The Key to Accomplishing More: Having Fun

UPDATED: May 22, 2023
PUBLISHED: January 24, 2017

For the deciding game of the National League Championship Series, I was in a neighborhood grill on Chicago’s northwest side, watching the Cubs vie for their first World Series berth since 1945. I’ve been suckered by plenty of mediocre Cubs baseball in the past 20 years, as well as by the occasional decent team—always, for one reason or another, or a dozen, doomed to fall short late in the season, never able to create the breaks that other teams caught. Yet the current group seemed different somehow, not least in the fact that they were just really good together.

Late in the game, a Los Angeles Dodgers batter popped up an easy out to first base. There, per protocol dating back at least to Little League, first baseman Anthony Rizzo called that he had it, churning his arms in the air as he tracked the ball, to wave off other fielders. Then, a strange thing: The deft second baseman Javy Baez drifted over… and over… and stood right in front of Rizzo, until their gloves were practically touching, a disaster unfolding. Baez calmly poached the out, and then as he jogged back to second, he and Rizzo shared a laugh. This ritual, it turns out, was a season-long inside joke of theirs, now playing out in one of the highest-pressure games the Cubs organization had encountered in some 70 years.


“This is why they’re going to win this game and go to the World Series. Because even with the stakes this high, they’re still just playing around.”


“This is why they’re going to win this game and go to the World Series,” a buddy of mine, a local who’d watched the team all year, said then. “Because even with the stakes this high, they’re still just playing around.”

This same friend of mine burst into tears when the Cubs completed the win an hour or so later, and later reported that when he woke the next day, he remembered the Cubs were going to the World Series, and joyously wept through his morning shower.


Sounds weird to ask, but: Wouldn’t you just love to run a business like the Cubs? Best performance in more than a century. Great camaraderie. World champs, holy cow. Shedding so much baggage along the way that their fans—clients?—are emotionally overwhelmed, and all the more in love with that C on their hats.

Related: 5 Ways to Make Your Business Better Than the Competition

Parallels between sports and business can be perilously simplistic. (How many clichés in your workplace, you must wonder sometimes, began in ballparks?) But it’s worth asking how a culture shifted so completely. The answer, I’d argue, is that the Cubs figured out how to have more fun at work. That, I’d also argue, is something you might as well try yourself.

The organization has been winning more since hiring Theo Epstein as its president of baseball operations in 2011. Most of Epstein’s great moves have been, in some fashion, tearing the roster down to the floorboards and rebuilding around fantastic young talent. Another masterstroke was, in 2014, hiring Joe Maddon as the team’s manager. Maddon, a plumber’s son, had recently guided a formerly moribund team, the Tampa Bay Rays, to the World Series. He also had a temperament well-suited to a franchise whose long-term memories were all about losing. He came to work each day with his sleeves rolled up and a wisecrack at the ready, making the Cubs’ clubhouse a chill, enjoyable place to be. Late in the Cubs’ surprising 2015 season, for instance, he invited an arkload of zoo animals to hang with his players before a game: In attendance were a flamingo, a penguin, a sloth, a baby snow leopard. In 2016 the most emblematic Cubs gear was a T-shirt bearing Maddon’s distinctive eyeglasses with some advice he offered to Baez when the second baseman came up from the minors: “Try not to suck.” It became an unlikely team mantra.

The Cubs’ success and their stay-loose clubhouse caught the attention of sportswriter Jonah Keri. He groups Maddon with other coaches who have fostered cultures of fun in their respective organizations. Keri believes this can create a competitive advantage for those teams. The trend in sports hiring, in fact, has swayed from authoritarians to the Maddon-types of the world. In the NBA, the Golden State Warriors in 2014 fired a very good coach in Mark Jackson and hired the easygoing Steve Kerr, who immediately led the Warriors, in consecutive years, to the team’s first NBA title since 1977 and the NBA’s record-best number of wins in a season. One of Kerr’s memorable moves, to keep his team relaxed, was to screen assistant coach Luke Walton’s board-stiff cameo on the soap opera The Young and the Restless for the players before a practice.

“There’s an institutional bias against people smiling,” Keri told me. “But you can be positive and still work hard and be driven and be goal-oriented and still keep your head down.”

Even the NFL, the No Fun League, has handed a championship trophy to relative gadfly Pete Carroll, the coach of the Seattle Seahawks. He’d been a dynamo coach at the college level, at the University of Southern California, and yet in his first tour as an NFL head coach in the ’90s he washed out with the New England Patriots, where his upbeat chill didn’t translate on a middling team. He took flak for seeming to screw around by playing pick-up basketball with his players in the stadium parking lot. “Did the Patriots play worse as a result?” Keri says. “No.” He didn’t immediately set Seattle afire; his first two years there were losing seasons. “But Carroll was very, very positive from the get-go,” Keri says, “and finally they got there.”

The Key to Accomplishing More: Having Fun

In Keri’s reporting, one word that kept coming up around Carroll and Kerr was “discipline.” Seemingly people felt compelled to mention it amid the praise for their playfulness, because even in sports, a culture literally predicated on games, the perception remains that only the most serious have a monopoly on structure, planning, and resolve—the basic elements of leadership. This may contain an element of truth. Yet it also makes irascibility and inaccessibility the refuge of insecure managers.

“If you’re running a staff, sometimes they need to at least be guided,” Keri acknowledges. A manager can’t be everyone’s friend all of the time. All he’s saying, though, is that hiring need not prize stormy personalities over sunny ones. “Flip the default,” he says, “from negative to positive.”

Related: It Takes a Positive Attitude to Achieve Positive Results


The question of how to build positivity into a growing company is one dear to Michel Buffet, Ph.D., of the London-based management consultancy YSC. He has worked in the field of leadership assessment and development for 18 years, consulting dozens of Fortune 500 companies and teaching at Teachers College, Columbia University. Some years back he found himself with colleagues trying to build a small company on the values they wanted to see in their workplace. Key among them: making a profit while remaining, well, fun. They found that approach took them only so far. “We hit a wall,” he says. “We had to grow up a bit. We had to face this notion that if we wanted to grow the business, we had to be more about management and building infrastructures.”

This is a point of departure from sports, in that the structures are largely going to be in place when any coach takes over a team. If you don’t run a sports team, you probably have to figure out the dance mid-tune. So how do you maintain profits along with your sense of high play?

If possible, start as you’re scaling up. When Buffet works with companies that are hiring, they begin by making a profile of a person who is likely to be successful in a given role. This step isn’t about credentials or experience; it’s about the rest of the person. How social are they? How adjustable? Are they inquisitive? Are they good at diplomacy? When they’re under stress, what behaviors do they exhibit?

And, shoot, do they like to have fun? A trait that Buffet measures for is, in fact, hedonism. And it’s not in conflict with ambition, commercial instincts or adjustability.


“Being part of an organization is more than just doing a task. It’s more than selling a product. It’s also about experience and who do you care about. What kind of community do you want to be a part of?”


“Being part of an organization is more than just doing a task,” Buffet says. “It’s more than selling a product. It’s also about experience and who do you care about and who do you want to hang out with on a daily basis. What kind of community do you want to be a part of?” For Buffet, an openly gay man who’d never worked in a company with other openly gay people, coming to YSC was a pleasant jolt. “Here were three openly gay men in a small company,” he says. “It was inclusive at every level.”

Inclusivity is a key. People who feel included in discussions will be more easily forthcoming with what they know. As leaders rise in a business, they still have to work from the best information they have, and then take some sort of action. But the larger the organization, the further leadership is from the ground-level work of the company, the greater the need for leaders to act on intuition. Having people at every level of an organization feel comfortable to offer their knowledge, without siloing it off or fracturing into factions, can only inform the decisions that you, the person in charge, have to make.

The aim becomes finding people who can cotton to the wider workplace culture while you build with a range of personality types, and then make everything work in concert as you expand. “You want an organization that has some diversity,” Buffet says, “but it’s a fine balance. You do want to have a center of gravity, enough people to define a culture.”

I asked Buffet which companies are exemplars these days for corporate culture. Some pharma companies come to mind, and expectedly so because they tend to be profitable and carry a sense of mission: healing people. Tech naturally has some standouts as well: “It sounds like a big cliché,” Buffet says, “but Google has been really good at that.” Facebook, too. “The banks have a very hard time,” he says. “Because their purpose has been so tainted in the last few years. What do they stand for?”

At the core of all of these sectors, though, is profitability. I’ve worked for companies where the idea of fun is supposedly baked into the company’s identity—yet ownership never makes clear exactly what it expects to give up to make the office a place where people look forward to spending time.

The Key to Accomplishing More: Having Fun

At one such company, we rank-and-file were having trouble getting the owners to provide the elemental perk of snacks in the kitchen. Around the same time, I happened to take a tour of a Google office, where the employee who led me and a couple of other people around took us through a small cantina and offered this factoid: On average, a snack costs Google less than $2 and results in an employee spending 40 more minutes at work. I do not know what the average Google employee earns, but I presume it’s higher than $3 per hour. This seemed like one of those win-wins where one side (the company) actually wins a lot more.

I mentioned this math to the owners. Sure enough, soon after, snacks routinely appeared in our kitchen.

Related: 8 Tenets of Good Company Culture—Does Yours Have Them?


A naked profit motive doesn’t conflict with workers enjoying their jobs any more than a wisecracking coach derails championships. A modest investment in Goldfish crackers and pretzels might in fact save a company tremendous amounts of money. And if you want to foster the sort of environment where people shoot parking lot hoops with their managers, you can still win a Super Bowl.

There’s hope for bosses who don’t have the charisma of a Pete Carroll. I asked Keri who in sports builds a less-obvious culture of workplace fun. He named the Pittsburgh Steelers’ Mike Tomlin—the youngest-ever Super Bowl-winning coach. And the San Antonio Spurs’ Gregg Popovich, a famously prickly interview subject and five-time NBA title winner. “His public persona is that he doesn’t suffer fools at all,” Keri says. “But he’s the biggest softie ever. He loves his players. I don’t mean he likes his players. I think he loves his players.”

Here’s how this plays out in sports—again, not always the clearest corollary to the workplace, given its general machismo, but often a laboratory for culture shifts. Keri was admitted to the Baseball Writers Association of America, which controls hall of fame voting. He’s one of the younger members, and he took his first opportunity to vote for a forgotten former Montreal Expos outfielder named Tim Raines, whose support was so low that he was about to fall off the hall of fame ballot. Raines wasn’t, in Keri’s words, an easy guy to peg as a hall-of-famer. But he was strong in some categories such as on-base percentage that, in part due to the Moneyball revolution, have come to hold greater sway in player evaluation and appreciation. Raines wasn’t voted in. A poll of younger baseball writers, though, showed much higher support for his worthiness—a sign to Keri that, as in so many realms, younger leaders may simply have to wait for the older generation to retire before they can reflect their values onto the system at large.

“As society goes forward and people in power change, we are getting more progressive in a lot of different ways,” Keri says. “We’re being less sexist, less racist, less hidebound. I feel more progressive now than I felt in my 20s. Millennials are going to be way less conservative than the 40-year-olds now, and way, way less conservative than the 40-year-olds of 40 years ago.”

The kids will inherit the culture they ultimately create. So it’s worth getting ahead of. For one, you stand to build a stronger company, if you handle it correctly, and ought to enjoy your life as you do. For another: The Cubs actually made it to the World Series, and then won the thing. Do not despair. It is, overall, a joyous time we live in, where apparently anything is possible.

Related: You Can Do Anything


This article originally appeared in the February 2017 issue of SUCCESS magazine.

Sam Eifling is an itinerant American reporter and editor who lives in Brooklyn, New York. His writing and documentary work has appeared in such outlets as the New Republic, Sports Illustrated, the Oxford American, Pacific Standard, Vice, the Associated Press, The New York Times, and The Tyee. His newspaper writing has won a Sigma Delta Chi from the Society of Professional Journalists and has been supported by a grant from the Fund for Investigative Journalism. A graduate of Northwestern University and the University of British Columbia, he enjoys beer and naps.