Today we’d like to introduce you to Wendy Conklin.
Hi Wendy, we’re thrilled to have a chance to learn your story today. So, before we get into specifics, maybe you can briefly walk us through how you got to where you are today?
I actually started out as a teacher in 3rd and 5th grades. Then I went back and got my master’s in Gifted Education. After that I spent years writing curriculum for publishing companies and traveling around training other teachers on best practices.
In 2012, I took an upholstery course just for fun, and it completely changed my life. I started selling pieces on Etsy almost right away. I had zero clue what I was doing on the business side…learned a lot of hard lessons about actually running something profitably. It took six and a half years of doing both before I finally worked up the nerve to quit my day job and go all in.
Since then it’s grown into Chair Whimsy — custom chairs, a full line of DIY upholstery courses, a book, and a coaching group where I help other creatives build their own businesses. Still feels like the same thing that hooked me back in 2012: chairs, color, and a lot of whimsy.
We all face challenges, but looking back would you describe it as a relatively smooth road?
Not even close. Pricing was probably my biggest early struggle…figuring out how to actually price my chairs so I made money, not just covered costs.
At one point I had chairs handcrafted in Italy and shipped over for me to design and sell, but the profit margin was brutal once you factored in everything. And I had no idea how to ship a chair when I started. I had several break in transit, and one set just went missing entirely. Try explaining that to a client.
The real lesson was learning to believe in my own higher prices and grow a spine about it. This work is hard, and when you price it like it’s hard, you attract a different kind of client — ones who don’t try to talk you down, because they already know it’s worth the artisan touch.
Thanks for sharing that. So, maybe next you can tell us a bit more about your work?
I design and build custom upholstered chairs, and I specialize in pattern mixing: taking prints that shouldn’t work together on paper and making them sing on a chair. Florals with stripes, checks with a bold color, a “hero fabric” as the anchor and everything else built around it. I teach this exact method in my courses, but on my own chairs I push it further than I’d ever tell a beginner to.
I’m known for chairs that don’t look like anything else in the room, on purpose. Most upholstery leans safe: one fabric, one texture, done. I go the opposite direction. I get an idea in my head, sometimes from a fabric, sometimes from something totally unrelated, and I chase it until it’s a finished chair. My Taylor Swift Eras chairs are probably the best example. That idea popped into my head, I ran with it, and it ended up on the cover of What Women Create Magazine.
What I’m proudest of isn’t any single chair, though. It’s that I figured out how to teach this: how to mix patterns and colors on purpose instead of by accident. Now thousands of women have used what I taught them to make their own homes bolder. That, to me, is the whole point. Not just making cool chairs, but proving anyone can learn to do it.
What sets me apart is that I don’t play it safe, and I don’t want my students to either. Rules are meant to be broken once you understand why they exist. That’s basically my whole design philosophy in one sentence.
Risk taking is a topic that people have widely differing views on – we’d love to hear your thoughts.
I am a risk-taker, but a calculated one. I don’t jump without looking. I look hard, then I jump.
Quitting my day job was the biggest risk I’ve ever taken. We needed my income, so this wasn’t a “just try it and see” kind of decision. But I already had evidence I could sell, since people were buying my chairs. The real risk wasn’t whether I could sell at all, it was whether I could get my prices right so selling actually turned into a living.
Selling my art under Whimsy & Co has been a different kind of risk. Chairs are functional, so even if someone doesn’t love your exact style, they can still see the craftsmanship. Art is just subjective. Someone either connects with it or they don’t, and there’s nowhere to hide behind function. That vulnerability is newer for me, and honestly, still uncomfortable some days.
My view on risk is pretty simple: get enough evidence to believe it can work, then commit fully instead of hedging. The calculated part is doing your homework first. The risk part is still being scared and doing it anyway.
Contact Info:
- Website: https://chairwhimsy.com/
- Instagram: https://www.instagram.com/chairwhimsy/
- Facebook: https://www.facebook.com/Chairwhimsy/
- Youtube: https://www.youtube.com/c/DIYwithChairWhimsy
