Awesome Woman of the Month: Jessie Oleson (aka Cakespy!)

Jessie and her Cakespy creations!

How would you like to be a dessert detective? You could eat your way through bakeries across every city you ever live in or visit, and tell people about your sweet discoveries. And people would listen. In fact, millions of people would reference your (very famous) blog every time they needed some advice about how they might best spend their calories.

What if you played with your food by using a pen instead of a fork? As a professional illustrator who focuses on fun and whimsical characters made out of dessert, you could use your artistic gifts to dazzle the eyes, not just the stomach.

Wait…here’s an even better question: what if you could do both?

You can! Especially if your name is Jessie Oleson!

Most people know Jessie as the head spy behind Cakespy, the blog that used to be an idea, but then became reality, which soon gave way to cookbooks, magnets, T-shirts, posters and lots of things with pink on it.

There is one important piece of information key to this story (besides all the pink, of course), and it’s this: before there was a blog or a cookbook or posters, there was first a belief. A belief so powerful that, without it, nothing would have ever happened. But, because of it, everything happened! So here it is:

Amazing things are possible.

“I don’t think I would have imagined as a young girl, ‘I want to be a minor internet celebrity blogger who draws and writes about cupcakes,’” Jessie jokes. “But, at the same time, I wouldn’t have been surprised. I have always been a big believer that amazing things will happen if you let them.”

Jessie, the aspiring artist!

She is quick to point out that she doesn’t believe anyone can do absolutely everything. “I am pretty sure I cannot be a professional basketball player,” she chuckles. “I believe it’s a matter of finding a language with which you can successfully communicate with the world. In my case, I found that when I combined my illustrations and writing and themed it around baked goods, it struck a chord with people – and, hooray – it made me happy, too! I believe that when you truly feel good about what you are doing, people will respond in kind.”

Dreaming is a vital part of life, but even if your head is stuck in a marshmallow cloud, Jessie believes it’s a good idea to have one foot firmly planted on the ground. She is also big on flexibility. When she was little, she submitted a story to a popular children’s magazine. On her envelope, she doodled a few things to make it stand out, and stand out it did. The magazine didn’t accept her story, but they wanted to buy her illustrations!

“Sometimes, life can throw us curve balls,” she says. “But, sometimes, this can be a beautiful thing. While there’s something to be said for being responsible and planning, it’s a good reminder to be flexible in your goal. Ultimately, in that case, I reached my goal of being published, but it wasn’t quite the way I thought it would be.”

The good news is there are never any rules when it comes to creativity, and Jessie has been enjoying the ride, given that it has taken her to some interesting places. A self-described “agent of delight,” she believes her job in life is to make people smile.

“I keep myself in a mindset of delight by wearing colorful clothing,” she says. “Why wear just one color when I can wear all of them? I also proudly wear my love of cupcakes, unicorns and all things bright, happy and sweet, both in everyday life and on my website.”

Her work was inspired early on by artists like Roald Dahl and Quentin Blake. She was even inspired by copying drawings from the Nickelodeon show, Doug, and by following books and cartoons where the artwork spoke to her in some way.

She attended Pratt art school in New York, and believes if you want artistic training, art school is an intensive way to attain it. “It is wise to supplement art courses, even if you’re at art school,” she advises, “with business and writing courses, because those will be immensely helpful as an artist.”

So what does this former Girl Scout believe helped her in life – besides art school, the color pink, delivering delight and always believing anything is possible?

“I did a lot of learning about friendship and teamwork in Girl Scouts,” Jessie says. “Those are seemingly simple things, but, really, are skills unbelievably important when running a small business – especially when you’re responsible for answering to so many different people.” Her passion for Girl Scouts, and especially Girl Scout Cookies, shines through in her blog posts, too! Whether it’s issuing a Girl Scout Cookie Milkshake Challenge to her readers, snapping a photo of the site of the very first Girl Scout Cookies sale or sharing a recipe for cookie sandwiches using Girl Scout Cookies, Jessie has found a way to keep Girl Scouts in her life.

Jessie also remembers being enamored by a project she did in Girl Scouts that involved making little dolls out of dried apples. Now, we’re not saying that making art out of food as a Girl Scout had anything to do with the success Jessie Oleson has experienced today, but we will say this: there really isn’t a better, or more delicious, combination.

Cakespy has clearly found a recipe for success, and we applaud her for having the confidence needed to believe in and pursue her dreams. Thank you, Cakespy, for bringing sweetness to people’s lives!

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