It started with a DM. In the fall of 2011, amid a midcountry job search from Baltimore to Chicago, I slid into the DMs of a local editor. That following spring I started freelancing for her and the rest, you can say, is not only editorial history—it was the start of a long-lasting friendship.
The boss-to-mentor-to-friend pipeline isn’t rare. Perhaps my favorite example of this often intergenerational relationship is that of characters Rebecca Welton and Keeley Jones in the Apple TV sports comedy Ted Lasso.
When we first meet Keeley, she’s a bubbling model-turned-publicist for football team AFC Richmond and Rebecca, as the club owner, is her boss. In fact, Keeley is a bit intimidated by Rebecca’s “strong and prickly” nature, but eventually the two become close friends—bonding over business, romances and life in general.
In the same way my mentor became more like a big sister to me than a boss, Rebecca helps Keeley grow into the powerful entrepreneur we see in the show’s third and final (?) season. After all, in one of the last scenes, we see Keeley present Rebecca with a business plan for an AFC Richmond women’s team (writer’s note: it was at this point that I started crying because this is the power of female friendship).
Juno Temple, the actress who plays Keeley, agrees.
“Also, just that final moment to have it be with Keeley and Rebecca, that to me was something that was so important because that relationship on and off camera has been something that has changed my life forever for the better,” Temple said in an interview with Deadline. “I also think it has created such an amazing conversation about how female friendships need to be viewed in this industry as extraordinarily important, powerful, brilliant, and uncompetitive, just loving relationships.”
As it turns out, there are both professional and personal benefits to intergenerational friendships in the workplace and beyond. But that doesn’t always mean they’re easy to forge or maintain.
“Before the pandemic, I would hear from millennial women all the time that they felt that their GenX and Boomer bosses were barriers to their rise at work,” says Ann Shoket, CEO of TheLi.st, a private community of high-impact women in media, technology and entrepreneurship. “Millennial women would say that they felt like they were being held back on purpose or that the more senior women at work saw them as a threat in some way. And the GenX and Boomer bosses would roll their eyes at how ‘entitled’ millennial women were or how uncommitted or disloyal they were—how they wanted to zoom ahead without putting in the time or paying their dues.”
Rather than viewing each other as competition, Shoket would advise women from different generations to see their colleagues as opportunities.
“For millennial women, the more senior leaders had insights into rooms they had never been in before,” she says. “And for the Gen X and Boomer bosses, they needed to see millennials as fuel for their continuing ambition.”
In a recent study conducted by TheLi.st and Berlin Cameron & Benenson Strategy Group, researchers found that nearly 60% of women say their feelings of loneliness or isolation have increased as their careers progressed and nearly 53% of women have declined a job, a promotion, quit or stopped working altogether because of the negative impact on their personal life.
“There’s a generation of women who are looking up the ladder at the women ahead of them and seeing what they’ve had to sacrifice, seeing how they’ve had to compartmentalize and they’re like, ‘no, thank you. I’m opting out of that,’” Shoket previously told Fortune.
Instead of opting out altogether, Shoket and others like her are calling on more experienced generations to reach back and pull up their younger counterparts who may also be aspiring to C-suite positions. The COVID-19 pandemic, she says, managed to level the playing field somewhat—offering flexibility at work and advances toward equity and social justice.
“The great reset made us realize that we all want and deserve more out of work,” says Shoket. “And the loneliness epidemic that we’re facing now has underlined how important it is for us to build community and togetherness. The pre-pandemic frictions have to fade away. The stakes are higher now—we’re not just talking about a race to the top. We all want to build careers of meaning. And that requires meaningful relationships with the people we work with.”
