Becky Simpson

Speaker / author / chipper things founder

Photo by Constance Higley.

Featured photos courtesy of Becky Simpson.

Illustrator, author, designer, speaker, and founder—all hats worn by Becky Simpson—an incredibly honest and talented creative entrepreneur. In the following chat, Becky shares with us her thoughts on channeling your creativity, learning that not everything started needs to be finished, and what it’s like to publish illustration books.

Can you share a bit about your journey as an illustrator and perhaps what you’re currently focused on? I always knew I wanted to do something artsy growing up. Before I went to college, I decided I wanted to be a graphic designer because that seemed like a practical choice. At the time I thought graphic design was designing window displays for Burger King, and I didn’t even care about Burger King, yet somehow I still chose this path. I had no idea how diverse and exciting this field is, but thankfully I went for it. I studied at Iowa State and after college, I landed my first job at a design and marketing firm. While I was there I wrote my first book as a side project. After I acquired the book deal, I moved to Austin to start freelancing. Now my husband and I are in Nashville (we love it!) and I’m pumped to see what the next phase is for freelance-job-life, while growing my product line, Chipper Things.

I love the product line. How long has it been around, and what are some of your takeaways from e-commerce? I launched Chipper Things in April of 2015 as part of my Adobe Creative Residency—it’s what I worked on for an entire year! I’m so grateful that I had the year to plan, design and launch my store. I have over 70 products and I’m pumped about what 2017 holds.

I started with all these collections, where I was trying to reach everybody, but the stuff that sticks is the gal pal collection. It’s really a celebration of friendship and play. It’s positive and humorous. A few things that I’ve learned that I’m starting to implement 8 months later: 1) If I do it right the first time, I don’t have to redo it 2) Figure out the why and then pivot from that place (it’s okay to not know the why right away) 3) Figure out ROI / finances right away. Don’t just wing it. Get the foundation down before say, adding contractors or investing in a new product.


Courtesy of Chipper Things lookbook.

I’d love to learn more about your illustration style. You’ve talked about experimenting with different drawing techniques before, but naturally gravitated back towards doodling and drawing less serious characters. I never set out to have a style. I’ve been drawing my whole life, so it has naturally evolved. I wish I had a more thoughtful reason, but it’s really just that what I’m doing is the most fun way for me to do it. When things are fun and easy, we tend to do them more. Doing what we like seems to be the most sustainable approach to finding our flow. 

I do want to acknowledge that it’s a lot easier to build momentum when you feel validated over and over again. I was always the token art kid. If I took up a new hobby today—playing guitar, for example—would I be able to grow and evolve at the same rate as I have with illustration? Probably not. It’s not impossible, it’s just easier to keep going when your teachers and friends and parents always affirmed that this is what you are made to do. 

But no matter what our path (smooth or rocky) or when we started (young or old), we will always—10 out of 10 times—get better and better (and thus evolve) so long as we stick to it and do it over and over and over again.

You’re also a speaker. It seems that your speaking engagements often revolve around topics of processes, particularly in starting and finishing. What do you personally find more challenging—starting or finishing a project? How do you break through those barriers? I think finishing is always the hardest part. I have this idea notebook filled with hundreds of ideas and if I had an infinite amount of time and resources, I’d start every one of them. But when the idea is something that’s so near and dear to my heart—where I feel defined by its success—that’s when it’s really hard to start. That’s bigger than just starting, it’s existential.

It seems like the last 10% takes as long as the first 90%, that’s why finishing is rough. You think you’re in the clear, but you have all of these decisions you’ve been putting off and tiny bits of work that take forever. That’s when it’s easy to say, “I’ll decide tomorrow”, and then tomorrow becomes next year.

Sometimes if things don’t get finished, it’s for a reason. When I first heard That Stephen King doesn’t finish every book he starts, I felt liberated for the first time to do the same. Not everything started needs to be finished, but you do need to know that you are a finisher. After we have the confidence to start and finish, it’s up to us to have the discernment to know what is worth pursuing (even when the excitement fades).

“Not everything started needs to be finished, but you do need to know that you are a finisher.

I didn’t know that about Stephen King, that’s really freeing to know. So, how do you personally identify when a project is worth finishing? After all the excitement fades, what is it about a project that makes you disciplined enough to follow through with it? Funny you ask, because I was just thinking about this moments ago as I was stirring turkey on the ol’ frying pan (it’s a cooking-at-9-pm-kind-of-night). In this moment, I think I do better—or at least follow through—when I can go at my own pace. I don’t know if that’s a good thing or not. I’d love to start something like a podcast but I don’t know if I can follow through every week (at this point). But if instead of a podcast, it was a season that was released all at once, I could probably get into that. I think it’s trial and error and observing failures and successes that lead us to not just the right projects, but the right processes. Much of it just comes down to a feeling. I did this 30 Days of Play Instagram challenge on my Chipper Things Instagram. It was all these fun little prompts to inspire people (including myself) to take time to play. A great idea in theory, but even I didn’t follow through. I probably only completed 5 days. I was embarrassed that I publicly gave up and never addressed it again. I kind of wish I just did the thing, but what I do know is that at the time it wasn’t for me. So follow through or not, now I know. I don’t regret giving up in that case. However, if I gave up out of fear, then I think I would have regret.

I don’t regret giving up in that case. However, if I gave up out of fear, then I think I would have regret.

Let’s talk about your books. I recently interviewed another author about the process of publishing illustration books, and it’s definitely no easy task. Having your hands tied into multiple projects at any given time, what is it about publishing books that gives you joy? I get this sort of long-game adrenaline rush from publishing. I don’t have kids, but these books kind of feel like my babies. I’ve spent so much time working on the concepts, outlines, etc. These things aren’t sexy at the beginning and the early stages bring zero guarantee of success. After hundreds of hours and drafts and tears and smiles and “I’d pay anyone any amount to finish this for me” moments, the book is done. And then a year later it is released, and I’m left with this archive of my work. It’s work that I will always have to look back on and remind me of that time in my personal and professional life. A book is a marathon, not a sprint. You can’t finish 150 pages and just be “meh,” about it. It’s impossible not to be proud, in my opinion.

The Roommate Book. Learn more about Becky’s books here.

Can you share more about not taking yourself too seriously? Why do you think it’s important to be more playful as an entrepreneur and a creative? I’m more serious than I come across, but I see most of life through a pretty jolly lens. I have a lot of structure in my day. I could be more spontaneous, but I have a feeling that this structure allows me to have play within these confines (I guess I am a child). My dad is very positive and has a good sense of humor. He always said, “If one person laughs, it’s funny.” [dad joke] and, “Is this a major, or is it a minor?” when we would complain about something trivial. I’ve just always enjoyed silly things and I’m naturally pretty optimistic. This lends itself to me watching old SNL sketches to start my day out in the studio. 

Not everyone is this way and that’s okay. If everyone can lean into their true selves and become the fullest version of that, I think we’d be in a good place. This is just where I’ve ended up (but I am partial to this way of life).

It’s one of your beliefs that everybody is creative. What’s your piece of advice for people having a hard time channeling their creativity or believing they’re creative? Everybody is creative! Every sentence you speak is improvisation…unless you’re reading a script.

For better or worse, we let these labels from our youth define us. Creativity is just connecting the dots. It’s a muscle that you have to exercise. Some people are born extra super creative, like some are born more athletic. But anyone can be creative (or athletic) if they practice.

One more thing. I don’t really like the label “Creatives.” I get it. It’s easier than saying “All you photographers and graphic designers and illustrators and…yadayadayada,” But that label makes it an “us” vs. “them” thing. We don’t call good looking folks the “Attractives.” Attractive people are more than their looks, plus that leads us to assume that they’re the only ones graced with good looks. We are all creative. Creativity isn’t exclusive. It’s inclusive.

If you want to be more creative, find more dots to connect. Step outside your comfort zone, keep a journal with you everywhere you go and meditate every morning. I’m still working on that, but I know that when I’m bursting at the seams with ideas, it’s because I’m healthy (physically, mentally, spiritually) and I’m consciously (and subconsciously) welcoming ideas and art.

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