17 Ways Extremely Busy Entrepreneurs Wind Down

Despite living and breathing their businesses, these smart small-business owners have all learned how to step back and recharge.
August 19, 2014

We all know how energizing it can be to run your own business. In fact, it’s not uncommon to hear entrepreneurs—who often live and breathe their businesses—say something like, “I’ve never worked a day in my life.”

But growing a business can also be mercilessly stressful—long hours, sleepless nights, little time to spend with friends and family. Despite that, just one in three of the 1,500 small-business owners surveyed in the recently released Office Depot's Small Business Index plan to make time for a vacation this summer. 

One of the big reasons it can be so difficult for entrepreneurs to take an actual vacation is that they feel the need to be connected to their business in a way that prevents them from, say, jetting off to a fabulous resort or traveling the world. At the same time, the most astute entrepreneurs realize they can’t work all the time. At the very least, finding ways to make downtime is a sure way to keep your productivity up and your creative juices flowing. 

To find out how entrepreneurs create downtime for themselves, I recently conducted an informal poll and heard back from some 300 entrepreneurs about the creative ways they make room for decompression and downtime despite their hectic schedules. 

While I heard from plenty of business owners who enjoy spending time with friends and family, as well as quite a few dog lovers and plenty of folks who enjoy yoga and meditation, what follows are some highlights of the more unusual and creative ways my survey participants said they like to take a break—along with their own photos and videos that show how much they truly enjoyed their downtime.

Enjoy this look at the diverse ways entrepreneurs wind down.

Restoring Vintage Cars

Relaxation is found in restoration for Rick and Ryan McGuire, a father-and-son team from Visalia, California, who own seven Valvoline Instant Oil Change franchises. Not only are the stores spread out around northern and southern California, they even have one franchise in Arizona. Before they teamed up in business, they bonded in the family driveway over a beat-up Mustang. Rick and Ryan have restored at least six classic and muscle cars over the years. You'd think that once they closed up shop for the night, they'd want to get away from all things car-related, yet they find fixing up old cars and restoring them to their former glory to be a stress-relieving hobby. 

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Rick McGuire (left), with a restored black Shelby GT 350, and Ryan McGuire with a 1968 California Special. Photo: MOO, Inc.

Rocking Out

Jon Rustad owns an animation studio, while his entrepreneurial wife, Julie, created a product line to teach children about wildlife in the desert. Julie says they de-stress by rocking out in their family band, The Nap Skippers, playing at home and at fundraisers. “We're busy, busy people with lots of ideas, but we understand the need to recharge our batteries, too,” Julie says. “How can you not smile and have fun playing music you love and watching the crowd dance?”

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The Nap Skippers: Syver Ray, Jon and Julie Rustand. Photo: SpryTime Photography

Cooking Up a Storm

Matt Michel, CEO of Service Nation, a contractor service organization, found out later in life that he was pretty good at cooking. His salsa recipes have even won first place in the Texas State Fair on four separate occasions—and he’s won other awards for his picante and barbeque sauces as well as his chili. When things heat up at work, spending some time over a hot stove helps the busy entrepreneur cool down.

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Matt Michel with his daughter Mackenzie, celebrating their four-time Chili Cook-off wins. Photo: Matt Michel

Sailing the High Seas

Benjamin Dyett, founder of Grind, a collaborative community and co-working space with two locations in New York City and one in Chicago, makes a point to unwind by getting out on his boat, either by relaxing or working the ropes during regattas. "I love the sea,” Dyett says. “Its vastness and unending movement is frightening yet familiar. The open water represents relentless beauty and inestimable power that dwarfs land-based contrivances of our own vanity. Sailing—especially competitively—allows me to clear my head and think only of the boat and our movements together in harnessing wind, wave and current.”

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Benjamin Dyett (center) finds time to unwind out on the water by competing in the New York Yacht Club Classic Boat Regatta in Newport. Photo: Benjamin Dyett.

Practicing Kung Fu

To wind down from her career as a busy author, educational consultant and professional speaker, Susan Fitzell says one of the ways she keeps her focus is by practicing kung fu. “If I'm not focused while swinging around a broadsword, it could be dangerous,” Fitzell says. Here's a video of Kitzell in action.

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Susan Fitzell working on her focus. Photo: Sam Wilson.

Lacing Up the Skates

Dahna Goldstein, founder of PhilanTech, an online grants management system provider, says the best stress relief she’s found as a busy business owner is to play hockey. “It's great exercise, engages my competitive spirit and gets me away from my computer and phone,” Goldstein says. “When running a business, it can be hard to get out of your head, to think about anything that isn't the business. When I'm on the ice, if I think about the business, I get hit, which is a pretty good incentive to keep my mind on the game.”

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Dahna Goldstein racing up the ice during a hockey game. Photo: Sarah Altschuller

Taking a Cat Nap

Brian Halligan, CEO of marketing and sales platform HubSpot, is a huge proponent of naps as a way to recharge during the day. He believes in them so much, he made sure there's a nap room in the company’s Cambridge, Massachusetts, office. “We ask a lot of our HubSpot employees,” Halligan says. “We're a fast-growing software company, so everyone from our engineers to our sales reps and support team work really hard to grow the business. Providing a nap room onsite means they can recharge in the middle of a long day, recover from a tough week of travel or just have a quiet place to think in the midst of a big project. Naps make our employees happier and more productive, which is a win for them and for the company long term.”

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The HubSpot nap room appropriately called the “Van Winkle” room. Photo: Matt Plays, HubSpot

Taking a Hike

When Ken Rutkowski, a venture capitalist, founder of METal International and host of Business Rockstars Radio, wants some downtime, he invites between 50 and 80 of his connections to join him on two-hour hikes in different locations across Los Angeles County. “The groups tend to function as mini TED events because of the creative people that join us,” Rutkowski says. “Someone is always tossing us ‘mind grenades’ during the hike. In fact, we've had people fly over to join us after CES and TED because it's a great way to unwind in a non-stressful environment and enjoy the amazing scenery Los Angeles has to offer.” Rutkowski says his outings began in 2013 when he started the group to help his friend, Nolan Bushnell of Atari fame, get back into shape. 

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Ken Rutkowski and friends on a recent trek through the hills of Los Angeles. Photo: Ken Rutkowski

Getting Dance Fever

John Turner is the founder and CEO of UsersThink, which provides usability feedback on websites. The best way he knows to unwind? By dancing. “I try to carve out time later in the evening when there's a dance event nearby, go for at least an hour, then go home and get back to work,” Turner says. “The refresh helps me come up with ways to solve problems, the creativity reenergizes me to work harder, and it serves as a cheap workout.” Turner says his dancing has even led him to travel to compete, such as the time he won a free trip to New York City to compete in a national event seen here (he’s credited as Sweatband John). 

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John Turner performing as part of a music video for a Big Freedia concert. Photo: John Turner

Making Time for Crafts

Jessica Greenwalt is both the founder of graphic design and Web development firm Pixelkeet and co-founder of crowdsourcing medical solutions provider CrowdMed, which explains why Inc. magazine named her one of its "10 Women to Watch in Tech." Since she’s working on multiple startups, she says she has very little free time, but she makes the most of the downtime she has by holding craft parties with her friends, creating everything from paper crafts and costumes to public yarn bombing projects. “The most stress relieving craft project for me is making sets of greeting cards,” Greenwalt says, which you can view here

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Jessica Greenwalt crafting with her parakeet Lord Jello Worthington II ("Jello" for short). Photo: Hugh Edmundson

Hitting the Open Road

When Sam Chandler, founder and CEO of Nitro, a leading provider of document productivity and collaboration solutions, wants to unwind, he likes to build and ride vintage motorcycles, which he also collects. “I’ve ridden motorcycles all my life,” Chandler says. “I own newer and vintage street bikes, and a dirt bike, and whether it’s an hour in the saddle or 10 hours, I love it. A few years ago, I rode all the way across Argentina, off-road, from the Atlantic Ocean to the Chilean border in the Andes, through Patagonia. It was epic. And more important, there was very little cell phone coverage on the whole trip! On anything with two wheels, you have to stay focused, especially if you’re moving quickly, so it’s almost impossible to think about anything else. What better way to clear the head?”

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Sam Chandler stops to snap a shot after a 10-hour day on his bike. Photo: @nitro_sam

Running Up a Mountain

Russell Benaroya, who co-founded health care and fitness startup EveryMove, is an avid trail runner and often escapes to Mt. Si in the Washington Cascades to clear his mind. “I'm a trail guy,” Benaroya says. “It's where I find my peace, where I feel accomplished, and where I calm myself down amidst the intensity of building EveryMove. I always come off the mountain more resolved and committed to make a difference and confident that we'll make it happen.” 

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Russell Benaroya taking a selfie with Washington’s Mt. Si in the background. Photo: Russell Benaroya 

Fixing Up Furniture

“When I was in my teens, I loved refurnishing old furniture,” says Josephine Geraci, founder and president of My Mom Knows Best Inc., which makes gLovies, a line of disposable gloves for kids. “I would sand and sand and sand the wood. Then my favorite part—the varnishing—took place. Ahhh, the sense of accomplishment. I decided recently that I'd go back to the joys of my teenage years and refinish my lawn furniture. I know it's nothing big, but I felt such a sense of calmness, peace and accomplishment as I sprayed the chair. I realize I may be different, but fixing old things and making them new again is a way I like to unwind after a long, busy week.”

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Josephine Geraci showing off her refurbished patio furniture. Photo: Nicoletta Geraci

Working Out

Husband-and-wife team Paul and Stephanie Jarrett are the co-founders of Bulu Box, a discovery e-commerce platform for health, wellness and weight-loss products. The Jarretts say that being married to your co-founder makes it even harder to turn that “work brain” off at the end of the day or on the weekends. One outlet they turn to is CrossFit training, which the Jarretts find is a great fit for pounding out that stressful energy and directing their mental focus away from work.

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Paul and Stephanie Jarrett working out at their local CrossFit gym. Photo: Stephanie Jarrett.

Feeding the Ducks

Jared Lerner, president of Just Live, which produces performance and lifestyle apparel, believes it's essential to wind down after work and clear your mind. His trick? Leaving his smartphone indoors and taking his kids out to feed the ducks in the lake behind his home in Florida. “Getting back to nature and taking the time do something as simple as tossing bread for ducks," Lerner says, "is a terrific way to disconnect from work, stress and the constant buzz of technology.”

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Jared Lerner unwinding by feeding the ducks near his house. Photo: Just Live

Learning to Play Chess (and Walking a Dog)

S. Ming Ooi is the CEO of two Brooklyn-based startups, tapTrakMed and tapTrak, both of which are pioneering apps. Ooi says he winds down in two ways: First, by walking his dog, Louie, before his day gets started and then again at the end of the day. Ooi also recently took up chess. “It’s a good way to exercise the mind and learn the lessons of strategy and failure,” Ooi says. “I have chess lessons regularly, and it's humbling to have an 8-year-old kick your [butt]. It’s a good reminder of where we stand in the universe.”

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S. Ming Ooi at the chessboard with his dog, Louie. Photo: Kathy Chan

Throwing Out Bait

Courtney Hurst, co-founder of Metis Communications, is a native of Provincetown, Massachusetts, a small, seaside town that was built upon the fishing industry. Hurst comes from a long line of commercial fishermen dating back to her great-grandfathers, and she continues that tradition as a way to escape from her “day job.” On fishing trips—which depending on the season, the weather and the catch, can last from five to 12 hours—she catches lobsters, oysters and ground fish that she then sells to a local wholesaler. “Commercial fishing on the weekends with my husband is hard work,” Hurst says, “but the physical labor while being out on the water, looking back at the coastline of Provincetown, my favorite place in the world, helps me work out the stress from the week before. It’s satisfying. It’s soulful. It’s stress free.”

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Courtney Hurst working out her stress on the open water. Photo: Courtney Hurst

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