In the decisive game of the National League Championship Series, I watched the Chicago Cubs fight for their first World Series berth since 1945 from a neighborhood bar on Chicago's northwest side. For 20 years, I'd endured mediocre Cubs teams and occasional contenders that crumbled late in the season. But this squad felt different—genuinely good together.
Late in the game, a Los Angeles Dodgers batter grounded out to first. First baseman Anthony Rizzo called for the ball, arms waving per Little League protocol. Then, Javy Báez, the flashy second baseman, drifted over, positioning himself right in front of Rizzo until their gloves nearly collided—a potential disaster. Báez calmly snagged the out, and as he jogged back to second, he and Rizzo shared a laugh. It was a season-long inside joke, unfolding in one of the highest-pressure games in Cubs history.
"That's why they'll win this game and reach the World Series," my local friend said, who'd followed the team all year. "Even with stakes this high, they're just having fun." He teared up when the Cubs clinched victory an hour later and wept joyfully in the shower the next morning, remembering they'd made it.
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Wouldn't you want to run a company like that? Over a century of futility transformed into peak performance, unbreakable camaraderie, and World Series glory—leaving fans (your customers?) more devoted than ever.
Related: 5 Ways to Make Your Business Better Than the Competition
Sports-business parallels can be simplistic (plenty of workplace clichés originated in ballparks). But the Cubs' cultural turnaround merits study. Since hiring Theo Epstein as president of baseball operations in 2011, they've rebuilt around elite young talent. The masterstroke: hiring Joe Maddon as manager in 2014. The plumber's son had taken the Tampa Bay Rays to the World Series and brought a perfect vibe to a franchise scarred by losing.
Maddon rolled up his sleeves daily, snacks in hand, fostering a cool clubhouse. After the Cubs' surprising 2015 season, he brought zoo animals—a flamingo, penguin, sloth, and baby snow leopard—to pregame. In 2016, his "Try not to suck" T-shirt (advice to Báez) became a team mantra.
Sportswriter Jonah Keri, author of books on baseball and hockey, groups Maddon with fun-fostering coaches who gain competitive edges. Sports hiring now favors laid-back leaders: The NBA's Golden State Warriors ditched solid Mark Jackson for easygoing Steve Kerr in 2014, winning their first title since 1975 and an NBA-record season. Kerr relaxed his team by screening assistant Luke Walton's Young and the Restless cameo before practice.
"There's bias against smiling," Keri told me. "But you can stay positive, hardworking, and goal-oriented without grinding away."
Even the NFL's "No Fun League" crowned upbeat Pete Carroll of the Seattle Seahawks. After early Patriots flak for hooping with players, he built winners patiently. "Discipline" often tags praise for such coaches, as if fun precludes structure. Yet it lets insecure managers hide behind gruffness.
"Sometimes staff need guidance—you can't be everyone's friend," Keri notes. "Flip the default from negative to positive."
Related: It Takes a Positive Attitude to Achieve Positive Results
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Michel Buffet, Ph.D., a London-based YSC consultant with 18 years assessing Fortune 500 leaders and teaching at Columbia's Teachers College, faced this scaling a fun-focused startup. "We hit a wall," he says. "Growth demanded infrastructure."
In business (unlike sports' ready structures), balance is key. Profile hires for fit: sociability, adaptability, curiosity, diplomacy, stress responses—and hedonism, which meshes with ambition.
"Work's more than tasks or products—it's community," Buffet says. As an openly gay leader, YSC's inclusivity thrilled him: three gay men in a small firm.
Inclusivity unlocks knowledge-sharing, vital as leaders rely more on intuition in big firms. Build diverse-yet-cohesive cultures: pharmaceuticals shine via mission; Google and Facebook excel; banks struggle post-scandals.
Fun demands investment. At one firm, owners resisted kitchen snacks. Visiting Google, I learned: snacks cost under $2 but yield 40 extra work minutes (at >$3/hour employee rates). Sharing this math got us snacks—a win-win.
Related: 8 Principles of a Good Company Culture – Does Yours Have Them?
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Profit and joy align: pretzels boost retention; hoops with bosses win Super Bowls. Pittsburgh's Mike Tomlin and San Antonio's Gregg Popovich prove quieter fun-builders succeed—Popovich dotes privately on players.
Culture evolves as generations shift, Keri says. Millennials will normalize progress.
Build fun now for stronger business and joy. The Cubs won it all. In this era, anything's possible.
Related: You Can Do Anything
This article originally appeared in the February 2017 issue of SUCCESS magazine.
