‘Still’ Working: Confessions of a 60-Something Hustler

By Diane di Costanzo

Let me start with the moment I realized how contrary the notion of a hustling 60-year-old woman is to the natural order of things, at least as defined by well-regarded research firms. To set the scene: I work in branded content, mostly, which means I read more than my share of decks written to define our clients’ target consumers. Called personas, these consumers are classified according to gender, age, and income. And the 60-plus personas, especially the women, are a case study in ageism.

More specifically, and according to a 2020 McKinsey report, a woman my age may “still” — this word is inserted a legit 100% of the time — be working. But she’s looking forward to “spending more time with family, especially grandkids” and pursuing her passions, which include — per every presentation with stock photos for added clarity — gardening, volunteering, and strolling barefoot in the sand with a white-haired fellow, both parties dressed in light-colored leisure attire.

I had just turned 60 when I looked at the image and had the revelation: This is who (they think) I’m supposed to be — or become —right now. And yet I find myself wanting the next writing assignment, the next project at work, the next big opportunity. No different from how I’ve always felt. No different from the other working women I know. And — here is the real point — no different from men whose careers are still on the rise. 

But back to the marketing presentation’s insight about how women in their 60s report feeling “less confident” about their professional skills, especially skills that involve technology. The conclusion: The best way to get in touch with the 60-something woman would be to send printed material via “direct mail,” as it’s called. 

First, allow me a tiny rant about the persona known as the “digital native,” typically millennials and Gen Z-ers. True, these consumers came of age with computers and digital devices in hand. Literally, in their hands, at all times. But since digital proficiency has been required for virtually every job since the 1990s, your beach-walking gal and her white-haired pal also have 30 years’ worth of experience using these devices, thank you very much. (I’ll also thank you for not sending marketing brochures to my house.)

My second gripe is the less overt but still pervasive assumption that a 60-year-old’s ambition and drive to progress in her career — which is to say her hustle — is on the wane. It is convenient that the job market tells itself (and us) that women in their sixties no longer want to work. That belief supports not hiring women my age and older. And also younger than me, especially in industries that favor youth, such as tech and media. 

That belief has been around for a while. And it’s always been bad for women looking for work. But then, during COVID, it got worse. As the ranks of the unemployed swelled, there was a marked increase in “sex-plus” discrimination — essentially, the compounding effect of being a woman in the workforce while also having another “protected characteristic” such as age or race. Per the New School’s Older Worker Report, employees aged 55 and older “lost jobs faster and returned to work slower than mid-career workers.” Additionally, “older workers who are Black, female, or lack a college degree experienced higher rates of job loss,” according to the same report, and are having a harder time rejoining the workforce. 

There are myriad triggers for what’s sometimes called “involuntary retirement” — and none of them are easily addressed. For one, older workers are more expensive than younger workers: they have higher salaries; their health insurance policies can cost companies more. And, according to a *report written for Millie by TueNight’s Stacy Morrison, applying for less-senior roles as an overqualified woman is seldom a successful strategy. 

Further, younger managers report feeling uncomfortable hiring people who look like their moms. And many corporate cultures are — or like to project themselves as — youthful. Having that older lady jump onto your Zoom call is a bit like having your mom descend the stairs to the basement rec room while you’re trying to chill with your friends. Not cool. And why isn’t she off gardening or enjoying her grandkids somewhere? 

So, what’s a 60-plus hustler to do? Persist, to reference the word made famous by Elizabeth Warren, an O.G. hustler herself. Find inspiration in stories about women who did a great thing — or more great things — at the age of 60 or older. Don’t accept the platitudes that tell us “age is just a number.” I mean, obviously it’s a number. But for women, the larger the number the harder it is to get — and stay — employed. 

Also, start drafting the next phase of your life, putting some of the pieces in place as soon as you can. Even small pieces. Think of it as a giant jigsaw puzzle (because it is). Work the edges. Give it a frame. While you’re at it, share your idea with friends or people who might be able to help you. Create a vision board if you are so inclined (and crafty).  

My plan? Buy a distressed complex of beach bungalows in Thailand, fix it up and live there six months out of the year, running the place, as well as an on-site wine bar and kitchen. Seriously, this is my plan. So, please keep 2025 open for a “TueNight in Thailand” event, where we’ll tell our stories under the rustling fronds of a grove of palm trees and also walk barefoot on the beach dressed in leisure attire. White-haired dudes, optional.

*report not yet published 

Originally Published June 1, 2021.