From Hobbyist to Online Teacher- What I Wish I’d Known Before I Started

In this heartfelt solo episode, Delores Naskrent shares the winding, decades-long journey that took her from hobby artist and craft show vendor to internationally licensed designer and full-time online art teacher.

🎨 From selling in local gift shops and big-ticket craft shows...
 📦 To licensing with Hallmark and teaching over 90,000 students online...
 👩‍🏫 To building a thriving membership and making art part of daily life again...

This episode is a raw, real, and reflective look at what it really takes to build an online teaching business as a creative — and all the things Delores wishes she’d known sooner.

You'll hear:

✨ How a “flop” craft fair led to a life-changing licensing contract
 ✨ The transition from classroom teaching to Skillshare to full independence
 ✨ The surprising workload of teaching online (it's not just recording!)
✨ Why asking for help changed everything
✨ The top 3 pieces of advice she'd give her younger self

Whether you’re just starting out or deep in the juggle, this episode will remind you: you don’t have to do it all at once — and you don’t have to do it alone.

🔗 Links Mentioned:

• Delores’ classes + membership: https://www.deloresart.ca
• Email Delores: info@deloresart.ca
• Instagram: @deloresartcanada
 

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Kaylie Edwards - Instagram - Website - Facebook - Threads

• 5 Day FREE Email List Kickstart Challenge
• New Handmade to Scalable Beta Course

Delores Naskrent - Website & Digital Art School - Instagram - Facebook - Pinterest - Youtube

• Procreate Foundations Course
• Affinity Foundations Course

Transcript

[00:00:00] Hey, my friends, it's Delores here again. Thank you for joining me on another episode of the Creative Juggle Joy. Today's a solo one and I'm recording it. While everything from my latest course launch, the Mastering Surface Pattern Design in Affinity Designer class is still very fresh in my mind. You might've heard the behind the scenes chat that I had with Kaylie on episode 46, but this one's just me and reflecting out loud with you.

Delores Naskrent: Heart to heart, I'd say I have another one that I've recorded that talks about the specifics of re. Recording and creating all the content that I have in my school and on Skillshare. But this one is a little bit more personal because even though everything might look polished from the outside, kind of, I know there's been a few [00:01:00] glitches, but it takes decades of twists and turns to get to this point, and a whole lot of learning things the hard way if there's a hard way.

Somehow I find it, if you've ever thought about teaching online or you're already doing it and wondering if you're the only one juggling all the tech and all the creative and the customer emails and the late night editing, you're not alone. I've been there. I actually am there. So today I'm gonna walk you through sort of a different aspect of how I got from local gift shop consignment to licensing art worldwide, and then also teaching over, I'd say 90, 95 maybe students online.

And most importantly, what I wish I had known when I first started. So this. Information may overlap with a couple of other episodes, but I think it's kind of a different twist on it that I really want you to know. [00:02:00] So I'll rewind a little bit. I know I've talked about a few of these things before, but I did start out as a hobbyist, you know, just drawing and painting and selling pieces on consignment at little local gift shops.

Eventually, I even partnered with two friends to open our own gift shop. It was creative and chaotic and we kept it going by doing a ton of graphic design work on the side. So we took on almost any job. Uh, we did a lot of catalogs, a lot of magazines, and. Even seed packets. We once had a contract for over 10,000 seed packets that we did the layout on.

Yeah, that was a big one. I also had a very long and fulfilling career as a teacher, so for 30 years I taught in the classroom watching everything shift from the really commercial art, original hand done kind of [00:03:00] work to kind of. Ushering in the whole digital era of design. So I was right there during that transition period in the 1980s.

I was there helping students cross the bridge into the digital world while I was also doing that myself, and at the same time, I was still freelancing and still creating, and still trying to figure out where my art could go. So then came the craft sale chapter. I originally tried doing this on my own.

The first show I did was at the local art gallery. A friend of mine had a booth. I got a booth and that was my, literally the first show I ever did, and it kind of ignited the interest for me. I started doing sales and by then I was single with three kids. My eldest daughter was about 15 or so, and [00:04:00] eventually became.

Really pivotal in me setting up my booth and my product line to what it was by the time we stopped doing craft sales. So she basically joined me as a partner when she was about 18 or 19, and we hit the Canadian Craft Show circuit really hard. We had been doing smaller shows, but the bigger the show was, we found the more money that we made.

So we went to the highest. Show that we could find the ones, I'm talking the really big shows where they have at least 50,000 plus people coming in, giant booth fees, hotels, product prepped. It was really a full-time business and. We were both working, I was working full-time still as a teacher. She was working at, uh, a local movie business Blockbuster that doesn't exist here anymore.

But, , we both kind of managed to do all [00:05:00] this work around all of our regular responsibilities and learned that we had to definitely, you know, pace ourselves and spread our workout throughout the year. It was great. It was really great. We continued to do that until she had her first child, which was about.

Seven years ago, and we have now stopped doing that. But what was really cool about that phase with was that for me, it eventually led to selling wholesale. So we decided to do a couple of wholesale gift shows where we were able to sell to gift shops and we got lots of pretty good contracts. You know, they weren't, it wasn't huge sales, but it was spread out throughout the year.

It was often when we weren't doing the retail craft shows ourselves. So there was always that little bit of money coming in from the gift shops. And really that was one of the things that [00:06:00] led to my very first art licensing deal. And here's where it feels like a storybook moment. I did a teeny tiny craft show one day at a car show that was, you know, huge.

But. The craft show, part of it was not the draw. There was a car show going on. That's where all the people were. We had had hardly anybody coming in to the arena where a, a bunch of us crafters had set up our booths and I really barely made any money. But the owners of hallmark stores, and I've told this story so many times, I hate repeating myself, but the owner of three local Hallmark stores walked in, a husband and wife team.

They stayed for a while and really took a good look at my work. We had a nice long chat. They laughed, they cried, and they left me with a [00:07:00] huge opportunity. So that meeting led to, first of all, getting, a really large order. I think the very first order from them was a $1,200 order, and then I got two other orders for, I think $800 and another one for about the same.

But what was really amazing about it is it led to a five year art licensing contract with their gift manufacturer, and my work ended up. Not only in the Hallmark stores that they owned, but in shops all across Canada, all through the us, in Australia and in Europe. Unbelievable. Like, wow, what an opportunity.

I, at that point, had never even really heard about art licensing, so it was, it was a huge learning experience for me. It was a really huge deal, and I was able to produce some of the best work. That I've ever done, [00:08:00] at least at that time. I look back at it now and I think, oh gosh, I could have done so much better.

But you know, that was a look that was around at that time, and that's what I was doing and it really got me, um, the full understanding of what art licensing was about. It sounds magical, right? Like just sounds like a dream come true. And it definitely was. But it was also a lot of hard work behind the scenes because I was still raising, raising those three daughters, still teaching full-time, still doing craft shows, and obviously still learning.

So another thing that happened was. At the end of my teaching career, I had that art licensing going and I decided to retire because my husband was sick with cancer. And I kind of went for a little bit, without doing a [00:09:00] lot of additional sort of freelance work. And I kind of found that I missed teaching and I did a lot of my own learning at that time. So I had found Skillshare and I'd taken many classes there myself. I actually really loved the platform and the community and learned from so many different teachers. Really started to understand the whole, what you'd call the teaching business, you know, online teaching business, and.

At one point just thought to myself, why am I not teaching here? Like, why not do this? So I jumped in and once I jumped into something, I pushed myself pretty hard. So I set a really strict pace. I wanted to really build up my, list of classes quickly. So I did a class a week for several months. I recorded, I edited, and I uploaded [00:10:00] consistently and.

Little by little, I built a really good audience. I think I have 127 classes or something on Skillshare. And at first I was doing all Photoshop and um, illustrator, and then procreate came. Into the picture and I started having fun doing projects with procreate, and when I switched over to teaching on procreate, my numbers went crazy.

Like my PROCREATE classes were filled with 10 times more people, so I knew immediately this was the way to go and kind of started switching over to teaching mostly procreate classes. Eventually the same thing kind of happened with Affinity Designer, and again, I saw my numbers were way higher in.

Procreate and Affinity Designer classes than they were for the Adobe classes. And [00:11:00] I, who knows why. I mean, it's possible, it's just because there were already well-established teachers in those two subjects. I don't know. But for me, the money was definitely in the procreate and affinity designer classes, so I really started to focus on them, and that's why there's so many more of those classes.

On skillshare of mine than there are of Photoshop and Illustrator. So over time, my classes have reached now over 85,000 students. And between that and my school, I'm sure I've easily taught over 90,000 students if you include the students. I've taught also in high school. So while Skillshare was an incredible stepping stone and.

It was one of the ways that I established my own membership because I definitely had fans and people who loved to learn from me. I found that things really changed [00:12:00] directly after the pandemic. I'm sure that during the Pandemic it was a boom for. Programs like Skillshare because right after the pandemic kind of ended, they cut teacher pay in half and it was a shock to say the least.

So, , a few of us teachers, myself included, started to imagine something different and that was having our own platforms, having our own schools. And having our own memberships where we could fully shape and grow and not be at the mercy of, you know, places like Skillshare who could just. Randomly cut your wages in half.

It was really tough, honestly. So now I teach through my own site membership, and that has been a rewarding move. I get to connect way more directly with my students [00:13:00] and offer more flexible resources, and I love just the fact that I'm designing classes that reflect what I truly love to do. But I'll be really honest, it has not all been easy.

One of the biggest misconceptions I had was that teaching online would feel like teaching in a classroom. Spoiler alert, it does not. It's not like being in a classroom at all. Teaching online means you're also the curriculum writer, the video producer, the tech support team, the copywriter, the social media manager.

And the person who answers emails at 10:30 PM when someone can't download a brush set. Yep. That's me. I, I don't know, like honestly, what surprised me the most was. The tech load, you know, the actual administration, just how many platforms and systems it takes to keep a [00:14:00] course business running. Honestly, there's so much.

I mean, there's all that video editing. There's the email automation. Thank God I have Kaylie. There's the community tools and the hosting platforms, and. You know, just, oh God, simple things like passwords and, you know, just managing all of it and keeping records of everything. Having, you know, my Airtable system completely set up and following it, you know, naming things, oh my gosh, organization.

It's, it's just so, so much like the admin is, is just crazy. And you know, really at the time I. Hadn't even really considered marketing when I first started. I didn't realize just how much marketing would be involved if I wanted to go out on my own. You know, when you're in a big, uh, program like Skillshare has, you don't have to do [00:15:00] any marketing.

Skillshare is doing the marketing. You don't just build a class, you know, and wait for people to find it as, that's what I found is I, yes, I did have a membership. I did have the classes. I was doing exactly the same as I was doing when I was on Skillshare, but I had to wait for people to find it and. You know what it is when it's business, you just can't wait.

You literally have to find the people. You've gotta talk about it, you've gotta share it. You've gotta invite people in, and you have to keep doing that again and again and again. And honestly, that part used to feel so uncomfortable for me. But over time, I started to realize I wasn't actually selling. I was just telling people what I love and giving them a way to join me.

I couldn't have possibly done it without Kaylie. And you know, we can talk [00:16:00] about a lot of the mistakes we've made along the way. We've had tech mishaps, we've had email flops, we've had broken links. I mean, just recently I accidentally, oh my gosh, this was the worst thing ever. But I deleted over 170 people from my membership.

Literally, yes. Deleted them and I'm still repairing the damage from that one. Just one of those stupid mistakes I made at 1130 at night, and oh my gosh, I had no idea I was deleting people specifically from a course and didn't realize I was actually completely deleting them from my membership. Thank goodness so many people have reached out and

I hope to goodness that I get everybody back. 'cause that is, you know, definitely the bread and butter right now of my earnings is from my membership. Thank you so much to all of you who have reached out and that I was able to get you all back in again. And you know what? [00:17:00] Honestly, it's, it's just sometimes it's just about being exhausted.

Like I. Just get so tired. There is no big team here behind the scenes. I have amazing help, especially from Kaylie, who's been an absolute lifesaver, and I've got a couple of others that I've hired that I absolutely adore. Lindy, my community manager, she still has to do a lot of stuff, but oh my gosh, I still wear a lot of the hats.

It's really easy to glamorize online teaching, but the truth is it's a load of work. It's worth it, but it is work you guys, and I so appreciate all of you who support me in even the littlest things, buying my, you know, artist resources that I create. All of those little things, paying for the monthly membership.

These are the things that make it [00:18:00] possible for me to do this kind of job. It. I couldn't do it without you. I really couldn't. People often ask me, do you still make art? And yes, heck yes, I have to. Teaching is what I do, and it's. Teaching of the projects that I create, but I know that there's a lot of times that I just do the art because I need to just relax and get lost in the painting or designing or whatever it is.

A lot of times these can end up as classes, but sometimes, honestly, I just do it for the relaxation at first. I do still license my work. I do still sell cards with abstract art. And I do carve out space to make art just for the joy of it. I was even working in my art journals the other day when we were at the beach.

I brought up just a couple of tools with me and I [00:19:00] flipped through my actual art journal and physically took a white marker most of the time, and added detail to probably 20 different pieces of artwork that I have in there because you know, I still license that stuff. So it's good for me to carve out space to make time for just that, that joy of it.

That stuff often is the basis of other things that I do, and I can transfer anything that I do in my analog art to be part of my digital art. And I think all of that is part of what keeps me connected to my students too. They know I'm still in it with them. I'm still learning and I'm still creating. I often think, you know, what would I go back and give myself as advice when I was just starting this online teaching thing?

And there are a couple things [00:20:00] that I would say. First of all. Pick one platform and learn it well before trying to juggle too many. I am right now really debating whether to stay on teachable or not. There have been some major costs increases and I'm not sure that I want to stay using Teachable for that reason, and support is not necessarily always.

You know, the top end, in my opinion. I also have heard and learned about a couple of different platforms that might work for me, costing way less. We're talking less than half, and I'm just hoping that I can make it work and integrate it. I don't know. I haven't done the research. I really need to do that.

But this is one of the things I would say is to definitely research that before you start, because now it's a whole big thing. Of trying to migrate from one [00:21:00] platform to another. The other thing I would say is like. In fact, this one should have been really the most important thing to tell myself back in the day was to build an email list early.

So that email list is golden. It's the most important thing to have, and that's because you're having a direct line, a direct conversation to your audience, and that is gold. Social platforms I haven't personally had a lot of success with any, you know, tangible building of my business or money coming from them.

They, they change algorithms change, but gosh, that email, that's what really gives you stability. So growing that email list, being really consistent with it, that's really important. And last but not least, one of the things that I would have given my. Given myself as advice sooner [00:22:00] was, oh gosh, I wish I had done this sooner, is to hire support.

So asking for help sooner. Gosh, why did I not do that? Even part-time support can really help save your sanity. So now I've got Kaylie with my marketing and tech support. I've got Che doing my video editing and helping me out in any other ways that she can. She often does my uploads to sites like Etsy and Creative Market.

I also have lindy as my community manager. So she's always in there, in the community talking and helping people. And I've hired also Michelle, who is gonna be helping me with setting up my systems in Airtable and getting them running smoothly so you don't have to do it all and you don't have to do it alone.

And it's really helpful to have other people there as soundboards and helping you with some of those things that you [00:23:00] could pass on. And in a way, save yourself money because that lets you do more of the things that really make you money. So if you're listening and wondering if you could teach online, let me tell you, if you've taught anything before, if you've got the skills to share, there is space for you to do it.

Please don't hesitate. It won't always be easy, but I can tell you it's very deeply fulfilling and don't wait until you're ready. Don't put that time, like don't waste the time. I definitely was not really ready for that first one. My first class is almost embarrassing, but I made it up as I went along like most people do, and I got better and I got faster.

Thanks for spending time with me today. If this resonated with you, I would love to hear from you. You can send me a message or tag me on Instagram or email [00:24:00] me info@deloresart.ca, Instagram. Facebook is Delores Canada. If you're part of my school or membership. Thank you for making this beautiful business possible.

And, and I will see you next time. Keep creating, keep juggling, and most importantly, keep finding joy in the process.