Wealthy After 40: Personal Finance, Budgeting, Retirement Planning, Savings, Spending, Financial Freedom, and How to Retire for Gen Xers

Ep 134 | How to Start a Side Hustle That Makes Money w/Chloe Winstanley

Dalene Higgins - Money Coach, Retirement Coach, CEO

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




Send me an email with your questions, thoughts, and takeaways from the podcast to: elevatefinancesllc@gmail.com

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Grab the free Retirement Ready Checklist to begin your retirement planning journey

  Welcome, Chloe. I am excited to chat with you. So if you'll just tell listeners who you are and what you do. 


Sure. 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 polar maclay workshops. Terrarium workshops. I did CoLab with a watercolor artist friend of mine.


So we did a more traditional paint and sip. So so those sorts of things. And we'd set up the space, invite people along, get a, a liquor license, people we'd 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 Paula Maclay airing, 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, if anyone else wants to try doing what I do, because it's been such a fun journey.


And I just think it's really helped supplement my small business income with when I was selling poly rockley 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.


Such an exciting story I can tell. So tell us some of your biggest highs and your maybe lowest lows of crafting for profit journey, just to help others as they're thinking 


about this. Sure. So I am someone who I didn'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 1-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 Maclay. 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 that, mailing them off. And that was really fun.


The profit margin was pretty good for Pauler Maclay 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.


I've been an entrepreneur for a while, but I hadn't really, like, I've started businesses and I've closed them because I 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 it's just a really great feeling 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 would be the high, high is just seeing success and, 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, for workshops to do them in.


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. That was the best feeling in the world.


And then I think the challenges in the lowers 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 a hundred dollars into advertising and not making a single sale.


So scrapping that idea, all those sorts of things. 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, 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, so.


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 doing this, 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 wanna 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. 


What great insights and what a journey and thinking as my listeners 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 in 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? Let's talk about both of those.


I think when you are 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, 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.


By supplement and just make my time worthwhile by hosting a workshop because I would be able to make, a good profit from teaching people. 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 gonna 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 need to go into it with open eyes and just, you need to, there are things that you need.


I was quite involved in the creative community in, in New Zealand and I, 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. So I just think that things like doing your research on the craft fair in particular. So if you, 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 depends obviously on the craft fair, but there would be a lot these days who kind of, are resellers and things like that. I see a lot 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 and I feel like that goes against the purpose of what craft Fairers 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 wanna be judgemental 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 these people are importing stuff from overseas, they're gonna be selling it really cheap. It's gonna be, people aren't gonna wanna spend on your, high quality handmade product if they can get a similar thing for two or $5.


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've bought something thinking that I was supporting a small business, but it turns out that was just something that was imported and mass producee.


So it's just really tricky. 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 multilevel 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. 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 wanna 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 gonna be going towards advertising advertising the fair so that there's gonna 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. 'cause 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.


There's always strategies that you can take to set yourself up for success. And that's just why I love talking about this 'cause it's so complex. There are so many layers to it. And it just gets into, so 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 that, there's always gonna 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 because some organizations are gonna have different priorities depending on their.


Personal ethos. 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 doing, taking the steps that you can to, maybe create multiple streams of income as well.


If it's, if hosting workshops is something that you're able to do, then explore that as well, just because. Depending on, on where you are and what your skills are, it could be a really lucrative a 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 product because people are, people love experiences and they love, going to classes. I think that it's just something that, , just opens a whole different door of opportunity if you are 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 wanna talk more about the workshops.


And so my first question is, how did you make that shift? Obviously 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. But 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?


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, 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, 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.


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. 'cause 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.


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 I. 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, I tried running them for shorter, but then I realized, this isn't something I wanna 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, where I would just, just move around the.


Move around the room help people make two piers of earrings while they were there. Helping, teaching people how to use jewelry pliers to and jewelry findings to, turn their masterpiece masterpiece into an earrings. So, and we'd also have the oven on site as well. So people would just bake their clay and they'd leave with.


With the product, which I really liked because people would just leave, wearing the things that they just made. And it was just so much fun. And people really loved it. And, 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, 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 her. I'm not an expert.


I haven't been making earrings for 20 years, but I've been making earrings a lot lately and, and I'm good at it now and I'm confident teaching people and, 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.


And they always do.


How fun. I love that. If anybody wants to connect with you where can they find you? 


I'm on Instagram. My handle is at one K artist. People can also email me if they want to, if they want any advice, any firsthand advice.


On, 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 100 k artist dot 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, any last words, any last piece of advice for 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. So I think just go for it. Just do it. Just seize the moment and, and if you're faced with setbacks, just keep going.


That's the main thing is you're not really gonna 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 gonna make you the best kind, 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. Absolutely. Thank you so much for talking to me.