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One of Jane Caldwell’s college professors described her as being “grindingly thorough.” According to Jane, the professor didn’t mean it as a compliment, but Jane has found her perceptive tenacity has been one of her greatest resources in life. 

Not only did it help her secure a career as a college professor, but it led her to start her own business, The Rowdy Ladybug. And ultimately doing what no one else has done. 

Jane’s inquisitive mind loves solving problems and facing challenges head-on. She thrives when she can fall down a rabbit hole, think outside the box, and create something entirely one-of-a-kind. Jane has what we call the mind of an entrepreneur.  

After several years in academia, Jane had her daughter and decided to become a stay-at-home-mom, but her brain wanted to work on something and solve problems.  

Jane watched how her daughter pulled at seams and changed her clothes several times throughout the day, and she saw a lack of durable children’s costumes in the market. 

After seeing a gap in the market, Jane took it upon herself to fill it by researching and analyzing how to make costumes that not only withstand children but allows them to use their imagination and think outside the box. 

She wanted to make something that no one else had even thought to make.

Jane began by making costumes for her daughters, then making towels and custom costumes for her friend’s children. Not only that, she put her innovator hat on and found ways that one costume could be made into several different outfits. To save parents time and energy from cleaning up a pile of costumes and give them more storage space. 

Her business began to grow gradually, especially once friends and customers began saying how shocked they were that her creations had lasted for years. YEARS! No kids’ clothing or materials these days are durable enough to last one year.

Jane began seeing traction, she raised her prices, began selling online, and The Rowdy Ladybug was born. 

Jane is dynamic, confident, and incredibly intelligent. She’s different from others in a way that’s her superpower and lead her to create a business out of imagination.

I hope you enjoy this interview as much as I did!



Jane Caldwell The Rowdy Ladybug website screenshot

How did you get started making children’s costumes and accessories?

Jane: I got started on the business because I had a baby, and I’d been working as an adjunct professor. And it just really wasn’t sustainable. 

But when I was at home, I needed something to do. So I picked up an old sewing hobby, and the business followed after a couple of years.

I started off making things that friends asked me for. “Hey, my toddler is exploding out of their infant bath towel. Could you make something?” Or, “My daughter’s having a birthday party, and the theme is superheroes, and we’re going bowling. Could you make something we could have as a party favor?” That’s how superhero capes got started.

I think some of it is I’ve always loved making things. I love sewing, it’s very soothing. And I love dressing up and as an adult. 

Making costumes for kids, I kind of get that vicarious thrill of putting together something that’s going to be fun for someone.

Pretty early on, I realized I wanted to help small people out there dress up, and play make-believe daily, not just on Halloween. 

I asked myself, what can I make that will put kids in charge of their playtime?

Jane Caldwell The Rowdy Ladybug Facebook screenshot

How long have you been sewing?

Jane: My mom taught me when I was around 14 to use the sewing machine. But I remember a couple of really awkward hand-sewn projects when I was around five or six with a really chunky embroidery needle that was blunt on both ends. So I’ve kind of always sewn. But if I were to do the math, it’s been well over 40 years.

How did you end up pursuing The Rowdy Ladybug full-time?

Jane: Once my daughter started school, it was decision time. Did I want to go back to some sort of part-time college teaching? What was going to allow me to be home when I needed to?

 I was really enjoying the business, and it seemed like the logical time to put more time and effort into it. But it came closer to full-time about seven years ago when my daughter started elementary school full time.

Then around five or six years ago, I started getting more interested in marketing. And I realized, “Oh, I can market things to people without it being this dirty, sleazy, sales pitch that I feel like I’m selling used cars, and people are going to run from me on sight.” 

It has been a gradual ramp-up.

Jane Caldwell The Rowdy Ladybug  Pinterest screenshot

What’s your favorite thing to design for The Rowdy Ladybug?

Jane: I think the costumes are my favorite thing to design at this point. I’ve managed to come up with enough materials that I can keep finding ways to turn costumes into things that kids can embellish on their own and change for each play session.

That’s what really gets me passionate, and I’m like, “Okay, how do I put the kid in charge of playtime?” Granted, kids will be imaginative and can put on a coat, and it can become a spaceman’s encounter suit or a doctor’s coat. 

Kids can imagine a costume to be anything, but I’m like, “What if I could bootstrap that a little bit? Give them a bit of an advantage where the costume can be decorated and changed up to help get that creative process started so that it’s really child-driven.”

So really, designing costumes has become a favorite for me now, partly because it’s a challenge for me. It’s like, “Okay, what kind of spin can I put on this so that it’s not just one costume that only does one thing?”

I also think from the parent perspective; no one has infinite space for storing costumes, no matter what you try to do. I’ve seen all of these plans for adorable dress-up corners, but you know, kids. 

Hangers are not easy to use; sooner or later, it ends up in a pile or the dress-up box. Otherwise known as the impenetrable tangle where they dump the entire box out and rummage for what they want that day.

Jane Caldwell The Rowdy Ladybug  Instagram screenshot

What tips do you have for someone designing clothes for children?

Jane: Well, certainly, any time you make things washable, dryable, and easy care, that’s huge for any parent. I think many of us have had the experience of taking something faux fur and running it through the washer and dryer and having it come out crunchy because it melted. 

I’ve noticed many clothes have the most conservative care instructions to clean and dry so they won’t get damaged. We’re seeing a lot of things being labeled with the safest method because the care routine hasn’t been tested, so a lot of things are line dry, flat dry, and drip dry. 

Sooner or later, you run out of space, especially if you have eight bazillion articles of kids’ clothing in your house. 

For kids’ items, easy-care is a big thing. Organic materials, when you can get them, are great. However, I tend to go for cotton/polyester blends just because they don’t wrinkle.

Jane Caldwell The Rowdy Ladybug Instagram screenshot 1

Do you outsource any help with your business or do you do it all yourself?

Jane: Yes, I have a couple of local people. Often, they’re moms who are working from home because they either have kids who are not yet in school or kids coming home from school, and they need to be home. So if they’re working, it’s part-time. 

Then I have one or two friends who work full time who also like to sew, so I will outsource small jobs to them to take care of a lot of the basic steps in production.

I do outsource a fair bit. And I’m slowly gearing up the courage and sets of instructions to outsource some of the more detailed tasks. It helps to have been a teacher. I trained many teaching assistants in one of my prior jobs, and it’s like, “Okay, how do you boil down this stuff to the basics?” 

As a crafter, some of it is, “Well, what am I even doing?” Then, I take that and try to explain it in a way that another human can do it.

Jane Caldwell The Rowdy Ladybug pin

How did you shift your business to become more profitable?

Jane: Really, I had to adjust my pricing. It’s tricky because if you sell locally, there’s a lot of “No one’s going to want to pay that” and “Who do I think I am charging that much?” 

Eventually, selling online has helped with that because then you can reach other parts of the country. 

What was the process like trying to find high-quality items that stand up to kids’ rough and tumble play?

Jane: Well, friends would bring me costumes and be like, “This is all shredded out at the shoulder seams. Could you fix this?” I mended those things and tried to figure out, “How are we even going to salvage this? There are shreds of shiny fabric threads sticking out everywhere. What do I do?” 

Which has gone into my thinking about construction, wondering, “Okay, if will this pop or shred? What is a kid going to do?” Having my own little boundless energy machine here at home, I was like, “What’s she going to do?”

That helped and some amount of testing it myself. “Okay, I sew a seam in terry cloth.” When it’s in a towel, towels seem so durable, but all you have to do is cut a piece of terry cloth, and suddenly it is this fragile thing where all of the little loops fall out, and the edges start raveling. 

Figure out that process took a lot of trial and error, some investment in new equipment, and then finding ways to misuse my equipment. “This is not typically done. Can I do it anyway? Yeah. Can I add a pop stitch needle to this? What’ll happen?” 

I went down many internet rabbit holes and threw money at the wall to see if it stuck.

Just playing around has really helped and testing it myself, along with being picky about it.

The Rowdy Ladybug Instagram screenshot 2

What has been the hardest part of owning your own business?

Jane: Time management. And finding a balance between the fun things to do and the things that have to be done. 

Also trying to get that stuff done so I can be present mentally and physically for my family. 

I get tunnel vision when I’m excited about something. That’s a battle, especially without traditional hours or a boss outside of the cats supervising me. 

I went down many internet rabbit holes and threw money at the wall to see if it stuck.

Just playing around has really helped and testing it myself, along with being picky about it.

As a business owner, what tips do you have for not letting it take over your life?

Jane: Planning, it’s not my strong suit. When you work for someone else, you can go through work on autopilot. But not if you’re an extremely motivated business owner and you want career advancement. 

When I worked for other people, whether it was a teacher or researcher, I never really had that much drive. There would be plenty of days where I could go and do the thing and then come home, but now I have to be strategic, so I’m planning it ahead of time. 

It really comes down to planning and having some sort of cycle, like whether you’re doing a quarterly review with yourself or checking your books at the end of every week or once a month you record all of your stats. 

Having a regular check-in process to say, “Okay, am I staying on-task with the business? How about the rest of my life?” 

Jane Caldwell The Rowdy Ladybug photo

What’s your favorite part about being a business owner?

Jane: Getting to do what I want. I don’t have to worry as much about my carbon footprint, which has been wonderful. And having a flexible schedule so that I can be here when my kid gets home from school yet still be doing some work. I can check in with her about her day at middle school and be present without getting in her way. I love that I still get to be around and available to my family. 

And just the flexibility to pursue new things, along with all of the mental challenges. I guess I don’t really have one favorite thing about having my own business, but it’s been great.

Why did you decide to use Tailwind?

Jane: Once the pandemic hit, I wasn’t doing craft fairs, so I started making online sales. As part of that, I needed to do online marketing, and Pinterest seems to be a great way to drive traffic to a website through pins. 

Pinterest is frequently changing. They’re always trying to refine how their platform works. It takes a lot of work to keep that rolling. Having some sort of scheduler like Tailwind is almost essential if you’re pinning on Pinterest for business and you want time to focus on anything else.

That’s what got me started with Tailwind because it seemed to be a really good platform for doing that. 

I knew a few other makers who were using it. And now I’m finding out other things that they’re adding, like Tailwind Create. I’m still only dipping my toes into that, but it’s like, “Huh, that took my picture and made 62 different graphics with it.”

I like that once I fill up the schedule pins, it will keep pinning, and I don’t have to stay focused. It will just carry out the schedule for me as long as I can keep that scheduler full. It gives me a lot of leeway and creative freedom to mess around with my schedule doing other things. It’s one ball I don’t have to worry about dropping.

Jane Caldwell The Rowdy Ladybug Instagram screenshot 3

What’s your favorite Tailwind feature and why?

Jane: I’m really fond of the interval setting for pinning so I can have it pinned to one board, and that can be exported and populate a calendar so quickly. 

And lastly, what’s next for The Rowdy Ladybug?

Jane: It’s back to work, and the fact that it keeps working even when I’m not poking at it is just a beautiful thing. 

Plus more costumes. I’m playing around with a design for a knight-king-queen costume that includes a design-it-yourself coat of arms or something on it.

Where you can find The Rowdy Ladybug

You can buy Jane’s costumes, bath mitts, and towels on her website or Etsy. And you can also follow her journey on Facebook, Pinterest, and Instagram!

I hope you enjoyed this interview as much as I did. Jane is as original as her innovative creations.

Until next time, friends!

Psst! This Pin was made in seconds with Tailwind Create. Try it for yourself

From college professor to small business owner - Jane Caldwell turned her lifelong hobby of sewing into a one-of-a-kind business of enhancing imagination!

Lauren Noble

Lauren Noble is a Content Marketer at Tailwind who has been published on Scary Mommy! Lauren owns her own self-love and worthiness coaching business, Noble Guidance, and lives in Oklahoma City with her two daughters, Madelyn and Roz, and their cuddly cat Theo Moon.

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