"He was the co-founder of a growing startup with devoted users, a beloved product and millions of dollars in the bank when Stewart Butterfield made a curious decision.
He quit.
Mr. Butterfield spent a sleepless Sunday night in November 2012 and emailed his investors on Monday morning to return their money. He had calculated that his videogame company's chances of financial success were too slim to make it worth his time or theirs and he refused to waste another minute of it.
His search for the next big thing began almost immediately and didn't take very long: It led him back to the software his company had developed for its own internal communication. It was such an afterthought that it didn't even have a proper name. By that Wednesday, two days after he quit, Mr. Butterfield picked the shorthand for "Searchable Log of All Conversations and Knowledge." Today it's known as Slack.
The unlikely origin story of Slack, which Salesforce bought at the height of the pandemic for $27.7 billion, is one Annie Duke tells in her new book, "Quit," because she believes it exemplifies one of the most important, least understood lessons of business.
"Quitting on time will usually feel like quitting too early," writes Ms. Duke, a decision strategist and retired poker player.
Her book is about when, why and what it means to quit, which sounds to many people like the dirtiest of four-letter words. We have become so biased against quitting that we try not to even say it. We prefer jargon like "pivot" instead.
Meanwhile, unless you've quit modern life, you've probably heard about "quiet quitting," a phenomenon similar to slacking at work. But quitting should be loud and proud, Ms. Duke told me in an interview. For all the reasons people quit, she offers a new one: It can be a competitive advantage.
"Success does not lie in sticking to things," Ms. Duke writes. "It lies in picking the right thing to stick to and quitting the rest."
She makes the case for thinking like a quitter by arguing that we fundamentally misunderstand something about quitting: It's not losing.
"Contrary to popular belief, winners quit a lot," Ms. Duke writes. "That's how they win."
Of course, there's a reason most people aren't in the habit of quitting their jobs, and it's not because there is a stigma around quitting or because they don't want to. They can't.
But there are unexpected benefits to quitting, which Ms. Duke understands from personal experience. Five years into studying for a Ph.D. in cognitive psychology at the University of Pennsylvania, she took a leave from graduate school because of chronic health issues. She had to quit right before she could land a job or defend her dissertation.
Only because she was desperate for cash did she follow her brother into a line of work where she could apply her training in judgment to pay the bills: poker. Her education continued in casinos and smoky card rooms and earned her millions in prize money and, even more valuable, one World Series of Poker title bracelet.
It also provided fantastic material for writing this book: There are few people with greater expertise on quitting than exceptional poker players.
In fact, one of the biggest differences between most players and the world's best players is how often they quit. My favorite stat in Ms. Duke's book is what happens in Texas Hold 'em poker after professionals and amateurs peek at the starting cards they're dealt. The pros play fewer than 25% of their hands before other cards hit the table. The amateurs play more than 50%.
"Amateurs usually hold 'em," she writes. "Professionals usually fold 'em."
Folding isn't a sign of failure. It's a prerequisite for success.
Ms. Duke says we should all fold more. We spend too much time on too many pursuits that are no longer worthwhile to avoid feeling like we have failed. But in poker, that's a good way to go broke. Because elite players are obsessed with optimal quitting, it has been on Ms. Duke's mind for decades.
"Was I thinking about it as quitting?" she said. "No. Was I trying to get better at the game where this skill was incredibly important? Yes."
It happens to be incredibly important in business, too, which Mr. Butterfield knew long before many of the world's most efficient companies made their employees use a product called Slack.
"When you've invested in an idea that just isn't working, it's incredibly tempting to draw down to your last dollar looking for any way to save it," Mr. Butterfield said in an email to me.
He knew better. He was an experienced quitter by then. Mr. Butterfield was the co-founder of a company building a videogame in 2004 that was running out of money and couldn't secure funding after the dot-com bust. Mr. Butterfield was dealing with a case of food poisoning when he felt something other than nausea: inspiration. He decided to kill the game but save one of its tools for sharing photos. That became Flickr. It was sold to Yahoo in 2005 for $25 million.
His next brush with quitting would lead to a much bigger payday.
This time, his company was hard at work on a game called "Glitch," and a six-week marketing push to attract new users meant business had never been better. That's when Mr. Butterfield realized it still wasn't good enough. He felt the growth was unsustainable, and he wasn't going to let sunk costs drown him. "When he looked at the range of possible outcomes," Ms. Duke writes, "the probability was just too high that the game would end up being a money pit."
Everybody thought he was nuts for cutting his losses when he did. Mr. Butterfield thought he probably should have done it six weeks earlier.
"Once you face the facts and cut the cord," Mr. Butterfield added, "you can refocus that energy into efforts that have better odds of success."
Like a poker player, Mr. Butterfield was thinking in expected value, Ms. Duke says. He calculated that his expected value of quitting was higher than gritting his way through it.
"He could see the writing on the wall," she writes. "But when you are a good quitter, often you're the only one able to read it."
What he couldn't see until he quit was the idea that had been sitting right under his nose. After "Glitch" died, Slack was born. His backers could keep their investments and his employees would keep their jobs. Slack hit the market less than one year later, went public in 2019 and was acquired last year. Mr. Butterfield quitting was quite lucrative.
It wasn't the right decision because he invented Slack. It was the right decision, and then he invented Slack.
It's hard for the human mind to overcome hard-wired tendencies and navigate uncertainty. We know how sunk costs and loss aversion play tricks on our brains from pioneering research by Daniel Kahneman, Amos Tversky and Richard Thaler, while economists have shown that even wealthy investors are smarter about buying stocks than selling them. The experts with every financial incentive to get quitting right still get it wrong.
The best way to get better at quitting is practice, but that's not the most practical advice. Ms. Duke recommends a "quitting coach," or someone you trust to tell you the truth, especially when you don't want to hear it.
My second-favorite fact in her book: Mr. Kahneman considers his quitting coach to be Mr. Thaler -- a fellow Nobel Prize winner.
Ms. Duke can relate to the difficulties of quitting. She says she was unhappy playing poker as far back as 2006 but didn't stop until 2012. Mr. Butterfield went six weeks too long. Ms. Duke took six extra years. "I should've gotten to that decision a lot earlier," she told me.
Now she's doing something else later than she anticipated. More than 30 years after leaving academia, Ms. Duke recently went back to school to finish her degree in cognitive psychology. As it turns out, she's almost done with that dissertation." [1]
1. EXCHANGE --- Science of Success: Business Lessons From the World's Best Quitters --- A former professional poker player argues that everybody should know when to fold 'em
Cohen, Ben.
Wall Street Journal, Eastern edition; New York, N.Y. [New York, N.Y]. 01 Oct 2022: B.1.
