It’s hard to believe I’ve come full circle in my career. At one point, I was the mentor. Today, one of my former mentees is my boss. Crazy? Absolutely. Surprising? Not really.

I’ve always taken a lot of pride in helping the people around me succeed. I’ve always felt that if the people around me were succeeding, then I was succeeding too. Looking back, I realize that has been one of the threads connecting nearly every chapter of my career.

It started with a professor who knew me better than I knew myself.

I entered the working world during my last semester at Fitchburg State University as an intern. At the time, I had a very specific idea of what I wanted to do. I wanted to go to downtown Boston, walk the streets, and work at one of the big advertising agencies. My professor, Helen Obermeyer Simmons, had a different idea. She knew me better than I knew myself and placed me at a small design studio in Watertown, Massachusetts. That studio was FableVision. And what a decision that turned out to be.

I never would have guessed that my first real design job would involve creating digital assets for animator and storyteller Peter Reynolds, only to go home after my internship and make stuffed animals based on his characters. From there, I crossed the hallway into the parent company, CF Video & Interactive, and found myself working on video and interactive projects.

Looking back, I couldn’t have asked for a better place to start my career. It felt like home — filled with great people, interesting clients, and the kind of creative energy I wanted to be around. I just didn’t realize at the time how much that experience would shape me.

I ended up staying at that same desk for 10 years, watching a family-owned business evolve and eventually get acquired by a New York agency. At the time, I was just doing the work. Looking back, I realize I was building a foundation.

The intern who became the boss

During those years, I started bringing interns in from Fitchburg State. I loved working with them. I could give them real projects, real clients, and real-world experience while working shoulder to shoulder with them and the rest of the team. One of those interns was Jason Drury. Jason was an eager beaver. A sponge. He wanted to learn everything. And apparently, I was a little intimidating.

When we recently reconnected, Jason described me as someone he feared because I was so direct with him. Why are you doing this? Why did you make that choice? And, apparently, I had no problem grabbing the mouse and showing him exactly what I thought he should be doing, usually while telling him he was moving too slowly.

Looking back, it makes me laugh. But it also makes me incredibly proud. That intern from more than 20 years ago is now the owner of a wonderful company, DC&Co, producing great work for clients around the world. And somehow, I’m now working for him.

Full circle.

The long way around

After Watertown came Vistaprint. Nearly 15 years at a global billion-dollar company. That chapter taught me a completely different set of lessons, but one of the biggest gifts was the people I met. I had the opportunity to work with amazing, creative people from the US, Spain, Germany, Tunis, India, and beyond. I was surrounded by people with different backgrounds, cultures, experiences, and perspectives.

I learned so much about people. I made friends for life. And some of those people still show up in my LinkedIn feed today. It was a pretty incredible experience to work with people from all over the world and see how differently we could approach the same creative challenge. It changed the way I think about people, collaboration, and good work.

Then came a small stint at a SaaS company, and eventually DC&Co. Along the way, I’ve worked at agencies and in-house. I’ve worked across print, digital, video, interactive, branding, and just about everything in between. I’ve seen the creative business from a lot of different angles, and I’m grateful for every one of them.

From Chasing to Choosing

Early in my career, I was in a racecar. Everything was about speed. Chase the next project. Solve the next problem. Learn the next thing. Take on whatever was coming at me.

Go, go, go.

And honestly, I loved it. But almost 30 years gives you something speed can’t: perspective. Today, I’m still moving fast. I’m just much more intentional about where I’m going. I know when to push. I know when to step back. I know when something needs to be perfect and when “good enough” is actually good enough.

I know which questions to ask. And, perhaps most importantly, I know that I don’t have to be the smartest person in the room. Sometimes my job is to find the smartest person in the room and give them the space to do what they do best.

That’s probably one of the biggest changes I’ve noticed in myself. Early on, I wanted to prove I could do it. Now, I’m much more interested in helping the people around me do it.

What comes next

I don’t think you can really understand a career while you’re living it. You’re too busy doing the work. You don’t know which boss will teach you something you’ll carry for 20 years. You don’t know which coworker will become a lifelong friend. You don’t know which intern will eventually become your boss. You don’t know which seemingly random project will give you a skill you’ll use years later.

You just keep showing up. You learn. You make mistakes. You meet people. You move on.

And eventually, if you’re lucky, you get to look back and see how some of those seemingly disconnected pieces fit together. That’s probably what these years have given me more than anything else: perspective.

When I look back, I think, “Wow, look where this took me”. From agency to in-house and back again. From print to digital, video, interactive, branding, and just about everything in between.

I couldn’t have planned any of it. And I wouldn’t trade any of it. So here I am, almost 30 years in. Still chasing good work. Still learning. Still surrounded by people I want to be around.

I’m just a lot better at choosing where to put my energy. And honestly? I’m pretty excited to see where it takes me next.

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