From Spit-Up to the C-Suite: My Journey with Imposter Syndrome

Five days after bringing my daughter Audrey home from the hospital, I was still in my pajamas, trying to stay awake through the haze of sleep deprivation and newborn chaos, while chasing after her 2- and 4-year-old siblings. That is when my dad called. “Sarah, we need your headshot for the business plan—now!” I looked at myself—unshowered, spit-up on my shirt—and thought, "This is not what an entrepreneur looks like." But I showed up anyway. If that sounds familiar, you are not alone.

I want to talk about something we all experience but rarely discuss aloud: imposter syndrome. And I want to flip the script on it.

If You Feel Like an Imposter, High Five Yourself

For years, I thought feeling out of place meant I was doing something wrong, and I gathered evidence to support that belief. I told myself: I had been around the roofing industry but never worked directly in it. I was a stay-at-home mom with no experience hiring or firing. I had sales experience before staying home, but I had never been a manager or started a business. My partners? Longtime industry veterans, a decade or more senior, who seemed to know everything I did not about running an operation. I was responsible for creating the company's infrastructure and corporate office. When I walked into meetings with attorneys, bankers, and insurance agents to launch Elite, the look said it all: "Do you belong here?" "You're making these decisions? Who is really in charge?"

Own Your Power, Do not Give It Away

If you walk through life reacting to how you think people see you, you give away your power. And once you give away your power, the weight of others' judgments can be soul-crushing.

What I have learned is that people who made cutting comments simply had not seen anyone like me in that role before. I had not yet shown them how capable I was. That realization took years. I had to learn to filter feedback—sometimes people’s opinions do not align with what you know to be true about yourself. It is not personal; often, it is just a disconnect because they have not yet seen your full potential.

Now I know that the butterflies in your stomach and the voice asking, "Do I have what it takes?" are not signs of weakness. They are evidence of growth. If you are feeling imposter syndrome, high five yourself. It means you are stepping out of your comfort zone—where real growth happens!

Every Step is a Step Toward Confidence

I often share a story about feeling overwhelmed at my daughter’s first club volleyball tournament. I looked around and thought, "These other moms know exactly what to do; I’m lost!" But the truth is, they had just done it more times. Confidence is not innate; it's built by

crossing the bridge from "I don't know what I'm doing" to "I've got this," one step (and one mistake) at a time.

During my 12 years at Elite Roofing Supply, I learned everything on the job. I asked countless questions, even when it felt awkward. (I once read a 100-page bank agreement line by line and refused to sign until I understood every word. The banker told me no one had ever asked so many questions—but we got better terms!) I made mistakes, bad hires, and launched projects that flopped. I learned that falling down is part of building something great.

Attending my first IRE after launching Elite was overwhelming. I didn’t know many people and felt like the new kid compared to my partners. But my partners and father served as allies, introducing me around and helping me learn the ropes. Most people enjoy helping and mentoring—you just have to be vulnerable enough to ask. Now, years later, I go to IRE with a clear agenda and a network of friends and peers. But it took time, practice, and persistence to get there.

Your Perspective is Your Power

Being an outsider turned out to be my superpower. While many of my colleagues came up through the industry, I brought a fresh perspective. When people rolled their eyes at my suggestions for a website or business cards, I learned not to take it personally. Sometimes, people resist what’s unfamiliar because it makes them uncomfortable, not because it's a bad idea.

Each role within a company comes with different priorities. It took me years to realize that sometimes conflicting priorities aren't personal, they’re simply the reality of a complex organization. I learned to trust my gut and to view feedback as a gift, while staying anchored in my own knowledge and instincts.

If you’re new to a role or industry, don’t hide it—lean in! Ask questions. Challenge the status quo. There is no single “right way” to lead or succeed. And if you’ve been in your field a long time, stay curious. Innovation often comes from outsiders who think differently.

Practical Tips from a Recovering Perfectionist

If you’re thinking, "I could never do what she did," let me share some survival strategies:

- Embrace discomfort. It’s the price of growth. - Find your people. Mentors, allies, and peer groups are your lifelines. - Advocate for yourself and others. Champion overlooked voices in meetings. - Keep asking questions. Curiosity is your most powerful tool. - Let go of perfection. Authentic leadership connects more than polished appearances. - Stop seeking external validation.

You are Not Alone—And You Belong

It is easy to think everyone else has it all figured out. But the truth is, we are all figuring it out as we go. The key is to keep moving forward, one step at a time, and to support each other along the way. Imposter syndrome is gender-neutral; everyone, including your male colleagues, has fears and insecurities.

Walk into every room knowing you belong. You are there to add value. If someone doubts you, remember they just have not seen your full potential yet. But you know your value—and that is what matters.

Let Us Cross the Bridge Together

If this resonates with you, I hope you will do three things. First, high five yourself for being brave enough to show up—at work, at home, or anywhere new and intimidating. Second, do not do it alone. Watch the webinar replay, join the conversation, and connect with peers. Third, celebrate your progress. Notice each skill you improve, each step you take.

Together, we can turn imposter syndrome into a badge of growth, not a signal to stop. Let us walk that bridge—one skinned knee and high five at a time.

Ready to step forward? Click here to watch the webinar and access more resources. Let us do this—together.

 

Sarah Weiss is a dynamic entrepreneur and business leader who co-founded Elite Roofing Supply in 2012 and played a key role in growing it from a startup to a $600 million company with 26 branches across 9 states. Starting as Chief Operating Officer and later stepping into the CEO role in 2019, Sarah helped scale the business by building strong teams, streamlining operations, and leading with authenticity.

In 2024, she led the successful sale of Elite to a family-owned company in Tampa, Florida, achieving a major milestone for the organization and its shareholders.

Now, Sarah is embracing a new chapter—investing in female entrepreneurs, mentoring emerging leaders, serving on advisory boards, and speaking openly about her journey through imposter syndrome, self-doubt, and growth as a woman in a male-dominated industry. Her story is proof that leadership doesn’t have to fit the mold to be powerful.