Hillary Sobel: Championing Women, Leadership, and Unapologetic Authenticity
Photographed by Priyanca Rao | Trailblazers Empowerment Project
Get to know Hillary Sobel, From Courtrooms to Boardrooms
Hillary Sobel spent more than three decades as a practicing attorney representing clients and protecting their businesses. Over time she realized she wanted to move from “fighting against” to “fighting for.” That insight sparked the birth of Minerva Turning Point Strategies, her consultancy dedicated to helping small businesses grow without trapping their founders in a 24/7 grind.
“If you can’t trust anybody else to do the work, your business becomes your own personal prison.”
At Minerva Turning Point Strategies, Hillary now channels her legal experience into strategic consulting for business owners especially women who want to refine operations, build sustainable teams, and reclaim their weekends.
Watch behind the scenes from Hillary’s trailblazer shoot
A Lifelong Advocate for Women
Hillary grew up surrounded by strong, intelligent women. Her mother, a divorcee in the 60s and 70s, raised her while co-owning a business that eventually traded on the New York Stock Exchange. Her aunt was integral to that success. These experiences cemented Hillary’s commitment to female leadership.
“I’ve always been a champion of women. They are the inclusive leadership. I’m not bringing it to them. I’m supporting it.”
That philosophy extends to her consulting work. Hillary seeks out businesses founded or run by women to help them scale, streamline, and build confidence.
Teaching Women to Tell Their Stories
Hillary is currently developing a course that teaches women to recognize and communicate the power of their personal stories not just in newsletters or bios but in everyday interactions, emails, and meetings.
“I can convey what I want in my pajamas. If I’m doing it well, you won’t even notice.”
Her upcoming class combines writing and speaking exercises for high school students, college women, entrepreneurs, and retirees alike, equipping them to walk into any room with confidence.
“Everybody has a unique story. Tell it your way, every day.”
The Writer Behind “The Cowgirl, the Shark, and Stilettos”
A disciplined writer, Hillary begins every morning with coffee and three handwritten “morning pages” to clear the cobwebs. She publishes regularly on her Substack “The Cowgirl, the Shark, and Stilettos”, a title she first coined in 2012 as a playful answer to what her memoir might be called. Today, that Substack reflects the multifaceted nature of her voice—strategist, advocate, and storyteller.
She is also at work on a deeply personal memoir about growing up Jewish in America, confronting antisemitism, and weaving her own life with broader events in the world.
“It’s a new kind of vulnerability just like being photographed. But it’s something that really matters to me.”
Writing Her Own Story
Beyond her Substack, Hillary is working on a full-length memoir that blends personal history with social commentary. The book explores what it was like to grow up Jewish in America, how she navigated antisemitism, and the ways her own experiences intersect with pivotal events in the wider world.
She sees the project as both a chronicle and an act of courage showing the same vulnerability she asks of her clients. The manuscript threads together themes of identity, resilience, and women’s voices, echoing the lessons she teaches in her upcoming storytelling course.
“This book is my way of telling the whole story of what shaped me, what I’ve learned, and why authenticity matters.”
Hillary’s goal is to help readers see how individual narratives can illuminate universal truths, and to model for other women that they too can claim their story in full.
Building Networks That Feel Like Community
Hillary rejects transactional networking. She has joined LeadHERship Global, founded by Linda Fisk, to create authentic, supportive connections for women worldwide. She’s also served on nonprofit boards and is continually looking for platforms where she can amplify underrepresented voices.
“Find the rooms where you feel comfortable, not the ones others define for you.”
For Hillary, true leadership is about helping others speak first, then finding the courage to step out yourself.
“Your voice is yours. Nobody else can say or do what you can say or do. Use it.”
Unapologetic Authenticity
Hillary’s career and life have been defined by refusing to fit into other people’s boxes from leather jeans and spiked jackets outside of court to her unapologetic approach to leadership. She never confused professionalism with conformity.
One day she spotted one of the judges she regularly appeared before while shopping at Bergdorf Goodman. Hillary was in leather pants and a jacket with chains. The judge, too, was dressed in a beautifully styled, colorful outfit that reflected her personality. Hillary walked right up, smiled, and introduced herself outside of the courtroom. In that moment they both saw each other not just as “attorney” and “judge” but as two women with style and lives beyond the bench.
It’s an encounter Hillary often recalls when she talks about authenticity. To her it proves that authority and individuality can coexist and that showing up as yourself can open doors instead of closing them.
“Be quirky. Be yourself. If people don’t like who you are, they’re not your tribe.”
The Trailblazers Photoshoot Experience
Hillary recently participated in the Trailblazers Project with photographer Priyanca Rao. For someone who hated having her photo taken, the shoot was transformative.
She describes the day as “a warm, comforting cocoon” where she felt completely safe to be herself. The resulting portraits have garnered enthusiastic reactions on LinkedIn, amplifying her professional presence and personal brand.
“I never felt like, ‘Oh my God, she’s taking my photo.’ It was fun. I felt completely safe in this process.”
The experience mirrors the empowerment she brings to her own clients: vulnerability leading to strength, and authenticity leading to impact.
Connect with Hillary Sobel and Minerva Turning Point Strategies
To learn more about Minerva Turning Point Strategies, Hillary’s upcoming storytelling course, or to follow her writing, visit her LinkedIn page or subscribe to “The Cowgirl, the Shark, and Stilettos” on Substack.
Hillary Sobel is redefining what it means to lead with authenticity, to speak with courage, and to build businesses that don’t just grow—but thrive.
Hillary, after successfully practicing law, refocused her attention on advising growing,
mostly women-founded, businesses. Her legal experience with investors, bankers,
accountants, board directors and c-suite executives across a various industries led to a
unique perspective on risk, operations, governance, and market opportunities. With that
knowledge, Hillary brings a distinctive outlook to entrepreneurship for small individual
businesses, franchises, and growing regional and global organizations.
Through her consulting business, Minerva Turning Point Strategies, Hillary combines
strategic thinking and curiosity to identify new pathways to growth. She has been
published in Forbes Women on the intersection of profits and people, and in Medium on
opening hard conversations to expand our understanding of each other. Hillary believes
that business and social responsibility do not sit at odds with each other and supports
clients who participate in and grow with their communities.
Hillary’s passion for storytelling and advocacy find an outlet in speaking and writing.
From her appearance on “The One Problem Podcast” with Avil Beckford to her
Substack, “The Cowgirl, The Shark, and Stilettos” (and upcoming memoir), Hillary
connects current and historical events to the stories of our daily lives.
About the Trailblazers Empowerment Project
The Trailblazers Empowerment Project was created by Priyanca Rao, a portrait photographer who helps women step into their most powerful selves. Each session is designed to honor who you are and reflect back to you the strength that’s been there all along.
Priyanca combines luxury portraiture with deep listening and storytelling, creating images that not only look beautiful, but feel like truth. This project is about visibility, confidence, and transformation. You leave with powerful wall art that reminds you everyday of your highest self.
Apply here to be part of the project.
Be Seen. Be Heard. Be Remembered.
You have a story. You have something to say. Let’s show the world who you are becoming.
📍 www.priyanca.com/trailblazers
📸 @priyancaraophotography
As part of the Trailblazer Empowerment Project by Priyanca Rao, we were honored to photograph Hillary Sobel an inspiring leader whose work aligns deeply with our mission to celebrate women in leadership through intentional, powerful imagery. Priyanca Rao Photography specializes in eco headshots and personal branding photography tailored for women in executive, creative, and leadership roles, including CEOs, COOs, mentors, business coaches, accountants, consultants, lawyers, and authors. Known as a top NYC and Westchester photographer, Priyanca also serves clients throughout Connecticut (CT), New Jersey (NJ), and Long Island, delivering branding photos that elevate websites and social media presence. Whether you’re a founder, healer, or change maker, this women’s empowerment project continues to spotlight authentic voices through meaningful portraiture designed to help you stand out and lead with confidence. These business consulting personal branding photos hopefully help inspire and empower other women who are entrepreneurial and have consulting dreams.
