From Freelancer to Small Biz Owner

In preparation for this year’s Creative Freelancer Conference (one of the four components of the HOW Design conference), we sat down with Jenn David Connolly, the owner, founder, and creative director of Jenn David Design in San Diego, CA. Jenn will be one of the featured speakers this year, appearing on two panels covering best practices for freelancers and the process of transitioning from freelance to small business.

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HOW: When did you first realize you wanted to be a graphic designer?

Jenn David Connolly: I’ve been into art as far back as I can remember, but I knew graphic design was it when I took my first design class in high school. Working with type, color and imagery to solve problems opened my eyes to a new way of being creative.

HOW: What was your first design job?

JDC: I interned at Bergdorf Goodman’s advertising department in NYC as an undergrad, but my first real paying job was doing production on black-and-white “help wanted” newspaper ads. It might not have been the most exciting, but I was working under a talented creative director and learned a lot about information layout, typesetting, prepress and the printing process—all things I didn’t learn in school.

HOW: What advice do you have for other designers aspiring to a similar career path?

JDC: Put a little bit of yourself into your work—that’s what will set you apart—and never stop learning no matter what stage of your career you’re in. The worst thing is to plateau. Keep pushing yourself out of your comfort zone. That’s where the magic happens.

HOW: What’s been one of your most favorite projects?

JDC: Early in my career, when I was working at Williams-Sonoma designing packaging, we were laboring over a taco sauce line design. Multiple designers had submitted concepts for review and all had been turned down. The concept literally came to me in a dream one night. I came in the next morning and said, “I’ve got it!” and proceeded to nail out a design that instantly won over the decision-makers. To this day, I find that letting ideas simmer in my head for a bit before taking action on them is incredibly effective in finding strong solutions, and the concepts tend to form organically.

HOW: What’s the strangest thing that has happened to you during your design career?

JDC: As an undergrad I always thought I would be a creative director at some big firm in NYC someday. That career path changed when hen my husband and I decided to move from Boston to San Francisco. Since the dot-com bubble had just burst, nobody was hiring in San Francisco, but there was a wealth of freelance work to be found. When the job offers did start coming around, I was really enjoying freelancing and wanted to see where I could go with it. I never looked back, and here I am running my own studio by the beach in San Diego, quite the opposite of my NYC dream. I never planned this route, but I’m so glad life led me along this path.

HOW: What self-promotion strategies have been most successful for you?

JDC: Determining my specialty and developing a content strategy around that—basically putting out a lot of content, sharing my expertise and positioning myself as an expert in my field. The more you specialize, the more in demand you are. The clearer we’ve gotten on our specialty as a studio, the more ideal prospects have sought us out.

HOW: Do you have a pet project—a side business, passion project, or a charity to which you donate time or services?

JDC: We do occasional pro bono projects as a way of giving back. Donating our services to nonprofits we’re passionate about is worth so much more than donating cash, and it’s rewarding.

I also do illustration and have made posters, calendars and other products we sell online ( Currently, this is strictly a side project for fun as I focus on growing my graphic design business, but eventually I might like to take the illustration business to the next level and get into some retail.

HOW: When you get stuck in a creative rut, how do you break free?

JDC: I find that taking a break, not focusing on it and doing something totally different and unrelated to work at all (go for a run, play at the beach, make crafts, cook in the kitchen) either helps the ideas to come to me naturally or helps me return with a fresh approach that enables me to get around that roadblock.

HOW: If you weren’t a designer, what would you be?

JDC: A chef or something to do with food. I love good, healthy food and being creative in the kitchen. It’s not surprising to me at all that I’ve chosen to specialize in working with gourmet food companies.

HOW: What does San Francisco bring to mind? What do you plan to do while you’re there?

JDC: It brings to mind the years I used to live here! My husband and I lived in Cole Valley near the entrance to Golden Gate Park. We had kids years later when we moved to San Diego, and we named our son Cole after the neighborhood we loved so much.

HOW: Where did the ideas for your session topics come from?

JDC: When I attended the CFC for the first time in 2012, I had been struggling with how to go from being solo to having a studio with employees. I knew it was what I wanted, but I didn’t know the steps to take to get there. Something Sarah Durham said during her presentation really struck me: “I realized I wasn’t running my business—my business was running me.” That was my situation exactly: I had two young kids, a growing business that was choking me and I wasn’t attaining the quality of life I wanted. It was my tenth year in business, and while it had been a very successful and exciting decade, I knew I didn’t want to spend the next ten years the same way. Life is short and the timing is never going to be perfect, so I decided, “Now is the time.” The CFC was a big catalyst for me to embark on that path to find the knowledge I sought and make the changes I wanted, and I want to share that with others who are in the same situation I was.

HOW: What are you most excited to share with session attendees in San Francisco?

JDC: I’m excited to share my experience of how I went from being solo to having a studio with employees. As a freelancer, you start out with the idea that you are your own boss, and there is a honeymoon period where everything is peachy. But then you get to a point where the work is really rolling in, and the honeymoon is over. You are a one-person business, you’re wearing too many hats and you start to suffocate. Either you make the decision to scale back or grow. I’ve heard from too many in this situation to know it’s not uncommon at all. Scaling back is easy, but how do you grow? I couldn’t find easy answers so I forged my own path and accomplished what had been my five-year goal in just six months.

Meet Jenn in person at this year’s Creative Freelancer Conference!

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