From Boardroom to Grocery Aisles: Rebuilding Confidence in a New Industry

Transitioning from a senior executive role at the Department of Homeland Security to the entrepreneurial world of Consumer-Packaged Goods (CPG) wasn’t just a career shift—it was a transformative journey that tested my self-perception and confidence. Leaving the familiarity of the boardroom to embrace the challenges of grocery aisles, I faced the daunting task of building credibility and confidence in an entirely new industry. This is the story of my transition and the lessons I’ve learned along the way.

The Big Career Leap

After years of leading initiatives in high-pressure environments, my decision to leave an esteemed federal position was met with skepticism. My role wasn’t just a job—it was a way of life. I took my responsibilities as a public servant seriously, believing deeply in the principles of good governance and public service. My entire adult life had been devoted to this mission, and leaving it behind felt like I was giving up or quitting on the many people who counted on me; how could I leave them behind?

Friends and colleagues questioned my reasoning. Why leave a secure, stable career for an uncertain future in a family business? My answer was simple: I believed in my husband’s gift as a baker, in my family, and in Sweet Maddie’s Cookies on Demand. I knew we had something special—something that could be a game changer in the cookie dough space.

Though I was confident in the vision, stepping into a completely unfamiliar industry brought its own set of challenges. Entrepreneurship required me to build confidence from the ground up, and the process was far from easy.

Rebuilding Confidence in a New Industry

Stepping into the role of entrepreneur came with a steep learning curve. After years of operating as a subject matter expert in federal operations and management, I suddenly found myself in unfamiliar territory, learning about consumer engagement and retail distribution from scratch. It was humbling, and I was eager—perhaps too eager—to know everything as quickly as possible. My drive to master this new industry sometimes made the process feel overwhelming, as I tried to absorb years of knowledge in just weeks.

To keep myself grounded, I developed the TRUST factor:

T ~ Trust in who you are.

R ~ Be resilient in the pursuit of your goals.

U ~ Be unapologetic in communicating your value.

S ~ Stay connected to those who lift you up and hold you accountable.

T ~ Be tenacious in holding on to what matters and brave in letting go of what doesn’t.

Staying connected, for me, meant not going it alone and finding my community—a group of peers I could grow with and learn from. That was a game changer. Having a support system helped me stay grounded and provided me with encouragement, perspective, and accountability when I needed it most.

This framework had been my guiding principle during my federal government career, particularly in moments of uncertainty when I entered meetings wondering if I truly belonged in the room. Reapplying it to my entrepreneurial journey gave me the clarity and focus I needed to navigate this new space and build on my strengths rather than fixate on how much I had to learn.

The Family Dynamic: Building a Business Together

I am not alone in this journey—it’s me, my husband, and our five adult children, all working together to build Sweet Maddie’s Cookies on Demand. My husband, who is my best friend, is now also my business partner. It’s been an interesting dynamic, one we wouldn’t have imagined years ago, but one I wouldn’t trade for anything.

There have been times when he’s said, “I could never work for you,” to which I jokingly reply, “Well, I would’ve fired you!” We both laugh because working together in a family business is nothing like the structured environments we’ve known before. He occasionally reminds me, when he thinks I’m being bossy, that I no longer have a staff or an executive assistant. We laugh, but it’s a dynamic that requires patience, communication, and a lot of love.

Building this business together has been an incredible experience, not just as entrepreneurs but as a family. It’s taught us to lean on each other in new ways and strengthened bonds we didn’t know could grow deeper. I’m grateful every day for their support, their ideas, and the memories we’re creating along the way.

From Consumers to Connection: Hands-On Experience

From briefing Congress and managing federal operations to standing in a grocery store asking, “Would you like to try a Brown Butter Toffee Caramel cookie, finished with smoked sea salt, freshly baked?” my daily life has changed dramatically—and I laugh out loud, sometimes unprovoked, when I think about it. The image of myself preparing for high-stakes Capitol Hill meetings versus cheerfully engaging with unassuming customers over cookies never fails to amuse me.

It’s humbling and joyful all at once—especially when a customer tries one of our cookies and immediately asks, “Where can I find these?” My response: “In the frozen dessert section.” Yep, my new norm feels good.

Old Skills, New Lessons: What I Brought with Me

One of the greatest surprises in my journey was how transferable my previous skills were. My expertise in strategic thinking, risk management, and leadership—all honed in federal service—proved invaluable in navigating the unpredictable nature of entrepreneurship. For example, my background in crisis management prepared me to adapt quickly, make data-driven decisions, and address challenges head-on, ensuring Sweet Maddie’s remained competitive in a crowded market.

The transition also taught me to embrace humility. In federal service, I operated from a place of authority. In the CPG industry, I started as a novice, relying on time, trial and error, and small wins to build my confidence.

The Road Ahead: Embracing Growth

Looking back, I recognize the tremendous personal and professional growth this journey has given me. Yes, the path of entrepreneurship is riddled with challenges and moments of uncertainty. Yet, I’ve come to see these discomforts as signs of growth and progress. Success doesn’t come overnight—it’s cultivated through effort, resilience, and patience.

To anyone considering a similar leap, know this: rebuilding confidence is possible. Embrace the unknown, TRUST in your vision, and allow yourself to grow through the process. While the discomfort of change may feel overwhelming and like an emotional roller-coaster at times, it’s part of the journey—and absolutely worth the ride.