Help! I’m failing at retirement

There you were, a senior executive. Charting the direction for an organization. Setting and achieving ambitious goals. Building and mentoring a team. Having an impact.

Then you realized your ultimate objective, a well-deserved exit into retirement. And suddenly, the world stopped.

At least that’s how many retiring CEOs describe their experience stepping away from full-time employment. In a go-hard culture that views a life of leisure as the reward for all those late nights on the job, few people expect to find the transition to retirement such a letdown.

How is it that one can experience ennui over another day on the links? Who could be bored at the mere thought of another umbrella drink? What if grandkids, books and a whole host of hobbies just aren’t enough?

For many CEOs who have done it all, even having such emotions can bring on disappointment or guilt. In the backs of their minds, they can’t help wondering if they’re failing at the easiest challenge they’ve ever faced — enjoying the good life.

If this sounds familiar, there is encouraging news. You can reimagine your retirement. The process starts by admitting that you’re not yet fulfilled and then asking the big question, “why?”

You’re not alone

“I think the vast majority struggle,” says Vistage Chair Barbara Zerfoss. “There are very few people who have so full a life outside their work that they actually retire well.”

As a former vice president for a $5 billion global corporation, Zerfoss empathizes with executives who experience distress after an exit. “When you stop that type of role, I can’t explain what it feels like. It’s definitely a loss. And you need to fill that up with something or you’ll be in trouble emotionally and mentally.”

Longtime executive coach Allan Fried agrees. “When somebody is used to having a fast-paced career and then wakes up one morning with no place to be and nothing to do…” he drifts off in contemplation before continuing. “Most people I know still want some sense of purpose. They want something to do. They want to keep their minds and souls and spirits active.”

Editing your next chapter

Fried has witnessed numerous flailing retirements. One colleague, he says, “sold his business and made a lot of money and he was so unhappy.” That’s why Fried prepares clients for what to expect. “You have to help them clarify what they want the next chapter of their life to look like.”

This perspective aligns with Zerfoss’s experience. She has devoted her retirement to helping businesses and executives, while also exercising her imagination as a fiction writer. Her first novel will be published this spring.

Zerfoss found her way by getting in touch with her purpose. “Everyone needs to stay engaged in some way and use their talents in a manner that aligns with their purpose,” she says.

Take note: Your personal mission in life may be different from the meaning you pursued in the C-suite. It might take some introspection to figure out what inspires you now.

What’s motivating, but missing?

Once you confront your negative emotions about retirement, you can begin to ask what’s causing them. What are the missing pieces of a meaningful life?

Consider whether any of the following factors resonate. Then ask yourself how you could incorporate these features into your daily activities. Keep in mind, these are tough questions. Don’t expect all the answers to come easily, but trust that they will come with time.

Live your legacy

Think failing retirements are only an issue for those of Social Security age? Not so, says Fried. Anyone who walks away from a rewarding career can feel empty.

“There are lots of people who sell their businesses. They could be in their 40s and 50s and looking at what’s next. They’ve made money. Now it’s more about legacy and impact.”

Can you relate? If so, you may want to consider:

• Is the legacy you left behind in business important to you? If so, how could you carry that mission forward?
• What about your impact? How can you continue to make a difference?

Lifelong learning

Asked about what executives miss in retirement, a quote by Henry Ford quickly came to mind for Zerfoss. “Anyone who stops learning is old, whether at 20 or 80. Anyone who keeps learning stays young. The greatest thing in life is to keep your mind young.”

Did you especially value the learning and growth you experienced in the C-suite?

• How can you apply that youthful inquisitiveness today?
• What topics interest and intrigue you? Where and how might you explore them?

A yearning for connection

Talk to nearly anyone in live theater, and you’ll hear about the deep camaraderie that emerges over the course of a show. The same can be said of the high-wire act of business. CEOs connect with their teams almost every day and they network within their industry, profession, and community.

That means stepping back can leave a CEO feeling isolated. Fried, pulling from his wealth of stories, mentions a coach and speaker who worked well into his 90s. He lived in a gated retirement community and his neighbors would frequently ask, “What’s it like on the other side?”

His goal, according to Fried, was to remain in touch with the outside world, which he did through his encore career.

Do you feel like your universe has gotten too small?

• How could you reconnect with individuals from your professional life?
• What new connections might you be interested in building?

For Zerfoss, this reaching out phase is a vital step for reimagining retirement, after identifying your purpose. “Talk to a lot of people and have conversations.”

You may not know what you’re looking for in those discussions, especially at first, but they’re still worthwhile. “Almost everything that’s created starts with a conversation,” she says.

It’s OK to reconsider

Successful CEOs are willing to abandon a business plan when it doesn’t pan out. They accept when they must rectify a bad hire or redevelop a product. In other words, they change course. Don’t be afraid to do the same in retirement.

Constant leisure isn’t the only option. From occasional volunteering to full-fledged unretirement with an income stream and plenty of schedule flexibility, you have choices to find meaning, purpose, and fulfillment and make this chapter everything you hoped it could be.

Related Resources

5 paths CEOs consider once they retire

Life After the Sale [Vistage Perspectives Fall 2021]

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