Jen Sterling & Red Thinking
GLOBAL TOP PLACING WINNER: Been there. Solved that. But what's next?


Jen hung up the phone in her office at Red Thinking, a branding and marketing company. Her company is experiencing "growing pains" yet again and it is time to make important decisions. Balancing scale, identity and time available. 

The clock was ticking. Jen looked over to her right at her calendar, ever looming, carved up in tight daily schedules: Red (for her company), blue (household), green (daughter) and purple (volunteer work, business networking, speaking engagements, hosting her monthly working moms support group, community events, webinars, chambers of commerce meetings, five different board of directors meetings, award presentations, etc.).

Right next to her calendar proudly stands a new wireless digital photo frame with a rotation of over 100 family photos that her husband gave her for Christmas. "Look!" says Jen to a friend/woman business owner sitting near her desk. "There's one my husband took of our daughter Rachel that I have never seen before."

 "I'm dedicating this case study to my daughter, Rachel, and hope it helps to instill in her an awareness and balance of values, volunteerism and adventure."



Jen is an entrepreneur so full of ideas that she keeps turning pages to her next chapter. One of her first "aha" moments was in high school when the light came on literally. Her Junior Achievement group created flashlights from wires, bike handles and cords that plugged into an automobile cigarette lighter. Jen produced and sold lots of those flashlights. "It helped me to realize my entrepreneurial, type-A drive. I went from that to working retail part time and I was managing a men's store by senior year of high school."

The entrepreneurial light kept shining when she graduated from George Washington University where she received a BA in Visual Communications with a minor in Psychology (always thinking). It was no surprise to her family, friends and teachers that she didn't last long following the usual path of corporate employment. She found out quickly that she "was not a good employee" and instead followed her passion to build her first design and branding company.

In 1999, Jen had an unexpected "aha" moment soon after she and her husband moved to Loudoun County in Virginia where she was working from her basement. She received notice in the mail from the local government that it was against the rules for a home-based business to have "more than one full-time employee who is not living in the home." Jen had five employees and suddenly a big problem. "No one will ever care as much about your company as you do. I think of my company as my first child. Like family, you have to keep learning as you go to keep up. That was a huge moment for me. I realized it was time for me to ask for help."

With a deadline looming to halt her business, Jen started making calls and found the connections she needed to a real estate agent, moving company, etc., through the president of the Loudoun Chamber. She returned the favor by volunteering hundreds of hours to the Chamber. She later became the youngest person to chair that Chamber in 2005.

The Chamber is also where Jen found her passion for volunteering. "I joined the Chamber to learn about my new community. People kept telling me, 'If you really want to get involved, you have to get on a committee.' So I volunteered to get on the marketing committee. I could see how easy it was to fix something that the rest of the committee 'didn't see' because it wasn't their industry. I could do a couple of small things and they'd go, 'Oh, wow.' Then they'd say, 'Can you do this?'" That helped Jen feel good about what she was doing with her business skills. The more response she got, the more she started looking for more ways she could have the same kind of impact to help others."

Then came the next pivotal moment. "My husband and I were talking about having a family and I was very stressed about how to have a family and still do what I needed to do at work. Because at the time, I really was my company. I was doing the sales, the marketing, the art direction and I was the primary contact to the community. If I decide to have a baby and go on maternity leave, what would happen? Does the company shut down? Who runs everything I was running? I wanted kids, but I didn't know how to go about it from a business perspective. So I sent an email out to 20 women business owners just like me around the U.S.

"I went on Google and found women-owned firms that were like mine and wrote: "You don't know me, but here's who I am and I have a company like yours and I'm struggling right now with this decision about if and when and how to have kids. Other than the basics. I know how the birds and bees work. (LAUGHS) But how do I make it work with everything else? And what did you decide to do? And how did it impact your business? If you're willing to share it with me.

And every single one wrote me back. The answers varied. Some women said, "You can't do it. You have to pick one or the other." Other women said, "Of course you can have both. You just have to accept you'll never be good at either one of them.

I didn't necessarily have to agree or like the answers. It just helped me sort through some of the things I had been thinking about and it gave me the ability to think about it from different points of view. One woman was local and invited me over to talk about what happened when she first had her it had impacted her business...what kinds of things she put in place to offset those impacts.

Knowing that you can reach out to the world and get help is huge because as an entrepreneur, most of us are not wired to think that way. Most of us are wired to try and do it ourselves. Figure it out. We should be able to do this on our own. And we talk ourselves into a corner and then we don't get the help we really need. We feel stalled and helpless. Don't be shy. Ask for help?


Professional issue

"I've always been challenged with how to best support my business and plan for its growth. When I started it, I wasn't married. Then, I got married and we moved and I had to 'scale' up from home-based to leased space. Then we decided to have a child. Then I moved to the next level and new space by joining with partners.

You have to be able to grow and support the business as it grows, but not grow so fast that you are going to have to turn around and let people go. Or go in directions you might not really like to work in. And once you've had a child, there are many even more important demands on your time and life. (LAUGHING) You should see the master calendar for our family."


Personal issue

"Everybody talks about 'work-life balance.'

For me, it's not so much about where to spend the time, but how to make it happen. I did a lot of soul searching this past year. Stress can build up and I was thinking 'What do I want out of life?' My company was my first child and it's part of my family. I don't see my company as work. I see my role here as work. I want the company to thrive.

So I can cut back on my job, but I can't cut back on the company because it's my family. Complicating this, I'm trying to decide 'Who am I individually?' I talk to people who have dozens of friends they've kept in touch with their whole life. I don't have that. My friends are all through my 'work.' They all know me through my role with the company. That is a big identity struggle for me."


What's next?

"I am no longer obsessed with finding traditional balance. Instead, I will be ecstatic to reach a smooth integration of all parts of my life. So now I must figure out how to approach it. But in this process I really need to figure out where my company is going next...and at the same time...find me."