“It’s hard to teach determination, but if you’ve had setbacks, and you’ve had to fight to get to where you are, it is built in you to keep going,” says Nicola Free. “It’s how quickly you bounce back, what learnings you take away, that can make you even stronger.”
With a career shaped by determination, hard-won resilience, and a commitment to leading with integrity, Free does not just navigate change — she drives it. She reflects on how embracing risk, learning from inspirational leaders, and trusting in both her existing skills and her capacity to grow have been central to her journey.
Taking Risks and Having Faith in Herself
From an early age, Free learned to be a self-starter. She reflects, “I came from a very working-class background and went to the worst school in Warwickshire. I had to teach myself my GCSEs because the classes were so disruptive.”
Determined to “do something with my life and make my parents proud,” Free was the first in her family to attend university, where she pursued law. However, it did not take long for her to realize that the legal path, while hard-earned, was not where she wanted to stay. When a client she had supported on a major securitization project invited her to help launch a CMBS platform, she made a decision that would completely change her career.
“It was definitely a big risk,” Free admits. “I would never have anticipated that I would have left the law a year after qualification, but this new opportunity sounded really interesting.”
Jumping into a completely new environment, Free recalls that “a third of it was in my comfort zone and two-thirds I was learning from scratch.” Free leaned on what she knew: her work ethic and resilience.
“Have confidence in the skills you bring, work hard to learn what you don’t know, and don’t give up at the first hurdle. Be willing to take a leap of faith. Ultimately, it’s about believing in yourself; that you’ll get there, and that you can do it.”
That mindset has carried her through ever since. Today, Free is a recognized leader in her field. As Head of Commercial Real Estate (CRE), EMEA for Wells Fargo, she is driving the firm’s CRE strategy across Europe, strengthening its capital markets capabilities, and deepening client relationships in the region.
“It’s a hugely exciting time to be a part of this business and the opportunity ahead of us…this is the year that the strategy is all coming together.”
Leading with Humility and Authenticity
When reflecting on her leadership approach, Free emphasizes the importance of clarity, humility, and authenticity.
“I always try and bring people along with me,” she says. “Give them a vision of what the strategy is, what we’re trying to achieve…make them feel like they’re part of something really special.”
She continues, “it’s about leading with integrity, humility, and doing the right thing for the business, the clients, and the strategy we’ve set for ourselves.”
Mentoring and feedback are important elements to how she leads. “The only way I managed to make a success of my career change was having good people around me who were prepared to coach and teach me,” Free says. “It’s incumbent on us all, particularly as leaders, to be that player-coach where you take the time to give people feedback and help them develop.”
She recognizes that it is also about holding oneself accountable when things go wrong and ensuring others are recognized when they go right. “When things are going really well, make sure people are getting the credit.”
Find a Culture that Aligns with Your Values and Leadership who Embody It
While Free is unquestionably guided by a strong internal compass, she also highlights the vital role that external factors, particularly an organization’s culture and leadership, play in shaping meaningful career development.
“One of the things I’ve learned throughout my career is to ask: What’s the culture? What kind of institution do you want to work for? At Wells Fargo I enjoy working for a bank that has a strong culture that I can relate to while being guided by truly inspirational leaders.”
Free is particularly inspired by Kara McShane, Head of Commercial Real Estate at Wells Fargo, “who is seen as one of the most influential women in finance.”
“To be able to work for somebody like her is really inspiring…and when you have leaders you trust and respect, you want to do your best for them.” It’s a dynamic she now pays forward to her own team. “I want them to come in and feel they’re part of something great, and that they want to succeed because they believe in me, in the business, and in the leadership above me.”
Be Bold. Own It.
Surrounded by leaders she respects, and serving as one herself, Free is acutely aware that leadership is not just about results; it’s also about presence. For women in real estate finance, that presence is still too rare at the top.
“If you’re a woman running a lending business in this industry,” she recalls reading in Real Estate Capital, “then you’re pretty extraordinary.” The line gave her pause, not out of self-congratulation, but reflection. “I come in and do my day job because I love it and want us to succeed. I don’t think of myself as any different than any other leader. But seeing that made me realize there’s a responsibility that comes with being one of the few.”
It is a responsibility that Free takes seriously. As she has risen through the ranks, invitations to speak and serve on panels have increased, and she uses them to push for broader representation. “I’m always conscious about making sure there are other women at the table, that the panels are diverse, and that we’re holding ourselves and others accountable.”
Her visibility is intentional. Instead of blending in, she embraces standing out.
“There’s a big real estate conference I go to every year,” she says. “You queue to board the flight, and it’s just a sea of men in navy suits. I make a point of wearing something bright and own the fact that I’m not the guy in the navy suit. I’m the woman in the bright red dress. It’s an opportunity to be seen.”
She emphasizes, “Being different can make you more memorable. It’s not just about gender. You might be younger, newer, or from a different background. Whatever it is, don’t be afraid to be visible. Have confidence and own it.”
Outside of work, Free applies the same conviction and focus to her personal life. She’s a mother of two daughters, and a competitive CrossFit athlete.
“I’m a strong working mom, and it demands a lot of my time, but I’m showing my girls what working hard and loving what you do can lead to and I’m not apologetic about it.” CrossFit is her outlet, her reset. “When I am training hard, I’m not thinking about anything other than being in the moment… it’s a really good way of switching off.”
That thread of determination runs through everything she does, whether it’s qualifying for a legal career, shifting into finance, growing a business, mentoring a team, or lifting a barbell.
“When things get really tough, don’t give up,” she says. “If you keep digging in, you’re going to feel so great at the end of it.”
By Jessica Robaire
Business Travel for Professional Women in a Volatile World
Career Advice, Career Tip of the Week!In our latest global World Travel Protection online survey of more than 2,000 business travelers, 70% of women said they believe travel is riskier for them than for their male colleagues. Across every category measured, women expressed greater concern about business travel. Harassment and discrimination were cited as major concerns by 65% of women, compared to 53% of men. Nearly one in six women also reported having either experienced or witnessed harassment linked to gender or sexuality while travelling.
Worries about sexual assault were also high, with 64% of women expressing concern while 46% of men (which is almost half of men surveyed) also were afraid of sexual assault. This is a serious crime and these are not abstract fears, they are real concerns.
To navigate these challenges, individuals can take specific precautions to protect themselves, but organizations also have a duty of care to put robust travel risk management plans in place. At World Travel Protection, we use a practical framework built around three key areas: the Traveler, the Destination, and the Activity.
The Traveler: Knowing Your Profile
Your gender, age, ethnicity, seniority and travel experience can all affect how you’re perceived and treated abroad. A senior woman executive might command respect in one region while facing cultural resistance in another because of societal restrictions. Organizations should invest in inclusive policies that consider travel risks through a woman’s viewpoint – not just generic safety advice.
Before you travel, have an open and honest discussion with your company’s security or HR team. Are you comfortable with the destination? Will you be traveling solo or with a companion? It’s important to voice any concerns, preferences or support needs.
The Destination: Digging Deeper
While most companies assess destinations for obvious risks, such as political instability or health concerns, they may overlook subtler cultural challenges. How are women in leadership perceived? Will legal systems support you if something goes wrong? Are there local dress expectations or religious customs that impact how you should behave?
It’s essential to understand how society functions before setting foot in it. That includes knowing what areas to avoid, what cultural faux pas to steer clear of, and even how local elections or protests might disrupt transport or safety. Travel safety apps, such as our Travel Assist app, send location-specific, live insights and alerts, and help a traveler stay informed, particularly in a changing environment. These tools are essential for understanding whether, say, a local election might increase protest activity, or a cultural event could impact transport links.
The Activity: What You Do Matters
Different business activities expose travelers to different levels of risk. A journalist covering a political story may draw public scrutiny or unwanted attention, while a woman attending closed-door meetings may avoid such exposure. In contrast, a woman hosting a client dinner in a conservative society might even face hostility or discomfort. We recently supported a woman executive travelling to rural Pakistan. Every element of her trip was carefully planned – from how she dressed and conducted herself to how she navigated armed checkpoints. We also addressed medical access and emergency protocols, ensuring she had support for everything from potential evacuation to food access during Ramadan fasting hours. This is responsible planning.
We offer training specifically for women travelers – covering everything from emergency protocols to situational awareness, how to handle harassment, recognize manipulation, and stay digitally secure. These sessions, whether online or in-person, empower women to travel with confidence and give companies assurance that their duty of care is being fulfilled.
What Can Women Travelers Do
While company support is essential, there are practical steps women can take to feel more confident and in control while traveling. It starts with the fundamentals: dress appropriately for the destination’s climate and cultural expectations, leave expensive jewelry or valuables at home to minimize unwanted attention and assess the safety of attending after-hours meetings when traveling solo.
Accommodation is another critical factor. Always stay in vetted hotels, ideally with robust security procedures. Larger hotel chains often have dedicated security teams and are better equipped to support business travelers. When booking, request a room that is not on the ground floor and is away from isolated stairwells or emergency exits. Consider using simple tools like a portable door lock or wedge to enhance hotel room security.
Above all, trust your instincts. If something doesn’t feel right, it probably isn’t. Don’t hesitate to remove yourself from a situation whether that means stepping away from an uncomfortable conversation or asking hotel staff or security for assistance.
Alcohol and Food Safety
One often-overlooked threat, especially in Southeast Asia, is the risk of tampered alcohol. Methanol poisoning is often undetectable and usually comes from counterfeit or home-brewed spirits. Only consume drinks you’ve seen opened or poured, avoid suspiciously cheap cocktails, and be particularly cautious with local liquors.
Drink-spiking is another real risk, especially for solo travelers. Never leave your drink unattended and don’t accept drinks from strangers even if they seem friendly and well-meaning. It’s vital to stay alert in social settings.
The Taboo Every Woman Should Be Prepared For
Menstruation remains one of the least talked-about but critical travel issue for women. In conservative or remote locations, sanitary products can be difficult to find or even considered inappropriate to sell in public.
For example, there is the story of a woman at Istanbul International Airport who spent hours searching five terminals for tampons. She left feeling humiliated and paid nearly $20 for a basic pack. Another woman in China was told that sanitary pads were considered “private items” and not available for sale on public transport. Always carry what you need, even if you don’t expect to need it.
Stay in Touch
A simple tip is to check in regularly. According to our World Travel Protection survey, many women say they want more frequent contact from their employer while travelling, and a third report checking in with family or colleagues as part of their routine. Also, share your itinerary before departure, keep emergency contact information saved and written down, and let someone know if your plans change.
If you have access to a travel assistance app, make sure it’s turned on. The Travel Assist app offers flexible geolocation settings, allowing users to preserve privacy with a 5km radius or, with a quick adjustment, switch to precise location sharing when needed. This means that during a crisis – whether it’s a natural disaster, political unrest, or a terror incident – organizations can accurately locate and assist travellers. Travel should never mean going off the radar.
In today’s volatile world, business travel requires more than just a flight and a printed itinerary. With the right preparation, awareness, and support, executive women can navigate the global landscape not just safely, but with confidence and authority.
By: Kate Fitzpatrick, World Travel Protection’s Regional Security Director (EMEA). Kate has lived and worked in the Middle East, Africa and Europe. In Afghanistan, she was Security Risk Manager for the European Union Delegation in Kabul; in Nigeria, she worked as Security Risk Manager and a Senior Intelligence Analyst for the Bill and Melinda Gates Foundation; in Switzerland as Corporate Security Manager for the TAP Trans Adriatic Pipeline (Europe); and, most recently in London as Director of Security and Safety for Bvlgari Hotels and Resorts.
(Guest Contribution: The opinions and views of guest contributions are not necessarily those of theglasshammer.com)
Heather Plumski: President, Stearns Bank
People, Voices of ExperienceAs President of Stearns Bank, Plumski brings a rare blend of head and heart. She shares how her leadership is driven by values, grounded in purpose, and distinguished by forward thinking with a readiness to own both the good and the bad.
From Part-Time Teller to President
Plumski’s journey started in forensic science before pivoting to accounting, completing her degree in two years. While classmates chased big-city roles, she chose central Minnesota and a part-time teller job that turned into a career.
“I didn’t even know what a credit analyst was,” she recalls. “But it let me work with numbers and small businesses both objectively and subjectively to understand their needs…which I found to be incredibly rewarding.”
Since joining Stearns in 2005, Plumski has led through every phase from underwriting through the Great Recession to helping build the SBA and equipment finance programs. As CFO, she drove strategy. Now, as President, she leads a women-owned, employee-owned institution committed to helping people reach their full financial potential.
“We walk the walk. As employee-owners, we understand the challenges our customers face, and we build solutions that serve them.”
Authentic, Inclusive Leadership
Plumski’s leadership style is rooted in authenticity. “You can’t fake it,” she says. “When you’re aligned with who you are, your decisions get clearer, your leadership gets stronger.”
Her collaborative approach encourages open thinking. “I used to wait until every idea was perfect. Now, I bring it to the table early. It invites feedback and makes the work better.”
She credits her growth to staying curious and stretching beyond her comfort zone. One major stretch? Leading technology. “It was like learning a new language. But I learned I didn’t need to know everything I needed to trust the experts around me.”
Just Keep Going
Plumski pushes back on perfectionism and encourages boldness. “Women often hesitate if they don’t check every box. My advice? Don’t count yourself out – say yes before you say no.”
Her mantra: “Don’t quit on a bad day.” That resilience, she says, has made all the difference.
Coaching, Clarity, and Perspective
Executive coaching has been a game changer for Plumski. “It pulls me out of the weeds. I walk away with clearer thinking, stronger communication, and better perspective.”
Even when she feels too busy to take the call, she never skips it. “I always leave better than I came.”
Empowering Employees, Growing Communities
Looking forward, Plumski is focused on deepening Stearns Bank’s impact from growing employee ownership to expanding inclusive financial solutions nationwide.
“Our Employee Stock Ownership Plan isn’t just a model. It’s a movement,” she says. “When we help our customers succeed, our employee-owners build generational wealth.”
That sense of shared prosperity also drives Stearns’ focus on underserved markets. “We listen first. Then we build whether it’s through our Salaam Banking Division or nonprofit solutions. And by the time the rest of the industry catches up, we’re already on to what’s next.”
Family and the Mountains
When she’s not leading a national bank, Plumski is hiking, running, canoeing and simply soaking in family life with her four kids, husband and extended friends and family.
“There’s something about the mountains,” she says. “They remind me how small we are, and how big our purpose can be.”
By Jessica Robaire
Op-Ed: 5 Ways Women Leaders Can Build a Respect-Rich Workplace Culture
Career Advice, Career Tip of the Week!Workplace incivility, or persistent disrespect, now costs U.S. businesses a staggering $2 billion per day, according to Gallup estimates. That’s not just a human problem – it’s a bottom-line problem. A Harvard Business Review study found that 50% of employees who experienced workplace incivility reduced work effort, and 12% left their jobs.
And for women in leadership roles, the stakes are sometimes higher. When we lead, we’re often scrutinized more harshly and held to different standards. But we also have a powerful opportunity to model a leadership style that encourages loyalty, psychological safety, and measurable success.
As the former CEO of Syms Corp., the first off-price retailer of its kind, I learned early on that cultivating respect wasn’t a luxury. It was a leadership imperative. In a male-dominated industry, I rose to become the youngest female president of a company listed on the New York Stock Exchange. And I did it by building a culture where people felt seen, valued, and heard. That’s still rare. But it shouldn’t be.
In my upcoming book, Leading with Respect, I argue that creating a workplace grounded in dignity is no longer optional – it’s the most sustainable way forward in today’s anxious, fast-moving professional landscape. With 31% of employees feeling disengaged, according to Gallup, now is the time for leaders to focus on improving performance, collaboration, and retention.
Below are five ways women executives can lead with respect and reshape the cultures they’re part of, from the top down.
1. Set the Tone Early and Often
Respect starts at the top. Leaders who model respect and inclusion empower others to do the same. If you ignore microaggressions, tolerate dismissiveness, or let egos dominate meetings, your silence sets the tone. So does your presence.
Whether you’re onboarding a new analyst or presenting to the board, show up in a way that centers clarity, presence, and attentiveness. Respect isn’t about being “nice” – it’s about creating space for everyone to contribute meaningfully.
In team meetings, implement a simple practice of rotating who leads or facilitates. This democratizes airtime and signals that hierarchy doesn’t override value.
2. Listen Like It’s a Leadership Skill (Because It Is)
Too often, leadership is associated with speaking. But in high-performing firms, real power comes from listening. Employees, especially those in early or marginalized career stages, might not volunteer truth unless they trust you’re genuinely open to hearing it. And we know women are interrupted 50% more often than men in professional settings, so let’s interrupt that pattern with active listening. This also builds psychological safety, which makes employees feel more comfortable. When people feel heard, they stay engaged. When they don’t, they quietly check out.
Replace “Any questions?” with “What’s not clear yet?” or “What am I missing from your perspective?” These prompts unlock better dialogue and better data.
3. Respect Boundaries – Yours and Theirs
Respect also means knowing when to pause. In industries where overwork is normalized (“hustle culture”) and availability signals loyalty, boundary-setting can feel risky. But leaders who respect their own limits model sustainability. And those who acknowledge their team’s personal and professional boundaries earn deeper trust.
It’s especially vital for women leaders to reclaim time and enforce boundaries as part of workplace culture, not despite being ambitious, but because of it.
Normalize “focus hours” on team calendars. Publicly support people who decline late meetings or take full parental leave. Set the example without apology.
4. Reward Integrity Over Optics
Too often, loud performers get the spotlight while quiet excellence goes unnoticed. If your culture rewards only visibility, you risk alienating the very people who keep your business running with consistency and integrity.
Women leaders are uniquely positioned to challenge performative cultures by rewarding substance over showmanship. Promote those who lift others, not just themselves.
In performance reviews, build in metrics for collaboration, mentorship, and ethical decision-making, not just revenue or output.
5. Be Explicit About Inclusion and Act on It
Don’t assume that respect will trickle down. Cultures of inclusion must be intentionally built. That means regularly reviewing who’s in the room, who gets airtime, and who’s being overlooked.
When women in leadership elevate others, especially across lines of identity and background, we disrupt exclusionary systems that thrive in silence.
Create sponsorship programs, not just mentorship ones. Advocate for underrepresented voices when promotions, stretch projects, or visibility opportunities arise.
Respect Isn’t Soft; It’s Smart
In the boardroom, courtroom, or C-suite, respect is not a sentiment. It’s a strategy. And while it costs nothing to implement, it pays dividends across every business metric that matters. According to Deloitte, leaders who model respect and inclusion significantly outperform those who don’t.
For women in leadership, leading with respect is also a form of defiance. It says: I don’t have to emulate toxic models to succeed. I can build something better, and I can bring others with me.
In a world where too many companies are quietly cracking under the weight of incivility, women executives have the power and responsibility to lead differently. To lead with respect.
By: Marcy Syms is a social entrepreneur, philanthropist, and the former chair and CEO of Syms Corp., the first truly off-price retail chain in America. Her forthcoming book Leading with Respect: Adventures of an Off-Price Fashion Pioneer (Citadel // August 26, 2025) explores how respect-focused leadership fuels performance and purpose in today’s workplace.
(Guest Contribution: The opinions and views of guest contributions are not necessarily those of theglasshammer.com)
Sally J. Clarke: Entrepreneur and Author
Extraordinary Lives, PeopleFrom leading communications at some of the world’s largest fintech companies to writing novels, building a business, and advising boards, Clarke has consistently evolved while staying true to her values of creativity, integrity, and impact.
Clarke shared with The Glass Hammer her experiences in shaping a career defined by movement, meaning, and a refusal to be boxed in.
On embracing a portfolio career:
“At the world’s largest financial technology companies, I led global marketing and communications over an eleven-year period. I’ve built and sold an online arts business, won multiple awards in the technology industry, published my fiction novel Ringside Gamble, established the advisory practice of Asia’s leading think tank, visited Iran and Kazakhstan on writing assignments, sat on several boards across both the arts and technology sectors, and am now writing two new books. One non-fiction and the other fiction.
“It took me a long time to realise that I am a verb, not a noun. That’s why I now have a portfolio career. From my home in Singapore, I divide my time between advising technology companies solving complex problems, writing, and participating on boards. My career continues to be an evolutionary process, not a ladder, but a landscape.”
On the personal qualities that shaped her path:
“I’m an optimistic team player — resilient and reflective. I was born into a working-class family and had my first job at the age of 14, delivering newspapers in rain, sunshine, sleet, and snow on my not-so-trusty, rusty bicycle. To this day, I can still remember the click-clacking sound the pedals made! I supported myself and earned scholarships through university and two postgraduate Master’s degrees — one in International Finance and the other in Asian Art History. I work hard to stand in the other person’s shoes.”
On living her values in high-stakes moments:
“Thanks to my parents, I have an internal compass forged in tungsten, a North Star I’ve trusted throughout my life. I take time to reflect and rely on qualitative as well as quantitative data when forming decisions.
“In Singapore, I faced significant pressure to tell a potential customer at one firm that we had paid pilots — when the company did not. The same founder misinformed about the readiness of the software, employed bullying tactics and took credit for other people’s achievements. As a consequence I found opportunities aligning to my integrity and transitioned from the firm.
“The second challenge was leading the development and rollout of a content management system (CMS) and the front-end client interface. I pitched and secured USD two million in funding to lead a team of developers, designers, and project managers to rapidly build a web platform for data distribution. When it came time to go-live, self-doubt crept in. Many people told me the CMS would be rolled back — I had countless sleepless nights. But I trusted the process, and the so-called Greek chorus of naysayers was wrong.”
On mentorship and the power of stories:
“I’ve had the honour of working on the teams of some incredible people, such as Michael Rushmore who was pivotal in contributing to the growth of IHS Markit, a company I joined as head of marketing and communications in 2007. Data giant S&P Global agreed to buy IHS Markit in a deal worth $44 billion in November 2020. Michael had phenomenal insights, which I still share to others. For example, “don’t make them have to work it out.” This golden nugget refers to the importance of communicating in such a way that your ideas land.
“Cristobal Conde former President, Chief Executive Officer and FIS and Chief Executive Officer at SunGard is a leader I admire. He was incredibly supportive of the sustainability framework I helped build during my time at the latter firm. At SunGard I won the President’s 100 per cent award.
“I read. A lot. Both fiction and non-fiction. Some of my favourite start up books, Shoe Dog by Nike co-founder Phil Knight, Start Up CEO, by Matt Blumberg, Play Nice but Win, by Michael Dell, and Venture Deals: Be Smarter than your Lawyer and Venture Capitalist by Brad Feld and Jason Mendelson are examples. I am inspired by stories. Indra Nooyi , former Chairman and CEO of PepsiCo, is another business leader I follow, and can thoroughly recommend My Life in Full.”
On how she leads with positivity and empathy:
“One piece of advice that shaped me early on was: “Don’t wait for permission.” It gave me the confidence to lead with conviction, long before I had a formal title. That mindset has served me well: whether I am building global brands, launching a start-up, or navigating difficult company mergers.
“But perhaps more influential than any single piece of guidance has been the example set by the leaders I’ve most admired. They led with clarity, composure, and care, especially in high-pressure situations. They didn’t command attention with noise; they earned respect with consistency. And they made people feel seen.
“Something I’ve carried with me through every chapter of my career is this: always role model the positive. Culture is shaped by what we tolerate, and by what we choose to amplify. So even when things are tough, I make a conscious choice to lead with optimism, empathy, and purpose. It’s not about pretending everything’s perfect; it’s about showing up in a way that helps others believe in what’s possible.
“And finally, I’ve learnt that how you leave matters as much as how you lead. It’s easy to focus on beginnings, but endings reveal who we really are. Whether moving on from a role, a company, or a chapter, I try to exit with the same integrity and thoughtfulness I brought to work itself.”
On redefining success:
“I often tell those I mentor that you can define success on your own terms, but only if you’re brave enough to step outside the conventional path. Early in my career, I tried to fit into other people’s expectations. It wasn’t until I started backing myself that I truly began to build things of value.
“I’ve learnt that leadership isn’t about knowing everything; it’s about being willing to go first, to take risks, and to bring others with you. I’ve built global brands, scaled start-ups, and now manage a portfolio career, and through it all, what’s mattered most is clarity of purpose, emotional resilience and having smart colleagues who challenge you.
“I would also say this: creativity is not a luxury; it’s a leadership superpower. Whether you’re building a business or writing a novel, the ability to imagine something that doesn’t exist yet and make it real is what sets great leaders apart. That, and the ability to walk away from what no longer serves you.
“Your career is not a ladder, it’s a landscape. Don’t be afraid to move sideways, take a leap, or build something of your own and test a hypothesis. Solving a big problem is where the real growth lies. If you opt to build a hobby business that’s fine too. Just define what success means to you.”
On blending purpose with creative pursuits:
“I aim to continue supporting the efforts of sustainable companies using technology to make the world a better place. One particularly impressive firm I have worked with is Yokahu, a leading innovator in parametric insurance.
“That same sense of purpose carries into the passion projects that are a part of my portfolio career. In 2023, Ringside Gamble, a universal story about a young boy with a big dream, was published. Christopher Hatton (Star Trek: The Next Generation, Raven’s Hollow) is attached as producer for the feature film adaptation. I donate a percentage of the royalties to support the purchase of books and school equipment for children in Khao Lak, Thailand.
“With Deborah Overdeput, Chief Operating Officer of Innovative Systems, I’m currently working on a non-fiction book. It features a series of interviews with C-suite women, many of whom have founded their own successful companies or hold senior roles at the world’s leading banks and technology firms. More than a series of personal narratives, it is a testament to resilience, ambition and the power of choice. Each story shares hard-won insights, lessons in leadership and practical guidance for those looking to shape their own future. We’re currently seeking a publisher, with submissions expected to begin in September 2025.
Spacious Presence: The Power of Self-Exploratory Writing
Career Advice, Career Tip of the Week!Whereas when you feel spacious in your presence and perception, you are more capable of holding the whole of life: the ups, the downs, the words and behavior of others, the changes of emotional weather within, and the ever-shifting waves of life.
You’re also able to act from a wider vantage point and feel more energetically centered at work and home. You are less reactive to circumstances, not allowing them to dictate your sense of yourself or the world. Instead, you are grounded in your inner truth.
One simple tool for returning to that truth is self-exploratory writing—a practice that invites clarity, emotional spaciousness, and inner alignment.
The Underrated Value of Simple Practices
The habits that serve wellbeing and inner harmony are so basic, so mundane, and so immediately available, we tend to overlook them—good sleep, anyone?—in search of a magic fix or a peak moment experience. Culturally, we undervalue what matters the most.
Burnout is a consequence of a culture, or internalized culture, that does not prioritize wellbeing. Managing burnout becomes a coping strategy. Within that context, self-alignment and self-care are the origin points of a woman who knows her innate value and that the paradigm won’t change unless how you regard yourself does.
Inner spaciousness can be cultivated through practices such as meditation, breathwork, mindfulness, contemplation, myofascial release, dance and movement practices, grounding—and reflective and expressive journaling.
Writing To Support Emotional Wellness
Author Natalie Goldberg wrote to the power of spontaneous writing to access your first thoughts: “The aim is to burn through to first thoughts, to the place where energy is unobstructed by social politeness or the internal censor, to the place where you are writing what your mind actually sees and feels, not what it thinks it should see or feel.”
When we recognize that emotions are energy in motion, we can get curious about them on the page, which can also help clarify what motives are at play in decision-making. Exploring your feelings, especially the ones you often resist, can deepen your self-understanding, expand your emotional bandwidth and resilience, and point you toward aligned action with your values and intuitive knowing.
Reflective and expressive journaling, which focuses on what’s truly on your mind and heart, has been shown to increase emotional awareness and emotional wellness while enhancing your overall outlook. Ultimately, it becomes a practice in emotional intelligence.
Cultivating An Orientation of Gratitude
People who orient in gratitude experience lower levels of stress and depression and better relationships. With practice, you can improve your ability to tap into the state of gratitude, elevating your “set point” of perception.
Practicing gratitude enhances wellbeing—for example, supporting better rest, less inflammation, and peace of mind while reducing symptoms of anxiety or depression.
Writing to express gratitude can help shift attention away from rumination and heavy emotions, and train the brain to more readily access appreciation. Not only this, but the positive effects on mental wellbeing compound like interest, creating accumulating benefits over time.
Processing Complex Emotions
Writing can also help to unwind and process trauma caught in the body’s cellular memory.
When we feel safe, writing about traumatic events or emotional experiences can help to organize chaotic thoughts, release locked-up emotions, and facilitate mental clarity and resilience long term.
Expressive therapeutic writing has also been shown to support physical health and immune function across a range of conditions, while reducing stress, anxiety, and symptoms of PTSD.
Visioning Yourself in Growth
Expressive writing which focuses on self-reflection, gratitude, and imagining a positive future increases experiences of life satisfaction and happiness. In one study, people who journaled for 15 minutes a day felt significantly less anxiety, distress, and depressive symptoms.
When you uncover and explore a new insight on paper, remember a gift that’s gone dormant, or admit future visions or goals for yourself, you are bringing them into your awareness to galvanize energy towards them.
Neuroscience has found that when it comes to goals, people who very vividly describe or picture their goals on paper (men tend to do so more) are significantly (1.2-1.4 times) more likely to achieve those goals. Part of the reason is writing them down improves the biological encoding process by which your hippocampus drops a pin and says, remember this.
Creating Spaciousness Through Reflection
When you put what is inside on paper through reflective journaling, you create spaciousness—within yourself and between you and your thoughts. Often, you can discover how you truly feel through writing and increase your self-awareness.
When you are honest on the page and guided with revealing questions, you have the ability to externalize and explore the narrative, examine triggers, reveal thought and behavior patterns, recognize values, and reveal truths. Increasing your self-awareness, you can begin to see where you are locked into the past, or into thoughts and emotions, so you can come back to presence.
As Goldberg writes, “When you are present, the world is truly alive.”
Start Now: Five Prompts For Embodying Self-Respect
Why not start now? Here are five journaling prompts related to embodying self-respect that you can write to today.
In the practice of yoga, more than half the task is getting onto the mat. With expressive or reflective writing, more than half the task is getting onto the page.
So often, we stay stuck in the same mental and emotional energetic loops, but self-exploratory journaling in response to powerful questions can open new doors of awareness which allow us into more of ourselves—and more of our lives and our unique leadership.
Aimee Hansen is co-author of This Book Is a Retreat: 101 Soul-Nourishing Questions to Reconnect with Yourself to be released on August 22, 2025 (prior to that, available for pre-order), a co-creation with USA Today bestselling author, Marianne Richmond. She is the founder of Storyteller Within and has led the Journey Into Sacred Expression women’s retreat on Lake Atitlan, Guatemala for the past ten years. As a lover of the questions that open us, she’s inspired hundreds of women in writing their hearts into expansion.
(Guest Contribution: The opinions and views of guest contributions are not necessarily those of theglasshammer.com)
Marie Bober: Chief Compliance Officer and Senior Counsel, Moelis Asset Management
People, Voices of ExperienceFrom captaining sports teams as a kid to speaking up in moments of silence, taking charge has always felt instinctive for Bober. “I come from a really long line of very bossy women,” she laughs. “I think it’s probably genetic.” While her grandmothers ran their households with authority, her mother broke barriers, becoming one of the first women to earn a PhD in chemistry from NYU in 1972.
That inherited sense of purpose shaped Bober’s own unconventional path. She started college as a chemistry major but quickly pivoted to psychology. Drawn to forensic work, she earned a master’s and spent three years at a pediatric psychopharmacology lab at Massachusetts General Hospital researching ADHD and pediatric bipolar disorder.
“My plan was to go on to get my PhD, but research itself started to feel like a tough long-term path with low pay, questionable ethics in some corners, and not a great ROI if you wanted a sustainable career.”
Still captivated by the intersection of law and human behavior, Bober pivoted again, this time to law school at Northeastern University. Being a part of Northeastern’s distinctive co-op program allowed her to try a little bit of everything: working with a solo practitioner, in a judge’s chambers, the DA’s office, and an in-house legal team.
“In-house was by far my favorite, but you don’t just go from law school to in-house,” says Bober. Instead, she built her experience through small firms, auditing work, and ultimately opened her own practice while keeping her eye on the long game.
Bober’s diligence paid off when a friend offered her an in-house legal role at Gracie Asset Management, a Moelis subsidiary. The only catch was the job was in New York, which meant that Bober and her wife had to live long distance for a few years. When Gracie had a key man event resulting in steep layoffs, Bober moved over to the parent company. After a few internal moves – and the sudden loss of a friend that left a senior counsel role vacant – she was promoted into her current role as Chief Compliance Officer and Senior Counsel at Moelis Asset Management.
Breadth that Delivers
Looking back on what has helped her succeed, Bober points to adaptability and a breadth of knowledge, both of which are essential in a role that spans legal and compliance.
“To be in this particular role, you can’t be rigid or precious,” she explains. “We’re an entrepreneurial business…everybody’s got to do a little bit of something, and you have to be okay with that. We’re always thinking about new strategies, markets to tap and ways to get clients. It’s flexibility and a willingness to pick up the next thing and learn.”
Bober points to the growth of the business as another part of what requires adaptability: “when we started, we were private equity. Now we’re private equity, broadly syndicated loans, direct lending, seeding of emerging managers, venture capital.”
As the business expands, so too does Bober’s knowledge base, which is necessary for her to guide legal and compliance issues.
“I call myself a triage nurse because there are certain areas that I’m deep in, like fund formation or structuring, but then I also have to be able to direct counsel for things like litigation, tax matters, or employment. I might not be an expert on all those issues, but I must be conversant enough so that my subject matter experts can direct me effectively.”
What They Didn’t Teach in Law School
Beyond technical range and flexibility, Bober believes that one skill rises above the rest when it comes to lasting success: knowing how to navigate people.
“How to handle and approach people is key; it gets you so much further than even your technical knowledge,” she emphasizes. “One of the things law school doesn’t teach you is that if you’re a practicing lawyer in a firm, networking is 98% of your job. To be a partner at a law firm means that you bring in a good amount of business.”
Bober adds, “My boss likes to joke that he thinks that my psych degree sometimes helps me more than my law degree because it definitely gives you a framework for understanding people.”
That understanding shapes the way Bober communicates, builds relationships, and earns trust, especially in the context of leadership and knowing how to manage in all directions.
“Managing up is a skill that’s rarely taught, and it matters just as much as managing direct reports. I’ve learned how to communicate differently depending on who I’m talking to, and how to present something in a way that gets the right response.” As Chief Compliance Officer, she often needs people to act on specific requests and ideally, do so with genuine buy-in. “I’ve seen people try to lead through fear or pressure, but that only works for so long. Eventually, people tune you out.”
It is a message she impresses on junior staff as well: “be proactive, message appropriately, be polite and respectful, and if you make a mistake or get it wrong, have the ego to walk it back and take responsibility. It builds trust.”
Leadership as a Team Sport: Fostering Growth Over Competition
In an industry known for individual ambition, Bober takes a different approach to leadership; one that is shaped by hard-earned lessons and a clear sense of the kind of environment she wants to create.
“I’m a competitive person,” she says, “but I try not to be competitive at work. That’s not the environment I want to foster.”
Earlier in her career, Bober saw firsthand how toxic leadership can erode trust. She recalls a former manager who guarded her influence closely and refused to use any of her political capital to support others.
“When my mom passed away, I got two days of bereavement. Other department heads had given people the full week, but my boss told me if I wanted the extra time to attend the funeral, I’d have to use vacation days. She didn’t want to spend any of her political capital justifying why I was not billing or there for that week.” That experience left a mark, but also a guidepost: “It taught me exactly the kind of leader I don’t want to be.”
Now, as a senior leader herself, Bober sees mentoring others not as a threat, but as part of what defines strong leadership. She draws inspiration from Brazilian Jiu Jitsu, a sport she trains in outside of work.
“My coach always says he never hides the best parts of his game because if someone can master it in two weeks and beat him, they deserve to win.” The same philosophy, she says, applies in leadership. “Helping my associate grow, bringing her along and giving her what I can to help her succeed doesn’t threaten me; it strengthens the team, and if I ever move on, she’s ready to step in.”
Success, On and Off the Mat
Whether she is preparing for a Brazilian Jiu Jitsu tournament in New Jersey or aiming for another podium finish at Masters Worlds in Las Vegas, Bober brings the same focus and drive to the mat that she brings to her role at Moelis. A two-time Masters World Champion as a brown belt and now a black belt competitor, she thrives on the discipline and challenge of competing and on the fulfillment it brings outside the office.
That mix of ambition and purpose is intentional. “I strove to have an in-house position. I strove to have work-life balance in my career,” she says. “And I think I’m in a spot where I can do both.”
For Bober, success is not about chasing the highest title or the biggest paycheck. It’s about feeling grounded, challenged, and able to pursue what matters. “I can sing in a rock choir on Tuesday nights. I can do jiu jitsu. That’s what makes it all worth it.”
By Jessica Robaire
Why Protecting Time for Deep Thought Makes You More Productive and More Alive
Career Advice, Career Tip of the Week!And yet, consider how many leaders spend their days: back-to-back meetings, two-line email replies, quick notes on a presentation or report. It’s all understandable—the organization’s engine is humming, employees need decisions, and a leader’s job is, among other things, to stay in touch broadly across a team or organization. It’s no wonder leaders often feel that they succeed based on their ability to task-switch as much as their ability to set a vision and galvanize a team.
Or more simply: Your calendar is probably packed. If there’s no time for lunch breaks, or even a bathroom break, there’s definitely no time for leisurely, expansive, deep thought. According to Dorie Clark in Harvard Business Review, 97 percent of leaders say long-term thinking is critical, and 96 percent of leaders say they don’t have time for it.
The reason frenzied executive calendars continue to exist for so many executives is that, in the short term, it is a functional way to get things done. Peers, teams and clients want discussions, an answer, an approval. That’s what they need to do their jobs. What we sometimes forget as leaders, amidst all the organizational bustle, is that it’s our job to tend to the visionary, strategic questions before they become threatening, existential questions. When we operate only in a place of stimulus-response, we’re actually playing out of position—like a goalie who’s left the goal. This might work for a while, but when a competitor shoots and scores because we weren’t protecting what was most important—our ability to think broadly, creatively, strategically—we lose.
Deep thought is important because as leaders we’re not usually measured by the quantity of our output. We’re measured by the quality of our thought. A brilliant vision. A unique understanding. A counter-intuitive strategy. A prescient decision. These are things that drive careers and businesses. No one was ever promoted for their email response time. Warren Buffett knew this and once said, “I insist on a lot of time being spent, almost every day, to just sit and think. That is very uncommon in American business.”
Deep thought is also important because it’s a beautiful way to spend our time! Warren Buffett ended the quote above not by saying, “I [sit and think] because it drives shareholder value.” He ended it with, “I do it because I like this kind of life.” It can be incredibly nourishing and invigorating to be lost in thought; to find a state of “flow” in which we’re so immersed in our thoughts that everything else seems to slip away.
Unfortunately, deep thought, as you likely know, is not easy to protect. And women managers often face the additional, biased expectation of being “a pleasure to work with”—available and attentive to others’ needs. It’s completely understandable why a female leader would be more inclined to return the email quickly, bolstering her reputation for being responsive, even when her time is better spent thinking deeply. It’s not an unbiased world. And yet we can still find ways to thrive within it.
Here are four things you can do in the next week to start protecting your time to think:
By: Bree Groff is a workplace culture expert and author of Today Was Fun: A Book About Work (Seriously). She has spent her career guiding executives at companies such as Microsoft, Pfizer, Calvin Klein, Google, Atlassian, Target, and Hilton through periods of complex change. She is a Senior Advisor to the global transformation consultancy SYPartners and previously served as the CEO of NOBL Collective. She is a graduate of the University of Pennsylvania and holds an MS in Learning and Organizational Change from Northwestern University. Bree lives in New York City with her husband and daughter.
(Guest Contribution: The opinions and views of guest contributions are not necessarily those of theglasshammer.com).
Nicola Free: Managing Director, Head of CRE, EMEA, Wells Fargo
People, Voices of ExperienceWith a career shaped by determination, hard-won resilience, and a commitment to leading with integrity, Free does not just navigate change — she drives it. She reflects on how embracing risk, learning from inspirational leaders, and trusting in both her existing skills and her capacity to grow have been central to her journey.
Taking Risks and Having Faith in Herself
From an early age, Free learned to be a self-starter. She reflects, “I came from a very working-class background and went to the worst school in Warwickshire. I had to teach myself my GCSEs because the classes were so disruptive.”
Determined to “do something with my life and make my parents proud,” Free was the first in her family to attend university, where she pursued law. However, it did not take long for her to realize that the legal path, while hard-earned, was not where she wanted to stay. When a client she had supported on a major securitization project invited her to help launch a CMBS platform, she made a decision that would completely change her career.
“It was definitely a big risk,” Free admits. “I would never have anticipated that I would have left the law a year after qualification, but this new opportunity sounded really interesting.”
Jumping into a completely new environment, Free recalls that “a third of it was in my comfort zone and two-thirds I was learning from scratch.” Free leaned on what she knew: her work ethic and resilience.
“Have confidence in the skills you bring, work hard to learn what you don’t know, and don’t give up at the first hurdle. Be willing to take a leap of faith. Ultimately, it’s about believing in yourself; that you’ll get there, and that you can do it.”
That mindset has carried her through ever since. Today, Free is a recognized leader in her field. As Head of Commercial Real Estate (CRE), EMEA for Wells Fargo, she is driving the firm’s CRE strategy across Europe, strengthening its capital markets capabilities, and deepening client relationships in the region.
“It’s a hugely exciting time to be a part of this business and the opportunity ahead of us…this is the year that the strategy is all coming together.”
Leading with Humility and Authenticity
When reflecting on her leadership approach, Free emphasizes the importance of clarity, humility, and authenticity.
“I always try and bring people along with me,” she says. “Give them a vision of what the strategy is, what we’re trying to achieve…make them feel like they’re part of something really special.”
She continues, “it’s about leading with integrity, humility, and doing the right thing for the business, the clients, and the strategy we’ve set for ourselves.”
Mentoring and feedback are important elements to how she leads. “The only way I managed to make a success of my career change was having good people around me who were prepared to coach and teach me,” Free says. “It’s incumbent on us all, particularly as leaders, to be that player-coach where you take the time to give people feedback and help them develop.”
She recognizes that it is also about holding oneself accountable when things go wrong and ensuring others are recognized when they go right. “When things are going really well, make sure people are getting the credit.”
Find a Culture that Aligns with Your Values and Leadership who Embody It
While Free is unquestionably guided by a strong internal compass, she also highlights the vital role that external factors, particularly an organization’s culture and leadership, play in shaping meaningful career development.
“One of the things I’ve learned throughout my career is to ask: What’s the culture? What kind of institution do you want to work for? At Wells Fargo I enjoy working for a bank that has a strong culture that I can relate to while being guided by truly inspirational leaders.”
Free is particularly inspired by Kara McShane, Head of Commercial Real Estate at Wells Fargo, “who is seen as one of the most influential women in finance.”
“To be able to work for somebody like her is really inspiring…and when you have leaders you trust and respect, you want to do your best for them.” It’s a dynamic she now pays forward to her own team. “I want them to come in and feel they’re part of something great, and that they want to succeed because they believe in me, in the business, and in the leadership above me.”
Be Bold. Own It.
Surrounded by leaders she respects, and serving as one herself, Free is acutely aware that leadership is not just about results; it’s also about presence. For women in real estate finance, that presence is still too rare at the top.
“If you’re a woman running a lending business in this industry,” she recalls reading in Real Estate Capital, “then you’re pretty extraordinary.” The line gave her pause, not out of self-congratulation, but reflection. “I come in and do my day job because I love it and want us to succeed. I don’t think of myself as any different than any other leader. But seeing that made me realize there’s a responsibility that comes with being one of the few.”
It is a responsibility that Free takes seriously. As she has risen through the ranks, invitations to speak and serve on panels have increased, and she uses them to push for broader representation. “I’m always conscious about making sure there are other women at the table, that the panels are diverse, and that we’re holding ourselves and others accountable.”
Her visibility is intentional. Instead of blending in, she embraces standing out.
“There’s a big real estate conference I go to every year,” she says. “You queue to board the flight, and it’s just a sea of men in navy suits. I make a point of wearing something bright and own the fact that I’m not the guy in the navy suit. I’m the woman in the bright red dress. It’s an opportunity to be seen.”
She emphasizes, “Being different can make you more memorable. It’s not just about gender. You might be younger, newer, or from a different background. Whatever it is, don’t be afraid to be visible. Have confidence and own it.”
Outside of work, Free applies the same conviction and focus to her personal life. She’s a mother of two daughters, and a competitive CrossFit athlete.
“I’m a strong working mom, and it demands a lot of my time, but I’m showing my girls what working hard and loving what you do can lead to and I’m not apologetic about it.” CrossFit is her outlet, her reset. “When I am training hard, I’m not thinking about anything other than being in the moment… it’s a really good way of switching off.”
That thread of determination runs through everything she does, whether it’s qualifying for a legal career, shifting into finance, growing a business, mentoring a team, or lifting a barbell.
“When things get really tough, don’t give up,” she says. “If you keep digging in, you’re going to feel so great at the end of it.”
By Jessica Robaire
How to Thrive in the New Workplace: Why Learning Agility is Your Secret Weapon
Career Advice, Career Tip of the Week!Most humans are fascinatingly steeped in their contextual and subjective realities, combine that with stereotypical implicit beliefs and it is cognitively easy to believe that more effort would equal more success. Social psychology meets neuroscience very quickly here to result in false conclusions with real life negative impacts for people when surface thinking instead of systems thinking is applied by HR and leaders.
Why Learning Agility is Your Competitive Edge
Here’s where it gets interesting. The most successful organizations are shifting away from traditional merit measures toward something called “learning agility”— and this change could be your secret weapon. Learning agility isn’t just about taking more courses or earning additional certifications. It’s about demonstrating your ability to adapt, grow, and deliver results in new situations. Research shows that learning agility — the ability to learn from experience — is one of the key characteristics of high-potential employees. Even better, Korn Ferry research shows that people with high learning agility are promoted twice as fast as individuals with low learning agility.
This shift matters because it measures what you can do, not just what you’ve already done. For women who may have had fewer opportunities to build traditional credentials, learning agility creates new pathways to demonstrate your potential.
Four Ways to Build Your Learning Agility Profile
1. Become the Solution Finder
Instead of just executing tasks, position yourself as someone who tackles complex problems. Studies demonstrate that workforce agility enhances not only individual performance but also promotes innovation and effective knowledge dissemination. When challenges arise, volunteer to lead cross-functional teams or pilot new approaches.
Action Step: In your next team meeting, don’t just report on your progress. Come prepared with one process improvement suggestion and offer to lead the implementation.
2. Make Your Learning Visible
It’s not enough to learn—you need to demonstrate how your learning translates into results. Research indicates that learning agility directly affects employee engagement and innovative behavior, but only if others can see the connection.
Action Step: After completing any training or taking on a new challenge, send a brief summary to your manager highlighting what you learned and how you’re applying it. Include specific metrics when possible.
3. Seek Stretch Assignments
Learning agility is best demonstrated through performance in unfamiliar situations. Ask for projects outside your comfort zone, volunteer for challenging assignments, or request to work with different teams or departments.
Action Step: Identify one area where your organization needs improvement but lacks expertise. Propose a pilot project and position yourself to lead it, even if it’s not directly related to your current role.
4. Build Your Feedback Loop
Learning agility requires continuous improvement, which means you need honest feedback. Create a system for getting regular input from colleagues, clients, and supervisors about your performance and growth areas.
Action Step: Schedule quarterly “learning check-ins” with your manager. Come prepared with specific questions about your performance and growth areas, and ask for concrete suggestions for improvement.
Navigating the Transition
Not every organization has made this shift yet, and you may encounter resistance. In 2020 Robin J. Ely and David A. Thomas share in HBR a study named “Getting serious about diversity: Enough with the business case” as a follow up from their 1996 research paper called Managing Differences Matter which included a prediction of an emerging paradigm cited as the learning and effectiveness paradigm. This work may have provided answers if it had of been applied, but the work was not undertaken by most firms at scale. For meritocracy or “diversity” benefits to truly be realized, organizations have to adopt a learning orientation and be willing to change structures, and culture.
If you are in a more traditional environment or an environment now recoiling from their last twenty years efforts, focus on building your learning agility profile quietly while demonstrating clear results.
Your Next Steps
The workplace is changing, and this shift toward learning and effectiveness could be the key to unlocking opportunities that traditional merit systems may have denied you. Start building your learning agility profile.
1. Assess your current situation: Where have you demonstrated learning agility in the past year?
2. Identify growth opportunities: What challenges could you volunteer to tackle?
3. Make your learning visible: How can you better communicate your development to key stakeholders?
4. Build your support network: Who can provide feedback and advocate for your growth?
The traditional rules of advancement may have been stacked against you, but the new rules reward exactly what you bring to the table: adaptability, fresh perspectives, and the ability to learn and grow. It’s time to make that work in your favor.
Work with a coach – book in for an exploratory chat to see if coaching is right for you HERE
By Nicki Gilmour, founder and CEO of theglasshammer.com and Evolved People Coaching
Sam Rapoport: CEO, Blue80
Intrepid Women Series, PeopleSam Rapoport knows that there is value in playing the long game. When it comes to change, she knows that you have to put in an intentional effort. As an out LGBTQ professional, Rapoport also knows that being yourself means betting on yourself.
As a high school and college quarterback growing up in Canada playing tackle, touch, and flag football from a young age, Rapaport honed the ability of making rapid decisions under pressure.
“You have three seconds to get rid of the ball, and you are making a hundred decisions in those three seconds,” she says. “You have five people in your face trying to attack you. I taught myself at a young age to become calm in those moments.”
The instinct to remain focused, fast, and forward-thinking shaped not only Rapoport’s playbook on the field but also guided her career at the NFL (National Football League). Over two decades, she rose from intern to changemaker, pioneering trailblazing work in gender equity. More recently, she made the fearless decision to step away from her full-time role, choosing to share her hard-won lessons more widely as a consultant and keynote speaker.
“I want to help organizations around the world achieve progress more quickly,” she explains. “Because this work is so much bigger than the sport of football.”
Learning to Shoot Your Shot
Rapoport’s emergence as a changemaker in professional football began with an unconventional pitch. “In 2003, I submitted a resume to the NFL with an actual football. On the football I wrote, ‘What other quarterback could accurately deliver a pass 3,806 miles?’ which was the distance between my university and the league office. That stood out to someone in HR.” It earned her a coveted internship and foot in the door of a historically male-dominated league.
However, Rapoport’s proudest achievement was not just breaking in, but helping other women do the same.
“For the last 10 years at the NFL, I created a program that served to introduce women into coaching. I took on the Boys’ Club. I took on an establishment that had done things the same way for a hundred years, which was putting men in coaching roles, and I questioned it and then I created a platform that changed the game for women in coaching.”
She continues, “now as of this past season we have 15 women working in full time coaching roles, which is more than double any male professional sports league in the world.”
Rapoport emphasizes that the program’s success didn’t happen by chance. It was the result of years of focused effort and a deliberate strategy, or “a blueprint for accelerating change”. A key element of that blueprint is a framework she learned along the way: the 20/70/10 Rule.
“I have found that 20% of any organization understands what needs to be done to make the change – they’re bought in. 70% want to do the change but have no idea how. And 10% wants nothing to do with it,” she explains. “Focus your energy on moving the 70% into the 20%. Ignore the 10%. The ground moves from under the 10% statistically anyway.” For Rapoport, it’s about shifting the focus from fighting resistance to fueling momentum.
Today, Rapoport continues consulting to the NFL Women’s Forum and is helping build the league’s first professional flag football league, one of her childhood dreams. She is also advising organizations like the USTA (US Tennis Association) on engaging more women in coaching. And one of her latest accomplishments includes working with USA Flag Football on creating a path to the sport being featured in the next Olympics. Finally, she makes sure to leave time for keynote speaking, which she describes as, “probably my favorite part of my job because I can deliver a lot in a short period of time on how to create change.”
On Being Yourself – Truly
As she worked to open doors for others, Rapoport also navigated what it meant to “be herself” in the workplace.
“I wasn’t out in the first decade of my career at the NFL…Everyone always says, ‘Be yourself,’ but that’s easy when you look and act like the default person at an organization,” she reflects. “It’s a lot more challenging when you are a member of the gay community, or the Black community, or the Latinx community.”
She continues, “when I felt confident enough to make the change to come out and be myself unapologetically…I started to thrive.”
Beyond being out at work, Rapoport defines being herself as, “finding the middle ground between professional you and weekend you. It’s about dropping the act, ditching the corporate lingo, the need to sound like a textbook, or mimic your boss, and just being real.”
However, Rapoport is quick to acknowledge the privilege required to let one’s guard down. “There’s a privilege in seniority to be able to do that. Younger people have a harder time.” She emphasizes that safety is paramount, both in professional and personal spaces. “It’s up to the environment. The environment owes it to you to make it safe to come out. I came out when it was safe, and before, it didn’t feel that way.”
Betting on Yourself
When it comes to navigating moments of self-doubt, Rapoport is clear: it’s not about faking it until you make it. “In my opinion, that’s the worst advice you could give anyone. If you fake it, then imposter syndrome kicks in.” Instead, her mantra is “publish and iterate.” Try something, learn from it, refine it, and keep going.
“I have a lot of things, but I don’t have imposter syndrome,” she says. “I’m okay with putting something out there and maybe running away after I do, but I’ll fix it from there.”
She and her wife even have a motto: “We’re betting on ourselves.” Whether it’s stepping into a new gig or turning down one, the calculus is simple: “We’re literally putting all our chips on us. And if it works, great. If it doesn’t, we learn.”
A Pragmatic Path to Meritocracy
With years of experience in gender equity, Rapoport offers an informed perspective of what’s falling short in DEI and what has the potential to move it forward. “We need to stop with these massive pendulum swings,” she says. “It has to be apolitical.” She believes real progress is possible and meritocracy is about removing barriers so that everyone has the same access to opportunities. Rapoport is also adamant that true equity work must be intersectional stating it to be critical to ensure access to all women.
At the heart of her work is a long-term vision that stretches beyond any single organization or lifetime. “I think ahead 100 years, and I think of what the NFL can look like with all genders being ubiquitous,” she says. “With half of the head coaches being women. Half of the general managers. Half of the owners.”
Rapoport is not pushing for dominance, but for balance. “I don’t believe the future is female, I believe in balance, and I believe the future is everyone – equal representation of great people. That’s how you start to take down very destructive structures that hurt marginalized people.”
Outside work, Rapaport is “massively into plants,” plays three instruments, cooks, paints, and has a list of future hobbies she is excited to learn. But her greatest joy, she says, is her family. “I am so proud of how functional and healthy and happy my family is,” she laughs. “And I’m very passionate about putting my energy there over anything.
By Jessica Robaire