This was first evident more than a decade ago when she quit her job as the corporate executive of a Fortune 500 company during a Periscope livestream. “I’m not sure if there’s an alignment of [our] future trajectory. I’m going to work for myself. I'm promoting myself to work for myself,” she said at the time before flashing a smile at the viewing audience. As she resigned on camera, a constant stream of encouraging messages floated upwards on the screen.
By 2021, she’d fashioned her work as a corporate consultant and her personal life with her husband and three adopted daughters into a reality show, She’s The Boss, for USA Network. This year, she released the New York Times bestselling memoir Nothing Is Missing, written as she was in the process of getting a divorce and dealing with her eldest daughter’s struggles with substance use.
Convinced that there’s no way the 39-year-old has achieved all of this without intentional strategic planning, I asked her about it when we spoke less than a week before Christmas. I’d seen videos on social media of her working on 2024 planning for other brands, and I wanted to know what that looked like following her own year of success.
She listed a number of goals, including ensuring that the projects she takes on in the new year align with her identity “as a Black woman, as an African woman, as a mother, as someone who has lived a [rebuilding] season and is now trying to live boldly and entirely as themselves.” But, I was shocked by how much of her business planning also prioritized rest.
Despite the bestselling book, a self-titled podcast, and working with numerous corporations, Walters said she’s been taking Fridays off. This year, she doesn’t want to work on Mondays, either.
“A lot of us think we work hard until retirement hits. I want to progress towards retirement,” she said, noting that she’ll check in with herself around March to see how successful this plan has been. The goal, Walters said, is to only be working on Tuesdays and Thursdays by sometime in 2025. “It is intentionally building out what I know I would like to have happen and not waiting for exhaustion to be the trigger of change.”
"A lot of us think we work hard until retirement hits. I want to progress towards retirement... It is intentionally building out what I know I would like to happen and not waiting for exhaustion to be the trigger of change."
Walters said the decision to progressively work less was partially in response to her previously held notions about her career, especially as an entrepreneur. “When I first started, I thought burnout was a part of it,” she said. “What I didn’t realize is that even if you’re able to bounce out of burnout or get back to it, there’s a cumulative impact on your body. If you think of your body as a tree and every time you go through burnout, you are taking a hack out of your trunk, yes, that trunk will heal over, and the tree will continue to grow, but it doesn't mean that you don’t have a weakened stem.”
But, the desire for increased rest was also in response to the major shifts that occurred three years ago when she was experiencing major changes in her family and realized her metaphorical tree was “bending all the way over.”
Courtesy
“One of the things we have to recognize, especially as Black women, is that there is this engrained, societal, systemic notion that our worth is built around our productivity,” she added. “That is some language that I think is just now starting to really get unpacked.” In recent years, there’s been an increased awareness of achieving balance in life, with Tricia Hersey’s “The Nap Ministry” gaining attention based on the idea that rest, especially for Black women, is a form of resistance. Even online phrases such as “soft life” and “quiet quitting” have hinted at a cultural shift in prioritizing leisure over professional ambition.
"One of the things we have to recognize, especially as Black women, is that there is this engrained, societal, systemic notion that our worth is built around our productivity."
If companies are lining up to consult with Walters about their brands and products, then women have been looking to her for guidance on starting over since she invited them to livestream her resignation 12 years ago. As viewers continue to demand more from content creators in the form of intimate, personal details, Walters has navigated her personal brand with a sense of transparency without oversharing the vulnerable details about her life, especially when it comes to her family.
The entrepreneur said she’d been approached to write a book for several years and was initially convinced she was finally ready to write one about business. “I started to do that, and then I went through my divorce. When that happened, I said, why would I write a book telling people to get the life that I have when I’m not sure about the life that I have,” she said.
Instead, she decided to write Nothing Is Missing and provide a closer look at her life, starting with being born to immigrant Ghanaian parents (“You need to know my childhood to know why I’m passionate about entrepreneurship.”) through the adoption of her three daughters and eventual divorce. Despite her desire to share, however, she said she felt protective of the privacy of her family, including her ex-husband.
When discussing this with me, Walters said she was reminded of a lesson she learned from actress Kerry Washington, who released her own memoir, Thicker Than Water, just a week before Walters’ book release. Washington’s memoir grapples with family secrets, too, specifically the fact that she was conceived using a sperm donor and didn’t learn about it until she was already a successful TV star. While Washington reflects on how the decision and subsequent deception impacted her, she’s also careful to hold space for her parents’ experiences, too. “A lot of things she said was that she had to recognize where she was the supporting character and where she was the main character,” Walter said.
This is something Walter worked to do in Nothing Is Missing when discussing her daughter’s struggles with addiction. “I was very intentional about making sure that I did not reveal more than what was required,” she said. “If I say something about someone’s addiction, I don’t need to go into the list of the substances they used, how they used them, what I found. [I don’t need to] walk into a room and paint a picture of what it looked like for people to understand.”
Walters said some of the most vulnerable moments in the book barely made a ripple once it was released. She was extremely nervous to write about getting an abortion, she said. But no one has asked her about this in the months since the book was released. Instead, people have been more interested in quirkier revelations, such as the fact that she once appeared on Wheel of Fortune.
“I have bared my soul about this thing I went through in my youth that has changed me for people, and people are like, ‘So how heavy was the wheel when you spun it?’” she said, chuckling. “It just goes to show that people never worry about the thing that you worry about.”
With the success of Nothing Is Missing, Walters said she still isn’t planning to release a business book at the moment. But, as she navigates parenting a teenager and two adult children while also navigating a relationship with her new fiancé, Walters said she believes she has at least one or two more books to write about her personal journey. “There is sort of an arc of where my life has gone that I know I’ve got something more to say about this that I think is important, relevant and necessary,” she said.
In just three years, Walters’ life has undergone a major transformation. There’s no telling what the next three years will have in store for her, but it seems likely she’ll retain an inspired audience wherever life takes her.
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With each chop, many of us are wondering what is left of our stories. Issa spoke with Net-a-Porter's digital publication, Porter, amid Rap Sh!t's cancelation. “You’re seeing so many Black shows get cancelled, you’re seeing so many executives – especially on the DEI [diversity, equity and inclusion] side – get canned. You’re seeing very clearly now that our stories are less of a priority,” she said.
While there has been a push for more diversity in Hollywood, and the tides seemed to be changing (i.e., recent Black representation at Emmy's, Golden Globes, and Oscar noms), the number of cancelation of these series tell a different story. The American Fiction star is even looking to possibly change directions in her career. “I am pessimistic, because there’s no one holding anybody accountable – and I can, sure, but also at what cost? I can’t force you to make my stuff. It’s made me take more steps to try to be independent down the line if I have to,” she explained.
Issa Rae at 2024 Emmy Awards
Photo by Frazer Harrison/Getty Images
As of now, Issa is excited to get "back at it" amid last year's writer's and actor's strikes. The actress, writer, and producer has her hand in everything from music to spirits, and we love seeing the growth. However, we first fell in love with the Insecure star from the TV, or if you're an OG fan, the internet, and so we're always anticipating what she creates next.
“I’m writing a couple of different projects – one for myself and one to produce and create with others – and I’ve been feeling so inspired and excited to get back at it,” she said. “I’m embracing that challenge. The industry is in flux, so it’s really inspired me to focus and hone in on what stories I want to tell. I’ve been laser-focused on getting these projects up and running.”
Ten years from now, we may even see Issa in a whole new industry because, according to her, she plans to transition into a life of service. I know that's right!
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Feature image by Tommaso Boddi/Golden Globes 2024/Golden Globes 2024 via Getty Images
