Chalk It Up To Untapped Talent: How Boston's Joan Awylward Went From A Server To Certified ChalkBos - Lioness Magazine
Joan Aylward, a chalkboard artist better known throughout Boston, as ChalkBos. (photo courtesy of ChalkBos)
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Chalk It Up To Untapped Talent: How Boston’s Joan Aylward Went From A Server To Certified ChalkBos

“I winged it the whole way,” said Joan Aylward, a chalkboard artist better known throughout Boston, as ChalkBos. “I had no choice but to dive head first into everything and try to figure it out as best I could.

Today Aylward is something of a local Boston celebrity with her work featured in many bars and restaurants throughout the city. Having worked in the restaurant business for 20 years as a server, Aylward, a graduate of Massachusetts College of Art and Design, always thought of herself as an artist but never really saw how it would actually come to fruition.

In school, Aylward majored in photography and laughs today, confessing to having a camera she never truly knew how to use. Once she started a family she began a calligraphy business from home, which would turn out to be useful years later when she started her chalkboard art. It was a divorce that brought her to the restaurant business and eventually onto the path she walks today.

“The last restaurant that I worked at was on Boston Waterfront and they had floor to ceiling chalk walls as you walked in,” explained Aylward. “I just said to my boss, ‘Do you mind if I write our cheeses, our charcuterie and make it look really nice?’ So I started doing that and then I started doing other things just in my off times, just fun things on the walls.”

It wasn’t long after this that Aylward’s handy work started to catch the eyes of not only her bosses but of the many regular patrons of the restaurant. One boss decided to take Aylward’s talent beyond writing the daily specials and suggested they pitch custom walls to clients that would book rooms for business events, and have Aylward draw their logo on the wall.

“I would come in early and do a logo and a welcome and I would get maybe $35 or $50 and I thought that was fantastic, it would fill up my gas tank,” said Aylward “And then I would put my uniform on and serve the party.”

Quickly, Aylward’s work started to get recognized and she found herself with requests to do signs in other bars and restaurants. As this went on a co-worker suggested that she should be doing this full time.

“What a crazy thought,” Aylward said. “But he kind of put this pressure on me. He said, ‘you know what, think of a name. I want you to make up some business cards and I’m going to give you two weeks.‘”

Challenged accepted. Aylward came up with the name ChalkBos, a combination of the medium she works with, chalk, and an homage to the city she loves, Boston. The rest, as they say, is history. Working solely as a chalkboard artist for almost five years now, Aylward still works 100 percent by word of mouth advertising. When caught in action you can see her, “ChalkBos” written on the back of her shirt as she works on the wall in front of her.

“As a trained artist turned chef I know how important it is to do something that feeds your soul,” said Suzanne Lombardi, Aylward’s first client and Chef/Owner of The Plate in Milton, Mass. “Joan’s work has soul. She’s an amazing talent with a true love for her work. I would literally have her drawing all over my restaurants every day if I could. Her work just makes me happy. It’s been so great to watch her creativity blossom. A true ChalkBos.”

Today Aylward can be found on Instagram, her wall of posts looking more like a carefully curated art gallery than an example of her work for her clients.

“I was honing my skills every restaurant I worked at and I had no idea I was doing so,” Aylward said.

Having never had any intention of becoming a freelance artist and having never known anyone who was, Aylward really had to learn on her own and fast. From figuring out pricing, time schedules and maintaining and growing her clientele, Aylward had to draw upon on all her past experiences to help her create ChalkBos into what it is and performs as today.

“I believe in Destiny so I just feel like whatever happens to you is meant to happen to you,” Aylward said. “I feel like it’s a little bit of your own hard work plus a little predetermined escapades and things that happen to you that force you into what you do or how you wind up in life and also I think that being open to those ideas certainly has a ton of play into it.”

Not yet ready to divulge what she has planned for the future of ChalkBos, Aylward would only say more was to come.

“I get that feeling, that universe feeling,” explained Aylward. “The way that this company was sort of thrown at me, I just kind of know that it’s going to be better than and bigger than what I’m doing right now.”

About the author

Tara McCollum

Tara McCollum, a New York native, currently resides in Houston, TX where she has learned to trade in cosmopolitans for margaritas, and white winters for palm trees, but has held stead fast to her great love for the Yankees. She currently works full time as a middle school English teacher and is a loving mother to a little monster named Dean, who reminds her to never give up on her dreams and encourages her to keep changing them, and often.

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