How To Know When To Quit Your Job

Older workers have a problem. They don’t know when to quit.

As baby boom-era CEOs, professors, lawyers, engineers and others get older and keep their jobs longer, it is raising uncomfortable questions.

Is there an art to stepping down gracefully? “I’m not sure there’s an art. I think it requires will,” says Anne Mulcahy, who was 56 when she voluntarily gave up the CEO job at Xerox to make way for her successor, Ursula Burns. She is now 68. “It’s hard. It’s not something that happens naturally if you like what you do and you’re good at it. You have to set time limits for yourself.” You also have to know what your purpose is after you retire or “you go into this void that’s really very tough,” she adds. Leaving the C-suite was one of the hardest things she’s ever done, says Ms Mulcahy, who lives in Connecticut and is now actively involved with nonprofit organizations.

Mandatory retirement at 65 ended for most jobs in the mid-1980s, giving some people the impression they could work forever. Since life expectancy has increased—from 70 years old in 1959 to about 83 for today’s 65-year-olds—many people want to work longer, for both personal and financial reasons.

At their peak, boomers, those born between 1946 and 1964, numbered almost 79 million, and their ranks include the first generation of career women and lots of people who remained single or got divorced. For many boomers, work has taken on an outsize role. It provides purpose, fulfilment and community. It creates structure and routine.

Since many work at desks or in the service industry—not manual labour—boomers also have fewer physical limitations that could cut a career short. “Retiring at 65 makes no sense. Many people are still at the height of their game,” says Gillian Leithman, a Montreal-based retirement coach who conducts seminars and corporate workshops. Nonetheless, 65 is still the line of demarcation at which everybody else thinks you should be ready to retire, regardless of whether you agree. Another career coach says it’s like having an expiration date on your forehead.

“People are turning traditional retirement age and the gas tank isn’t empty,” says Robert Laura, a Brighton, Mich.-based retirement coach and financial planner. “They can easily work til 75.”

That’s why so many people avoid planning for it. Until the pandemic, boomers were retiring at a rate of about 2 million a year. By last September, 40% of boomers in the U.S. had retired, according to a recent report by the Pew Research Center.

Dr Leithman finds that most people, even high-powered executives, put off thinking about it until the 11th hour. When she asks them what will get them out of bed in the morning in retirement, most have no idea, she says. “They’re terrified.”

The transition is so difficult that it has spawned a new industry of coaching and consulting firms that focus solely on retirement. Many are run by former corporate executives who know the difficulties first hand, like Bob Foley, former CEO of Travelodge hotels and the former human resources chief of Pyramid Hotel Group. Mr. Foley says he was called in one day by his boss, the CEO at Pyramid, who asked out of the blue if he had a plan to identify and train his successor. “I thought, ‘What, are you out of your mind?’ ” he recalls. He was 53, and the company was growing fast. “I thought, ‘Is he pushing me out? Is my life about to end?’ You go through that fear stage. Everybody does.”

He spent eight years hiring and training his much younger successor, learning to appreciate the generational differences between himself and younger workers who are more tech savvy and champing at the bit to get their turn.

Mr Foley, now a Boston-area executive career-transition coach, tells clients to retire when their skills are no longer in vogue. At Pyramid, he was against texting—he thought it too unprofessional. He didn’t think customer service could ever be entrusted to an automated chatbot. When younger employees suggested replacing an obsolete HR system that he’d created, “Boy, did I say no to that,” he says. He finally realized “these guys are smarter than I am. I finally got out of my way.” At 61, he was ready to leave.

Retirement doesn’t just happen. “The heavens don’t open up, the world isn’t at your feet when you retire,” says Mr Laura. “Retirement is a made-up phase of life. It’s nothing until you put things into it.”

He asks clients to write down how they’d spend one day in retirement; then how they’d spend a week. Often they only make it halfway through. Once people figure out retirement could last 30 years, they realize that’s a long time to play golf, knit or help register voters. They want to find something to throw themselves into, says Chip Conley, who founded Modern Elder Academy, a school in Baja California Sur, Mexico, where mid-lifers and retirees can problem-solve a career transition.

The transition is often painful and messy, says Mr Conley, 60, who founded the boutique hotel business Joie de Vivre Hospitality at age 26, sold it 24 years later, and then for a time was a strategy executive at Airbnb. “I had to end the idea that I was a CEO. I had to right-size my ego and let go of all my hotel knowledge,” he says. He likens it to “ripping off a body suit of Band-Aids.”

He warns clients about “the messy middle,” the interim period when retirees have no idea what’s next. He has them create dream boards, asking themselves, do you want to be an angel investor, author, social worker, entrepreneur? He helps them figure out what skills and experience they can apply in a new venue, as he did when he moved from the hotel industry to tech. He tells them to follow their curiosity. “If you’re passionate and engaged and curious, people lose track of your wrinkles,” he says. “They are attracted by your energy.”

Stepping down works best when you follow a plan, experts say. Don’t expect execution to be perfect. Though Ms Mulcahy knew she wanted to be in nonprofits, “the need to fill your calendar is so strong that you say yes to things you shouldn’t,” she says. “You worry about your shelf life and staying relevant.” She found in hindsight that it hadn’t been necessary to add a stint as cable news commentator to her board and nonprofit work. “It solved my itch to feel I was still part of the business world,” but it didn’t suit her, she says. “I hated it.”

She settled into a seven-year chapter chairing the board of Save the Children, a nonprofit organisation that took her all over the world. She is now focused on helping younger career women navigate the corporate world, specifically a network of 25 who meet in her apartment every quarter. “We sit around and drink wine and solve each other’s problems,” she says.

I wish to protest the current ugliness. I see it as a continuing trend, “the uglification of everything.” It is coming out of our culture with picked-up speed, and from many media silos, and I don’t like it.

You remember the 1999 movie “The Talented Mr. Ripley,” from the Patricia Highsmith novel. It was fabulous—mysteries, murders, a sociopath scheming his way among high-class expats on the Italian Riviera. The laid-back glamour of Jude Law, the Grace Kelly-ness of Gwyneth Paltrow, who looks like a Vogue magazine cover decided to take a stroll through the streets of 1950s Venice, the truly brilliant acting of Matt Damon, who is so well-liked by audiences I’m not sure we notice anymore what a great actor he is. The director, Anthony Minghella, deliberately showed you pretty shiny things while taking you on a journey to a heart of darkness.

There’s a new version, a streaming series from Netflix, called “Ripley.” I turned to it eagerly and watched with puzzlement. It is unrelievedly ugly. Grimy, gloomy, grim. Tom Ripley is now charmless, a pale and watchful slug slithering through ancient rooms. He isn’t bright, eager, endearing, only predatory. No one would want to know him! Which makes the story make no sense. Again, Ripley is a sociopath, but few could tell because he seemed so sweet and easy. In the original movie, Philip Seymour Hoffman has an unforgettable turn as a jazz-loving, prep-schooled, in-crowd snob. In this version that character is mirthless, genderless, hidden. No one would want to know him either. Marge, the Paltrow role in the movie, is ponderous and plain, like a lost 1970s hippie, which undercuts a small part of the tragedy: Why is the lovely woman so in love with a careless idler who loves no one?

The ugliness seemed a deliberate artistic decision, as did the air of constant menace, as if we all know life is never nice.

I go to the No. 1 program on Netflix this week, “Baby Reindeer.” People speak highly of it. It’s about a stalker and is based on a true story, but she’s stalking a comic so this might be fun. Oh dear, no. It is again unrelievedly bleak. Life is low, plain and homely. No one is ever nice or kind; all human conversation is opaque and halting; work colleagues are cruel and loud. Everyone is emotionally incapable and dumb. No one laughs except for the morbidly obese stalker, who cackles madly. The only attractive person is the transgender girlfriend, who has a pretty smile and smiles a lot, but cries a lot too and is vengeful.

Good drama always makes you think. I thought: Do I want to continue living?

I go to the Daily Mail website, once my guilty pleasure. High jinks of the rich and famous, randy royals, fast cars and movie stars, models and rock stars caught in the drug bust. It was great! But it seems to have taken a turn and is more about crime, grime, human sadness and degradation—child abuse, mothers drowning their babies, “Man murders family, self.” It is less a portal into life’s mindless, undeserved beauty, than a testimony to its horrors.

I go to the new “Cabaret.” Who doesn’t love “Cabaret”? It is dark, witty, painful, glamorous. The music and lyrics have stood the test of time. The story’s backdrop: The soft decadence of Weimar is being replaced by the hard decadence of Nazism.

It is Kander and Ebb’s masterpiece, revived again and again. And this revival is hideous. It is ugly, bizarre, inartistic, fundamentally stupid. Also obscene but in a purposeless way, without meaning.

I had the distinct feeling the producers take their audience to be distracted dopamine addicts with fractured attention spans and no ability to follow a story. They also seemed to have no faith in the story itself, so they went with endless pyrotechnics. This is “Cabaret” for the empty-headed. Everyone screams. The songs are slowed, because you might need a moment to take it in. Almost everyone on stage is weirdly hunched, like a gargoyle, everyone overacts, and all of it is without art.

On the way in, staffers put stickers on the cameras of your phone, “to protect our intellectual property,” as one said.

It isn’t an easy job to make the widely admired Eddie Redmayne unappealing, but by God they did it. As he’s a producer I guess he did it, too. He takes the stage as the Emcee in a purple leather skirt with a small green cone on his head and appears further on as a clown with a machine gun and a weird goth devil. It is all so childish, so plonkingly empty.

Here is something sad about modern artists: They are held back by a lack of limits.

Bob Fosse, the director of the classic 1972 movie version, got to push against society’s limits and Broadway’s and Hollywood’s prohibitions. He pushed hard against what was pushing him, which caused friction; in the heat of that came art. Directors and writers now have nothing to push against because there are no rules or cultural prohibitions, so there’s no friction, everything is left cold, and the art turns in on itself and becomes merely weird.

Fosse famously loved women. No one loves women in this show. When we meet Sally Bowles, in the kind of dress a little girl might put on a doll, with heavy leather boots and harsh, garish makeup, the character doesn’t flirt, doesn’t seduce or charm. She barks and screams, angrily.

Really it is harrowing. At one point Mr. Redmayne dances with a toilet plunger, and a loaf of Italian bread is inserted and removed from his anal cavity. I mentioned this to my friend, who asked if I saw the dancer in the corner masturbating with a copy of what appeared to be “Mein Kampf.”

That’s what I call intellectual property!

In previous iterations the Kit Kat Club was a hypocrisy-free zone, a place of no boundaries, until the bad guys came and it wasn’t. I’m sure the director and producers met in the planning stage and used words like “breakthrough” and “a ‘Cabaret’ for today,” and “we don’t hide the coming cruelty.” But they do hide it by making everything, beginning to end, lifeless and grotesque. No innocence is traduced because no innocence exists.

How could a show be so frantic and outlandish and still be so tedious? It’s almost an achievement.

And for all that there is something smug about it, as if they’re looking down from some great, unearned height.

I left thinking, as I often do now on seeing something made ugly: This is what purgatory is going to be like. And then, no, this is what hell is going to be like—the cackling stalker, the pale sociopath, Eddie Redmayne dancing with a plunger.

Why does it all bother me?

Because even though it isn’t new, uglification is rising and spreading as an artistic attitude, and it can’t be good for us. Because it speaks of self-hatred, and a society that hates itself, and hates life, won’t last. Because it gives those who are young nothing to love and feel soft about. Because we need beauty to keep our morale up.

Because life isn’t merde, in spite of what our entertainment geniuses say.

How To Know When To Quit Your Job

Many baby boomers—especially those at the top of their game—struggle with the decision to step down. And when they leave, the transition is often ‘painful and messy,’ says one career coach.

Artistic culture has taken a repulsive turn. It speaks of a society that hates itself, and hates life.