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Mortal Leadership

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Latest Issue:

  • THE PROBLEM Western society doesn’t prepare people for death or retirement well.

  • WHY IT MATTERS Poorly handled transitions wreak havoc in the workplace.

  • THE SOLUTION Cultivating a deep sense of purpose and curiosity.

By Meghan Walsh

March 26, 2025

Enrique J. Fernandez had a deeper intimacy with loss than many. The 73-year-old had to say his first significant goodbye at the age of 10, when he migrated from his homeland of Cuba to Miami. Decades later, he mourned the loss of his wife and the mother of his children, when, at 52, she died of lymphoma. Even so, he wasn’t prepared to lose his professional identity.

Throughout life’s roller coaster of fate, Fernandez thrived professionally as a renowned reconstructive surgeon and president of the Florida Society of Plastic Surgeons. By 59, he had purchased his own medical facility. “I had intended to do succession planning, but I never did,” Fernandez says. Several months after moving into his new office, Fernandez learned he had colon cancer. While the cancer went into remission, chemotherapy caused the surgeon of 33 years to develop a tremor in his hand. Fernandez could no longer wield a scalpel with the precision his work required. If not a surgeon, the father of four, devoted husband, and outdoor photography enthusiast no longer knew who he was—and that loss of identity brought his entire existence into question. “One night, I hit a wall and looked up and said, ‘God, I need some wisdom,’” recalls Fernandez.

In a variety of forms, the story of the surgeon who could no longer perform surgery is a common one. It’s also the story of the executive who builds a successful career and keeps her head down—though the signs suggest it’s time to plan retirement—and plows forward as if all will go on forever. When the day does finally come to relinquish her post, she is unmoored. Or it’s the story of the CEO who refuses to pivot, the investor who doesn’t sell, or the burnout who can’t quit, all of them unable to let go and frozen by fear of what’s on the other side. A 2023 Employee Benefit Research Institute survey found that a third of workers plan to retire older than 70—or never. In reality, almost half are caught unprepared after being forced out of the workforce much earlier than expected.

Experts put it bluntly: Modern western society doesn’t do death well. It’s a taboo that takes place begrudgingly and behind sterilized steel doors, with minimal preparation or support. We don’t know how to talk about, plan for, or navigate the passing-on process. This collective inability to confront impermanence is reflected in the corporate world. Leaders fail to make adequate retirement or succession plans. Shuttering a business in the face of shifting markets, emerging technology, or new environmental realities is considered a failure, rather than a natural and inevitable part of the life cycle. “We’re trying to put off what comes after,” says Anita Hannig, an anthropologist and author of The Day I Die: The Untold Story of Assisted Dying in America. “There is an unwillingness to face finitude.”

Such reluctance leads to transitions that get unnecessarily messy—relationships turn toxic, business suffers, and innovation and growth are stifled. But since the pandemic, which forced us to confront loss on a global scale, there have been signs of a shifting relationship to death. Some say that if we can learn to deal with mortality with more grace, we will be better able to handle life’s multitude of transitions, including those in the workplace. And vice versa. Planning to retire from a job can be a prelude to the ultimate retirement. Indeed, for his part, Fernandez has dedicated the current chapter of his life to helping other professionals prepare to transition (though he doesn’t use the R-word). But he has a phrase that captures the issue: “We deny and delay.”

The outsourcing of death in the United States can be traced back to the Civil War. Masses of men were dying thousands of miles from their homes, which prompted entrepreneurial embalmers to create a business preserving bodies so they could be returned to grieving families. The death industry grew from there, professionalizing a process that until then had been handled in and by the community. Today the funeral-home market in the US is worth about $20 billion.

Advances in medicine further distorted the West’s relationship to dying. The end of a life is postponed by all means necessary. When the grim reaper does finally prevail, as the grim reaper always does, the cessation of breath is considered a failure, rather than an inevitability—and, in some cases, a mercy. Because death so often happens in medical facilities and bodies are promptly ferried away, people have become spooked by corpses. For the sake of loved ones, the dead must be made to look as if they’re still alive through the embalming process. “The less familiar we became with death, the more fearful people became,” Hannig says.

“There is life after retirement.”

Even medical schools, doctors will tell you, don’t provide the skills needed to prepare for death—just as business schools don’t teach how to successfully transition into retirement or handle a layoff. In his 1973 Pulitzer Prize-winning book The Denial of Death, anthropologist Ernest Becker writes that the repudiation of death “is one of the most basic drives in individual behavior, and is reflected throughout human culture.” People find all kinds of ways to skirt mortality, from anti-aging face creams to cryonics to ​​AI-generated ghost bots. But natural disasters, wars, recessions, and pandemics, all of which have ominously reared their ghoulish heads the last handful of years, can be powerful reality checks. Indeed, COVID-19 shook loose cultures of complacency that are continuing to unravel.

Since 2019, membership in the National End-of-Life Doula Alliance has soared 500 percent. Green burials are growing in popularity, communities are hosting public death cafés, and young people are writing living wills. A few rebellious elders are even throwing their own farewell parties. And again, this larger societal change has percolated into corporate culture. A growing number of employers, including Salesforce, now offer death-doula services to their employees that are on par with birth benefits. Other companies are implementing redundancy planning, while some business coaches are expanding their offerings to include end-of-life planning. “Even in moments we perceive as negative—whether a death or a departure—we can discover opportunities to live more intentionally and show up in a new and better way,” says Ora Shtull, an executive coach who recently went through a death-doula training.

One of Shtull’s clients, a C-suite executive, was nearing the end of his 30-year career at a large corporation. Like Fernandez and so many other leaders, he hadn’t started planning for his retirement until it was thrust upon him. He’d suffered a stroke and his language was impaired. But both the executive and corporation sought to navigate the transition with intention and care.

Shtull coached the man through letting go of his former responsibilities in favor of prioritizing passing on his institutional knowledge. “His struggle was internal,” Shtull says. “‘What is my value? Can I still be useful?’” Instead of ticking through to-do lists, he turned his focus toward bringing more heart into his interactions with colleagues. Across cultures and time, the transition into elderhood is commonly marked by a reorientation toward being rather than doing.

A shift in identity occurs whenever people go through a transition, says Alua Arthur, attorney and founder of death-doula training program Going With Grace. Many workers, especially the most successful, form their sense of self around what they do. When they no longer have that structure, they can feel destabilized. One survey found that last year a quarter of retirees aged 62 to 85 went back to work, some for financial reasons but others because they were unprepared to deal with the emotional loss. Executives “have to go through this critical period and answer the question of how best to utilize what they’ve learned in their careers to contribute in other meaningful ways,” says Dennis Carey, vice chairman and co-leader of board services at Korn Ferry. “It’s about finding a new identity.”

***

Retirement is only one of many endings experienced throughout a career. Workers move to new teams, switch careers, and quit. They face layoffs. They suffer disillusionment. But without the tools to process what’s happening, these losses often go unmourned and unrealized. “We need to honor even those minute deaths that occur,” Arthur says. “Even if they mean the business is growing, there is still loss and transition.” Simply acknowledging what a colleague is going through can help them to integrate the experience. Each of these moments holds the potential for reflection on life’s existential questions. What are my gifts? My purpose? What do I want my legacy to be? Sure enough, many books and philosophies on dying turn out to be instructions for living more intentionally.

“These are the bridges that lead to new possibilities.”

Making time to grieve and to contemplate requires slowing down. It requires a willingness to wade into liminality and maintain faith—or perhaps imagination—that what lies on the other side is worth the risk of stepping into uncertainty. As Carey reminds executives, “There is life after retirement.” As with all endeavors, even faith gets easier with practice. Small transitions become preparation for big transitions. “There is a hesitancy to embrace the last chapter of life, because the real thing you’re pivoting toward is your own passing,” Hannig says.

How endings are navigated sets up beginnings. But there is an important time in between the stop and start, which is the pause. Shtull says this is where reorientation happens. This is the moment when Fernandez turned from practicing medicine to helping people transition into new professional expressions. It’s when Shtull’s client went from doing to being. “These are opportunities,” she says. “These are the bridges that lead to new possibilities.”

Image credits: Iakov Kalinin/Getty Images; Artic Images Stone/Getty Images; Aliaksei Brouka, Serhii Brovko, Aliaksei Brouka, Takoyaki Tech, Great99 studio/Getty Images; Dulyanut Swdp/Getty Images