Becky Simpson Will Encourage You to Make It Up As You Go Along

Art director, illustrator, and educator, Becky Simpson, took a leap of faith when she launched her own brand and online store, Chipper Things. “I worked at a design firm for a couple of years after college,” she recalled in an interview with The Great Discontent. “I knew I wanted to eventually work for myself, but it wasn’t until I landed my first book deal that I had the confidence—or the savings—to take the leap.”

Her decision proved to be the right one, not only for her but for other people around her. Her art, you see, is made with the goal of cheering you up, and judging by her buzzing online presence, people are tuning into the message. Known for her relatable flowcharts and uplifting illustrations, her designs can be found on anything from paper goodies to apparel.

“Leaving that design job to freelance full time was a huge leap because I had absolutely no business sense, no practice freelancing, and no real plan at all,” admits Simpson. “Looking back, I can’t believe that’s how I dove in, but I’m so glad I did. I’m so grateful and excited about where I am now. I wouldn’t be doing what I’m doing today if it wasn’t for the route that brought me here.”

Now she encourages others to follow her lead and take that leap of faith. “It’s easy to look at people who are making things happen and think, ‘I wish I was like that. I wish I could be involved in interesting projects and take those sorts of risks.’ But the thing is: we all have that in us. Those people aren’t superheroes—they’ve just had practice.”

Follow her words of advice:

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