stepping away from work long enough to reset. That’s exactly what got me thinking during my conversation with sabbatical researcher and Harvard Business School lecturer DJ DiDonna. His take? Sometimes what we really need isn’t another long weekend. We need space. Real, extended, intentional space to rest, think, and figure out what we actually want.

A Sabbatical Isn’t Just a Really Long Vacation

So what makes something a sabbatical instead of, well, a very enthusiastic vacation? DJ defines it as extended, intentional leave from your job, ideally measured in months, not days or weeks. And that timing matters. In his research, many people said it took six to eight weeks before they really started feeling like themselves again. Six to eight weeks! A sabbatical can happen at all kinds of moments, too. Maybe you’ve left a job and don’t want to immediately jump into the next one. Maybe you’ve sold a business, gone through a major life change, or simply spent years working without enough actual rest. There’s no one “right” time to do it. The common thread is creating enough distance from your normal routine to actually reset.

What If You’re Doing Fine…But You’re Not?

One of the phrases DJ uses that really stuck with me is “functional workaholism.” It’s the idea that you can look completely fine from the outside. Productive, successful, reliable, getting everything done, while your relationship with work is quietly becoming unhealthy. And that’s what makes it so tricky. There isn’t necessarily some giant crash that tells you it’s time to stop. You’re still answering emails, you’re still meeting deadlines, you’re still showing up. Meanwhile, your body might have some thoughts of its own. DJ talked about people in his research experiencing things like sleep problems, stomach ulcers, trigger finger, and eczema while still performing well at work. Sometimes you don’t realize how much of your identity has gotten wrapped up in work until you actually step away from it. And that distance can give you something we don’t always have when we’re in the middle of the daily grind: perspective.

How Do I Actually Take A Sabbatical?

This is probably where most of us start getting nervous. A few months away sounds lovely in theory…but what about money? Your job, your responsibilities, your health insurance? The fact that your inbox is filling up while you’re gone? DJ’s advice is to start planning before you desperately need the break. He suggests picking a date in the future and working backward. Take a look at your spending, your housing situation, your insurance, and what you could realistically save. Maybe you downsize, maybe you sublet your place, maybe you change locations for a while. A sabbatical doesn’t have to look like an expensive vacation. And if you’re employed, DJ recommends starting the conversation with your boss early. Not with, “Surprise! I’ll be gone for three months!” but with something more like, “In a few years, I’d like to take two months off. How could we make that work for me and the team?” You don’t have to have every detail figured out. You just have to be willing to start the conversation.

Here’s the part I found especially interesting: a sabbatical doesn’t necessarily end with a dramatic career change. DJ shared the story of a lifelong lawyer who took time off to try writing a novel. After 90 days, he shredded the manuscript. And you know what? He realized he still wanted to be a lawyer, he liked the community and liked the intellectual challenge. He liked his work. The sabbatical hadn’t “failed.” Quite the opposite. It had given him the clarity to know what he wanted. Other people in DJ’s research talked about reconnecting with friends and family, making room for creative interests, recovering physically, or simply feeling human again. And honestly, that might be the most compelling part of the whole idea. You don’t have to come back from a sabbatical with a five-year plan, a new career, and a completely redesigned life. Maybe you just come back knowing yourself, and your life, a little better. And that sounds like a pretty good use of a few months to me.

Timestamps:

05:42 Defining sabbaticals versus parental leave

12:20 Re-entering the workforce after a sabbatical

15:53 Recognizing burnout and functional workaholism

20:14 Financial planning and costs of taking a sabbatical

23:34 Talking to your employer about time off

27:20 Resisting the productivity trap during planning

34:05 The emotional and human benefits of taking time off

40:56 Practical steps to start planning your sabbatical

48:41 Homework: Planting the seed for your future sabbatical

Links:

DJ DiDonna’s Article: The Urgent Case for Sabbaticals for All

LinkedIn Course: Why a Break from Work Might Be the Best Career Move You’ll Ever Make

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