True Career Success Doesn’t Have A Shelf Life

To say it’s not easy to be a woman is a vast understatement. Still, the idea of “having it all” is ages old, a cliche by now certainly, and yet it still colors so much of what we do. But what if we broke away from those ideas and simply created our own ideas for success by which to measure our lives? And what if we chose our own time frames in which to achieve them? Our worlds of possibility might expand beyond our imaginations.

In this entrepreneurial age, we’re looking to some women whose careers have taken them on magnificent journeys into their work, and also into themselves. They all found success, as they define it, after the age of 40 in industries ranging from prose and performance to beauty and business. Incidentally, all of these women also view success for themselves in unique ways, from time well spent to community development to personal balance.

When, for generations, women have been told they have an expiration date, Mira Jacob, Jo Weldon, and Rea Ann Silva prove what a laughable idea that truly is. Ahead, they each speak to TZR about their interesting (and often disappointing) journeys to the top ... however they choose to define it.

Mira Jacob, 50

Professor at The New School & Author of A Sleepwalker’s Guide to Dancing; Good Talk: A Memoir in Conversations

For 20 years, Mira Jacob had been trying to get her work published. She had spent time “failing up the corporate ladder,” as she says, in editorial positions at various media companies before she sold her first book, The Sleepwalker’s Guide to Dancing, a novel about a patriarch who starts talking to his dead mother, in 2014 at the age of 41. For context, this project was 11 years in the making. And while Jacob was delighted to be able to publish her novel, her own definition of success started elsewhere. “For me, success actually meant less getting published, [and more] spending my days doing mostly what I wanted to be doing,” she said. “As often happens to brown women, you get promoted a little and take on the workload of all your superiors. [With my first novel,] my days were spent working from eight o'clock in the morning to eight o'clock at night with a short break to feed my son. And then I would try to write from 11 o'clock at night to one in the morning. And so I knew that was not the balance I wanted, obviously.”

Selling her first book changed her life, but the only reason she was able to finish it was because she was unexpectedly laid off. At that point, she didn’t want to be tied to her desk anymore, and for six months she and her partner moved to Barcelona with their son. “I edited my novel, and I did my freelance assignments, and it was six months of living this other way,” she says. “What I learned in that moment was, if you get to control what you are doing with your days [...] you are, oh, I don't know, like 100 to 150% happier.” Success for her now means finding that fine balance between work and personal projects, though she says some weeks are still better than others.

Another version of success for Jacob was, of course, literary, specifically in the form of reader responses to her novel, especially from those who had tragically lost loved ones, as in her book itself. “It occurred to me in a much deeper way that this thing that you do just for you is actually a thing that can reach other people in a real way. Just to be seen that way felt enormous…to be needed for the things that I alone can bring to a piece of paper, which is my humor and my intellect and my heart.” Jacob explains that she had been writing in a vacuum for so long, that she felt nothing she did mattered, that the world would keep spinning without her. But hearing validation from readers that her work indeed mattered to them was deeply moving and inspired her to take more risks.

“As a woman of color who is publishing over [the age of] 40, I can tell you not many people are looking for you to be a success, and certainly not [back] in 2014. You're lucky to be in the room and constantly told that, especially in those years,” she says. “I remember understanding this thing about myself that I knew they didn't know about me, which is that I can try and become more than they could ever imagine.”

For her next project, 2019’s graphic memoir Good Talk: A Memoir in Conversations, Jacob taught herself how to draw, how to use InDesign, and how to make her own fonts. “I did it because I knew they were not looking for a woman in her mid-40s to teach [herself] how to draw to tell that kind of story,” she says. “I set up rules and a world where I could make a format to tell a story in a way that I had never seen it told before.” Others saw the beauty in it, too: Good Talk’s review in The New York Times noted its “grace and disarming wit.”

Jacob’s inspiration to create and move forward continues: “If I'm gonna bet on something in this world, it's gonna be me,” she says. “I do think that we are primed to believe that aging is a horrible disease, that you must look away from when it happens lest you also catch it…but you do realize that if you're not aging, you're dying,” she says. “Like, those are the only options, guys.” Now, Jacob has learned to continue cultivating trust in herself, finding creative challenges rewarding. “Never take somebody else's word for your own expiration date. Nobody else can possibly say when you're no longer viable to do something. Nobody knows that but you.”

Jo Weldon, 60

Headmistress, The New York School of Burlesque; Author, The Burlesque Handbook, Fierce: The History of Leopard Print; Anti-Censorship and Sex Workers’ Rights Activist

Jo Weldon initially became a stripper because she was fascinated with the tease-y show style that we now know as vintage burlesque (although it didn’t have a label at the time). She quickly learned modern stripping wasn’t like that, though she did still enjoy it. “I liked the cash, I liked the flexible hours, I liked the spandex…I wanted an intense lifestyle as well, and I got that,” she says. But upon moving to New York in 1997 to become a writer, which had always been one of her goals, Weldon discovered the neo-burlesque scene and a place for herself in it. It was everything she liked about stripping and creating acts, but with none of the club management, she says.

Weldon also found the writing community in the city supportive. “The only artistic community I'd spent a lot of time around was rock and roll, the music industry, and hair metal bands, and they were not nice to each other for the most part. Then, going out among writers, artists, sex workers, and burlesque performers, everybody was out to help each other,” she says. She sought out other writers and performers and created a community and connections for herself.

In 2004, Jo Weldon founded the The New York School of Burlesque, and named herself Headmistress. “Every time I tell somebody who doesn't know very much about burlesque that I'm the Headmistress of [the burlesque school], they'll ask, ‘How did you get that job?’ [I tell them] I made it up, I gave myself that title, I started that business. And I don't think everybody should have to be an entrepreneur to be successful, but I think for me that was the way to go,” she says.

A few years later another dream of Weldon’s materialized, when she went on to publish and sell her first book, The Burlesque Handbook, at the age of 47. Some 13 years after its release, the guide remains an essential burlesque text. Weldon felt successful publishing the book because she says it servs both herself and her community of burlesque artists. “I'm not a martyr, but I also don't feel like I'm doing enough if I'm just meeting one of my own ends,” she says, adding that she defines success “mostly in terms of whether or not I'm doing what I say I will do. I tend to take on too many things at once, so when I feel like I'm delivering on my promises, fulfilling people's needs, and getting my needs met, I'm in a successful moment.”

Weldon’s career is also multifaceted. She’s proud of her work as an anti-censorship activist; of working as a lobbyist at the UN for sex workers’ rights; of working and writing for the sex workers’ rights movements alongside activists like Carol Lee, who came up with the term ‘sex work.’ She has also become a fashion historian. In 2018, she published the book Fierce: The History of Leopard Print, and in the last three years has been writing and presenting about sex workers’ influence on fashion in academic journals and conferences. She is currently a resident scholar with the New York Public Library’s Center for Research in the Humanities. In 2022, she contributed an essay to director Lizzie Borden’s anthology Whorephobia: Strippers on Art, Work, and Life.

For Weldon, a career is an ongoing process, one without an end game. "Success is a fluid thing, not a static thing. I had some successes before I was 40, but I felt like I really went after what I actually wanted in my 40s,” she says. People shouldn’t second guess themselves out of opportunities, she continues. “I had assets and resources and health when I was young that I don't have now. But I have experience and knowledge and networks and connections and people that are true to themselves in my life now that I did not have when I was young. It isn't a trade off. These aren't crumbs,” she says. “Assets shift. Value what you have going for you, value the people that support you, and do not sweat the people that don't.”

Rea Ann Silva, 60

Founder and CEO, Beautyblender

Rea Ann Silva’s path to being the founder and CEO of Beautyblender is by her own description a zigzag. She began as a makeup artist for music videos, and later film and television. Then she began doing makeup for celebrities on the red carpet, and later became the makeup department head for Girlfriends, one of the first television shows shot and broadcast in high definition. Her career has included movies that have since become iconic, like Friday and Set It Off, television shows like Moesha and The Hughleys, and artists like Whitney Houston and Eve.

Beautyblender came to be in 2003, when Silva was on the Girlfriends set and needed to make touchups seamless. “I had no idea what I was doing at the time, in terms of being here 20 years later still talking about Beautyblender. I thought I was creating a tool for makeup artists only, I didn't expect it to be a consumer product,” she says. “That happened, and then that provided me the opportunity to be able to dream bigger and focus on what I like to call the hot dog and the hot dog bun…you can eat a hot dog on its own, or you can eat the bun on its own, but it's so good together, right?” Indeed, Beautyblender has since expanded from tools to makeup itself. “So these two kinds of categories, between tools and complexion, that I'm honored to be able to play in now are like the culmination of just everything.”

Silva’s career has not been without hardships, she says. She had to learn how to understand finance and all of the ins and outs of her own business, from forecasting and planning to production schedules and job delegation, things she didn’t initially think about as a makeup artist. “Through those challenges, I learned more. And I'm smarter now. And I'm stronger now,” she says. She encourages people to do the same. “Learn everything. Don't become complacent because you can afford to, either timewise or financially, offset your responsibility to someone else. I have to delegate, I can't do everything, but don't delegate blindly. If you're delegating a task in an area that you don't understand, take the time to delegate it to a person who you believe is an expert and then learn from them. You have an opportunity to learn and become smarter, and you'll only become stronger as a business person, as a leader, as an inventor by doing that.”

Now, Silva defines success as balance, something she’s been learning throughout her 25 years as a makeup artist. “I didn't know how to relax. I always felt like there was something I needed to be doing. Now I can pace myself a little bit better. There are days still where my life is out of balance,” she says. “But at least I know the difference. Before I only knew pedal to the metal.”

Silva is concerned that social media forces us to put pressure on ourselves and feel like we’re running behind, but she believes that being an entrepreneur is actually about the long game. “Entrepreneurial experience is taking yourself through all the paces, the ups and downs of growth, and challenge and success and celebration, all those things that go into creating a well-rounded brand,” she says. “If you're just winning, winning, winning all the time, what do you really know?” She believes failure is essential to growth, that it’s an opportunity to make yourself better, and that success has no time limit.

“Hello, we are now as human beings living a lot longer. So is after-40 really later in life? Or is it midlife? I don't know. There are people who are 80 years old, still being vibrant and productive in life and active in their physical bodies. I don't think those old standards apply anymore,” she says. “My advice would be to not act your age. See the world through the most positive and beautiful lens you can find because life is great. And it's only that way if you make it that way, you know? You can make things bad, you can make them good. I choose good.”