7 hard truths about leaving the C-suite

Serving as a senior executive is a job, often a high-stress one at that. Leaving the C-suite should, therefore, come as a relief, shouldn’t it?

Speak with leaders who made the transition out, however, and you’ll hear something very different. For example, Kevin Trout, who owned and sold a multimillion-dollar medical equipment distributorship, says this about leaving the day-to-day: “It’s like quitting cold turkey.”

David Zerfoss, whose illustrious career included a long tenure as president of Husqvarna, says that “most CEOs probably have to detox after that role because it’s such an adrenaline rush.”

As hard as the job of a C-level executive may be, it turns out that the departure can be even harder. Here are some of the difficult issues recently retired executives and exiting leaders often confront.

1. You may feel isolated.

The first difference many executives notice when they don’t go into the office — the house is empty by comparison. For Kevin, there was a sense of loss. “I missed the people I worked with. I missed the people who were on my team,” he says.

The degree of isolation can come as a shock. Marty Stowe, who spent several years in the C-suite for a large HR and payroll services provider, explains that many executives “find out their entire network was about ABC Corporation. They have nobody outside of that bubble.”

What’s more, discovering that some cherished relationships were transactional can be emotionally distressing. Marty relates comments a retiring friend once made to him. “The reason people stood in line to kiss the ring is because I was the managing partner. When I left, I had no value to them. There was nothing I could do for them.”

2. You could struggle with your sense of identity.

“I know a lot of CEOs and business owners who define their personal identity by what they do for a living,” Kevin observes. “It’s a bit of a trap.”

David sympathizes with executives whose sense of self takes a hit. “You thought you had it figured out when you were in a corporate role. The whole world was on your shoulders, so you think, this must be who I am.”

According to Marty, “The hardest thing about leaving is the amount of your self-esteem and ego that is tied directly to your title. And when you leave, your title doesn’t go with you.” He concludes, “Why do so many people die soon after they retire? It’s because they’ve lost themselves.”

3. You may mourn the prestige and the perks.

“They say the saddest person in the world is the CEO of a large company with a private jet when they walk their wife back to coach after they retire,” David comments wryly.

The topic of lost prestige may not be discussed terribly often, but the impact is real. As a senior executive, Marty says, “you get treated differently. Two thousand people reporting to me — yeah, that’s pretty sweet.” Then, he says, “All of a sudden, when you stop, it all stops.”

Marty admits, “when I get on a plane and see everybody in first class, I get a little nostalgic.” No longer having those outward signs of success, he says, “it can be a devastating blow to your self-esteem, your ego, your place in the world.”

4. Your relationship with money may change.

Another hard truth, “Not everybody has a million Apple shares,” David points out. Senior executives are likely to retire comfortably but nonetheless may experience a shift in their attitude toward money.

“When you retire, you have a lot of time on your hands,” David explains. “There’s a tendency to want to spend money. But you also don’t want to spend money because you don’t have money coming in on a regular basis.”

For Marty, the biggest change is departing “Bonus City,” as he calls it. “When you’re in the C-suite, you know you’ll get a big bonus at the end of the year. Many times, you have stock options. So you get these large amounts of money dropped in.”

Budgeting without these periodic payouts can be frustrating, all the more so when an exit comes unexpectedly. That’s why Marty recommends planning “maybe not for the worst-case scenario but for a second or third act,” he says. “Have a plan in case where you’re at right now doesn’t work out, or you get acquired, or the company wants fresh blood.”

5. You might want to work for pay.

Kevin points to his own genetic good luck. “Everybody in my family lives to 100. One of the issues for me, I retired at age 59. What am I going to do for the next 40 years?” For him, that was a financial and a personal question.

Ironically, even well-off individuals may want to pursue paid work. David points to studies that indicate that money matters, “no matter what that pay level is. There’s a reward side.” As he explains, “People say, ‘I’ll just do this stuff at charities.’ They start out with a lot of energy.” But as time goes on and interpersonal conflicts and other realities arise, he notes, “they start going there less and less.”

Paid work changes the equation. “It doesn’t matter if you’re a greeter at Walmart or in some large role coaching or consulting. It’s doing something to get paid, which means you have to show up.”

6. Rewarding options may be difficult to find.

Unfortunately, senior executives frequently find it more difficult to transition from a full-time career to the type of encore engagement they’re seeking. Marty says, “I wanted to be like doctors who go from working five days to four days, then from four days to three days. But if you’re in the corporate world, there’s no such thing as scaling back, so C-suite people struggle with what’s next.”

A big problem is that many exiting leaders are accustomed to opportunities emerging without effort. Headhunters and executive search committees have always come calling. Marty breaks the news that you may no longer be in such high demand. “They expect a lot of people knocking on the door but they don’t,” he says. “So you’ve got to go out and figure out what you’re going to do.”

All is not lost, however. “What people have to remember is all that wisdom and experience you have is still very, very valuable,” Marty says. “People don’t understand that leadership in itself is its own skillset that’s highly transportable.”

7. You’ll need to mind your state of mind.

What makes the difference in enjoying life after the C-suite? Attitude, mostly. David, for one, couches his departure in positive terms. “I tell folks I never retired. I just graduated.”

Kevin, too, is fulfilled years after he walked away. “I think it depends on your frame of mind and that, I think, depends on how prepared you are,” says Kevin. “Some people can see it as a rebirth, something new.”

To lean into a better perspective, David counsels former executives to look forward, not backward. “The most boring thing in the world is some ex-CEO going on ad nauseum about what they did in the past. If your whole life is about what you did in the past, there is no future.”

Three executives, one answer.

For Kevin, David, and Marty, some of these hard truths hit harder than others. But they all found their “bridge back to the present,” as David calls it, through the same organization: Vistage. 

Today, each of them values the opportunity they enjoy as Vistage Chairs to give back, remain relevant, connect with others, and even tend to their finances.

Perhaps Marty puts it best when he says, “This is the most rewarding job I’ve ever had, the most fulfilling job I’ve ever had. Monetarily, it’s fantastic. I pinch myself and I can’t believe I found this.”

The takeaway — the life you seek is there for the taking. Or as David says, “You have a chance for as many new seasons as you want. The most powerful thing we do is choose.”

Related resources

Life After the Executive Suite [available for download]

Help! I’m failing at retirement

How CEOs stay relevant in retirement

2355 views