Jen Sterling’s Stories, Lessons & Insights

Jen Sterling shared their story and experiences with us recently and you can find our conversation below.

Hi Jen, thank you so much for joining us today. We’re thrilled to learn more about your journey, values and what you are currently working on. Let’s start with an ice breaker: Are you walking a path—or wandering?
WOW. This question stopped me in my tracks. I didn’t realize it until now, but I think for the past several months I have been wandering. I go through phases in life and business where I have very clear goals and I am following a determined path to reach them. But then there are times, like right now, where I feel a bit lost. I know I am doing the right things, and I am happy I am doing them, but I have misplaced the drive to pursue them doggedly. I think of these times like the “winter” of my business. My creative drive is more subdued… almost hibernating. I am handling more administrative and generic tasks. I am resting more and taking better care of my personal health. I know these things are required in order to make the other “seasons” of my practice the most fruitful as they can be. So rather than feel frustrated or depressed at being lost or wandering… I am grateful that “spring” is right around the corner, and my days will fill with passion and purpose again.

I obviously needed to hear this right now. Thank you for asking!

Can you briefly introduce yourself and share what makes you or your brand unique?
I am a creator. I am an entrepreneur creating businesses (7 over the past three decades). I am always thinking up projects to address a problem at home or in my community. Other times, I am an artist painting large, colorful abstracts based on my emotions and intuition. In all of these cases, I am creating something that did not exist before.

Currently, I am focused on being a full-time fine artist, and I run a nonprofit organization to benefit all visual artists in Maryland through an annual open studios tour and a year-round online community.

I thrive on creation. I find it challenging to address an issue, problem, or situation with my ideas. My brain is my toolbox, and I love to apply it!

Amazing, so let’s take a moment to go back in time. What relationship most shaped how you see yourself?
I have been impacted in different ways by a lot of people in my life. Some that I am related to or know very well, and others that only came into my life for a very short time. But who most impacted how I see myself? Definitely my dad. In my early years, as I grew up, and even into adulthood, my dad had a way of seeing me, even when I didn’t, and he was able to provide insightful guidance when it was needed most.

When my sister and I were little, my dad would often razz us by saying things like “you can’t do that… you’re a girl.” He never meant it. He knew it would make us throw our shoulders back, step up to him, and say, “Yes, I can, watch me!” That inner confidence and strength have served us both as we grew into professionals, each of us surpassing what we would have thought possible.

Do you remember a time someone truly listened to you?
It’s going to sound so small… but it meant the absolute world to me. When I was dating my current husband, John, he asked me to join him on a short road trip to visit his friend at their place of business. His friend showed us around and explained his business model and processes. He shared his financials and spoke with John about his interest in a possible loan or investment in his business. We left to drive home, and before we even got out of the parking lot, John turned to me and asked what I thought.

What did I think? He was asking me? When I questioned him, he stated that I ran a million-dollar business and was obviously successful. He truly wanted to know how I saw the business, what could be improved, and did I think it would be a good investment.

I think that was when I first fell in love with John. My first husband always treated my companies as if they were hobbies and was always pushing me to get a “real job.” John saw me as a peer. As a business person in my own right. And he truly wanted to hear what I had to say.

Sure, so let’s go deeper into your values and how you think. What are the biggest lies your industry tells itself?
So many artists think that if their work is “good enough,” it will sell itself. Or if they have a gallery representing them that they don’t have to worry about selling themselves.

These thoughts could not be further from the truth.

Art is a business like any other. I need to invest in my brand, execute on my marketing, and continually work to achieve awareness of my art. This is the case even if I have a gallery that chooses to show my work. AND I need to make sure my creative output is the best I can make it on top of all of that. No artist can just hide in their studio all day, every day, painting. We must invest ourselves in our business just as much as in our craft.

Okay, so let’s keep going with one more question that means a lot to us: If you knew you had 10 years left, what would you stop doing immediately?
I asked myself a version of this question six or seven years ago. Life is short. Am I spending my days doing what I truly enjoy? And, for that matter, do I like who I am while I am doing it? The answer was no. And a rather emphatic no at that. I decided to immediately take steps to rectify that.

I wanted to divest myself of my last creative agency and throw myself into my fine art. The work we were doing had changed so much since I had first started the company. I no longer felt the creative passion and inspiration for the work we were doing or the clients we were doing it for. I started seeking a buyer and eventually chose to sell it to my staff in order for it, and them, to continue blooming in the way that best worked for them.

Then I started fresh. I had been painting for years as a hobby, but now it was going to become my full-time gig. To do it right, I needed to start a company and set certain legal and financial groundwork in place. I needed to switch my mentality from working in a team selling our services, to working on my own and selling myself. My artwork was a raw expression of my thoughts, my feelings, and my creativity. Opening that up to the world is a scary thing to do.

I have not regretted it for a second. It has been five years, and I can honestly say that I love every day of it. I could win the Mega-Millions Lottery tomorrow, and this is still what I would choose to do with my time. I am free to choose my activities, the way I spend my days, and who I work with. Freedom has always been my number one value. Now I get to fully live it.

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Image Credits
Portrait by photographer Mary Gardella

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