These Women Are Proof That It’s Never Too Late For A Career Plot Twist

Most of us have heard some version of the same professional success story: Grind hard in high school to get into a good college. Grind even harder in college to land internships that’ll lead to your ideal career path. Parlay said experiences into a first job. And once you break through at the right place, grab onto the nearest ladder and start climbing like hell to the top.

This straight and singularly focused path has well served many a striver, of course. But it’s also a plan that doesn’t account for the fact that life constantly shifts, and we as humans are ever-changing. We constantly outgrow personal interests, relationships, places of residence — and, yes, professions as well. But what happens when the itch to completely change jobs comes after years of investment in another field?

Turn out, if you have an open mind and curious attitude, some pretty incredible things. This is a truism that designer Vera Wang has long understood, even before famously launching her now-cult-favorite bridal line at age 40, an endeavor that has since blossomed into an empire spanning ready-to-wear, accessories, and perfume.

“I’ve done a lot of pivoting in my life; it wasn’t only mid-life, it was mid-teens,” the designer tells me over the phone, right after assuring me with me a wry laugh that 40 is hardly too old to make a significant change. She is turning 76 this year, after all, and is still constantly adapting her professional strategy to both meet her creative needs and the demands of the rapidly evolving fashion industry. But none of that was something she could imagine at age 19, when she was passed over for the Olympics after training as a competitive figure skater for over half her life.

“I had a nervous breakdown, and dropped out of college for a year. I took a year in Paris just to collect my thoughts,” she says, continuing on to share that it was a subsequent summer job at the Yves Saint Laurent boutique in New York City — and a chance encounter with former Vogue fashion director Francis Stein at the store — that led to her working at the legendary magazine for 17 years as an editor. She later left to oversee product design at Ralph Lauren and, well, the whole wedding gown thing? It was something of a fluke. “I got engaged and couldn’t find a dress,” she says simply, noting that this was a time when there weren’t many fashion-forward options for brides beyond working with an haute couture house.

“I was very hesitant to [start my brand] because it’s huge money, huge risk, huge everything,” she says. “But I think when you get to a certain point, there is a moment in your life where you think, ‘Well, this is going to be a big change. I may be taking 10 steps backwards.’” Indeed, it was the kind of moment where you decide whether to lean into the trepidation or run away from it — and Wang decided to go for it, doubts be damned.

Leslie Tessler, founder of cult beauty brand Hanni, felt the same now-or-never pull to begin her line of hero body care products. Over a call one sunny afternoon, she explains the non-linear chain of events that brought her to entrepreneur-hood: burning out in the world of New York City beauty marketing, moving to Argentina with no job or contacts, meeting her husband, having three children, weaving in and out of various consulting gigs, a short stint as a cape designer. It wasn’t until over a decade into this winding journey that she decided to launch her line in 2020. She says by then, at age 40, she cared less about making a change than finding a passion to follow.

“I wanted to do something, but I wanted it to be right,” she says, “And if anything, starting a business later in life teaches you that it’s never too late. There’s no rush: It’s so much better when you feel it in your gut, and you know that it’s the right thing.”

Both Wang and Tessler, of course, had the benefit of at least understanding the industry they were moving within. But each founder discovered that baseline knowledge and years of connections can only get you so far — sometimes you just need to embrace the chaos of trying something new. “When I left Ralph [Lauren], all the fabric people I dealt with, all the embroidery, all the licensees — I supervised 29 lines there — those doors closed,” remembers Wang. “You think you’ll be able to work with all the big fabric houses, but when you go on your own, suddenly no one knows you anymore. So it was a startup for me.”

It didn’t help that this was the early ’90s, when it was less common to veer from one’s set career track, especially as a prolonged work tenure often meant solid heath benefits, a substantial 401(k), and corporate perks. (Remember those?) In some ways, though, being an outsider was the secret to Wang’s success. “I was like, ‘Why do we have all these rules [about wedding gowns]? I didn’t know the rules, and I didn’t care,” she says. “I think that’s sort of what brought the fresh inventiveness to bridal that we’ve done these last 36 years.”

When Tessler began her reinvention in 2020, she had a whole different set of challenges to navigate: “When I left New York City in 2010, digital marketing wasn’t a thing, so I was coming back to a totally different landscape,” she says. “I felt like a fish out of water.” Meanwhile, she was realizing that her brand’s first hero product — a razor — wasn’t resonating with shoppers the way she had hoped, and it was time to change direction. “It was so much harder for me to take this business that was heading one way and just pivot it completely,” she says, noting she’s stronger for the misstep. “So would it have been easier if I had started with body care right from the beginning? Yeah, probably. But would I be as savvy and good at what I do now? Probably not.”

Now, five years in, she’s more passionate about her ultra-hydrating products than ever, an infectious zeal that has helped her land her range in Sephora and build an Instagram presence of close to 50,000 followers. Her story, in many ways, is the antithesis of the breaking-barriers-in-Gucci-mules-and-a-Reformation-top Girl Boss myth, which perpetuated a culture of young, workaholic female founders in the 2010s who hustled around the clock without complaint. Instead, she paused from a draining job that wasn’t serving her and really took the time to figure out what was the right fit for her and her talents. Enter the aspirational career power player of the 2020s: someone with a long, rich, and varied professional background and the fearlessness it takes to use it in a totally fresh way.

This description could definitely be applied to longtime power publicist Sarah Bonello, who made the decision to step away from the world of media wheeling-and-dealing and create her essentials-focused brand, The Park, in her late 40s. Inspired by a well-worn skirt-leggings hybrid she had asked her tailor to recreate, she saw a gap in the market for premium, buttery-soft foundation pieces that’ll fit right into the wardrobe of a woman who wears the likes of Chanel and Thom Browne.

“I noticed that I kept getting stopped wherever I went — like, ‘Where’d you get those pants? Oh, my God, I love those pants,’” she remembers. “You know, my PR career was fine. But it took a lot of my time, and I missed being creative. I was ready for something new.” And while she says her fledgling brand is still too young to be profitable (it just debuted last summer), she’s already landed accounts at Elyse Walker and Net-a-Porter and counts style insiders like podcaster Liv Perez and stylist Dani Michelle as fans. She recently added a range of classic cotton pieces to her lineup; the new season will see some sumptuous velvet offerings. Things are slowly growing, perfect-fit basic by perfect-fit basic.

This is, naturally, one major benefit to beginning again in the midst of your second, third — even fourth — act of life: Life experience generally helps one be measured and strategic in their decisions. It was surely an asset to prolific food and spirits journalist Julia Bainbridge when she decided to join a master’s program to become a psychoanalyst mid-COVID lockdown. Although she was 38 when she decided to make this move, by the time she emerged both from the course and the last vestiges of the pandemic, ready to begin in-field training, she was in her early 40s.

“I do think I definitely lean on some of my past lived experiences to help some of my female patients in their 20s,” she says, observing that some clients have even specifically chosen her based on her therapist headshot. “I guess the fact that I don’t have Botox or do anything to myself shows because they say, ‘We could tell from your photo that you [are not in your 20s] — a lot of the other people who work here are so young, and we wanted to work with somebody who has some life experience.’”

I find this statement both makes me smile, but also fills me with a bit of sadness for the specific ways and work sectors in which our society values age — and the ones that very much do not. As someone firmly enriched in the fashion and lifestyle industry, I know the wisdom of more years is not something cherished equally across all sectors of business. Fashion and beauty are both avenues in which youth is prized as a general aspiration; they tend to be professional circles that are unforgiving to someone who’s had other commitments and priorities outside of their job. This fact is on my mind when I talk to Bonello a few days later. As someone who’s run in the high echelon circles of New York entertainment, fashion, and beauty for nearly three decades — and is both a mother and stepmother — age certainly must have been on her mind when she decided to create a new brand.

“Nobody’s ever made me feel uncomfortable about my age; I think I do it more to myself than other people do it for me,” she says thoughtfully. She notes that she doesn’t exactly broadcast her age, but it’s not something she goes out of her way to hide. “I feel really good about being a working mother, and being able to show my kids you can do anything in life.”

Tessler, a mother of three, offers a similar thought when I ask for an unfiltered take on entering the fast-paced world of beauty founder-dom in her 40s. “My life is a lot more complicated [than it was in my 20s],” she says. “I remember traveling for my job and you’re just up late at night working, and [there’s no crying children].” That said, she’s is far more self-possessed than her younger self. “I think I have more confidence for sure, I see it so clearly,” she says. “I want this for myself, and I want it for my kids. They see what I’m doing. They’re so excited every time they walk into Sephora. That fuels me in a way that I probably wouldn’t have been fueled before.”

And isn’t that kind of clear-eyed drive all anyone needs to get something done, regardless of how many turns they’ve taken around the planet? Plus, Bonello points out, it’s narrow-minded to think of a mid-life career change as totally going back to the beginning. “Trust your instincts, keep learning, and remember: Starting over doesn’t mean starting from scratch,” she says. “You bring your entire past with you.”