My daughters, who are 4 and 2, have requested the same bedtime story almost every night for the past month: When I Grow Up by “Weird Al” Yankovic. (Yes, that Weird Al.) If you haven’t had the absolute delight of reading it yet, a boy named Billy gets up in front of his class to answer the age-old question, “What do you want to be when you grow up?” And his answer is long-winded, to say it politely. He starts going through a lengthy and very unique list of potential professions. He might be a snail trainer, a giraffe milker, a gorilla masseuse and roughly a dozen other things, in rhyme, while his classmates and teacher try to keep up.

Somewhere around the 20th reading, I started thinking about the question the whole book is wrapped around. “What do you want to be when you grow up?” is singular. It asks for one tidy noun. And every adult in a kid’s life asks it in earnest, usually in the same tone we use for “what’s your favorite color,” as if there is one correct answer out there and the job of childhood is to find it.

Also, for the record, the book was written by a man who earned a degree in architecture before becoming a famous accordion-playing parody artist, which I’m guessing is not a career path any guidance counselor has ever suggested. I’m open to being proven wrong on that point, though.

Earlier this year I wrote about “ the career-confused era ” and leaned on Herminia Ibarra’s research showing that, when it comes to careers, knowing is the result of doing. This article started as a follow-up to that one with a fairly neat thesis: we ask children what they want to be as if there’s one answer, but most careers now run in seasons. So I reached out to Ibarra to test it.

The Question Assumes A Ladder

The question “What do you want to be when you grow up?” made a lot more sense when the career it was preparing kids for looked like a ladder. One field, maybe even one employer, and a steady climb that eventually leads to a retirement party with a dry sheet cake.

That model was already starting to wobble for the baby boomers. According to the Bureau of Labor Statistics, people born between 1957 and 1964 held an average of 12.9 jobs between the ages of 18 and 58, and more than 40% of those jobs came before they turned 25 . Today, the median worker has been with their current employer for 4.1 years, and for workers ages 25 to 34 it’s 3.0 years .

Ibarra, the Charles Handy Professor of Organisational Behaviour at London Business School, has spent decades studying what happens in between those jobs. Her book Working Identity and a 2026 Annual Review paper with Sarah Wittman and Kendall Smith both describe careers that move in nonlinear transitions, each one requiring people to renegotiate who they are professionally. Not just once, but over and over again, like riding It’s a Small World at Disney World on a loop.

Basically, the question we nonchalantly dish out to every 5-year-old is asking them to plug a destination into Google Maps, even though most of the adults asking it no longer have one themselves. What they have instead is a sequence.

During our phone conversation, I asked Ibarra what we’re teaching children about identity when we ask what they want to be. She paused before answering. “I hadn’t thought about it like that,” she said.

Her research is built on the idea that identity is multiple. So instead of asking “who do I want to be in five years’ time,” she favors keeping a running list of possible selves that intrigue you right now, and then testing them. But she wasn’t convinced kids were the ones who needed the lesson. “I don’t know if I would do that with kids, though, because I think kids are agile,” she said. “They’re like, ‘Okay, I want to be a firefighter today.’ It doesn’t mean that they’re not going to be a football player the next day.”

In other words, the kids are OK, because they treat the question as just a question and not with the rigidity of an obligation. Adults, however, tend to put more pressure on themselves and how they answer the question. “We ask everybody, ‘Who do you want to be in X amount of time?’ Like there was a singular answer,” she said. “And of course, I think that’s wrong.”

Her fix for kids isn’t a new question but rather a better follow-up. When a child announces they want to be a police officer on Monday and a fashion designer on Wednesday, she’d skip the career counseling and go straight to “That’s great. How can I support you to do that? What can we do to check it out? What would your day look like? What is it you actually like about it?” My take as a parent: leading with inquisitiveness instead of definitiveness is what helps instill a journey mentality as opposed to the need to find a singular destination.

‘It’s Very Hard To Express Them All At Once’

The idea of careers running in seasons is exactly where Ibarra’s next book is headed. The Bonus Years: Reinventing Our Longer Work Lives , out January 2027, looks at workers over 50, a group living and working longer than any generation before it, and she hears the seasonal language constantly. “I’ve done this, and now it’s time to do that,” is how she summed it up. Not because the earlier chapter was a mistake, but because that chapter reached an end.

One common version goes a lot like this: “I did follow my passion or my calling, and I gave it all, but I don’t want to kill myself for it. And now what I want is to have a more sustainable life.” Another is the person who climbed high in one field and now wants room for a different kind of creativity.

“We have a lot of different facets to who we are and things that we value,” Ibarra said, “and it’s very hard to express them all at once.” Which, when put that simply, makes sense.

A season isn’t a lack of commitment but rather a way of taking turns. Ibarra added one important caveat, though. Seasons aren’t entirely self-selected. “It’s a combination of what you want and what the market values,” she said. “You’re always talking between both of those things.”

‘What We Need Is Allowed To Change’

Ibarra’s book is about people over 50, but the seasons don’t always wait that long. Kayla Kleinman , a writer and creator who spent several years as the entire social media team at Bookshop.org, the online alternative to Amazon that supports independent bookstores, has already lived through a few of them, and she isn’t anywhere near 50.

Before the pandemic, she taught 16 yoga and barre classes a week, which she loved and which was running her into the ground. When studios reopened, the pay didn’t come back. So she went back to what she’d studied (she has a master’s in social media and mobile marketing) and landed at Bookshop.org, where she ran its social media, including Threads so enthusiastically that Meta noticed. She was also, by the end, racking up at least nine hours of screen time a day across six platforms. “I have a permanent dent on my pinky from when Threads launched,” she joked when we spoke on Zoom.

She left to go all in on her own content, and it didn’t pan out. Then came more than 100 job applications in a market she described as “atrocious.” The hardest part for her wasn’t the rejections. It was accepting that the thing everyone saw her as good at was no longer the thing for her. “What do you do when you know you don’t want to do this thing that you’re, quote-unquote, ‘good at’ and really specialized in?” she said. “I have my master’s degree in this.”

Today her work looks a lot more like Billy’s list. She works the front desk at a Pilates studio, a job she describes as “the right amount of mindless.” She co-leads a social media coaching program with an author. And she writes her own Substack and takes on brand partnerships. “There’s the two things that are stable in my portfolio career, so it gives more room for the other thing to be less stable,” she said.

She has made peace with the earlier chapters, too, including the woman teaching 16 classes a week. “That was a season of my life, and I’m grateful for that season and what it taught me,” she said. “But now we’re in a different season, and what we need is allowed to change as well."

‘Being Able To Leave And Feeling Ready To Leave Were Two Different Things’

Kleinman’s seasons ran one after another. For Kamana Bhaskaran , a content creator with more than 270,000 followers on Instagram, two of them ran on top of each other for more than a decade. While she built a corporate career, first at Meta in Singapore and then as a program manager at Medtronic, she was also building an audience around South Asian home hacks, many of them passed down from moms and grandmothers, which took off during the pandemic. Her days started at 5 a.m. with an hour of editing and brand emails before getting the kids to school, then filming at lunch, more editing after bedtime and batch filming on Saturday mornings. “It absolutely felt like running two marathons at the same time,” she recounted to me via email.

For five years, brand partnerships and affiliate income matched or exceeded her corporate salary. By the market’s measure, the next season had already started. She stayed anyway, which is the part of Ibarra’s caveat that’s easy to gloss over: sometimes the market signs off on a new season long before the person living it does. “Being able to leave financially and feeling ready to leave were two different things,” Bhaskaran said. She wondered who she would be without a corporate job. Having been raised by a single mom, she put a premium on financial stability. And she still wasn’t sure about the durability of content creation as a career. What finally moved her to commit to it in August 2025 wasn’t one viral video or a single big brand deal. It was years of consistent income from multiple sources, and wanting more time with her kids without feeling stretched in two directions.

Even now, she treats the move as a season. She’s giving herself a year to see how full-time content creation goes, her content is shifting toward practical ways moms can use AI at work and at home, and she hasn’t ruled out a return to corporate work. “I’m starting to give myself permission to have seasons,” she said. The slowest thing to change has been her answer when another adult asks what she does. At first she led with the résumé: “I previously worked at Meta and Medtronic, and now I do social media.” Lately it’s simply, “I’m a content creator, and I run my own business.” It’s the grown-up version of Billy’s list of possible professions.

Which brings me back to my own two munchkins, who laugh wildly at Billy the giraffe milker and his extraordinary list of potential professions. They, and their peers, are going to grow up watching adults navigate a lot of different things: layoffs, AI reshuffling entire job categories, parents changing directions at 40 or 55.

When I spoke to Ibarra, I asked her what we should be saying to them while they watch us figure it out.

Her answer was to let them in, at an age-appropriate level. Talk to kids about how you make career decisions, she said, partly “so that they infer the right things,” and partly because if you’re going through a tough stretch, saying “I’m trying to figure it out” gives them “license then to go through times when they’re not so sure.”

I pushed back a little, because that’s honestly hard. Every parent I know wants to project stability, and ambiguity feels like the opposite of that. She agreed there’s a line. “This is an anxious generation of kids coming up, and we don’t want to raise their anxieties unnecessarily,” she said. Nobody needs to walk a 6-year-old through a midlife crisis. Her suggestion was refreshingly old school: bring your kid to work. Give them a window into what your days actually look like, and let them decide what they like and don’t like about it.

Bhaskaran’s kids get a version of that window because she’s often recognized at Indian grocery stores and restaurants. When a stranger stops her to say a hack made their life easier, her kids hear firsthand that what their mom does helps people.

‘All These Things Are Possible’

Toward the end of our call, Ibarra mentioned she was planning to order When I Grow Up for her step-grandchildren. Not because children need to be taught about their 10 possible selves, but because “it’s nice to be able to say, ‘Okay, today I want to be this, and tomorrow I want to be that,’ and all these things are possible.”

When I mentioned the book to Kleinman, who grew up on Weird Al with her brother, she immediately decided her 4-year-old nephew also needed a copy.

The question we ask every kid was built for a career that no longer exists. But kids, it turns out, already know how to answer it, just like Billy did. They answer it in seasons, without anyone teaching them how.

Somewhere between career day at school and a first performance review, the question picks up a deadline, and we start believing that the plan we had at 20 has to be the one we’re stuck with at 45.