Can Don Draper Pivot? Lessons From Second-Chance CEOs Howard Schultz, Steve Jobs, And Mickey Drexler

Draper’s dark past and debaucherous present finally caught up with him on Sunday’s season finale and he was shown the door. But if he follows the lead of these three business legends, then please *do* call it a comeback.

Can Don Draper Pivot? Lessons From Second-Chance CEOs Howard Schultz, Steve Jobs, And Mickey Drexler

We’ve watched him show up intoxicated (from liquor or sex, or both), yet seamlessly spin a captivating pitch for anything from cigarettes and baked beans to a slide carousel and a Chevy. But as Mad Men’s sixth season drew to a close, Don Draper’s pitching prowess took a sharp detour into a dark night of the soul–at the conference table with potential new client Hershey’s.


Raw and emotional, he revealed his roots and sucked all the air out of that conference room. It was a tipping point for the partners of SC & P, who’d had enough of his lateness, daytime disappearances, cutting remarks, and general imperiousness. They called a meeting–for which he showed up on time–and asked him to “take a leave of absence.” Draper’s replacement was waiting in the wings, er, elevator, and asks pointedly: “Going down?” apropos of the a**hole boss finally getting his comeuppance.

Don Draper’s character joins a group of top dogs who were asked to leave the executive suite. Some CEOs were undoubtedly insufferable jerks, others not able to stem the tide of losses (hello Andrew Mason), another maneuvered himself into bizarre circumstances and legal scuffles. Others have boomeranged to success.

There are lessons for Draper in these stories of resurrection–and for all of us.

Howard Schultz, CEO of Starbucks
Like Draper, Schultz sprouted from humble stock (sans the whorehouse). The difference is Schultz’s candor. He’s been quick to tell the tale of growing up in a Brooklyn housing project and supported by a father who worked odd jobs, and Schultz was first in his family to attend college. He worked his way from Starbucks’ sales and marketing to CEO in six years and held the position until he resigned in 2000.

But he couldn’t stay away. In 2008, when Starbucks was faltering due to unwieldy expansion, Schultz took the helm again. In an interview with Success magazine he said, “This has been my life’s work, as opposed to a job. I didn’t come back to save the company–I hate that description–I came back to rekindle the emotion that built it.”


Starbucks landed on our list of Most Innovative Companies in 2012. It’s there because Schultz sees more than a market for new Starbucks goodies, and he contends it’s all part of a mission. “Profit as a singular goal is a fairly shallow aspiration, and it’s not enduring,” he says. “I’ve always said that you can’t create long-term value for the shareholder unless you create long-term value for the employees and the communities you serve.”

And the billionaire boss puts his money where his mouth is. During that interview, our writer observed that he wiped his own spill, took his own empty cup to the counter, and grabbed someone else’s cup as well.

Lesson for the Draper in all of us: Adjust this attitude from season four: “We’re gonna sit at our desks typing while the walls fall down around us. Because we’re the least important, most important thing there is.” Be more respectful of those who work with and for you instead of demanding they simply worship your ideas. And get your own damn coffee.

Steve Jobs, founder, chairman and CEO of Apple
In death, this lauded visionary has joined the upper echelons of legendary leaders in history. In life, though, Jobs and the company he founded, have been alternately loved and loathed by a cadre of coworkers, consumers, and not-so-casual observers.

Like former fur salesman Don Draper, Jobs talked his way into a position at Atari, even though he had no experience in electronics. Like Draper, Jobs was a restless seeker who eventually grew to be passionate about his ideas–a fact distilled into a most inspiring commencement address.


But all the passion in the world couldn’t save Jobs when he clashed with Apple CEO John Sculley, who was brought in to boost sales and establish order out of Jobs’s creative chaos. Twelve years and two startups later, Jobs was reinstalled and the rest is history–starting from when he pulled Jonathan Ive from the depths of design doldrums to create the iMac.

Jobs may not have been able to code or engineer a product’s design from the drafting table. Yet his ability to captivate any audience by introducing them to functional design was what sealed his greatness.

Lesson for the Draper in all of us: Go back to an idea from season two: “You are the product. You feeling something. That’s what sells. Not them. Not sex. They can’t do what we do, and they hate us for it.” The ability to tap the thrill of holding innovation in your hand is what makes any endeavor great.

Mickey Drexler, CEO of J.Crew
“Merchant prince” Millard (Mickey) Drexler has turned around not one, but three businesses including an early revival of Ann Taylor. After a 19-year stint at the Gap, where he turned selling jeans, T-shirts, and khakis into the height of cool, Drexler got a well-publicized pink slip. Plenty of ink was spilled on his outrage and he’s made no secret of his schadenfreude-laced feelings for his former employer.

For his third act, he landed the top spot at J.Crew and took the preppy retailer from publicly traded growth to an ever-more burgeoning retail empire one micromanaged move at a time. To ensure this strategic success, Drexler leans heavily on the tastemaking sensibilities of executive creative director and president Jenna Lyons, who’s helped elevate the retailer’s threads to cult status.


Drexler’s self-deprecating humor seeps into his advice for CEOs such as current Apple chief Tim Cook. “The best job to have: Take over a company that’s doing poorly,” Drexler said. “Never take over a company that’s doing great. You know, I love Tim Cook, but I wouldn’t want his job!”

Lesson for the Draper in all of us: Don’t bother squawking about what’s been lost. Reinvent the wheel–and yourself–someplace else.

[Photos courtesy of AMC | Jamie Trueblood]

About the author

Lydia Dishman is a reporter writing about the intersection of tech, leadership, and innovation. She is a regular contributor to Fast Company and has written for CBS Moneywatch, Fortune, The Guardian, Popular Science, and the New York Times, among others.