My Journey as a Creative Business Owner

If you are lucky, there’s a point in your business journey when you realize you’re not worried about making enough to put food on the table. I can’t remember the exact day that happened for me, but one day I woke up and realized that hard climb was over. And what a relief that was! Not that there aren’t more mountains to climb and problems to solve, but the hardest part was over.

I “started” my business back in 2012 after finishing a couple of upholstery courses. I put some chairs up for sale on Etsy and had my first sale in just 2 weeks! Never mind that I sold my chair for a ridiculous price…because I had no idea about pricing or how to actually make money, but I had a sale which was enough to get me interested in switching from my day job as an educational consultant and author into a more creative field.

One of the road blocks for me was what exactly was I going to do? Not chairs, of course! Because who does just chairs? Well, that was one difficult lesson to learn…that niching down in a business is the only way to stand out, but that literally took years for me to really understand and lean into. Here I am below in 2014 at my first flea market in my home town. I bribed two of my friends to help me! I barely made enough to cover my expenses.

That was the year I also had a booth at Round Top, and boy, I thought I had made it! This was the pinnacle of success…so I thought. Again, I broke even after a full week there. It was depressing and I honestly felt like a failure. There was no way I was ever going to be able to leave my day job to do this full time. It was soul crushing. Lots of tears were involved…ask my friends.

But I picked myself back up and just kept working really hard, seeking advice and help from others. I finally got a mentor who met with me every few months to give advice, and then I joined a coaching program that gave me the direction I needed. I needed “the know-how” to grow a business. I’m a big believer in coaching programs and am still part of one…and always will be.

I also began to understand my role with social media…it was more than just putting out a post on FB or Instagram. I began to understand that my posts were meant to serve others, not myself with how likes and comments I got. (I write all my own posts by the way.) That this blog I had been writing for years was about serving others and helping them live better lives. I was meant to inspire others.

And creativity has been a big part of my journey. I have to take time out to play more. Ask any entrepreneur about what they do to play, and I bet there will be a long pause…maybe even some push back. But playing is a huge part of keeping the joy and creativity alive in your life and business. EVERYONE needs it, especially business owners.

Being a creative business owner has been an incredible journey for me. I’ve learned from experience and from others. And you lean on your friends heavily for advice and sounding boards. One of my friends is Sara from Simply Southern Cottage. We have a lot of fun together, as you can see!

We’ve collaborated on various projects including photoshoots and chairs. We’ve listened to each other and offered support and ideas when the going got tough. You need friends like that!

And I’m excited to tell you about a new venture we are doing together for creative women business owners. It’s called Pink Creatives, and we’ve already hosted our first retreat back in April 2022. You can read more about that adventure by clicking here.

You can follow Sara at @simplysoutherncottage on both FB and Instagram. And of course my handle is @chairwhimsy.

If what I’ve written above touches a nerve for you, then click here to get more information about the retreat. We can’t wait for you to join us!


I'm Wendy Conklin, The Chair Stylist.

What brings me joy is helping others live more creatively. I design antique-inspired, boutique chairs, and I teach others how to do what I do. Check out my shop, services, and courses to bring more whimsy into your home and life!

Check out my online courses to spark your creativity and upgrade your joy, starting today!

10 Best Statement-Making Fabrics from Spoonflower

10 Best Statement-Making Fabrics from Spoonflower

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