When 65-year-old British Uber driver Malcolm McClean receives a call to pick up passengers at a hotel in Santa Monica, he’s under the impression they just need a ride to the airport. But when he arrives, a millennial couple hops into the back of his Hyundai Sonata and explains that their friend has swallowed a bunch of pills and locked himself in the lobby bathroom. McClean, a certified drug and alcohol counselor who’s been in and out of recovery for years, parks the car and offers to help.
When he enters the bathroom, McClean hears someone flopping around in one of the stalls and knocks on the door. “Greg,” he says calmly, “this is Malcolm, your Uber driver, and I’ve come to help you. Would you be more comfortable sitting in the lobby with me?”
As the door slowly opens, a man nearly half McClean’s age emerges, puts his arm around him and shuffles out of the bathroom. A paramedic is called, who takes Greg to UCLA Medical Center in Santa Monica while McClean, as promised and originally intended, drives Greg’s friends to LAX. Once they arrive, McClean asks for Greg’s number so he can check on him later.
When he does so the next morning, Greg is en route to Passages, the luxury addiction treatment center in Malibu, for a 10-day detox. McClean stays in touch, and Greg invites him to lunch at Passages on his final day, during which he opens up about his depression, pill popping and wealthy family. Despite multiple relapses over the next year, Greg never abandons McClean, who receives a text from him while I’m riding shotgun on his Halloween evening Uber shift.
“Headed back to Passages,” it reads.
The rise of hustle culture is often attributed to millennials, but when it comes to grinding in the gig economy these days, Boomers like McClean are leading the way. According to Uber, 25 percent of its millions of workers are over 50, with more drivers over 50 than under 30. Meanwhile, Boomer homeowners are the fastest growing demographic for Airbnb, and last year, Boomers earned the most money, took on the most gigs and earned the highest ratings on Wonolo, a platform where companies find short-term employees.
“We hear from a lot of older workers and retirees about their interest in part-time work and flexibility,” says Susan K. Weinstock, a vice president at AARP, who adds that the sharing economy provides both, as well as the ability to sharpen cognition by meeting people and learning new skills. More importantly, she says, “A lot of people have never financially recovered from the Great Recession.” Indeed, a 2017 survey revealed that 70 percent of Boomers have less than six months of savings.
My father is among them. After a 40-year career as a management consultant, he was abruptly forced into retirement when the agency he co-owned lost its largest client. And so, at age 74, my dad is now a full-time Uber driver. He only works during the day because he “doesn’t want to be driving a lot of drunks.” Instead, he predominantly shuttles local college students to and from class in my hometown of Fairfield, Connecticut. Dad averages twenty trips a day, seven days a week, resulting in about $2,000 a month. Combined with Social Security, the Uber income results in him taking home between $4,500 to $5,000 a month, which barely covers his expenses.
Still, he tells me that he finds his interaction with Gen Z passengers “fun.” A lifelong New York Yankees zealot, he enjoys busting chops of the predominantly Red Sox fans he drives. “They’re good kids, and I get a kick out of wearing my Red Sox hat with the backward B on it, which drives them crazy!” He’s even driven a student all the way to Ohio — an eight-hour, $580 fare — before turning around and driving home the same day.
Granted, being what amounts to a full-time cab driver wasn’t the retirement plan my father (nor his children) envisioned. For generations, the ideal in the U.S. was to stop working at 65 with a pension and gold watch to live for 20 more years on pensions and government subsidies in Boca Raton. But the combination of Social Security benefits beginning two years later, the abrupt stock market decline of 2008 and humans simply living longer, the notion of “retirement” has become as elusive to many Boomers as it’s long been for millennials. To wit: In 2017, the labor force of Americans 55 and older accounted for about 23 percent of the average annual workforce. (The Bureau of Labor Statistics estimates that by 2024, that percentage will likely surpass 25 percent.) Basically, guys like McClean and my dad can’t afford to quit working, which is why more than 400,000 seniors are doing gig-economy work, according to a study by the JPMorgan Chase Institute.
Forced interaction among younger and older adults in the gig economy is an unspoken component of the current “OK, Boomer” meme — i.e., a collective eye roll from younger generations in response to Boomers’ outdated ideas. Of course, generational griping and stereotyping is nothing new — Gen Xers like me have long been called “slackers” — and not everyone agrees that “OK, Boomer” speaks to deep, underlying tensions. Weinstock, for one, was surprised by it, “because we have a lot of research that shows how much employees actually like to work together, no matter the generation.”
The interaction is also shedding light on a misguided millennial assumption that all Boomers are riding off into the sunset with swollen pensions and million-dollar plots of land purchased for pennies during the Nixon administration. “Like millennials, Boomers working gig-economy jobs are victims of a system in which only the One Percent profits,” says Taylor Lorenz, who recently broke the story on the “OK, Boomer” meme for the New York Times. “Your dad is fucked over by the same policies his generation instituted. No one should be old and have to drive Uber. We live in a rich country and should be better providing for our citizens. When people say ‘OK, Boomer’ they’re talking about the stereotypical old rich white person with power. Boomers working in the gig economy have also lost out, so it makes sense that they’d be able to better relate to younger generations.”
That said, Lorenz balks at my suggestion that increased interaction inherently equates to intergenerational bliss. “Working in a gig economy means you have to treat young people as legitimate because they’re paying your salary,” she notes. “But you could put a racist, traditional Boomer in an Uber all day, and they’d just aggravate their passengers.”
That’s certainly not the case with early eightysomethings James and Inja Yates, who have been rated AirBnb “Superhosts” every quarter for five consecutive years. The biracial, octogenarian husband and wife of 59 years rent out the two-room penthouse suite of their sprawling, 100-year-old home beneath the Hollywood sign — “A View From the Top” — for $159 per night, which comes with an all-you-can-eat breakfast prepared by Inja that includes bacon, omelets, French toast and selections from the guests’ native cuisine. (Mexicans, for instance, might be served fresh tortillas and salsa, while Chinese guests are offered rice porridge.) “Our home is a haven for both the friend and the stranger,” Inja tells me. “You can be white, black or green and walk into my house through the front door. Let’s have something to eat first, then let’s talk.”
Upon my arrival, I’m greeted like a grandson coming home from college. Inja reveals a plate of Asian white pears and persimmons as James, wearing a striking Vietnamese necklace with a shark tooth and white seashells, explains how the challenges they faced as a mixed-race couple help them empathize with diverse guests from around the world. “The earth is one country, and humankind its citizens,” he says, their chosen mantra. “We have students from all over the world stay with us — Korea, France, China — for weeks at a time.” In 2016, the Yates were recognized as one of five of Airbnb’s “Best Hosts” worldwide, and James was selected to carry the Olympic torch during the 2016 Olympics in Rio de Janeiro.
“Nearly half of senior hosts rely on Airbnb to make ends meet,” explains Sam Zuo, a self-professed “Airbnb & Lifestyle Entrepreneur” in his late 20s, who tells me the two biggest challenges facing Airbnb hosts — flexibility and availability — give retirees an advantage since they typically have more time on their hands. (Eighty-five percent of reviews of senior hosts in 2017 were five stars.) “Boomer hosts are unique because they tend to like meeting their guests, socializing and telling stories,” Zuo says. “When I stay with older people, I want to know their life story and hopefully receive low-grade wisdom that I can apply to my life. Such hosting niceties make a big difference to the positive guest experience.”
In warm weather, at the Yates’ home that wisdom is imparted at breakfast served on the roof deck, overlooking the Hollywood sign. Otherwise, a table is set in the small kitchen. During their best years, the Yates have made $75,000 through Airbnb — half of which is used to fund a scholarship for mixed-race students of African-American and Asian ancestry — but Inja says the most valuable component is connecting with younger guests.
“I need the interaction because I get lonely,” she says, noting that it’s easier to talk to young people since her age group is set in its ways. “For example, I think gay marriage is perfectly alright. Look at my husband and me! Do you think it was easy for us to be married in the 1960s? When I think about Airbnb, I feel like God has sent me a gift in the last years of my life. He wants me to be happy. That’s how I feel connecting with young people, sharing our story and learning about theirs.”
Gig work for Boomers extends to public education. Don Blackman, a pseudonym, wakes up at 5 a.m. every morning awaiting a phone call from a staffing agency that coordinates substitute teachers for a charter high school in suburban L.A. Responding to the call is extremely competitive, he says, as it’s usually a matter of seconds before the opportunity slips away. “If I’m too late accepting and some other motherfucker sneaks in I’m out of luck,” he tells me. The gig pays $140 for six hours of chaperoning students and executing a lesson plan provided by the school.
Most important in this role, Blackman says, is an ability to connect with teenagers. “I’m loose and slip in little jokes to kinda shock the kids — like, ‘Do you know how we won the Revolutionary War? We kicked British ass!,’ which gets a lot of laughs. The kids think I’m fun because I don’t give a fuck. You don’t want to do the work? Fine, you’re not cheating me.”
For a journalism project, Blackman’s students asked if he’s experienced ageism in the workplace. “That’s like asking if I think there’s inequality for women in the workplace,” he says. “Of course there is. The older generation is never welcomed into the workforce by the younger generation because nobody wants to hire their father! Let’s not forget that Eskimos put seniors on a fucking ice floe and pushed it out to sea because they couldn’t afford to feed them.”
In addition to subbing, Blackman and his wife house and feed international students for $1,000 a month, which roughly covers their food budget. The financial support certainly helps, but he says having millennials and Gen Z borders keep them relevant, as the students come to depend on him and his wife for advice on career decisions, education and life goals. “We Baby Boomers have been greedy,” he admits. “We haven’t shared shit, haven’t done a goddamn thing for the climate and want it all. That’s a legitimate complaint.” Poor intergenerational relations, though, he views as a one-way street: “There’s no antipathy from Boomers toward millennials and Gen Z, at least not in this house.”
Likewise, while riding alongside McClean, I observe him effortlessly engaging with young passengers about buying first homes and founding startups that create air traffic control systems for drones. One young rapper plays a yet-to-be-released song on his phone, after which McClean bursts with enthusiasm about the “socially aware lyrics” representative of the human dilemma. “It’s wonderful that millennials have a completely different style of the future,” he says. “This generation gets pigeon-holed as being lazy and entitled, but I don’t see that at all. They’re inspirational.”
Obviously, to Lorenz’s point, McClean’s rosy attitude toward young people is likely partially due to being reliant on them to pay his salary. After all, McClean was well on his way to becoming another “old rich white guy” after decades earning six figures as an executive with Univision, K-Rock and founder of a handheld laser company. But a contentious divorce drained roughly half of his net worth and left him paying $4,000 a month in child support on top of a $6,000 monthly mortgage. Shortly thereafter, the mind-altering substances took hold. “I got into a relationship with a woman in Denver who introduced me to Molly, and I soon found myself wallowing and directionless,” he says, explaining he began smoking crystal meth and dropping acid daily on a beach in Santa Monica. “I was selling the last of my [stock] to survive.”
And now, he’s shuttling costumed millennials on Halloween, and doing so with a smile. A female passenger in a bee costume frantically calls to explain she’s mistakenly left her wings in McClean’s trunk. “I hope you didn’t leave your stinger!” he says, happily returning them at no cost. As he pulls up to Urgent Care to drop off Alfredo, a young man whose wife has just given birth to their first child, McClean jokingly requests that they name the baby “Malcolm,” after him. “It’s a girl,” Alfredo corrects, to which McClean replies, “Okay, Malcom-cita?” When a young mother dressed as a cat gets out of the car in Manhattan Beach, he waits in the parking lot while she walks to her apartment building. “I feel a responsibility with women to make sure they get home safely,” he explains.
Upon confirmation that she’s okay, he switches the Uber app to “offline.” He’s made $49 on seven trips in under three hours, matching his morning shift, which calls for a stop at his favorite on-the-job restaurant — 7-Eleven, which he tells me “has great burritos, especially at 2 a.m.” Tonight, he only orders a hot chocolate, his go-to end-of-shift treat, sipping it on the ride home. Satiated and content, McClean reiterates the joy he finds in assisting younger passengers, offering wisdom and receiving connectedness in return.
He could potentially receive much more from Greg, the millionaire addict he rescued from the hotel bathroom, who has expressed interest in investing in BiOptix, McClean’s stick-on bifocals invention, for which he’s seeking $300,000 for a 35-percent ownership. Greg says he wants to help, after he pays his parents $8 million to buy them out of the family business, which he anticipates doing in six months.
McClean remains cautiously optimistic, but either way, he’s grateful for having connected in the first place. “If it happens, it happens, and it will be magical given how we met.” Until then, though, for five or six hours a day, seven days a week, like my dad, he will continue chauffeuring people born after his 30th birthday, grinding the gig economy while sneaking 7-Eleven frozen burritos — very possibly until the day he dies.