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Evelyn Henson: How to Thrive in Every Season of Business

APPLE PODCASTS | SPOTIFY Every entrepreneur has experienced the panic that comes with a slow sales month. After 10 years in business, our latest podcast guest has learned to deal with the ebbs and flows to make the most out of every season. Evelyn Henson is a watercolor artist based in Charlotte, North Carolina. She […]

Photo of Evelyn Henson in her art studio


Every entrepreneur has experienced the panic that comes with a slow sales month. After 10 years in business, our latest podcast guest has learned to deal with the ebbs and flows to make the most out of every season. Evelyn Henson is a watercolor artist based in Charlotte, North Carolina. She creates whimsical art designed to brighten people’s homes and bring them a little sunshine.

One thing I really admire about Evelyn is that she’s always kept a love for her work at the forefront of what she does. Whether she’s in a busy season or a quiet period, she stays focused on her mission of creating art that connects people.

In this episode, Evelyn shares the behind-the-scenes of her creative journey – from starting a business at just 22 years old to managing unpredictable income and learning to set better boundaries around her work. 

Press play for the full interview or keep reading below!

Life Before Business

“I was always doing creative things,” Evelyn says. When she was young, her mom sent her to art camps every summer and she spent hours working on creative projects – but she never saw it as a career option.

“I never thought about the fact that there were people designing the cards and bedspreads that I loved so much.” Back then, Evelyn thought that having a creative career meant being a starving artist in New York City. 

So she decided to study art history with the goal of eventually working in an art museum. In the meantime, she kept painting on the side.

Opening Up Shop

After graduating from college in 2013, Evelyn started applying for entry-level art museum jobs. When she didn’t hear back from anyone, she decided to open an Etsy shop to add something extra to her resume. 

“I thought it would show that I was entrepreneurial. I had all this art I’d painted, and I thought I might as well sell it until I got a real job.”

The first weekend that Evelyn opened her shop, she almost sold out. That was when she realized there was real potential in working as an artist. She decided to stay at home with her parents for a little while longer to see if she could make a living selling her paintings

A year later, Evelyn’s shop had grown into a full-time business.

The Power of Personalization

Evelyn got her start selling paintings to her personal network – mostly friends from college who were looking to decorate their first homes on a budget. She also attracted an organic audience on Pinterest and Instagram, both of which were in their early days of popularity. 

After that exciting first weekend, Evelyn was disappointed when her sales dropped off over the next few months – but she kept at it, knowing that if she’d been able to sell that many prints once, she could do it again.

The Turning Point

Evelyn’s first major success was selling map prints of different cities; that was when she realized how many people were interested in personalized art. 

She got to work creating other personalized collections, paying attention to which items were most popular so she could replicate that success. “That was the biggest thing that allowed me to grow.”

In December 2013, Evelyn switched from Etsy to selling through Shopify on her own website – another major turning point in the business.

Finding the Gaps in Your Business

A few years into business, Evelyn was still working hard but felt like she was spinning her wheels. She knew she needed help to drive more growth.

“I’m not a math person at all, that was always my worst subject in school.” Evelyn wanted to be more strategic about where she spent her time, so she signed up for The Blueprint Model, my finance course for entrepreneurs, to learn the number side of her business.

What Evelyn Learned in The Blueprint Model

“I feel like I’ll always have something new to learn in finance and business. Even now, I’m always curious about how I can run things better.”

Taking The Blueprint Model helped Evelyn identify her most profitable products and showed her where to concentrate her growth efforts. She also learned how to price her artwork more effectively. 

When Evelyn started her business, she was 22 years old. She priced her art based on what her college friends could afford. “I just didn’t know any better at that age.” Now, she’s able to charge higher rates with confidence because her prices are based on a proven strategy.

Art Marketing Tips

Although Evelyn got her start on Instagram, she’s the first to admit that the platform has changed. 

As an artist, Evelyn used to be flooded with encouraging comments and DMs – something that, as the app has grown, doesn’t happen as often anymore. It’s been a hard adjustment for a lot of creatives. 

“Back in 2013, I could send something to an influencer and they were happy to post it on their feed for free,” Evelyn says, aware that the same art marketing tactic wouldn’t work today. 

Although Instagram is still a great place to make connections, these days Evelyn prioritizes other platforms for art marketing. The bulk of her sales come from her email list.

Managing the Ebbs and Flows of Business

One advantage of starting her business so young is that Evelyn never worked a full-time corporate job. She didn’t need to adjust to self-employment because “that was always my norm.”

That’s not to say it was always easy – like any creative business owner, Evelyn has been through highs and lows. Some seasons are busier than others and the slow months can be stressful.

“In the beginning, I was living with my parents so I was in a fortunate place where I was more in save mode.” But once she moved out, that first bill for her rent was intimidating. 

Evelyn was raised by money-conscious parents, so she took a slow and steady approach, living frugally and keeping her expenses minimal. Over time, she adapted to new bills and was able to grow her confidence alongside her business. 

“Seeing that year-over-year growth helped me maintain my sanity.”

How to Set Better Boundaries

Like most new entrepreneurs, Evelyn worked long hours for the first few years. Without a day job, she struggled to maintain boundaries and often ended up working through the weekend.

“It was hard for me to slow down and learn that rest is necessary. But you need time off or you’ll run yourself into the ground. Unfortunately, I learned those lessons that hard way.”

One lesson that Evelyn had to learn was that not every message needs to be responded to ASAP. She’s slowly transitioned from checking email constantly to a few times a day, and recently, setting an autoresponder so she can step away completely. 

When it comes to maintaining work-life harmony, it’s often small adjustments – something as simple as an autoresponder – that make the biggest difference in our peace of mind.

Staying Calm Through It All

Now 10 years into running her business, Evelyn still keeps her love of art at the center of everything she does. She’s become known for her unique and whimsical style and been featured in publications like Southern Living Magazine.

Looking back to her 22-year-old self who had just launched an Etsy shop, she would tell herself, “Don’t compare your beginning to someone else’s middle.” 

Although there are still ups and downs, Evelyn has learned to approach slow seasons with calm, knowing there’s always another busy season ahead.

More from this Episode

To hear the full story and more about Evelyn Henson, press play on the player above for the full interview or click here to download the transcript.



Free Monthly Art Downloads from Evelyn

Evelyn Henson Featured on Draper James

The Blueprint Model by Shanna Skidmore

Photo of Evelyn Henson in her art studio

Evelyn Henson

Brushed with a love for all things creative, Evelyn grew up in Columbus, GA where she always had an appreciation for art. She first discovered her love for painting when she attempted a floral still life as a Mother’s Day gift in college. After that, she couldn’t put down the paintbrush and opened an Etsy shop shortly after. What started as a few art prints on Etsy slowly evolved into a colorful and happy brand featuring stationery, gifts, wallpaper, and, most recently, textiles, and has been featured in Glamour, Domino, Redbook, People, and Southern Living. With everything she creates, Evelyn hopes her art brings your home sunshine for years to come. Her studio is currently based in North Carolina.


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October 19, 2023

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