Navigating Career Change: From Agency to Family Business

Join Molly Baker, founder of Indie Consulting, and Orli LeWinter, as they dive into the nuances of running a family business, making bold career changes, and turning ambiguity into opportunity. From strategic redirection to uncovering creativity in so-called “boring” businesses, this episode unpacks what it really takes to be a leader in an  entirely different landscape. This is the perfect episode for you if you're facing change and ready to make it work for you.

MB (Molly Baker): What’s top of mind for you professionally right now?

OL (Orli LeWinter): I recently made a major pivot in my career and now run a small business in a completely new industry. It's a family business that operated for 25 years without much strategy—successful, but very shoot-from-the-hip. I’m bringing in structure, purpose, and operational rigor, and learning how to navigate this shift on a deeply personal level. It’s been challenging and incredibly rewarding.

MB: Is your family involved?

OL: Yes, I work with my dad. It’s a gift, honestly. He’s 75, and it became clear he needed an exit plan—he deserves that. This opportunity lets me spend quality time with him and see him through a different lens. I’m grateful for that every day.

MB: Has he done this his whole career?

OL: Not exactly. He’s a photographer by training and an immigrant who started in the printing business in the '70s and '80s. He’s always been entrepreneurial but never had a corporate job, so he built the business in a very scrappy, intuitive way. When printing started to decline, he pivoted into this business and grew it himself.

MB: What are you really good at?

OL: I’m a trained strategist, so I’m great at seeing the big picture and creating actionable plans. My strength lies in operating in ambiguity, figuring out where we are, where we want to go, and building the path to get there—then actually executing. I set a high bar for follow-through and quality. That’s always been true, even back in high school—I found an old science notebook that was color-coded and basically a study guide. I’ve always needed a clear plan.

MB: What’s been the most pivotal moment in your career?

OL: Definitely this pivot to running the family business. Before that, quitting my agency job in 2018 was huge. I’d been there for over 11 years, and one day I just woke up and said, “I don’t want to do this anymore.” I had three little kids, including a newborn, and it was terrifying. But I gave notice and stayed for a few more months while I figured things out. Consulting after that gave me freedom and taught me essential business skills that I rely on now.

MB: Who has been the most impactful professional relationship in your life?

OL: Two mentors come to mind. My first boss was a strong mentor—tough, brilliant, and intense. Then there was Lee Mikan, who eventually became my boss. He was the polar opposite—calm, empathetic, never reactive. Learning from both of them showed me how different leadership styles can be equally effective and shaped how I lead today.

MB: Okay, so now tell us who you are and what your business is.

OL: I’m Orli LeWinter, Chief Business and Marketing Officer at Sign Expo, a signage company. There's a lot of buzz about “boring businesses” being the real hidden gems, and I’ve found that to be true. After years of working on exciting brands, creative campaigns, and traveling for conferences, I didn’t expect to find such fulfillment here—but it’s awesome.

MB: Beyond your dad’s retirement, what else led you to make this move?

OL: In 2024, I was diagnosed with breast cancer. After treatment and recovery, I reassessed my priorities. I realized I had the opportunity to take ownership, build something lasting, and apply my creativity in a new way. Also, advertising is an industry where you can age out—especially as a woman. This path offers longevity, challenge, and creativity in a whole new form.

MB: You said earlier you don’t like ambiguity. Isn’t running a business full of it?

OL: It’s full of uncertainty, yes—like financial ups and downs, cash flow, payroll. But it’s not ambiguous because I get to set the direction. I make the plans, and we execute on them. That part brings clarity and purpose.

MB: What does your average day look like now?

OL: It’s very hands-on. We design, fabricate, and install signage—so there’s a big technical component I’m still learning. I do site visits, talk with clients about their visions, navigate regulations, then help the team estimate and plan. We’re literally shaping the visual fabric of the city. I walk around NYC and think, “We did that.” It’s a great feeling.

MB: Biggest thing you’ve learned so far?

OL: Billing is not the same as cash flow! It sounds basic, but that was a real “oh no” moment for me. Also, just how much logistics and planning goes into making beautiful, physical products.

MB: How has your leadership style had to adapt?

OL: The people I work with now are very different from the agency world—hands-on, technical, not from traditional corporate backgrounds. I’ve had to adapt how I communicate, motivate, and build trust. But at my core, I stay true to who I am: empathetic, direct, and mission-driven.

MB: Is your dad ready to hand over the reins?

OL: Not entirely. It’s hard to let go of something you’ve built for decades. But he’s open to evolving and starting to imagine what life could look like if he stepped back—even a little. I think we’re both learning how to share leadership and plan for the future.

MB: Did you ever think you’d be doing this?

OL: Absolutely not. At 21, I thought I’d be writing the next great American novel. But maybe that dream isn’t totally gone—my plan is to write a book about this experience. A mix of memoir and business guide.

MB: What’s one thing you wish you’d known earlier in your career?

OL: That a career requires strategy. I spent years doing strategy for brands and never once applied it to my own path. I was lucky to love my job, but it made me passive. I wish I’d been more intentional earlier.

Find Orli on Linkedin and visit Signexpo.com to learn more.

As for us, follow @namedrop.pod on Instagram & LinkedIn and@molbakes on Instagram for all future episodes and insights.