A Sabbatical Can Look Any Way You Want It To—if There’s Intention Behind Your Time Off, Says Modern Elder Academy Founder Chip Conley

Chip Conley is a big believer in investing in what he calls “time affluence”—escaping the boundary-less world we’ve created for however long we can take a break and revel in the spaciousness of some well-earned time off.

In Conley’s early days as the founder of Joi de Vivre Hospitality, a boutique hotel chain he founded in 1987 and was CEO of for nearly 24 years, he implemented “The Radical Sabbatical”: Every full-time salaried employee got to take four consecutive weeks off every three years. “That was the 1990s, and everyone told me people would take a month off and either not come back or return to work and yearn for that time off again,” says Conley. “But what actually happened is that people came back renewed, appreciative, and excited to stay on another three years so they could take another sabbatical.

“The reality is that the radical sabbatical inspired more intention in our employees. It led to renewal—and retention, too.”

Since then, Conley has remained a big fan of taking time off and infusing that time with intention, whether it’s setting better boundaries that help you achieve work-life balance or setting a higher goal of taking a chunk of time off.

“Sabbaticals can sound like such a radical idea,” says Conley. “Sometimes you have to start with the radical idea that you can take a Sabbath. A sabbatical may be what you work toward, and taking one day off a week may be the stepping stone to getting there.”

As The Sunday Paper team prepares to take the month of August off from publishing our weekly newsletter, we thought it would be an ideal time to talk to Conley about what, exactly, a sabbatical entails, how to plan on taking one, and why all of us can benefit from it.

A CONVERSATION WITH CHIP CONLEY

Tell us a bit more about why you believe it’s so important to take time off from work or life as you usually live it.

We’re all familiar with time poverty—the world of spinning plates and so many things happening. This was true even before we had smart phones and created a boundary-less world. People have always felt overwhelmed by all of the demands placed on them.

Now, as we’re living longer—we’ve added 30 years of longevity in the United States in the 20th century!—we’re spending more time in midlife. The cultural anthropologist Mary Catherine Bateson talks about the concept of creating a midlife atrium, and I think it’s beautiful. Imagine if you had a home and you added 30 percent to the home, she said. The way we tend to think of this 30 percent is like adding a few bedrooms to the backyard. But instead of doing that, what you’re really doing is creating a mid-life atrium. Right in the middle of your life, let’s say that’s age 50, what you want to do is create the space and air and light to reflect on how you want to live the rest of your life. A sabbatical can help you do that.

When you first implemented the concept of taking a sabbatical for your employees in the 90s, you called it radical. Taking a big chunk of time off is still considered radical! Why do you think this is?

Taking time off really should be the Un-radical sabbatical, shouldn’t it?

Why is it still radical? I think many organizations have built hamster wheels dedicated to the idea that people have a full calendar, and that a full-calendar ethos doesn’t allow for people to take creative breaks.

Yet if your effectiveness is a function of your ability to be creative, innovative, emotionally intelligent, and responsive rather than reactive, these are things a sabbatical can enhance. I believe sabbaticals can create better raw materials of your organization. But they do require some planning.

What’s your best advice on how to make the most of a sabbatical, no matter how long or what it looks like?

Do and be something you’d have a hard time doing or being over a weekend or during a weeklong vacation. Test your boundaries and do things you couldn’t do with that much time affluence.

For example, I’ve done silent retreats in the past, usually for a week or 10 days. It can be really hard to transition in and out of a retreat like that when life is full-on before and after the retreat. So that might be something I do during a sabbatical because it would give me bumpers on both sides.

Maybe you want to write your memoir or take a Spanish immersion course. Do the thing that wouldn’t be as well served if it was done while you’re living life as usual.

How can more of us take some time off with the intention of feeling renewed and recharged when we return to work or our everyday lives?

I think each one of us can start by asking, “How can I infuse more awe in my life?”

We have to make space for awe. Our lives are so congested that we often don’t notice the awe when it’s right in front of us.

I started a practice during Covid that I used to do three times a week and still do it at least once a week: I take three hours off, from about 2 p.m. to 5 p.m., and I do something I call “spying on the divine”. I go on a walk in nature with our dog, and I try to be as attentive to nature as our dog always is. I look for what nature has to teach me. For example, I might notice the interdependence of plants or their resilience. I might notice that amidst all the new growth on a palm tree there’s also a skirt of old leaves.

To spy on the divine is to see what’s in nature and what’s in my human nature, too.

What would you say to retired folks who might say, “Why take a sabbatical? Retirement is a sabbatical!”

Life is a run-on sentence without any punctuation. A sabbatical provides some punctuation. It helps you break out of your habitual ways of being and create a new kind of ritual that allows you to reimagine who you are and what you do. I think the time you need a sabbatical most is in retirement, when you might be falling into habits that don’t necessarily serve you—whether it’s watching too much TV or gossiping or playing Bingo.

Think of a sabbatical as an opportunity to try something new. After all, curiosity is the elixir of life! Openness to new experiences is correlated to living a longer, happier life.

Taking a sabbatical gives you an opportunity to stay open to new experiences, which means you can retire for a longer time. You can live a regenerative life. At the Modern Elder Academy, we call it “long life learning” not “lifelong learning”.

We want people to ask, “How can I live a life that’s as deep and meaningful as it is long?” That’s what life should be.

Chip Conley is the co-founder and CEO of Modern Elder Academy—the first-ever “midlife wisdom school” dedicated to guiding and supporting adults through periods of transition in life. Chip is also a New York Times bestselling author, the former CEO and founder of Joie de Vivre Hospitality, and the former Head of Hospitality and Strategy at Airbnb, where he served as a “modern elder,” offering wisdom to the company’s three founders. His book, Wisdom at Work: The Making of a Modern Elder forms the core of Modern Elder Academy's curriculum and is inspired by his experience at Airbnb.