What’s Next: Reinventing Yourself and Your Organization

BY Katie Chambers | December 21, 2023

“While all marginalized groups face barriers, women are especially likely to reinvent their careers, and women of color are even more likely to do so. In part, that’s because the workplace has been alarmingly slow to acknowledge the needs of working moms,” renowned journalist and bestselling author Joanne Lipman writes in her new book Next! The Power of Reinvention in Life and Work. Workplaces have an opportunity to better support and engage with all employees–women included–by recognizing the role of personal change and its impact on career development. 

People are searching for meaningful transformation in their lives and work. For employers, it means they need to know how they can support their workers as they advance in their careers and personal lives. This month, From Day One hosted the webinar “What’s Next: Reinventing Yourself and Your Organization,” a conversation with Lipman about her new book to discover what’s behind this trend and how to reinvent your organization, your teams, and yourself. Fellow speaker Liz Pittinger, VP of global customer success for Stork Club, illuminated how her organization is helping to innovate family-building and reproductive health benefits.

Normalizing the Concept of Reinvention

Lipman was inspired to write the book “when the world shut down” during the pandemic, and she realized there was no roadmap for what was next. “I set forth to look for stories of people who had successfully reinvented themselves, their careers, and their lives; for companies that had successfully made it through major transitions; and to the researchers who study these kinds of things,” Lipman said. 

But career reinventions aren’t limited to times of global change. Pittinger herself experienced career upheaval first-hand, starting with a transition from a role in the Department of Justice dealing with political economic development to a communications role at a Fortune 100 company following her marriage and move to Atlanta, followed by 15 years as a stay-at-home mom, a breast-cancer battle, a second master’s degree, and a return to the workforce in a flexible remote role. “I want to make sure all women know it's okay to follow your own path. These are all different chapters and our own books,” Pittinger said. “The whole idea of a linear career was so 20th century. It didn’t really happen then, and it’s certainly not happening now,” said moderator Steve Koepp, From Day One’s chief content officer. 

Through her work at Stork Club, Pittinger helps provide crucial support to employees facing important life transitions. Stork Club, which sponsored the webinar, is a comprehensive, flexible end-to-end family-building solution. It provides inclusive care for all individuals with family-planning benefits. The company supports various pursuits of parenthood, including covering fertility treatment irrespective of an infertility diagnosis, as well as adoption and surrogacy.

The Reinvention Roadmap

Reinvention is not always the “dramatic pivot” as portrayed in popular culture, Koepp noted. But it does usually follow a pattern. Lipman has developed what she calls the Reinvention Roadmap, with four distinct steps:

Search: Gathering information that will ultimately lead to your transition (even if you don’t realize it yet). 

Struggle: “This is where you're sort of leaving your old life behind, haven't figured out the new one yet,” Lipman said. This may feel like you’re stuck, but you’re actually moving forward and growing. 

Stop: In this phase, you are pulled out of your routine and gain new perspective–this is where transformation truly begins. 

Solution: With newfound clarity through struggles and change in perspective, you finally land in your new transformed form.

Incorporating Inclusive Women’s Healthcare Into HR Policy

As Lipman notes in her book, personal change has a profound impact on the careers of women. “Women typically leave the workplace when they have a baby or when they hit menopause,” Pittinger said. When women are starting families, they are typically in manager-level positions; during menopause, they are in the C-suite. So Pittinger emphasizes the need to support women in those roles especially as they hit these crucial moments in their lives as part of an organization’s DEI strategy. “At Stork Club, we ensure that we are giving a dedicated care navigator to each of these people, who is uniquely positioned to provide longitudinal care. We’re focusing on supporting the member and making sure they have positive outcomes, and providing additional support for their mental health,” Pittinger said.

The speakers, counterclockwise from below left: Author Joanne Lipman, Liz Pittinger of Stork Club, and moderator Steve Koepp of From Day One

In an increasingly remote working world, it becomes that much more important that employees feel supported rather than isolated. Employee benefit programs like Stork Club, Pittinger says, allows women space to have highly personal (and even embarrassing) conversations with experts outside of their organization, rather than with co-workers or HR colleagues, to get the exact support their need. “What I’m seeing HR teams do is they’re creating a culture of trust. They’re pulling the information from their teams, they’re incorporating that information. And then they’re enhancing this parental leave policies, and they’re creating bereavement policies that also include pregnancy loss,” she said. This also means developing benefits inclusive of all identities and lifestyles, such as fertility benefits that are not contingent on a diagnosis of infertility. 

Women’s Aptitude for Transformational Change

Lipman notes that studies at Harvard Business School have shown that when women hit their 30s, regardless whether they have children, they begin seeing a widening income gap between themselves and their male peers, as well as fewer promotions. “That said, the research suggests that women are actually better at navigating change and massive disruption,” Lipman said, because their self-identity is less attached to their job title. They find it much easier than men do, Lipman says, to pivot to alternate identities during times of career change, which can only serve to benefit them on their journey. 

Lipman shares that Prof. Deborah O’Neil at Bowling Green State University has found that women’s career paths are more jagged than men’s. “She calls the last stage of women's careers ‘the reinvention’ because very often as they reach seniority, they are either boxed out by the glass ceiling–they don’t get promotions–or they have careers and are ‘mommy-tracked’ and can’t get the attention to get revved up again,” Lipman said. 

Forced to reinvent themselves, women will often focus on giving back to others or bringing other women along with them on a greater cause. “Women who are 50+ have so much energy and ambition and they are virtually invisible to employers. We are losing so much incredible talent,” Lipman said. Companies should not be afraid to hire older workers, as in reality they may be even more focused than their younger, child-rearing counterparts. 

The Impact of Small Moments on Mental Health

“We're reading in so many different news sources about how unhappy the American workforce is today,” Pittinger said. Lipman writes about the importance of “weak ties” to boost one’s mood, such as a positive interaction with a barista or doorman. This small attitude shift can have big results. “If you have that boost in mood, that optimism, that growth mindset, you're more likely to be able to solve the business problem or the puzzle that you’re trying to work out,” Pittinger said. 

Personal experiences can have a profound impact on our outlook, Pittinger says, which is why Stork Club works to make sure members never have to deal with an impersonal call-center approach to service, especially with something as sensitive and emotionally fraught as fertility and reproductive care. “All of our nurses are also certified mental health coaches,” she said. “We have to be supporting people in a very human and empathetic way.” 

Transformation on an Organizational Level

“In personal life, I talk about the ‘expert companion,’ somebody who knows you well but can reflect back to you your strengths, talents, and potential in a way that is objective,” Lipman said. “There is an equivalent version of that in corporations.” Lipman shares that reinventions often come from not from experts but from people in the trenches who understand a company’s product or culture intimately. She notes several examples–including Viagra and the Mr. Clean Magic Eraser–of products that failed for their initial use but were found to fill an entirely different need through discoveries along the way. “Employees, customers, vendors need to be heard,” Lipman said. Employee listening, whether its tied to benefits needs or product innovations, can be key to an organization’s transformation. 

Editor’s note: From Day One thanks our partner, Stork Club, who sponsored this webinar.

Katie Chambers is a freelance writer and award-winning communications executive with a lifelong commitment to supporting artists and advocating for inclusion. Her work has been seen in HuffPost, Honeysuckle Magazine, and several printed essay collections, among others, and she has appeared on Cheddar News, iWomanTV, and CBS New York.

(Featured illustration by Wildpixel/iStock by Getty Images)


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