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How to Redesign Your Life After 50 with David Stewart

“Stop talking about it, and start doing it. I don’t want to hear about you talking about what your problem is or why you can’t do this. Just do it.”

These are words of tough love from David Stewart. Not exactly what you might expect from someone at the helm of AGEIST, a global collective focused on the 50-plus generation. The fact that we don’t talk that way to anyone over 50 is exactly the point. 


“If you’re talking to somebody who is younger, it’s all about aspiration, right?” says Stewart, founder of the self-described ‘global movement of people living better and longer than ever before.’ “Then suddenly, at a certain age—40, 50, 60—it’s not about aspiration anymore. It’s about treatment of medical symptoms, and it’s like, who wants that?” For the last four years, Stewart has been running a company with a mission to inject more aspirational imagery and messaging for the over-50 set. It was working as a photographer in the heart of a youth-centric industry that brought him here.


“I’ve done maybe a thousand advertising campaigns,” says Stewart, whose body of work includes photographs for Harper’s Bazaar, Esquire, multiple covers for The New York Times Magazine, and more. “I started to notice that I kept taking pictures of people the same age. When I started, I had my first ad in Vogue. I was like 23 and, 30 years later, I’m still taking pictures of people who are like 20. I thought, ‘Well that’s kind of curious, isn’t it?’ All of the stuff that was aimed at people my age—it was all this really disempowering, medicalized, and ultimately infantilizing imagery and messaging. I thought, ‘I don’t feel like that. Nobody I know feels like that. What’s up with this?’” With AGEIST, Stewart and his thoughtful team are working to reinvent how life after 50 is lived, embodied, experienced and—perhaps most importantly—understood. 

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A shift often happens at mid-life, and it’s not typically a desire to retire. “For the people that we know,” says Stewart, “what happens is, in their 40s, they start to have this glimmer of something. They’re not quite sure what it is. There’s just something, and then it seems like in their early 50s…this tipping point of experience has been reached. This becomes really the first time in people’s lives that they’re able to look back at what they’re good at and what they’re not and what they like and what they don’t like.” 


According to Stewart, when that shift happens, people say one of two things: “I love what I do. I’m going to double down,” or “Let’s do something else.” The first is more common, with the shift coming in the form of a second parallel career, but there are also radical pivots, like going from investment banker to yoga teacher. But how do you reimagine life after 50 when culture focuses on youth? To Stewart, it was simple: focus on possibilities. In AGEIST’s case, that means rich stories of second careers, journeys, and unconventional switch-ups. The goal? “To change the framing of people in our age group as something aspirational,” he says.


“We want to expand people’s imagination of what is possible,” he continues. “We’re all only limited by our imagination, right? So, if I show you, and I say, ‘Oh, you can go to law school at 59, and you can learn all this stuff, you can learn Japanese. You want to move to Shanghai and learn Mandarin and run a company? You can do that. Absolutely. Here, this person did this. They’re not different from you.’” 


Stewart talks excitedly about a recent interview with set designer Jocelyne Beaudoin. “Three years ago she was saying, ‘I don’t know what I’m going to do. Digital has crushed the whole print advertising business. I’m not quite sure. I’ve got a kid going to school.’ Three years later, she has this international modeling career. She’s represented by Art Department and she does big-level cosmetic campaigns.” Yet, in order to make these transitions, Stewart is quick to point out, “you need to have a certain level of consciousness and you need to be in the right life circumstances that allow you to reflect. If you’re dealing with other crises, this doesn’t happen.”




Radical shifts don’t happen in a vacuum, says David. “We show how people did it and the process. But that’s not enough. You need to talk to another human being. We’re filled with this whole set of delusions of who we are and what we’re good at. Some of that we know really well, but a lot of it, we’re clueless. We need to have somebody else say, ‘Oh, well actually you’re really good at X, Y, Z. You should maybe look at that, and here’s how you do that.’” You can hire a career coach or guru for this, sure, but Stewart’s own experience proves that the new perspective you need might be much closer to home.


“I’m lucky enough to be married to an incredible person, and she’s told me probably for 10 years, ‘You’re really good at telling stories. You’re really good at explaining things. You should be a public speaker.’” Stewart took those words to heart, and his speaking career is now flourishing.




“There’s a societal assumption that [as you age], you’re incapable of learning or growing, you’re not curious,” says Stewart. “These are only limits that you put on yourself, but people oftentimes believe that to be true, and people, employers, and coworkers, may believe that to be true. That’s a problem.”


How did we get here? It turns out youth-obsessed mania is a fairly new phenomenon. Up until the late 1920s, your age was immaterial, says Stewart. Nobody cared how old you were. Aging was revered. He points to movies from the 1950s. “Grace Kelly was dressing like she’s 50. Why? Because she wants the gravitas of somebody who’s 50.” The sexual revolution in the 1960s changed that. “There was all this energy, and it was great. Everything became focused on that, and that kind of hasn’t gone away.” 



The lack of aspirational messaging doesn’t just affect lifestyle choices. American culture is rife with what Stewart calls “age siloing.” It’s affecting work culture and resulting in homogenous teams and ideas. “The most robust ecosystems are diverse ecosystems,” says Stewart. “If you have an organization that’s entirely people of one age group, they are going to be entirely blind to a whole set of things. Fostering intergenerational relationships is absolutely key.” To understand the importance of intergenerational relationships, Stewart points to what happens without it. “If you only have younger people from a certain culture running a company, you get the whole tech bro—you get Uber is what you get. You get a train wreck.” 




Just four years old, AGEIST’s growth has been tremendous—and its demographics surprising. “We started this extremely primitive newsletter for 50 of our friends, which is now close to 20,000,” says Stewart. It’s not just 50-plus readers who are tuning in. According to Stewart, almost half of AGEIST’s readers are under the age of 45, and about a quarter of them are under the age of 30. “We don’t do any promotion, we don’t advertise. The only way someone knows about us is if someone told them,” he says. “And in spite of that, about 65 percent of our audience is in the U.S. We have people in Pakistan, Guangzhou, Brazil, Singapore…we’re big in the Gold Coast of Australia. What we’re talking about here is a global movement.”


Underscoring AGEIST’s growing impact is that brands are turning to Stewart for his insights on an older age group. “In the beginning, nobody wanted to talk to us. They were just like, ‘Oh, this is all old people.’ We were the people that they ran away from,” he says. “But now, I get a major brand calling me probably once a week that wants to work with us. That was not the case back then. In the last eight to 10 months there’s been a huge shift. The difference that we feel is rather dramatic. We’re doing a really major event in June with really heavyweight people.”

The big brands are pivotal for wider changes. “This isn’t going to be driven by somebody passing a law or making a refrigerator magnet or some other silliness,” Stewart emphasizes. “What’s gonna happen is—and I know this is happening because we’ve worked with these people—you’re going to see the big, major brands moving into this area. That’s what’s gonna move the culture.’’


Who’s already doing a good job? “Rachel Comey is the bomb,” Stewart enthuses. “She gets it. You look at her Instagram feed, there are people of all colors, all ages. And when they’re showing people that are a little older, they’re not showing them as these circus acts. Which is what a lot of the default stuff is. Like purple-haired granny on the turntables. Really? It’s infantilizing. So, what I like about Rachel Comey is she says, “No, these people, they are who they are. They’re this age; they’re really strong and they just own it.’” 



To make those life-changing arcs after 50, Stewart believes you have to stay two things: curious and healthy. “All of these things come down to being curious and taking action. What works for you may not work for me,” he says. “For me, there’s a whole set of behaviors that I do. I’m very careful about what I eat. I’m very careful about exercise. I’m super careful about my sleep.”

It’s no surprise that Stewart isn’t one for one-size-fits-all advice. AGEIST’s profiles speak for themselves. In the end, it boils down to mindset and motion.


“It’s about actually doing things and being out there manifesting things. That’s where the magic happens,” he says. “It’s not so much about thinking. Somebody said to me, ‘You don’t think yourself into right action. You act yourself into right thinking.’”

Story by Pam Majumdar as featured in the ninth issue of UNDO MAGAZINE. 

Photos by Jack Mckain


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