Risk is often painted as reckless, but for many entrepreneurs, the most meaningful growth comes from risks taken with intention, clarity, and courage.
In this feature, Dreamers & Doers members reflect on the smartest risks they’ve taken in their businesses and the pivotal moments that required them to trust themselves despite uncertainty. From bold decisions to quiet leaps of faith, these stories reveal how calculated risk can unlock unexpected opportunity.
Ambreen (Amber) Chaudhry
Founder & Pharmacist of Noori Skincare, a Pharmacist Mom formulated skincare brand for teens and tweens.
Ambreen Chaudhry
My smartest risk: Taking a job on the sales floor of Sephora as a Beauty Advisor despite being a pharmacist with 20 years of experience.
The payoff: I gained real, unfiltered insight into how young consumers think, shop, and misuse skincare—insight that shaped Noori’s entire mission and formulation strategy.
Why I went for it: I began to see how teens were damaging their skin by following trends without understanding the science behind what they were using. I trusted that being on the ground with them would offer deeper, more meaningful insight than any market report.
Anouck Gotlib
CEO of Belgian Boys, creating whole ingredient breakfast options that allow families to prep less, smile more, and indulge better.
Ursula Prinz
My smartest risk: Joining my husband in running Belgian Boys, even though it meant saying goodbye to my job in fashion. At the time, I knew nothing about the industry. We had just gotten engaged, and some people said we were crazy to go into business together.
The payoff: I have loved building Belgian Boys into a brand in over 10,000 retail stores, including Walmart and Target!
Why I went for it: I trusted my gut. My instincts are usually pretty reliable.
Mari Milenkovic
Founder & CEO of With Mari, supporting founders through high touch marketing strategy and immersive retreats.
Jess Koehler Photo
My smartest risk: Building both of my businesses as a fully nomadic founder. Income stability felt uncertain, and growing companies while living across time zones and constant movement required a completely different way of operating.
The payoff: I’ve built work that feels sustainable long term while living in more than 12 countries. Once my business supported my life instead of competing with it, everything became more sustainable and expansive.
Why I went for it: I trusted that the life I wanted required me to build differently and focused on creating systems that could move with me.
Mandi Young
Owner & Founder of Juniper Gardens, a set of mid-century modern wedding venues in rural Missouri that host weddings for couples across the country.
Love Leigh Photography
My smartest risk: Quitting my solid corporate career while simultaneously taking out a massive loan to construct a second location in hopes of making Juniper Gardens my main hustle. The decision could have bankrupted me or just set me back in my career path.
The payoff: Two years later, we have two wedding venues that are fully operational. Our part-time team has continued to grow, too!
Why I went for it: As I left corporate, I couldn’t shake the feeling that it was time to bet on myself. I had made a really big bet to go into a million dollars in debt while being confident that I could still support my family, my small team of employees, and myself. Gathering the courage for that step was simply delusion and blind faith.
Ciara Siegel
Brand, Marketing Strategist & Founder of CJC, bringing the strategy behind billion-dollar brands to small businesses.
Katie Ward
My smartest risk: Walking away from work that looked impressive on paper—big-name brands, award-winning projects, and constant momentum—to build a business I could shape intentionally and grow on my own terms. This meant moving away from a very clear definition of success.
The payoff: I gained sharper positioning, better-aligned clients, and a business that grows on its own terms, while giving me the flexibility I wanted as I started a family.
Why I went for it: I asked myself what would still matter five years from now. The answer wasn’t visibility or speed. It was impact, control, flexibility, and alignment.
Sydney de Arenas
Founder of The Etho, The Hive, Summit Chasers Network, Ítaca, a founder, operator, and strategic force behind multiple purpose-driven brands.
Sydney de Arenas
My smartest risk: Making the terrifying decision to fire almost all of my clients five years into business. I kept only two, because the rest were toxic—draining my team, eroding our standards, and pulling us away from the work we actually wanted to do.
The payoff: I rebuilt a company rooted in aligned values, high-quality work, and mutual respect. What could have been seen as reckless at the time ultimately created a business that generates both sustainable revenue and genuine joy for me and my team.
Why I went for it: Watching my team burn out and my business drift further from what I wanted to build wasn’t sustainable, and the risk of staying was greater than the risk of leaving. Once I accepted that protecting my values and people mattered more than short-term revenue, the decision was unavoidable.
Patty Williams-Downs
Founder & CEO of BreakingBounds®, a consulting firm delivering high impact solutions for business transformation.
Stevie D. Reid
My smartest risk: Starting two businesses at the same time. It stretched me in ways I didn’t anticipate, but it also sharpened my focus. Now, I intentionally keep a few irons in the fire, guided by advice from a business professor who taught me to operate across three horizons: strengthen and protect the core, scale what’s emerging, and continuously build the next viable option.
The payoff: This approach has helped me move from managing chaos to leading with strategy and confidence.
Why I went for it: Ideas flooded my heart and mind in a way I couldn’t ignore, so I knew it was a spiritual calling. From there, I brought in trusted people to shape those ideas into a clear business model.
Fatima Teos
Founder of Vita Nova Media & NJK Partners, a creative studio that helps purpose-led brands grow with clarity through content strategy, brand development, and intentional storytelling.
Nev Photography
My smartest risk: Walking away from a finance career where I was climbing toward the goal I’d announced at 22 (to be the first Latina CEO of a Fortune 500 company) to start over building businesses no one had heard of. I was trading external validation and a clear path for something undefined that only made sense to me.
The payoff: It taught me that legacy isn’t about titles you earn; it’s about the tables you build and the people you sit with.
Why I went for it: I was chasing a version of success I’d outgrown. Staying on that path just to prove a point would cost me everything that actually mattered.
Linda Du
Co-Founder & CEO of Moola Money, a financial guidance platform helping millennials understand their finances, define meaningful goals, and make smarter money decisions with confidence.
Alina Rudya
My smartest risk: Setting up my investment firm with the explicit goal of generating passive income to cover my own salary. It felt risky to step away from traditional employment and to rely on capital structures rather than a paycheck.
The payoff: I decoupled my time from my earnings. Today, the investment firm funds two salaries and gives me the freedom to build long-term projects like Moola Money without financial pressure.
Why I went for it: I reframed risk as staying dependent on an external income stream rather than building my own resilient one. Designing for financial independence first gave me the confidence to pursue more ambitious, long-term work and to enable others to do the same.
Dom Farnan
Founder of DotConnect, embedded recruiting for high growth startups.
Hailley Howard
My smartest risk: Going from solopreneur to building my company back in 2019. My imposter syndrome made it feel risky, and my negative self-talk was at an all-time high. I also used my life savings to fund the payroll for my first team as I tried to land additional customers.
The payoff: Once I jumped off, I never looked back.
Why I went for it: I felt confident that the clients I had would be interested in expanding our scope of work together. I trusted my gut instead of having an in-depth business plan.
Prabhneet Girn
Founder & Chief Executive Officer of Arize Care Consulting, a global award-winning women- and minority-owned public health and social impact consulting firm.
Prabhneet Girn
My smartest risk: Walking away from the institutional legitimacy, predictable income, and safety of a government job to start my company—without a family blueprint or financial cushion to fall back on since I’m a first-generation founder.
The payoff: It allowed me to build work that is fully aligned with my values, voice, and leadership philosophy, and to partner with organizations that trust me not just as a consultant, but also as a thought partner.
Why I went for it: I realized the cost of staying comfortable was becoming greater than the fear of leaving. I recognized that the kind of leadership I wanted to practice—slow, relational, and equity-centered—couldn’t fully exist inside rigid structures, making the decision less about bravery and more about honesty.
Naga Das
Founder of Alternative Coaching Methods, redefining health and wealth through plant medicine.
Jay Barhelios
My smartest risk: Launching a business rooted in psychedelics and plant medicines felt risky because they sit in a gray area. The legal landscape alone limits research and makes it hard to rely on anything other than inner knowing and integrity.
The payoff: Thanks to my leap of faith, hundreds have walked through our doors with broken wings and left grounded, empowered, and ready to fly again.
Why I went for it: By the time I began walking this path, I had nothing left to lose. I was willing to take any risk in pursuit of healing, inner peace, and a sense of true fulfillment. That willingness gave me the courage to move forward without guarantees.
Emma Tessler
Founder & CEO of Ninety Five Media, a woman-owned and operated digital marketing agency.
Emma Tessler
My smartest risk: Deciding to build a team of employees rather than relying on a network of outside contractors. This move directly impacted our profit margins and required a complete shift in how I thought about company structure, team culture, and long-term growth.
The payoff: This decision has shaped how we scale, how we support our employees’ lives, and the level of ownership and commitment our team brings to our clients every day.
Why I went for it: I spent time clearly defining what I wanted the future of Ninety Five Media to look like. With that long-term vision in mind, it became obvious that we needed a team deeply invested not only in their work, but in our clients and the company itself. That clarity gave me the confidence I needed, even knowing the decision would stretch us in the short term.
Lauren Bercuson
Trademark Attorney of Storylock Legal, a modern trademark and IP law firm focused on helping founders build, protect, and scale brand assets.
Daniel Wakfield
My smartest risk: Leaving a stable job as a divorced mother to pursue entrepreneurship. Failure wasn’t an option; I had two children depending on me!
The payoff: Betting on my skills and conviction gave me the freedom to build a firm aligned with my values and ambition. That leap reshaped our family’s future.
Why I went for it:If I succeeded, the greatest payoff would be flexibility, and since one of my children has ongoing health needs that require me to be present and responsive, this was a big incentive.
Bilen Mesfin Packwood
CEO of Change Consulting, a Black-owned impact communications partner that helps movement leaders, nonprofits, funders, and progressive campaigns build narrative power and community.
Bilen Mesfin Packwood
My smartest risk: Hiring my first full-time team member as a communications coordinator. At the time, I already had seven years under my belt as a solo consultant, and I was scared to navigate payroll and go through the hiring process.
The payoff: I found an amazing and committed collaborator and colleague. We are now a team of 14 people, and that first hire is my chief of staff.
Why I went for it: I turned to coaching to help me understand both the mindset and the process needed to hire and manage a team. I continue to invest in coaching to grow my leadership.
Domonique Worship
CEO & Founder of The Institute of Exceptional Alignment, a high-touch leadership development experience reimagining success for high-achieving women and the organizations that invest in them.
Soflo Inspires
My smartest risk: Exiting my career in law and corporate leadership to run my coaching practice full-time. Walking away felt like abandoning everything I’d built—and everything I’d been taught about success.
The payoff: I stopped building a resume and started building a legacy. I now work with Fortune 500 companies helping high-achieving women lead without losing themselves. Recently, I delivered my signature keynote on perfectionism to over 1,200 women.
Why I went for it: Sticking around was the bigger risk: to my values, my well-being, and the work I felt called to do.
Nicole Leon
Founder of L Leon Virtual Assistance LLC, providing high-level virtual and executive support that anticipates needs before they’re spoken, stands steady through high-stress seasons, and delivers unmatched assistance with genuine care.
Samantha Fandino
My smartest risk: Letting go of clients who were no longer aligned with my values, pace, or vision, even when it meant walking away from consistent income. Stability can be enticing, especially when you’re responsible for more than just yourself.
The payoff: I found space for higher-aligned clients, stronger boundaries, and a business that feels sustainable, spacious, and deeply fulfilling.
Why I went for it: Misaligned clients were costing me far more than money; they were draining my energy, creativity, and confidence.
Amanda Hofman
Chief Swag Officer of Go To Market, the anti-boring branded merch and swag experts—changing the way the world handles swag.
Julia Guignard
My smartest risk: Starting Go To Market without any formal background in merch, print-on-demand, or even retail. I was very aware I was stepping into an industry I didn’t know, and there were real moments of doubt as I figured things out along the way.
The payoff: I’ve been able to solve a problem I had experienced firsthand and create a more intentional, sustainable way of doing merch.
Why I went for it: I gave myself permission not to have the entire playbook figured out and focused instead on learning, asking questions, and building thoughtfully as I went. Approaching the industry without assumptions made it easier to see what needed fixing.
Lakeya Cherry
CEO & Founder of Lakeya Cherry LLC, a dynamic executive coaching and consulting business that empowers leaders and organizations to maximize their potential.
Danielle Finney
My smartest risk: Leaving my role as a nonprofit CEO after nearly nine years to pursue full-time entrepreneurship. It felt risky to walk away from a stable salary, a strong reputation, and the work I had spent years building to step into the uncertainty of generating my own clients and income.
The payoff: I built a more profitable business, became debt-free, and paid off my student loans in cash, something that likely would not have happened as quickly had I stayed on a traditional path.
Why I went for it: In one year of running my business part-time, I generated nearly the same income as my full-time executive role, which made me question what was possible with my full focus. I gathered the courage by looking at the data, building a financial cushion, and leaning on a strong community.
Peri Finkelstein
Founder & CEO of Team Peri Foundation, driven by justice, compassion, and the belief that true inclusion celebrates diversity.
Peri Finkelstein
My smartest risk: Severing ties with a nonprofit I had volunteered with and fundraised for over 15 years, knowing I would likely lose my network and long-standing donor base and have to start from scratch. I was walking away from security but I knew I had my own goals, including my lifelong dream of starting a nonprofit of my own.
The payoff: While I did lose supporters who didn’t understand the new mission, the leap allowed me to build something fully aligned with my purpose.
Why I went for it: I knew it was time to build my legacy, even if it meant confronting lifelong fears of being in the spotlight.
Ellen Hockley
Founder & Community Connector of Ellen Hockley Consulting and SAGE Women, a seasoned entrepreneur and a mother dedicated to empowering women to build sustainable businesses.
Jen Chanyi
My smartest risk: Putting it out into the world that I was ready to sell my first business. I was terrified that no one would want to buy it or see the value in the company.
The payoff: I made it happen! I found the right team and, four years later, they and the business are still thriving. I love that I get to watch from the sidelines.
Why I went for it: There were a lot of pro/con lists! I was beyond burned out and something needed to change. I figured I could either sell or close my business, but both options felt like insurmountable challenges. I also knew I didn’t want to just let go of what I’d spent five years building, so selling seemed like the more manageable answer.
Amanda Northcutt
Founder & CEO of Level Up Creators, a strategic advisory firm that helps founder-led businesses install clear operating systems, predictable revenue, and leadership-level clarity.
Greg Kahn
My smartest risk: Leaving my Silicon Valley executive role (and a substantial salary) to help consultants build sustainable recurring revenue businesses. I was assembling a team and pouring everything (18 months, 80+ hour weeks, every dollar reinvested) into creating the business I wished had existed when I started, with no guarantee it would work.
The payoff: We’ve now built a proven methodology that helps our clients achieve multi-five-figure MRR, and I get to do deeply meaningful work alongside an incredible team.
Why I went for it: During the pandemic, I realized I didn’t want to spend the rest of my career making the wealthy wealthier. My work was financially rewarding but lacked the purpose and impact I craved. I used the same strategic frameworks I now use with clients to ask myself the hard questions about legacy, then assembled my dream team and went all in.
Kelly Hubbell
Founder & CEO of Sage Haus, helping busy parents reclaim time by building their village, recruiting house managers and family assistants to lighten the mental load.
Lion & Oak Photography
My smartest risk: Hiring the team before we had the revenue to justify it. I was investing significant capital into salary and benefits when we were still building our foundation.
The payoff: By investing in exceptional leaders first, we were able to build the high-quality team and service delivery that our clients needed, which then drove the revenue growth that validated the investment.
Why I went for it: My mission is to provide quality help for families while creating meaningful jobs for caregivers, and that required me to practice what I preached—investing in incredible talent even when it felt premature. I had to trust that prioritizing people over immediate profitability would ultimately create sustainable growth.
Ingrid Zapata Read
Founder of Grow With Community, a consulting agency that helps community-led businesses build and strengthen their communities in ways that support sustainable growth.
Nev Photography
My smartest risk: Leaving my corporate role to build communities full time without having every step mapped out.
The payoff: That decision grew not one, but two businesses! What felt uncertain at the time became the foundation for everything that followed.
Why I went for it: Even as I was being promoted, I was feeling limited in my role. At the same time, founders were coming to me for advice and perspective outside of my job, which showed me that my ideas had value beyond my title.
Catharine Montgomery
Founder & CEO of Better Together Agency, a Black woman-founded, AI-forward communications agency that creates integrated campaigns for mission-driven work.
Catharine Montgomery
My smartest risk: Parting ways with investors who wanted me to compromise my mission and starting Better Together Agency from scratch. Overnight, I lost almost all my clients because those investors made it nearly impossible for them to follow me, and I had to rebuild everything with no financial cushion.
The payoff: Now, I only work with organizations whose values match mine, and I’ve built an agency where we never have to choose between revenue and doing what’s right for the communities we serve.
Why I went for it: Staying with those investors meant choosing financial security over my values, and I’ve never been good at that kind of math. I knew I could rebuild the client base and revenue, but I couldn’t rebuild my integrity if I stayed somewhere that asked me to compromise it.
Lauren Graham
Founder of Velvet Frame, an impact philanthropy consultancy for next-gen philanthropists motivated to fund systems change.
Leslye Tischenko
My smartest risk: Rebranding a company more than a decade in the works. We moved from social impact strategy for mission-driven organizations to impact philanthropy advising for next-generation donors.
The payoff: I’ve moved from broad, cross-disciplinary ecosystems work into a narrow, highly visible niche with a specific set of offerings.
Why I went for it: The gap became impossible to ignore: the organizations I had worked with were increasingly underfunded and overexposed, while a new generation of donors wanted to act but lacked clear pathways and issue-specific expertise to move money strategically in this moment.
Lorrie King
CEO of Caire Beauty, a science-driven skincare brand for women over 40.
Rodman Blanchard
My smartest risk: Leaving a successful career building billion-dollar beauty brands to pursue a long-held dream and start my own company. I was moving away from security, status, the familiar rhythm of corporate life, and predictable income to build something the industry hadn’t fully acknowledged yet.
The payoff: Women tell us they finally feel seen, respected, and spoken to like adults. That validation—combined with building a brand rooted in science and truth rather than trends—has confirmed that this risk wasn’t just smart; it was necessary.
Why I went for it: The problem to be solved was personal, persistent, and clearly underserved. Once I understood the gap in the beauty industry for women over 40, I couldn’t unsee it.
Monita Sun
Co-Founder of Building Abundance LLC, a real estate development company creating healthier homes through thoughtful design and non-toxic, building science–driven materials.
Monita Sun
My smartest risk: Slowing down in an industry that prefers speed, which felt really risky because it meant walking away from shortcuts, fast flips, and quick wins. It required trusting our instincts—and our values—even when it would have been easier to move faster.
The payoff: We secured our work, our reputation, and the people who live in the homes we build. As a result of our patience, we reduced costly surprises later, too.
Why I went for it: We trusted that taking more time upfront—on design, materials, and risk prevention—would protect long-term value, health, and trust.
Bethany Halbreich
Founder & Executive Director of Paint the World, a nonprofit reimagining the arts as essential infrastructure for social change.
Amy Doak
My smartest risk: Having a child at a moment when my work felt like it was finally hitting its stride. I was terrified of interrupting years of momentum, especially for my nonprofit work with Paint the World, which briefly had to pause.
The payoff: Motherhood actually sharpened my focus and intensified my income-earning work, creating stability and clarity. Now, as I return to scale and evolve my impact work, I can see that I’m not running behind at all. In fact, I’m perfectly aligned.
Why I went for it: I saw that momentum doesn’t disappear, but transforms. Trusting that I could rebuild, recalibrate, and evolve alongside motherhood gave me the courage to move forward.
Elle Wilson
Founder & CEO of Met Through Friends, home of the Plus-One Party™.
LinkedIn Headshots
My smartest risk: Starting something before I knew how to turn it into a business. The first event I ever threw was a party for my friends in my own apartment: no tickets, venue rentals, expensive materials, or business plan. In hindsight, I realize that it was the first prototype for what my business would eventually offer, but at the time it was an exercise in putting myself and my ideas out there before I was ready.
The payoff: I followed my hunch about a problem my friends were having, and the rest is history.
Why I went for it: Although I had no idea what it would turn into, I knew that I saw a problem—that my friends were struggling to find meaningful partnerships—and that I had some ideas about how to solve it.
Lis Best
Founder of Girls Club Collective, the intentionally intimate leadership lab where impact leaders and entrepreneurs ready to reimagine our world join forces.
Mag McMillan
My smartest risk: Leaving consulting—which, at the time, made up approximately half of my business revenue—in order to focus my energy on building the Girls Club Collective (GCC) community. I couldn’t do justice to the Collective when my energy was so split.
The payoff: Over the next year, I was able to not only show up for and grow GCC, but I also gained a fresh perspective and appreciation for the role I wanted both of these pieces (community and consulting) to play in my life and business.
Why I went for it: I reasoned that, even if I decided to go back to consulting (and it turned out I very much did!), I could turn it back on when the time was right; the work I had put into building my reputation as a consultant wouldn’t expire while I focused elsewhere.
Kelley Troia
Founder of Clandestine Events + Experiences, blending creative direction, environmental design, and discreet execution to shape the moments where influence is built.
Suzanne Covert
My smartest risk: Pitching a national insurance brand to let us manage their Indy 500 Presenting Sponsor activation, despite having no prior experience in motorsports. The visibility was enormous, the margin for error was zero, and the founder’s reputation and relationships would live or die by the environment we created.
The payoff: We walked away with a four-year partnership across IndyCar activations and later expanded to Formula 1, including managing an F1 Miami Paddock Club Suite in its inaugural year.
Why I went for it: The opportunity was rare and perfectly aligned with how I operate. I am deeply confident in my ability to figure things out quickly, build the right structure, and take full responsibility for the outcome, even without precedent.
Kellie Chen
Co-Founder of 8Rue Branding, a boutique branding agency bringing big-brand thinking to emerging Beauty, Health, and Fitness CPG brands.
Kevin Vu
My smartest risk: Rebuilding our business by stripping the agency all the way back and starting again as freelancers. We did this so we could get close to founders, listen deeply, and rebuild our strategy from real needs instead of assumptions.
The payoff: That humbling reset led to 8Rue becoming an award-winning agency that has partnered with over 70 beauty founders and supported launches into more than 1,200 retail doors.
Why I went for it: Staying comfortable was actually the bigger risk. The work no longer energized me, and I trusted that rebuilding around fulfillment and curiosity would lead to stronger, more meaningful growth in the long run.
Marissa Pick
Founder of Marissa Pick Consulting LLC, providing high-level strategic consulting for brands ready to lead the digital conversation.
Marissa Pick
My smartest risk: Deciding to launch my own consulting firm was the ultimate risk. I traded the comfort of a stable career for a path with no guarantees and plenty of room to fail.
The payoff: I discovered that “all-in” is more than a mindset—it’s a strategy. Despite the fear that followed me through those early days, I stayed grounded in one simple truth: My expertise is my edge.
Why I went for it: I trusted my expertise. The biggest risk isn’t failing; it’s never finding out what you’re capable of when you’re truly in the driver’s seat.
Julie Zhu
Marketing Strategist of Julie Zhu LLC, an award-winning marketing strategist and adjunct professor based in NYC.
Julie Zhu
My smartest risk: Agreeing to my first speaking engagement before I felt 100% ready! Public speaking terrified me, and this opportunity forced me to be seen in a bigger way than my business had ever required.
The payoff: This engagement opened the door to my ideal audience, and that visibility turned into real community and new life and professional opportunities.
Why I went for it: I built courage by developing strong material, rehearsing with friends, getting feedback, and focusing on being useful and relevant.
Rosalie Ennes
Founder of Portecua Consulting, a business and risk consulting firm helping impact-driven entrepreneurs build profitable and sustainable businesses with confidence.
Nev Photography
My smartest risk: Writing a book. When I started my business in 2023, it quickly became clear that doing so would help me further my mission and impact at a larger scale, and I spent 15 months dedicated to the process. It was one of the hardest things I’ve done, but it was well worth it.
The payoff: In the book’s first year, I’ve connected with hundreds of entrepreneurs, surpassed 100 five-star reviews, generated leads for consulting and speaking engagements, and received two book awards.
Why I went for it: There are very few business books written by women and people of color, written by someone who has an understanding of our experiences and challenges. I was motivated to create that representation.
Anjali Purohit
Creative Director & Founder of Studio Variously, creating modern home décor and lifestyle accessories using natural certified and verified materials.
Laur Nash
My smartest risk: Choosing not to delegate the foundational work of building my company—from registration to logistics—when I started as a first-generation immigrant entrepreneur and new mother.
The payoff: I gained a level of clarity that could not have been outsourced. Eventually, I was ready for responsible delegation, rooted in understanding rather than assumption.
Why I went for it: Building a company while becoming a mother taught me that leadership is learned the same way parenting is: by showing up fully, even before you feel ready.
Yewande Faloyin
CEO & Founder of OTITỌ Leadership & People Development, transforming how you show up so you can achieve more success for yourself, greater impact for your business, and increased satisfaction in your life.
Yewande Faloyin
My smartest risk: Stepping away from a career at McKinsey that looked perfect on paper but had led to burnout twice. It was the end of a clearly defined path.
The payoff: That decision created the space to build a coaching business rooted in integration, and allowed me to create experiences like my upcoming Women’s Leadership Retreat in Switzerland.
Why I went for it: After burning out twice, I realized the bigger risk was continuing in a system that required me to fragment myself to succeed. By trusting my intuition and allowing myself to experiment, I found a more sustainable, integrated way of leading.
Kylee McGrane
Founder & Executive Director of A Moment of Magic, harnessing the power of play to spark joy, foster connection, reduce isolation, and support the mental health and emotional healing for medically vulnerable children and their families.
Bahadir Gurel
My smartest risk: Hiring myself as a full-time employee right after college, when A Moment of Magic expanded from one chapter to ten. It felt risky to bet my livelihood on an early-stage nonprofit with no roadmap, no salary history, and rapid growth ahead.
The payoff: I quickly created the stability and leadership continuity we needed to scale responsibly, embed with hospital partners, and grow into a national organization serving tens of thousands of children every single year.
Why I went for it: The organization had outgrown volunteer leadership and needed full-time stewardship to match its momentum. Investing in leadership was what allowed the mission to scale with integrity and impact.
Gretchen Rickards
Founder & Executive Coach of GR Coaching and Consulting, helping leaders navigate growth, lead through transition, and amplify their impact.
Laura Robinson
My smartest risk: Resisting the pressure to narrow into a highly specific niche. Conventional wisdom says to focus on one very specific industry or audience, and it felt risky to go against that advice early on.
The payoff: I built a practice coaching leaders through growth and transition across healthcare, nonprofits, and mission-driven organizations, where insights from one context often prove unexpectedly useful in another.
Why I went for it: I’m a generalist at heart, and my experience has shown that the core challenges leaders face transcend industry. I trusted that depth of work and perspective would matter more than narrow positioning.
Nikole Hobson
CEO & Founder of Attaché & Co., a fractional Chief of Staff and operations firm helping founders navigate complexity, build strong operating rhythms, and lead with clarity as their companies scale.
Tibrina Hobson Photographyamber
My smartest risk: Leaving the security of a big bank and a carefully curated network to work in the startup world. During my interview, someone told me, “In a startup, there’s nowhere to hide.” At the time, that felt terrifying —but it turned out to be exactly what I needed.
The payoff: That leap reframed how I see my career and myself. What once felt “too broad” became my greatest strength, and it ultimately led me to build a business centered on helping founders navigate complexity without carrying everything alone.
Why I went for it: For the first time, my generalist background wasn’t something I had to explain or defend. In a startup, wearing many hats isn’t a liability;it is the work.
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