In short
Starting and growing a side hustle through creative workshops (polymer clay earrings), plus how to choose craft fairs and avoid common pitfalls while building income for earlier retirement.
Guest
Chloe Winstanley, self-taught entrepreneur from New Zealand. She started multi-craft workshops (polymer clay, terrariums, watercolor collabs) and ran paint-and-sip style events with liquor licenses. In the US she hosts polymer clay earring workshops from her Seattle home studio; she also sells earrings and shifted to workshops during COVID.
Key claims
Prioritize enjoyment first, but track profit; craft fairs can be costly and risky—research vendor mix, fees, and foot traffic; avoid fairs that allow resellers/MLM; workshops create experiences and additional income streams. Pivot after failed offers.
Notable examples
Renting a Christchurch studio (low foot traffic) led to workshops; she scaled from 5 people to 20, running 2–3 hour sessions where attendees make two pairs and bake clay on-site. She advises that doubts can signal you’re on the right path—keep going through setbacks.
Guests
Chloe Winstanley (solo guest).
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOIntroducing Chloe Winstanley
0:46 to 1:56
Chloe shares her background and her crafting business journey.
“Welcome Chloe, I'm excited to chat with you.”
Highs and Lows of Crafting for Profit
1:56 to 4:49
Chloe discusses her experiences and challenges in her crafting business.
“I'm also just really looking to encourage people or provide insight and guidance if anyone else wants to try doing what I do, because it's been such a fun journey.”
Building Relationships Through Crafting
4:49 to 7:29
Exploring how crafting can create connections and financial benefits.
“responding to what you're putting out there in a really positive way.”
Participating in Craft Fairs
7:29 to 13:11
Chloe discusses the pros and cons of craft fairs and how to succeed in them.
“planning and moving forward and retirement with purpose and maybe making a little extra money.”
Shifting to Workshops
13:11 to 14:00
Chloe talks about the transition from selling products to teaching workshops.
“Some organizations are going to have different priorities depending on their personal ethos.”
Transitioning from Products to Workshops
14:00 to 18:07
Learn how to shift from selling products to offering workshops and creating experiences.
“I think that it's just something that just opens a whole different door of opportunity if you're offering to teach people your skills.”
Overcoming Imposter Syndrome as a Teacher
18:08 to 20:42
Explore the challenges of imposter syndrome and building confidence in teaching.
“Once we peel back one layer, it's just like, what's hiding under here that we have to contend with?”
Final Thoughts and Community Engagement
20:43 to 21:25
Discover the importance of community and support in the journey toward retirement.
“I hope we have inspired listeners as something they can do and look forward to.”
Transcript
Automatic transcript. May contain errors.0:03Welcome to the Wealthy After 40 podcast, the show for Gen X women and couples who are ready to ditch financial stress and feel confident about retirement. I'm your host, Dalene Higgins, financial and retirement coach, helping Gen Xers master their money and create a personalized retirement plan so they can stop spinning their wheels and step boldly into their dream retirement. If you're feeling behind, don't worry. Continue listening to this podcast as well as be sure to grab your free guide, 5 Must Do Steps to Start Retirement Planning Now at elevatefinances.us backslash must do. And remember, let's make retirement possible together.
0:50Welcome Chloe, I'm excited to chat with you. So if you'll just tell listeners who you are
0:56Chloe Winstanley:and what you do. Thank you so much. It's so great to chat to you and I'm very excited. My name is Chloe. I am originally from New Zealand and in New Zealand I started the first multi-craft craft workshop business. So what that means is it's a lot like paint and sip where people would come along and they'd paint a painting and have drinks with their friends. It's a lot like that, only I would focus on different crafts. So I would do things like polymer clay workshops, terrarium workshops. I did collab with a watercolor artist friend of mine. So we did a more traditional paint and sip. So those sorts of things.
1:31Chloe Winstanley:And we'd set up the space, invite people along, get a liquor license. People would serve people glasses of wine and snacks and they would just pretty much just craft and have a different kind of girls night out. So that was what my business centered around in New Zealand. And now I'm setting up a similar thing in the States where I host polymer clay earring making workshops from my home studio upstairs in my house. I'm doing that out of Seattle. I'm also just really looking to encourage people or provide insight and guidance if anyone else wants to try doing what I do, because it's been such a fun journey.
2:07Chloe Winstanley:And I just think it's really helped supplement my small business income with when I was selling polymeric earrings and because sometimes it was tricky it was during COVID and there weren't a lot of craft fairs at the time so it was just tricky to kind of find a way that kept my business afloat during a really strange unprecedented time it's that experience has just inspired me to try and connect with other creatives and just see if I can provide any insight and guidance and that helps them with their own crafty journey because I just love encouraging people to be crafty. And also, if they can make a bit of money from it, then that's all the better.
2:43Such an exciting story I can tell. So tell us some of your biggest highs and your maybe lowest lows of the crafting for profit journey just to help others as they're thinking about this.
2:57Chloe Winstanley:Sure. So I am someone who hadn't go to business school or anything like that. It's all been completely trial and error. There have been some high highs and some low lows with that because, as I said, I started this during COVID and I also had a one-year-old daughter at the time. So it was a crazy time in New Zealand. We were in lockdown and I was just wanting to find something that kind of kept me busy and also was something to enjoy aside from just raising my daughter by myself during a lockdown. That's how I got into Paula MacLea. I'm a self-taught artist. I'm a self-taught entrepreneur and all of it was just trial and error I was selling I was selling my earrings online marketing them on Facebook and then fulfilling orders there mailing them off and that was really fun the profit margin was pretty good for polymer clay because a little bit of it goes a long way when you're making earrings but then I think I just wanted to try something that was a bit different that had a bit bigger of a profit margin that led to trying craft workshops and so the high was probably just realizing success with it.
4:02Chloe Winstanley:I've been an entrepreneur for a while but I hadn't really like I've started businesses and I've closed them because they haven't really taken off so I know what it feels like to close down a business and I was more familiar with that feeling as opposed to actually seeing orders come in seeing the fact that I was putting something out there that people responded to. That was just like a crazy moment of success for me where I was like wow I'm making these earrings people like them and now I'm hosting workshops to teach people how to make these earrings and people like it. It was just wild. I think just as a small business owner, just seeing people respond to your business in a way that you're hoping for, being able to reach people where they're interested in what you're doing and they're wanting to pay money for what you're doing, I think is just a really great feeling.
4:44Chloe Winstanley:And anyone who has a small business knows how great it feels when you see an order come through. It's just the best feeling in the world to see that people are responding to what you're putting out there in a really positive way. So that would, I think that That would be the high high is just seeing success. And I was able to do workshops in other cities as well. So I grew my business a little bit and was taking special flights just for workshops to do them in Wellington, which is the capital city in New Zealand, and also in Auckland, which is the biggest city in New Zealand. So that was just a total game changer, having my friends come along to join my team and we would do trips together.
5:20Chloe Winstanley:That was the best feeling in the world. And then I think the challenges and the lows were just because when you're doing everything by trial and error, you have to be okay with pivoting. You have to be okay knowing that sometimes you might fail. Sometimes I would put a workshop offer out there and people wouldn't respond to it. Like it wouldn't resonate with them in a way that they wanted to try. It's just kind of like you have to be okay with going back to the drawing board, scratching that out, trying again, putting$100 into advertising and not making a single sale. So scrapping that idea, all those sorts of things.
5:54Chloe Winstanley:But it did help me get good at pivoting and just being okay with if people don't like what I'm putting out there, then that's just a sign that I just need to try something different. And so I would always just come back to the drawing board, take a bit of time, dust myself off and then figure out a new workshop or a new idea, something that people were interested in. And it always worked out in the end. It was just like you had to not give up and just keep trying. So yeah, it's challenging, but I think that I am who I am because of those challenges that I faced. And we grow through challenges and when we're out of our comfort zone.
6:31Chloe Winstanley:And I'm also an introvert, so it's like I've done a lot of growth throughout that as well. I'm an introverted, shy person, and I'm running this business where I have to engage with people. But I really love it, even though it's out of my comfort zone. serving people in workshops, helping them figure out what they want to make and seeing them make it, seeing the look on their face when they're at the start. They're like, I can't make anything. I'm not creative. And then by the end of it, they're having so much fun. It's just super rewarding. So I think if you're on the right track, those challenges are always worth it.
7:03What great insights and what a journey. And thinking as my listeners and preparing for retirement, there's a couple things that you covered. Very first, you said, I get to have these people, I get to connect with them, what kind of relationships you're building. And that's huge in retirement when you've lost coworkers. And then secondly, to be able to work through the challenges, but to make some money as well. I really love how your story aligns with their planning and moving forward and retirement with purpose and maybe making a little extra money. So what are some reasons to host either a workshop or be participating in a fair?
7:46Chloe Winstanley:Let's talk about both of those. I think when you're creating, a lot of people are creating because we love it, right? We're not doing it because it's a drag. We're doing it, I think, primarily to enjoy ourselves and enjoy how we're spending our time. And then if we're able to make money on top of that, that's just a bonus. But also it's like if you're having a side hustle, you do want it to be lucrative. I think prioritizing those two things, I would say always prioritize enjoyment and having fun over the profit, but then still keep in mind the profit. It is possible to have both. And that's what I've realized throughout my journey was that if I wasn't making enough money selling earrings, I would supplement and just make my time worthwhile by hosting a workshop.
8:30Chloe Winstanley:Because I would be able to make a good profit from teaching people. Or, you know, sometimes the profit margin of that, depending on how many people you have at your workshop, is just going to be more profitable than a craft fair, depending on what the craft fair fees are, depending on... There are so many things that go into a craft fair. I think it's a really interesting topic and it's definitely one of my favorite things to talk about is if you're going to do a craft fair, how do you make it work for you? How do you make sure that you are setting yourself up for success? because craft fairs, they're so great, but I think you'd need to go into it with open eyes and just you need to, there are things that you need.
9:08Chloe Winstanley:I was quite involved in the creative community in New Zealand and I would see a lot of small businesses closing down. I would see a lot of posts on social media because these businesses were kind of just solely focusing on attending craft fairs. And craft fairs in New Zealand are getting really expensive And I know that they're also getting expensive in the States. Inflation is a thing. People are talking about recessions and all that sort of stuff. So it's like, how do we do what we love, but still have it be accessible for us so that if we're a small business and we don't have millions to throw into a craft fair, how do we, how are we able to afford it and, and kind of protect against making a huge loss?
9:50Chloe Winstanley:So I just think that things like doing your research on the craft fair in particular. So if you are wanting to attend a craft fair, I would suggest kind of scoping out what other kind of vendors they have. I know it depends obviously on the craft fair, but there would be a lot these days who kind of were resellers and things like that. I see it all the time. Like I was just in New York recently and I was walking past all these tables of products that look handmade, but you just know that they're just importing them and selling them and they're making their way into craft fairs too. So it's just like, it's a real shame.
10:23Chloe Winstanley:and I feel like that goes against the purpose of what craft fairs were in the first place which was to kind of just uplift like unique creators in the community and uplift people who are actually making handmade things that's what their small business is they make earrings or they make crochet items and that's what they sell it's not people who it's not made for people who are just paying to import stuff from China I mean it's hard because I don't want to be judgmental about it people are free to do what they want but I think at a craft fair if that's what you're wanting if If these people are importing stuff from overseas, they're going to be selling it really cheap.
10:56Chloe Winstanley:It's going to be people aren't going to want to spend on your high quality handmade product. If they can get a similar thing for two or five dollars, it's just it makes it really hard for genuine creators to sell their products. And it makes it hard for the buyer to maybe discern what is actually handmade and what is not. I know people really love to support small businesses and I'm one of them. And I've been in that position where I bought something thinking that I was supporting a small business. but it turns out that was just something that was imported and mass-produced. So it's just really tricky.
11:25Chloe Winstanley:I've been rambling a little bit, but I think that's one of the things. If you're looking at a craft fair, try and go along in person if you can ahead of time to a different one, just to see what kind of vendors they have, the quality of their vendors. I would personally avoid craft fairs who are allowing people who are multi-level marketing and that sort of stuff, where Tupperware or Avon or anything like that. Any craft fairs that don't align with your beliefs or whatever in terms of what a craft fair is meant to be and what it's not meant to be. And I think most kind of small craft fairs are probably going to be prioritizing handmade, high quality small businesses.
12:02Chloe Winstanley:It's just when you get to the really big ones, maybe that I would be a bit more skeptical about and that I would want to check out firsthand. I think doing your research on the craft fair, you can ask them questions. You can ask out of my fee, is my fee going to be going towards advertising, advertising the fair? so that there's going to be good foot traffic, just things like that. It makes me so sad when I hear, see comments on social media about people who have had negative experiences at craft fairs because I just know that it's a thing. It's really hard to keep a small business afloat, but there are ways to do it.
12:35Chloe Winstanley:There's always strategies that you can take to set yourself up for success. And that's just why I love talking about this because it's so complex. There are so many layers to it and it just gets into like how society functions and all that kind of big picture stuff about consumerism and capitalism and all that kind of stuff. I mean, we don't need to get into all of that right now, but I just think there's always going to be a way to be successful. And it's just about doing research and being prepared ahead of time, knowing what you're getting yourself into. If it's a really high fee, if you're looking at$500 and above, just be really scrutinizing because some Some organizations are going to have different priorities depending on their personal ethos.
13:19Chloe Winstanley:And I think that if you're someone who has a small business, is looking to retire early, obviously profit is going to be important. So just taking the steps that you can to maybe create multiple streams of income as well. If hosting workshops is something that you're able to do, then explore that as well. just because depending on where you are and what your skills are, it could be a really lucrative direction to take to not necessarily replace craft fairs, if you really do love craft fairs, but just to have just different streams so that your business isn't solely relying on selling those, selling your products, because people love experiences and they love going to classes.
14:03Chloe Winstanley:I think that it's just something that just opens a whole different door of opportunity if you're offering to teach people your skills. Because if you're making products, you've obviously, you've already got the skills anyway. So it's just passing on those skills and making money from it and making the money that your time is worthy of. I like that. And I want to talk more about the workshops. And so my first question is, how did you make that shift? So you're selling earrings, which is somebody just looks at and do they want it or not, and they make the purchase, right? And then now I'm teaching it.
14:34But I also love how you also said creating an experience. So how did you make that shift to not only just teaching them and showing them how to do it themselves, but also creating that experience?
14:46Chloe Winstanley:So it was at the time I had a studio that I was able to rent affordably through the Christchurch government because there was an initiative there that was trying to get small businesses into the city center. I was very fortunate I had a space, but I was also struggling to fill the space with people and with products. It was just, it was a tricky time to be trying to have a studio where I was trying to sell products because there wasn't a lot of foot traffic. There were no tourists. It was just tricky. That's how I thought of filling the space with people for workshops instead. And so I started off quite small.
15:20Chloe Winstanley:As I've said, I'm introverted. I was so out of my comfort zone to even think of teaching people. I started off with a really small group. One of them was a good friend of mine and she came along, participated in the workshop and then gave me some really good advice at the end. She was just really supportive and encouraging. And she pretty much just said, this is really great. You should keep doing it. You should charge more because I had priced it very low because I had no idea what I was doing. I wanted to take the pressure off the fact that I didn't know what I was doing. I made it really affordable at the start and she was just keep going.
15:54Chloe Winstanley:And just because people enjoyed themselves and that was really encouraging because it felt like such a mess to me. But I mean, if people are enjoying it, I can make improvements and I can get better over time. And I'm still getting better at workshops. I've been hosting them since 2021. And every workshop, I still learn new things at each one that I host. You don't need to go into it feeling really overwhelmed about trying to get everything perfect the first time because it's just impossible to. There's no such thing as it being perfect. I think the main thing is to just do your best and keep trying to grow.
16:25Chloe Winstanley:After that first workshop with five people, I think I did. I tried another one with maybe 10 and then it gradually over time over about maybe one to two months by the end of that I was buying more materials more equipment that people needed for the workshops and then I was hosting workshops with 20 people and that was my kind of element in my comfort area I felt confident hosting that many people and just figuring out how to make it work and how how to structure it so that it flowed really well I was hosting workshops of 20 people and they ran for about two to three hours per workshop. So I had a few that ran.
17:03Chloe Winstanley:I tried running them for shorter, but then I realized this isn't something I want to rush. Always allow for extra time. Just like wanting to ensure that I'm like moving around groups and giving everyone one-on-one attention because there's only one of me, but there's 20 people. So it's a three-hour workshop was what worked for me where I would just move around the room, help people make two pairs of earrings while they were there. helping teaching people how to use jewellery pliers and jewellery findings to turn their masterpiece into an earring. And we'd also have the oven on site as well. So people would just bake their clay and they'd leave with the product, which I really liked because people would just leave wearing the things that they just made.
17:48Chloe Winstanley:And it was just so much fun and people really loved it. And it was just something so different because nothing really like that existed in New Zealand. so I think it just depends anyone can do this I didn't have anyone teach me I just taught myself how to how to work with work with the medium and then how to host workshops on it and it really was just practice and and building confidence over time and then also just things like imposter syndrome and stuff like that workshops are complicated as well it's just there's so many things as a small business owner I think that we have to battle and I think imposter syndrome is huge and I think it's particularly huge for women as well So it's like an onion.
18:28Chloe Winstanley:Once we peel back one layer, it's just like, what's hiding under here that we have to contend with? And I think feeling who am I to teach people? I think that's a big thing that people feel where they're just like, I'm not an expert. I'm not a, you know, blah, blah, blah. But I mean, the conclusion that I came to was just that I know how I'm not an expert. I haven't been making earrings for 20 years, but I've been making earrings a lot lately and I'm good at it now and I'm confident teaching people. and you just have to kind of just believe in yourself and just trust that you do know what you're doing and that people will value your experience and expertise.
19:04And they always do. How fun, I love that. If anybody wants to connect with you, how can they find you?
19:11Chloe Winstanley:I'm on Instagram. My handle is at 100kartist. People can also email me if they want to, if they want any advice, Any first-hand advice on how to host workshops or anything to do with workshops or craft fairs. I love talking to small business owners. So my email address is hello at 100kartist.com. Yeah, reach out, send me a message on Instagram or anything. I love talking to people, giving them insight, giving them feedback or just brainstorming things. That's awesome. I have loved this conversation, Chloe. last words any last piece of advice my listeners I think just the main thing this is usually the piece of advice that I give to close it down is just if you're feeling good about something even if you've got doubts if you've got doubts about something you're probably onto the right thing because society is really good at kind of making us feel inadequate or insecure or anything like that if we're thinking outside the box if you're thinking outside the box and you're a bit nervous, you're probably onto something great.
20:17Chloe Winstanley:So I think just go for it. Just do it. Just seize the moment. And if you're faced with setbacks, just keep going. That's the main thing is you're not really going to get far if you do face setbacks and then it's not meant to be. That's not the case. Facing setbacks is completely normal. Facing challenges is completely normal. So I think just pushing through those is going to make you the best version of yourself. Those are some great words. I love that. And thank you for sharing your journey. I hope we have inspired listeners as something they can do and look forward to. So thank you again, Chloe.
20:54Absolutely. Thank you so much for talking to me.
20:59Thank you for spending this time with me. If you're not already following the show, be sure to hit subscribe so you don't miss what's coming next. And I'd love to stay connected with you between episodes. So come join me inside my Facebook community, Retirement Ready Hub for Gen Xers. It's where we're having real conversations about money, sharing wins, working through challenges, and building a clear path toward retirement. And remember, retirement isn't just a dream it's a plan and you get to make it possible
From the publisher
[Ep 134]
If you’ve ever thought, “I need a side hustle” or “What side hustle can I do?”, this episode is packed with inspiration and practical advice.
My guest, Chloe Winstanley, shares how she turned her passion for crafting into a successful side business. What started as selling polymer clay earrings online during the pandemic has now grown into hosting multi-craft workshops in both New Zealand and Seattle.
In this episode, you’ll learn:
✅ How to start a side hustle that aligns with your creativity and lifestyle
✅ Tips for running successful craft fairs and in-person workshops
✅ How to pivot during tough seasons and keep showing up
✅ What to consider when trying to make money with a side hustle
✅ The value of persistence, community, and connecting with others along the way
If you’re curious about starting something of your own, be sure to connect with Chloe:
Instagram: www.instagram.com/100kartist
Website: http://www.100kartist.com
Ways We Can Work Together:
💰 Join the next Map Your Money Workshop. It's time to take a peek at progress and find a clear focus forward.
📩 Join the 7-Day Savings Reset Challenge and create a savings system, not just a theory.
✨ Learn about the Retirement Ready Strategy Session. Dive into clarity for today and confidence for retirement.




