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.”

Administrative cowardice. Rampant cheating. The soaking and scamming of undergrads and grad students. Performative wokeism. Intensifying competition for international tuition dollars from an expansive China.

These are either the latest dire headlines about American higher ed or the myriad subplots of “Lords of Serendipity,” an ambitious new novel by Randy Boyagoda. Unlike most campus fiction, its scope extends well beyond the cloister of the liberal arts classroom to whammy the entire university system, from its financial model to its function within a globalized economy. Along the way, it skewers its lightning-rod targets with a precision too sharp to be considered entirely fictional.

That its author is not only well-versed in satire, having written four other novels in the genre, but is also a professor of English at the University of Toronto and an experienced college administrator, further blurs the lines between comic fiction and brutal fact. It’s the kind of no-holds-barred book only a consummate insider would know to write—but only one who is also conveniently outside the American university system could get away with writing.

“This is someone who’s got the inside dope on what can go on at universities, especially with international students, and what kind of con games are going on,” said Margaret Atwood, a friend and fellow Torontonian.

The novel, like Boyagoda himself, is often very funny—even as the dilemmas its characters face read as tragedy. Its cast includes the bickering members of a Sri Lankan hotel cleaner’s family, insecure American freshmen, dead-end third-tier college professors and their highflying Ivy League counterparts and dispirited university functionaries. An old-fashioned Dickensian tale, it sweeps across continents and campuses, from a classic liberal-arts college to a stand-in for Harvard University to an urban technical school to the dilapidated buildings of a state-run university in Sri Lanka.

“I’m a joyful person,” Boyagoda said in an interview, though he prefers to see his outlook on academia as “hopeful” rather than optimistic. He smiles and laughs frequently. He bikes everywhere. He derives energy from his students and from his four daughters, ages 14 to 20. They help him and his American wife, Anna, also an educator, care for Boyagoda’s father, an immigrant from Sri Lanka who has dementia and lives with the family.

Randy Boyagoda speaks at a panel discussion. — Randy Boyagoda taking part in a panel discussion at the University of Toronto in 2024. Polina Teif/University of Toronto

The germ of the novel came to Boyagoda during the pandemic, when he was serving as a vice-dean. An urban legend was circulating about a statistics grad student selling passing grades to international students. The cheating scheme itself may well have been apocryphal, but it felt tantalizingly plausible.

“As a novelist, it stayed with me,” Boyagoda said. “Who would sell grades for a stats course? Why would someone buy grades? What’s motivating them? Why wouldn’t the university be doing something about it?” What he didn’t want to do, he explained, was write “another novel about a creative writing professor and his drama with students.”

In addition to writing novels—the first of which was a finalist for Canada’s prestigious Giller Prize; he’s written eight books in total—Boyagoda teaches literature full-time. For his students next semester, kids raised in a purportedly “post-literature era,” he’s assigning three 700-page novels, he noted mischievously, books by George Eliot, Ralph Ellison and Kiran Desai.

On RateMyProfessors, students remark on Boyagoda’s heavy assignments, tough grading and distaste for cellphones, but also hail his “comedy.” When alerted to these reviews, Boyagoda laughed. “Guilty as charged,” he said.

“Randy’s one of those people in academia who is very well educated but doesn’t have an ounce of superiority about him,” said John Irving, who frequently guest lectures in Boyagoda’s classroom. “It’s amazing to see how willing students are to talk in his classrooms, how little afraid they feel of being mocked or put down—he gets complete candor out of them.”

Negotiating competing interests seems to come naturally to him. Like many college campuses, after the Oct. 7 Hamas attack on Israel, the University of Toronto was embroiled in protests, encampments and discord; part of the school’s response was to convene a working group on civil discourse. Boyagoda was put in charge, serving for two years. It’s the kind of thankless task many professors would flee from, but Boyagoda relished the prospect and thinks the group, which is ongoing, made progress.

He has since pivoted to another formidable academic concern: the waning prestige of the humanities. In July, Boyagoda became the director of the Jackman Humanities Institute and special advisor on the humanities to the dean of arts and science. This fall, he is starting a series of gatherings he calls the Dead Book Club. (Dead writers feature heavily among his favorites: St. Augustine, Dante, William Faulkner, Evelyn Waugh, Saul Bellow.)

“The goal is to encourage students to read for its own sake and have conversation for its own sake,” Boyagoda said. “The importance of the humanities will be revealed to those who participate.”

Illustration of the book cover for "Lords of Serendipity" by Randy Boyagoda, depicting a woman wearing a hat with various buildings on top, against a blue background with a white airplane.

“Lords of Serendipity,” which publishes next week, reflects Boyagoda’s commitment to the pursuit of knowledge: “I’m supposed to say I learn more from my students than they do from me, but no,” Boyagoda said. “I enjoy sharing my excitement and joy about literature and ideas. There are these moments when you are teaching and you can see someone’s face change because they didn’t know something and then they did. That moment when you’re actually watch someone enlarge themselves is deeply satisfying.”

In literary circles, Boyagoda is often referred to as a Catholic novelist, a description he embraces. “A novelist willing to give shape and voice to contemporary religious experience is needed,” Boyagoda said. “I understand myself as a Catholic novelist, provided that I’m not only a Catholic novelist, I’m also a South Asian novelist and I’m a Canadian novelist. I don’t want to be captive to one label.”

His characters, he said, are subjected to what he calls “Graham Greene character situations.”

“They are trying to do good in a fallen world and realize the most they can do is less harm than someone else would do in that same role,” he explained. “They have to accept they are complicit in something that provides some good thing to others. It’s a very Graham Greene way of thinking about sacrifice.”

The campus green they inhabit is a febrile zone in which lofty ideals and cynicism regularly collide. It’s a place where a traditional holiday college celebration is now an occasion for political protest. Kids freely police one another inside and out of the classroom with social media their constant, ready weapon of choice. International students, knowing their family’s financial futures hinge on their degrees, operate in terror of failure and deportation.

Early readers of the book include Gary Shteyngart and Junot Diaz, both of whom have taught at universities and written comic novels. They each contacted Boyagoda midway through to say, in essence, “You nailed it.”

As biting as “Lords of Serendipity” can be, Boyagoda’s faith in higher education remains undaunted.

“It’s absurd that we live in societies that make the decision to take people between the ages of 18 and 22, when they are most physically capable of contributing to our nations and communities, and tell them, ‘Go away for four years, and read and learn and have conversations,’” he said. “I want students to be aware of what an incredible privilege that is.”

Corrections & Amplifications
Randy Boyagoda is a special advisor on the humanities to the dean of arts and science at the University of Toronto. An earlier version of this article incorrectly said he is a special adviser to the dean of humanities. (Corrected on Sept. 2)