Here Comes the 60-Year Career

Get ready for longer careers. Probably much longer.

Charlotte Japp is setting the groundwork for it. Since graduating from college 10 years ago, Ms. Japp has worked in marketing at three companies in different industries and simultaneously launched Cirkel, a startup that connects younger and older employees for two-way career support.

Currently head of platform at ff Venture Capital in New York, Ms. Japp, 32, doesn’t see her career as linear, and doesn’t picture her progression as moving up a single, well-defined ladder. Instead, she envisions her career as long and varied—a marathon that will involve changing directions, with stops and restarts along the way.

“I know I’m going to have a career over a very long stretch and it won’t be just one thing,” Ms. Japp says. “Plus there’ll be more fluidity between periods of work, school and family.”

Millennials like Ms. Japp, as well as the generations behind them, are starting to think about their careers in a totally different way from their elders. They have no choice: Because they are likely to live healthily into their 90s or longer, they must learn to navigate 60-year careers instead of the traditional 40-year span.

But such a change will require a new mind-set when it comes to planning a career. Instead of advancing vertically up a single path, for instance, people will need to move sideways—and even down at times—as they traverse different jobs and multiple careers. They will have to make sure they have adequate income to sustain themselves over lengthy lives. They will need to figure out where they derive the most job satisfaction so they don’t burn out after decades of working. They will have to keep acquiring new skills to avoid becoming obsolete. And, if they can afford to, they may want to take occasional career breaks to balance their personal and professional lives.

“Over the course of 60-year careers, we’ll need to work and pace our careers differently,” says Laura Carstensen, founding director of the Stanford Center on Longevity.

Currently, Dr. Carstensen says, men and women at midlife “tend to burn the career-and-family candle at both ends, with lives impossibly packed from morning to night,” while older people who are plateaued or pushed out before wanting to stop working feel underused. She imagines a model where people might work about the same amount of time overall as they do now, but spread that work over more years—thereby reducing the risk of burnout and giving themselves time for personal pursuits and skill enhancement.

All of this could pose challenges for companies, which haven’t structured ways for employees to stay productive and creative over lengthy careers. Few have established flexible routes in and out of the workplace, or “glide paths” toward retirement that enable older workers to work longer but at reduced hours. Less than 10% of Fortune 500 companies have re-entry programs for employees who have taken career breaks for family caregiving or other reasons, according to research by Boston-based iRelaunch, which encourages employers to establish such programs, and helps people return to work after breaks of one to 20 years.

However, if they want to attract the workers they need, employers will have no choice but to adapt. After all, their leaders will likely be in the same position.

Here are seven things for employees to think about as they plan for—and navigate—this new terrain.

Charlotte Japp has worked for several companies and launched a startup in her 10 years since college. ‘I know I’m going to have a career over a very long stretch and it won’t be just one thing,’ she says. PHOTO: MARY INHEA KANG FOR THE WALL STREET JOURNAL

1. Expect a career that resembles a jungle gym rather than a ladder

Already, a lot fewer workers expect to stay at a single company throughout their career. That trend will only accelerate as careers get longer. After all, few people will want to stay at the same job for 60 years, even if they could (a big if). It is a recipe for job and life dissatisfaction and stagnant income. And few companies have shown the kind of loyalty that would encourage such careers.

Instead, employees should imagine a career that involves making leaps sideways and across rungs rather than a straight climb upward.

Ms. Japp says she learned to expect this by observing her parents, who both lost corporate jobs in midlife and then successfully pivoted to self-employment. Her father, after a career in advertising, established a stamp- and coin-selling business on eBay, and her mother became an independent adviser to art collectors after working as an executive at a large art gallery.

“The idea of portfolio careers, and change being a positive, was implanted in me early,” Ms. Japp says. Over any career, but especially a lengthy one, you need to cope with two ever-changing variables, says Ms. Japp. “First is the business world, where new companies and many new jobs will be constantly emerging. And personally we change over time—and so do our interests, needs and curiosity.”

2. Lifelong learning, including breaks to return to school, will be essential

It is hard enough now to stay up-to-date with technology and other job requirements, and to train for new opportunities. Add 20 years to careers, and it becomes even more daunting. In addition, many employees will want to start second or third careers over the course of their longer working lives, which will require returning to school for training and maybe even new degrees.

Giulia Pines, who’s 38, worked as a freelance writer—first in Germany where she lived for a decade and then in New York. Two years ago, in the wake of the Black Lives Matter and other social-justice protests, she thought about becoming a lawyer and “trying to change policies and help people, but at first I thought I was too old to make that switch,” she says. Then, she realised she likely has decades ahead of her to devote to law.

Ms. Pines is now a first-year student at Brooklyn Law School, has met several other classmates in their 30s and isn’t concerned about starting a law career at 40. “If I’m going to be 40 anyway, I might as well do what I want,” she says. Plus, she adds, she was raised in a family that “never considered retirement, with both my grandfather and father, who were doctors, working until they were unable to do that physically and mentally. I think of what I’m doing now as a next step, without an age attached to it.”

3. Seek flexibility to have a better work/life balance

As people live longer, and careers lengthen, their priorities change. They’ll also face conflicting demands. For instance, for growing numbers of young and middle-aged adults, caregiving responsibilities for older parents overlap with caring for young children. Among the 48 million Americans who currently provide unpaid care to elders or disabled relatives, more than 40% are 18 to 49 years old, according to a 2020 study by AARP and the National Alliance for Caregiving.

“Everyone is going to be a caregiver at some point, and it should be an acknowledged part of a 60-year career,” says Susan Golden, who advises companies and venture firms about innovation and entrepreneurial opportunities created by longevity.

Ms. Golden is a living example of her argument. She was a partner at a venture-capital company in her 30s, and took only three weeks off after having her first daughter. But she took a break after having a second daughter when she also began caring for her mother. Now she’s encouraging her daughters and other millennials to consider caregiving breaks themselves “so you don’t miss out on the joy of raising children. You don’t have to work straight through 60 years,” she says.

After her own break of about 15 years, Ms. Golden attended Stanford University’s Distinguished Careers Institute when she was 61, or what she calls her “renaissance stage.” She took courses on such topics as entrepreneurship and board governance at Stanford Graduate School of Business, healthy aging at the medical school and on design thinking. And she was among others in their 50s and older who were considering transitions. “Having the support of that community was so helpful,” says Ms. Golden, who also co-teaches a course about longevity’s business opportunities at Stanford’s business school and is the author of “Stage (Not Age).”

4. Learn strategies for restarting a career after a break

In March 2022, LinkedIn introduced a new category—Career Breaks—for users who are building profiles to describe the highlights of their time away from traditional jobs, including family responsibilities, volunteerism and travel. The new label should help normalize the idea that careers aren’t always linear.

Carol Fishman Cohen, chief executive and co-founder of iRelaunch, advises employees to keep detailed notes throughout their careers, not just about achievements but about specific experiences they have had with bosses, employees and colleagues at different jobs. It’s hard enough to remember accomplishments five or 10 years later, but 40 or 50 years? “Those of us who don’t think to keep these records have to re-create the past from memory, which may not be nearly as vivid or compelling as when they occurred,” Ms. Cohen says.

Those who take breaks should keep up-to-date on licenses and professional membership, take online courses to improve and learn new skills and possibly do part-time volunteering or contract work. “Use time during a break to reflect on your strengths and whether you want to return to the path you were on or take a new direction,” says Ms. Cohen, and let prospective employers know that you’ve thought carefully during a break about your commitment to a particular field.

5. Build an intergenerational network

Over the course of a six-decade career, workers need to nurture relationships not just with superiors but with colleagues who are junior to them.

Colleagues who are younger may be more skilled with new technologies, and be able to help older colleagues learn and adapt to them. And because there aren’t clear career paths, it is more likely that positions will shift. A colleague who’s younger in age may advance beyond their former bosses and be in a position to hire them or connect them to other jobs. This happened to Ms. Cohen when she wanted to re-enter the workplace after an 11-year caregiving break: She got a job at Bain Capital, where a former junior colleague she had previously worked with at a different finance company had a key position. He remembered her and helped connect her to others at Bain who hired her, she says.

6. Explore new paths even when you’re enjoying your current career

It’s typical for people to keep their heads down and focus on the job and employer they have, especially if they are satisfied. But in an era of long, multiple careers, it’s important to think about alternative paths before you have to or feel pressured to make a change. The odds are much greater that you’ll need to take that path one day.

To that end, experts advise people to attend professional meetings or conferences in areas they want to learn about, and to spend time thinking about what they might want to do next, just in case. Maybe somebody has worked in operations or IT, but imagines moving into human resources or marketing. It doesn’t hurt to talk with those people in those fields about what might be required. A safety net is a lot more important when you’re staring at, say, 30 more years of working than if you’re looking at 10 more years.

7. Don’t try to plan it all out

It is impossible to map out what will happen over a 60-year career. Too many things—in our personal lives, in the economy, in the workplace—will change. Nobody has a crystal ball that can look that far into the future.

What’s important, rather, is finding jobs and work environments that are both enjoyable and challenging. In the past, when careers typically involved a vertical climb, it made sense for employees to set goals they wanted to reach by a specific time or age. But trying to do this can be counterproductive today. The ability to be agile rather than rigidly focused on a handful of goals will be essential when traversing a career that lasts more than half a century.

“It is all about following my gut, knowing what I’m good at and doing what I enjoy on a day-to day basis,” says Ms. Japp. “The lesson I’ve been learning is to be adaptable. You have to meet the moment.”

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.