Ed Ryan, former GC of Marriott, before and after retirement. Courtesy photos

Jetting along in high-powered positions, top in-house lawyers can make the mistake of failing to prepare for the day when their landing gear drops for the last time. But what happens after that final flight? What is it like when the phone goes silent and the constant flow of emails slows to a trickle?

“It almost feels like it's a plane that has hit the runway and the thrusters are on and you come to a complete stop on that front of your life. Everything just stops,” said Ed Ryan, who retired last year as general counsel and executive vice president of Marriott International Inc.  “When you leave a corporation, the door shuts pretty quickly behind you. Everything pretty much goes away. A lot of people are surprised by it.”

Retirement shock is due, at least in part, to a cultural tendency among GCs to ignore the Exit sign in the legal department as if it were a speck hovering far off on the horizon, more easily ignored than confronted, according to Ryan.

“People treat it like they don't want to talk about it, like it doesn't happen,” he said. “If you're not thinking about this, you should be.”

Former in-house leaders have certainly struggled to navigate through retirement. But in the process, they've also found some fulfilling—and in some cases very creative—ways to spend their time and even give back.

'No longer part of the money train'

Ryan, who spent 21 years in-house at Marriott, said that GCs who are standing on the precipice of retirement should prepare for their “work tribe” to essentially vanish. “You'll still have friends from work,” he said. “But that social circle, it's not around you anymore. And the people who are working, they're busy and you're not part of that.”

Marla Persky, who retired in 2013 as senior VP, GC and corporate secretary for pharmaceutical company Boehringer Ingelheim, said she knew it was time to stop when she realized she “no longer had the fire in the belly.” She was 58.

Other GCs lose their drive without knowing it and one day they get left behind as the company keeps flying forward—a fate that Persky was keen to sidestep: “I never wanted to be one of those people,” she said. “I was very lucky. I got to leave at my own time on my own terms.”

Perksy left, but she didn't slow down. She now works as a senior adviser at the consulting and recruitment firm BarkerGilmore and is CEO and president of WOMN LLC, which she co-founded in 2014 with the aim of helping women lawyers advance into executive roles and join the C-suite. The company offers mentorship and consulting services.

She said one piece of advice she'd give to retiring GCs who plan to go into business is to not “naively assume” that the outside law firms they'd worked with will morph into clients for their next venture. She'd thought that the “firms to which I'd given millions and millions of dollars of business during my career as a general counsel would reciprocate and hire me to help their women partners succeed.”

“But those firms that I gave the most business to didn't really have any use for me after I was no longer part of the money train,” she said.

Like many retired GCs, Persky also serves on nonprofit and for-profit boards. And she discovered a way to combine her love of food, travel and business by becoming the founder and CEO of Epicurean Travel, which puts together food-centric vacations for small groups seeking to “be immersed in the historical, cultural distinctiveness, and culinary delights of locations around the world.”

'I wasn't ready for retirement'

Having a “mosaic” of interests to pursue post retirement is key, said Ben Heineman, who spent 16 years as General Electric's senior VP and GC before he retired in 2005. Now, he teaches, writes and serves on several nonprofit boards.

“To me the biggest thing was freedom,” Heineman said. “I've been involved in big government, big law and big business for my whole career and I very much did not want to have clients calling me, CEOs calling me, meetings to go to. I wanted to be free.”

Freedom for Mike Dillon, who retired in July from his position as Adobe's top lawyer, the fourth GC post he'd held, meant baking sourdough bread, a lot of it—he said he made two loaves a day for the first three weeks after he left Adobe. Then Dillon turned to another passion: cycling. He'd already written a book about riding his bike across the country. Seeking a new adventure, he and his youngest son, a recent college grad, set off Aug. 8 to ride gravel bikes along a 2,768 mile trail that follows the Continental Divide between Canada and New Mexico.

Dillon also was part of a team behind a documentary film about climate change and the decline of sea ice.

“Just enjoy life. You really need to have a demarcation, a way of decompressing from decades in corporate culture,” he advised. At the same time, he cautioned, “Before you make that decision [to retire] put together a list of everything in the world you'd like to do so you're not just watching daytime TV and eating too much.”

Michael Callahan, who left his role at LinkedIn earlier this year, agreed. The former GC, who now runs Stanford Law School's Rock Center for Corporate Governance, said GCs who are considering retirement or a career change should “take the time and be intentional about the work” they want to do and talk with people who are doing that work.

“I wasn't ready for retirement,” said Callahan. The 50-year-old had been a GC for about 15 years, first at Yahoo and then at Auction.com, now Ten-X.com, before joining LinkedIn about four years ago. “I certainly thought about the transition for some time and felt like throwing myself into a new challenge, which has been rewarding.”

'Certain amount of impostor syndrome' 

For some GCs, including Mark LeHocky, who served as the head lawyer for Ross Stores, Inc. and Dreyer's Grand Ice Cream, Inc., walking away from the legal department was relatively easy. LeHocky had been doing pro bono mediation work on the side for years before he retired and became a full-time mediator. He's also teaching at UC Berkeley's Haas School of Business.

“It was seamless,” LeHocky said of leaving the GC life.

But he might be an exception. Jay Mitchell, the former chief corporate counsel at Levi Strauss & Co. and now a professor at Stanford Law School, said he was both “thrilled and terrified” when he left the in-house world. And he described the first couple of years as being “pretty rough.”

“There was a certain amount of impostor syndrome,” he said of entering academia. But he added, “In many ways, people who work in-house, and particularly general counsel, bring a lot of value to teaching inside a law school. You've seen things from a broader perspective than one gets at a law firm.”

While Ryan, the retired Marriott GC, has seen colleagues struggle in retirement, he said he's not had much difficulty adjusting.

“It's daunting if you define yourself by what you're doing with your work or your title,” Ryan said. “I was fortunate because I never really defined myself that way. But I think there's a natural tendency to do that.”

Like Dillon, the ex-Adobe GC, Ryan is a longtime cyclist. He said he'd been biking “off and on” while he was a GC—but in retirement, he was able to go all in. He recently spent a week riding in South Africa. Before that he was cycling in Spain. And now he's planning to bike from Pittsburgh to Washington, D.C.

“The decision you've got to make is, 'Am I really going to retire?'” he said. “Make that decision and don't go half-ass on it.”