How Wendy Conklin Became a Creative Entrepreneur: Betting on Herself

Why Wendy Chose Change

Wendy Conklin 0:00

You know, when you get more miserable and more miserable, uh it's easy uh it's easier to make the switch. And I don't think that you make that switch until your misery is greater than the fear of the unknown.

Judy Oskam 0:16

That's my friend Wendy Conklin describing the moment she knew she had to change. Life doesn't come with a roadmap. We're all figuring it out as we go. I'm Judy Oskam, and this is Stories of Change helping you navigate what's next. Wendy had built a successful career as a teacher, writer, and an educational consultant. Then an upholstery class changed her direction. That small experiment eventually became Chair Whimsy. But leaving a secure career to pursue it full time required Wendy to bet on herself. As I think about the next chapter of this podcast, I wanted to bring this conversation back because Wendy's story reminds us that betting on yourself doesn't mean you're no longer afraid. It just takes a special kind of courage. If you've ever wondered whether it's time to make a change, I think you'll find a little wisdom in Wendy's story.

A Hobby That Started Pulling

Judy Oskam 1:17

Here's my conversation with Wendy Conklin.

Wendy Conklin 1:21

I had always been interested in upholstery and kind of dabbled in it by looking at books, you know, long ago. And um, so I tried some things and it was just really hard. And so once I took my courses, I was like, oh, that's how you do it. And it was much easier. And it was something that um I think anything that stretched me at that point, I felt like, well, that makes me better, my job and what I do. So I had no inkling that I wanted to change jobs, that I wanted to change careers at that time. Um, so once I finished my upholstery courses, I decided, okay, I need to open an Etsy shop. That's the next step for me. And that challenged me as well. Cause I'm like, gosh, how do I ship across the United States? How do I ship a chair? Because that's what I wanted to do was chairs. And so um, everything was like a challenge, but it was a hobby and it was fun. And I really enjoyed it. I learned a lot, a lot of heartache too. And um, as time went on, that business grew. And I began to become more dissatisfied with my regular job. It wasn't as challenging to me anymore. You know, once you write so many books, what other book do you need to write to challenge yourself? And um, probably the only one on any topics would be math. And I didn't want to do it. So I realized, you know, I'm I really became dissatisfied. And I'm the kind of person I need a challenge. I need uh change to keep me fresh and I like to try new things. Um, so as my chair business grew, I became more dissatisfied with my job and what I was doing just because it wasn't um my heart's desire to do anymore. I felt like I had done everything I could and grown as much as I could. And yet being an entrepreneur, on the other hand, was very scary, but uh also something that was uh that pulled me in that direction. So I decided um, you know, when you get more miserable and more miserable, it's easy, it's easier to make the switch. And I don't think that you make that switch until your misery is greater than the fear of the unknown. You know, there's always that fear of the unknown when you go into business for yourself or you switch careers or you completely do something different like I was doing, and a lot of people are doing that now. Um, but there's a lot of people who want to that don't make that switch. And, you know, um, for me it was finances, having a family and having to contribute to my family. And uh my daughters were getting ready to go to college at the time, and and I'm like, how in the world can I do this? So, really, as my business grew, I could see a small path, and yet I was still very scared. But my misery became greater than that fear of the unknown, and that's when I leaped, you know, and quit my job, quit my day job, and decided to do this full time.

Misery Versus Fear Of Unknown

Judy Oskam 4:17

And I think a lot of people might have a passion and they have a hobby, but they don't ever do it. They don't ever do it. What really pushed you over the edge? You talked about the misery. It was my misery. But also I think it takes some real courage to act to take the leap.

Wendy Conklin 4:35

It does take courage. Um, so you know, courage is different than fear. You can have a lot of fear and still act in a courageous way. So I think maybe that's what it was for me. I just didn't like what I was doing anymore and became just more dissatisfied. And and yet I could see, oh, this is a way out, maybe. But then, you know, you wake up in the middle of the night scared to death, you know, hot, you know, you're sweating and you don't know, you know, if you're gonna make it and you're scared, but you know, you wake up the next day and you think I can't do this other job one more day, you know, and there's gotta be a path. So I went on like that for a couple years before I actually decided to make a switch.

Judy Oskam 5:17

And

Getting Better Through Mistakes

Judy Oskam 5:18

then when you did make the switch, talk about how you created your company and why. Because you've created, you had the designer's expertise and the eye and the creativity to make it work. Not everybody does that, but you also worked hard at it. Right. So talk about that if you would.

Wendy Conklin 5:37

Well, over the years, I became better and better at doing chairs. When I first started out, you know, the chairs weren't that great, uh, but I had to start somewhere and learn more about fabrics and learn more about color coordination and things like that. And so the more that I learned, I did have to make effort to get better at what I did. And and I'm that kind of person. I'm an achiever. That's a part of my DNA. And um that's how I function. And so whatever I do, I want to improve on. And so it over the years, I mean, and it took me a while, and and I had uh mistakes that I made um that I had to learn from and bad clients to deal with that I had to learn lessons from that um and still have lessons, still have more to learn. And I'm but the encouraging thing to me is I am still growing and getting better at my design. There is not a um a finish line in this. Every single month I can look and think, oh, I'm getting better at this. I'm I'm seeing something in a new way. So there's always something more to achieve. There's always a way to get better at what I'm doing. And that for me is very satisfying just because of the way I'm wired, you know.

Judy Oskam 6:58

Well,

Building Chair Whimsy And Teaching

Judy Oskam 6:59

and and and chair whimsy uh is it's more than just a chair design shop. Talk about chair whimsy and what it is growing into. Right.

Wendy Conklin 7:09

So what I do is custom chairs for clients. Um, they either um order from me a set of vintage or a vintage or antique chair. Um, and a year and a half ago, I created my own line of antique-inspired dining chairs. So they were made in Italy. Um, I had, but they look like antiques, so they're super strong. Um, and this that was really born out of the problems that I was seeing with antique chairs. You know, I like to upcycle, I like to recycle, and you know, I feel like it's better for the environment and all those great things, and plus I love the style of old things. So giving it a new life is very satisfying. But at the same time, a lot of the chairs weren't strong enough uh to handle even more wear and tear because maybe they're just too old. And so that's why I decided to create my own line of chairs. So I do both, and I so I have a line of antique-inspired dining chairs that I also customize for clients. So I have the old and I have the new, but they all look old. And so a couple months ago, I uh through people asking me to do this, and I had no idea anybody wanted me to do this, and I thought I had kissed my years of teaching goodbye. And it's interesting to see how things come back full circle. Um, I have an online upholstery course called DIY Upholstery with Chair Whimsy, and it's a course for beginners that teaches them how to do what I do. Um, you know, I know how to write curriculum, I know how to teach, and I know how to teach adults because that's what I've been doing for years now. And um, so it just kind of grew into that. And uh I'm releasing a new course called Fabric Mixology because I kind of think fabrics and pattern mixing and color coordination are kind of my superpower. And um and I enjoy it, and it's something that it is work, but it's not difficult.

Judy Oskam 9:06

And your clients are wanting it. Why it's not difficult is because it's part of your expertise. Right. You already have it, and now you're able to share that with others online and teaching them how to do it.

Wendy Conklin 9:18

Right. And so that's really satisfying. And and I've had tons of people say, oh, you're creating competition for yourself, and you're, you know, just by teaching other people to upholster or how to do fabrics like you do, but I don't view the world in that way. I believe that um there is enough work for everybody who wants to do this as a job. If people want to flip and sell chairs, more power to them. I think it's great, and I'm happy to help them and teach them. So I don't have that scarcity mindset of if I share this, someone's gonna steal my customers. I I just don't believe that way at all. Um, I do believe that um there's great satisfaction in helping other people to become the best that they can be. And, you know, we all have our own tastes, we all have our own slants on the way that we do things. So no one's gonna do it exactly like I do it anyway. And no one, if you were taking the class, would do it exactly the way you would do it. You have your own style and your own thing, and there's enough clients for everybody, right? You know, if you wanted to do that, or maybe you just want to do your own. And I'm happy for you to learn to do that. So these online courses, um, I'm opening and closing throughout the year. So now this is my third time to open a course coming up, and I'm hoping to maybe do a business course also this next year that may turn into like more of a coaching type course for people who want to get into the chair business, like what I've done, um, because I've learned so many lessons and I would like to help other people to bypass a lot of the heartache that I've had

Guitar Lessons And Calculated Risks

Speaker 1 10:50

to do.

Judy Oskam 10:50

Yeah, uh, yeah. And and and I think, you know, part of one of the things we always ask on this show is give us a little known fact about Wendy Conklin. Little known fact.

Wendy Conklin 11:01

I know how to play the guitar. And I started taking it when I turned 40 years old because my kids bought me a guitar for my birthday back then. And I thought, you know, I'd always complain. Yeah, and I had always complained. You know, it was my complaining story of when I was a kid, how I wanted to play the guitar and I begged my parents and they never let me do it and never got me lessons. And so I complained about it for long enough. I guess my kids thought, we're getting her a guitar. And I thought, oh shoot, now I have to learn. But um, that was another one of those things that it helped me with my job, you know, and I wanted to learn because it stretched me. Did that turn into a career? No, it didn't. But it was something I enjoyed doing. Um challenges, always put challenges. I think challenge is good for everybody. Um what and I know I'm extremely wired that way, but I just think it makes life more interesting. It makes it more worth the living. I mean, it makes uh life an adventure for us. When you when you put yourself in uncomfortable situations, and trust me, with the guitar thing, um, there is a story, but you know, I have I was in very uncomfortable situations having to do a recital and um where I bombed and everyone else besides one guy were young kids at this recital besides me, and there was this one older man, and he was really good. And of course, I'm a beginner, so I was not really good. And anyway, someone knocked over my guitar and I didn't realize that that put it out of tune. So when I went up to do my song, it was awful, awful, awful. And I mean it was just mortifying, it was terrible, but um now I laugh about it because it became a good story, you know. So it's those kinds of things of putting yourself in those situations and it makes it fun.

Judy Oskam 12:51

Well, and and uh you you have uh you and Blane have two daughters. What are you hoping your daughters learn from your from your journey here? Because I think um as a mom, I think you really are a role model because you're a mom, but because of what you've gone through with the business and your whole career.

Wendy Conklin 13:11

I'd like them to learn not to be afraid to take risks and um you know, not any kind of risk, but calculated risks and and um not to be afraid of change, that it's a good thing. I really hope more than anything that they see that life is about an adventure and not to be afraid of taking calculated risks, not to be afraid of change, if it be in their career or their life somehow, because we all have things we have to deal with, we all have changes that we encounter throughout life, and that those are things that we should welcome. And even when it's uncomfortable, um, it's a good thing to to be challenged, to be uncomfortable in certain times, that life isn't a bowl of cherries, and that, you know, and they've seen that with me. They've seen me struggle, they've seen me cry, you know, they've seen me happy about things with my work and the changes that I've done. And and they've been very supportive because I know that cannot be um an easy thing, especially my husband, to have to sit back and let me do this when there's no guarantee. Um, there's no guarantee that I was going to be successful in it. Um, so you know, I think my whole family and my my girls especially, I I hope that I'm the example to them of not not letting fear control you. Yes, we get afraid, we all feel it, but not letting that get the best of you and rob from you living your life.

Judy Oskam 14:49

Well, let

Two Practices For Braver Choices

Judy Oskam 14:50

me follow up with that. Yeah. We we always try and and try and gain something from our experts for the listeners about some strategies. What are two strategies that you might share that would help us do just that? Because it's the how that's the difficult.

Wendy Conklin 15:07

Well, I'm not sure if there's strategies, they're more practices. One is a practice. Okay. I think the first thing I think is good for anyone, but anyone who's contemplating change, I think that um some form of a ritual of meditation, whether it be prayer or just doing meditative practices in the morning. For five minutes, that's all I do. Is I have an app on my phone that's free, and I time myself for five minutes and it reminds me to be in the moment, to breathe, to not respond to things around me in anger or frustration. And it helps me stop the stories in my head because that's the biggest battleground for anybody, especially entrepreneurs or especially people who want to make career changes that seem scary. It is the battleground in your mind. And if you can harness that, and I think the best way to do it is through meditation. And I don't believe that it has to be hours and hours of it, but I do. I practice a five minute every morning, and it has made a huge difference. It's it's a whole mindset change for me. And it's helped me manage my fear of doing this because yes, it's scary. I mean, even still, you know, there are moments where things don't, you know, and I think, oh gosh, I hope I don't have to go get a regular job. That's what every entrepreneur artisan fears the most is having to go back to their old job. Or what kind of other job could they get that would be a regular income? Because the money matters, and that's why we're that's why we have to do what we do. We do our work, you know. So that's number one. And number two, I would say get some kind of business coach. I think everybody could benefit from this. Um, get and try to get one that you just don't think you can afford. That's a little more than what you think you can afford. Stress yourself. Yes, because it will make all the difference having some kind of mentor, business coach, even a group coaching. I had a business coach uh for uh a couple of years who was wonderful and really got me off and gave me great advice. And then I graduated this last year into a group coaching uh program that cost more money and I was afraid I wasn't gonna be able to do it. But I I just knew it was the right thing to stretch me again, and it has. And now I've just done it again with something that's even more expensive that you I every time I think, oh boy, I I don't know if I can afford this, you know.

Judy Oskam 17:48

But that goes back to your growth mindset. Yes, knowing when it's time for you to level up, right?

Wendy Conklin 17:53

Right. And and everybody needs that. I mean, I I don't know that anybody should ever stay with the same business coach forever. I mean, like it you need to be changing because different people offer you different things. They have different gifts that they can offer and help you and they have different viewpoints. So you need that in order to grow. And um, as a person and as a business person, um, because they're all gonna have different focus. They may have a financial focus, or they may have, you know, something with the marketing focus, or they may, you know, just have something with promotions, you know, or or whatever. Um, but I think both of those things, I think some kind of meditation, ritual practice, and then I think having a business coach, mentor, grouping program, mastermind program, whatever it is, you need to be in something. You cannot do it alone.

Final Takeaways On Courage

Judy Oskam 18:46

What stays with me from Wendy's story is that betting on yourself begins with curiosity, taking a new challenge, or one step forward in a different direction. Yeah, the fear might still be there, but as Wendy reminds us, courage means refusing to let fear make the decision. I'm Judy Oskam, and thanks for listening to Stories of Change helping you navigate what's next.