There’s a tender spot between launching your creative journey and feeling truly established.
In this co-hosted episode of the Creative Juggle Joy Podcast, Kaylie and I spent time talking about something we both see often in our communities: the “messy middle.”
It’s that stage where the excitement of beginning has settled a little, but consistent growth and sales still don’t quite feel steady yet
When excitement turns to heaviness
You’ve had sales; you know your work resonates—yet growth slows and complexity increases. You begin to question your direction and whether you should keep going. Please know this is normal. Kaylie and I both shared how common this stage really is, even though many creatives quietly feel like they’re the only one experiencing it.
Clarity over noise
What brought progress in the beginning doesn’t suffice now. Instead of trying everything, turn inward. Look at what has already worked. Listen to the small clues and refine them. During the conversation, Kaylie explained how this stage often requires moving away from “try everything” energy and toward clearer systems and intentional choices.
Simplify and structure
As creative souls, we’re drawn to possibilities, but too many paths split your energy. Simplify your offerings, build gentle systems and create a steady rhythm—whether that’s weekly emails, batching content or mapping a clear journey for your customers. One thing we both agreed on in the episode is that structure doesn’t remove creativity—it actually gives your creativity room to grow.
Stay awhile and ask for help
Don’t abandon your efforts too quickly; let ideas take root. If numbers aren’t your strength, it’s okay to seek help—from AI tools, family or a supportive community. Sometimes an outside perspective is exactly what helps you finally see the next step clearly.
Our Thriving Artist membership is built for creatives who need nurturing during this season.
We gather weekly to celebrate wins, answer questions and share over 250 skill-building classes.
If you need business guidance, Kaylie’s Spellweaver Creative Hub offers workshops and live implementation sessions designed to help creatives refine what’s already working.
Together, we hope to support creatives on both the artistic and business side of this messy middle stage.
Listener Support Note
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Passcode Thrive
"Thrive is a one-hour creative business meetup open to all—whether you're part of my membership or just stopping by to grow alongside like-minded creatives. It’s a supportive space to dive deep into the highs and lows of running a creative business, share ideas, tackle challenges, and hold each other accountable. We talk about everything under the sun, from setting clear goals to boosting motivation, all while offering fresh perspectives and genuine support. It’s not just about business—it’s about building a community where creativity thrives."
Resources or Businesses Mentioned in This Episode
• Spellweaver Creative Hub membership
• Thriving Artist membership
• Teachable
Affiliate Disclaimer
Some links in this post may be affiliate links, which means either Kaylie or Delores may receive a small commission (at no extra cost to you). We only share tools or products we genuinely love and use ourselves.
TRANSCRIPT:
[00:00:00]
Delores Naskrent: Hello, everyone, and welcome back to the Creative Juggle Joy Podcast.
Kaylie Edwards: Hi, everyone. Okay, this episode, I feel like this one is for those where people are going to pause and go, "Wait, that is me."
Delores Naskrent: Yes. I think a lot of people are quietly sitting in this stage and maybe thinking it's just them, when actually it's incredibly common.
Kaylie Edwards: And not even realizing it has a name.
Delores Naskrent: Exactly.
Kaylie Edwards: So today we're talking about the middle stage, where you're not a beginner anymore, but you're also not making consistent sales yet.
Where am I actually at? So let's ask this, have you ever felt like I've done a lot, but it's not quite working yet? [00:01:00]
Delores Naskrent: Yes, and I think this makes this stage feel really hard.
It's that you already have proven to yourself that you can do it, so you have that nailed. It's not a confidence issue in the same way as it was at the beginning. It's more like a clarity issue.
Kaylie Edwards: Yeah, that's such a good way of putting it.
Delores Naskrent: Yeah. You've created work, you've improved, you may even have had some sales.
So there's evidence that things can work.
Kaylie Edwards: Yeah, and that's the tricky part because it's not zero anymore.
Delores Naskrent: Yeah, and it's not consistent either.
Kaylie Edwards: Exactly, and you're sat there thinking, "What am I missing?"
Delores Naskrent: Yeah.
Kaylie Edwards: So can I ask you something, Delores? When your students hit this stage, what do you notice in them?
Delores Naskrent: There's [00:02:00] often a shift in energy. At the beginning they were super excited, there was lots of excitement, and this period becomes a little bit more uncertain, and sometimes a bit quieter or heavier emotionally.
Kaylie Edwards: Yeah, that's exactly it.
Delores Naskrent: Yeah. They start questioning their work and their direction.
They start questioning whether they're doing the right thing, and sometimes even whether they should actually keep going at all.
Kaylie Edwards: Yeah, and I think this is where it can feel quite heavy for people because you're not a beginner anymore, so you expect things to be working.
Delores Naskrent: Yeah, and there's that expectation now people saying to themselves I sold 1,000 cards in December, so I should be further along.
Why am I only selling 10 cards now in January or February?" They just can't quite figure it out,
Kaylie Edwards: yeah, it's not the lack of progress, it's the lack of predictable [00:03:00] progress, and I think that is where a lot of people forget about business and doing your own business or becoming a working artist.
Delores Naskrent: Yeah.
Kaylie Edwards: If you don't have systems in place and, you're not visible, you're not gaining the traffic, the lack of predictable progress just puts you off.
And this is where the research really helped, because it actually names the stage. It's called the messy middle, and there's plenty of artists and business people that get stuck in this messy middle and then quit. And one of the lines that really stood out to me was, "This stage is characterized by a slowdown in growth, increasing complexity, and a feeling of stagnation despite continued effort."
Delores Naskrent: Whoa, yeah. I think complexity really stands out to me, because it's not just [00:04:00] doing one thing anymore. You're not just creating your art anymore. Suddenly there is all of the things.
Kaylie Edwards: Yeah, because things aren't simple anymore.
Delores Naskrent: Nope. There's a lot more decisions, and there's a lot more variables, and those decisions start to really matter now.
Kaylie Edwards: Yeah, there's lots of moving parts when it comes to business, and the shift people don't realize. Can I ask you this? Do you think people are still using beginner strategies at this stage?
Delores Naskrent: Yeah I do think that, and I think that's where the frustration comes in. What used to create progress now just doesn't move the needle in the same way.
They're possibly trying too many things or not doing enough things. You know what I mean?
Kaylie Edwards: Yeah, same, because at the beginning, progress comes from doing more, learning more, trying things, but here [00:05:00] in that middle bit, that stops working.
Delores Naskrent: And
Kaylie Edwards: this is backed up in the research too. It's where progress in this phase requires a shift from visibility driven activity to a structured system and authority building strategies.
Delores Naskrent: Yeah. So it's not about being louder.
Kaylie Edwards: No, it's about being clearer.
Delores Naskrent: What would you give as an example of that shift, Kaylie?
Kaylie Edwards: Yeah. So beginner stage might look like posting regularly, trying different products, experimenting. But the middle stage looks more like refining what's already working, so you're understanding your audience better, you're improving how you communicate your work.
Delores Naskrent: Yeah. So less of try everything, like- the shiny object syndrome. Yes. It's more about making really intentional choices, like looking at what has been working and then [00:06:00] what?
Kaylie Edwards: Yeah. It's where you go from the beginner stage where you're trying everything, you're experimenting, you're trying to figure everything out, you've got all this information coming in, and you're trying all these strategies that people have given you.
But what you're not doing is you're not refining, you're not improving what's already working, and it's more about doubling down on what works. So what marketing strategies have you been using that we're seeing a little bit of traction? Then you need to double down on them and find ways to improve that.
Same goes with the product side of it. If you've got artwork that was doing really well, can get it more visible? Is there any way you can improve the listings or sell it elsewhere that you can test? It's about doing more of that.
Delores Naskrent: Yeah.
Kaylie Edwards: So can I ask you, what do you think keeps people stuck here the [00:07:00] longest?
Delores Naskrent: Personally, I think it's not knowing what they should be adjusting. They can feel that something is off, but they can't quite pinpoint it yet. They haven't had enough repetition or really examining it closely to fully figure it out.
Kaylie Edwards: Yeah. That lack of clarity, definitely. I think a lot of people get stuck with they see something or they post something or they have a product and they put it up, and they don't see any traction for it, or they don't see any engagement.
But then instead of actually having a look in the numbers, seeing what actually could be working or what the problem could be, they abandon it and then start something new.
Delores Naskrent: Yeah.
Kaylie Edwards: And people don't give things enough time To work, 'cause with marketing, there's so many things that you could do, and you might not see results for [00:08:00] three months, but it's compounding in the background.
Pinterest is another one. It's a long-term strategy.
Delores Naskrent: Right.
Kaylie Edwards: It's like you have pins that have been up for years and years, and they're still bringing traffic to your store, aren't they?
Delores Naskrent: Yeah.
Kaylie Edwards: So it's a long-term strategy. Same with blogging. It's a long-term strategy, and people abandon it 'cause they don't see results straight away, and I think that's a lot of people need to stick with it and see what's working and double down on what that is.
Delores Naskrent: Agreed. I don't think they need to start again, but a lot of times I think they just don't know what to refine, and that creates that stuck feeling.
Kaylie Edwards: Yeah. I've been there too, where I was doing a lot, but not improving the right things.
Delores Naskrent: Yeah.
Kaylie Edwards: So at this stage, it isn't about more effort.
It's about better direction, and sometimes that is just ... You need to just keep going. [00:09:00] Yeah.
Delores Naskrent: Let's talk about a couple things that really help here. Any ideas?
Kaylie Edwards: Yeah. First thing, number one, audit what's working. So look at what's already working. Ask yourself, "What has sold before? What content got engagement?
What do people respond to?"
Delores Naskrent: Yeah. There are clues. Even if they're small, they're there.
Kaylie Edwards: Yeah. It's like even if you found someone ask a question about something maybe someone liked a color that you used, it starts away. So if somebody tells you something, asks you a question, keep a note and come back to that, 'cause it's always gonna help you in the long run.
And two is simplify. Very important. Don't overcomplicate things. So if I can simplify everything, because this stage often becomes [00:10:00] too many ideas, too many directions.
Delores Naskrent: Yeah. And that definitely splits your energy, right? When you make everything feel harder than it needs to be. Oh, yeah,
Kaylie Edwards: yeah. Just build systems as well. So this is the third one. Build systems. Build simple systems. Don't overcomplicate it. I know this. I went down a an AI agent rabbit hole not long ago, and it got really complicated, and I abandoned it because, yeah, I was like, "This is getting too complicated.
I need to come back and simplify." Just come back and simplify. Not anything fancy, but things like a consistent content rhythm is something you need to do. We've got it with the podcast, so we know when we're gonna record, when I'm gonna sit down and batch edit. I know when we're gonna do the newsletters or the podcast episodes, when they're gonna go live.
And having that simple rhythm has helped so much, [00:11:00] and we're ahead.
Delores Naskrent: Absolutely. It's the most, I think, important thing that you did for me, Kaylie, was to create those systems of having a schedule. And it starts to feel really stable when you have that in place, and it gives you something to really build on.
Kaylie Edwards: Yeah, and a way to stay in touch with your audience, I can't say it enough. Email is so important. Even if you're just a beginner, get your email set up. Even if you're just posting once a month to one person- just get it there and start building that consistency in.
And a clear path from a new person finding you to them buying from you. Create that simple system of, how does somebody find you, and then how do you get them to buy from you? Yeah. What's the path that they need to take? And then simplify it. Remove the barriers. It's like people sometimes [00:12:00] overcomplicate things with their sales page or with their product page, and then it's makes it complicated.
What do they have to do? It's like with Teachable, with Delores' Teachable, there was a bit where we were making it a little bit more complicated than it should've been, and we seen a drop-off in conversion because it was starting to get complicated, so we had to pull back. "Okay, actually, what's the journey that someone's gonna go on from someone first meeting Delores to how to get this purchase done?"
And we had to simplify it again.
Delores Naskrent: Yeah.
Kaylie Edwards: And four, stay with things longer. Like I've previously said.
Delores Naskrent: Yeah.
Kaylie Edwards: This is a big one. Stay with things longer, because a lot of people change direction too quickly.
Delores Naskrent: Yeah, they... Don't give it time to work, so before they've even gathered enough data to know if it could work. So you have to follow through on things for a [00:13:00] while to have statistics that can help you, can inform you.
Kaylie Edwards: Yeah. And I know if you haven't got the mindset. Or the, your brain doesn't work with data and maths. I hate mathematics. I'm terrible. I hate mathematics. I will do research, like, all day long. But maths is not my friend. It never has been. I've always been terrible at maths. I was very shocked and fell off , I'll say a gate, but it was a stile.
I fell off one when my mum told me I had a C in maths because I genuinely thought I was gonna fail it. That's how bad. Like, my partner takes the mickey out of me because I struggle with multiplications, and he knows them, and I'm just like, "Yeah, I don't know what you're talking about."
But this is, going back to this, it's like I know there's plenty of creatives who are not good at maths or don't like looking at the data. Genuinely, get AI to have a look at it for you and give- [00:14:00] you the insights. Tell it to talk to you like you're a fifth grader. Get it to do this for you, and then work out the plan moving forward.
What do you need to improve? What do you need to cut back on?
Delores Naskrent: Yeah.
Kaylie Edwards: If you're not good at it, get AI to do it or get someone else to look at it for you.
Delores Naskrent: Yeah. I suggest a family member that possibly could help you out with it. AI, I think, is very helpful when you've got statistics. You can pile in a bunch of statistics.
You can even just dictate them, and it'll give you a really good report and actually identify things that could be moving the needle for you. And I think that outside perspective helps so, so much 'cause you're often too close to it to see it clearly yourself.
Kaylie Edwards: Yeah. It's very much that. I do it with you, don't I?
I'll tell you something, 'cause I'm just like, "I cannot figure this out."
And [00:15:00] then you'll be like, "Oh, yeah, this." And then I do the same with Delores. Delores will say this, and I'll be like, "What? Oh, you gotta do it this way."
Delores Naskrent: That's a great partnership for that reason.
Kaylie Edwards: Yeah, and this is where support becomes really important because it's hard to see your own gaps.
Delores Naskrent: Yeah. Absolutely. An outside perspective, like I said, is just something that will help you so much, especially if you have people in your family or people in your circles that can do some of the things that you don't like doing quite as much.
Kaylie Edwards: Yeah. 'Cause if you can't afford to hire somebody see if you can get the free effort from a family member who knows how to do it.
And this is exactly where the support can make the biggest difference because this stage, this middle stage, isn't about starting, it's about refining.
Delores Naskrent: Yeah.
Kaylie Edwards: And so if you're in this stage and thinking, "I've built something. I'm working on this. I'm getting some [00:16:00] sales, but I need help making it work," that's exactly what we focus on inside the Spellweaver Creative Hub membership that I created-
where we help you refine your business, improve your visibility, strengthen your marketing for your creative artwork, and we don't just leave you with a workshop. Each month we have a focused workshop that quarter's core theme. Then the third week of the month I do a live implementation session with accountability.
So if you tell me on the workshop that you're gonna do this, then I will tell you in that third week, "Have you done this?" And if you haven't, then we will work through it in that live session, and you can ask me anything, you can troubleshoot with me, and I will do a co-working session around that month's workshop.
So you're actually, implementing what you're doing, and you're refining it and getting support as you go.
Delores Naskrent: A lot of people talk about cowork- working sessions just being [00:17:00] such a great way to move the needle. Honestly, I think it's great, and if your challenge is more on the creative side, then I think you might get some value out of the Thriving Artist membership because we do the same thing.
We try to support you in many different ways. We've got the weekly Thrive meetings where you can come and ask questions or listen or we love celebrating wins, so we'll often have two or three people with big wins for the week. It's just so supportive and fun, and we've got all of the skill-based classes in the membership.
I think I've just recorded over 250 courses can you imagine? It's taken me a few years, my friend, taken me a few years. But we've got lots and lots of creative resources. Lots of the classes come with whatever you need to [00:18:00] get through a project and create a beautiful artwork.
So many different styles. I love the fact that I can teach all those different kinds of styles and techniques and different software programs. So if you are at that point where you're in that messy middle and you want a little bit of help just in knowing what to do next, then hopefully one of our memberships can help you out.
You can keep developing your work with confidence.
Kaylie Edwards: So yeah so you're supported in both.
Delores Naskrent: Yeah, the creative, the I'll be the creative one. How about that? And Kaylie- you're gonna be the business side. Yeah. And we're gonna get somebody else to do maths.
Neither of us can do math.
Kaylie Edwards: No, I just get AI to do it or a calculator. It's fine.
Delores Naskrent: So yeah, if
Kaylie Edwards: you're in the middle stage right now, you're not stuck, there is a way forward.
Delores Naskrent: You're growing, and even if it doesn't feel like it, you are growing. 'Cause [00:19:00] I've been through this stage, so I totally get it.
Kaylie Edwards: Yeah, and this stage is where things start to click, when you have the right clarity and support.
Delores Naskrent: Well said. Yes. And until next time, everybody, keep creating, keep juggling, and most importantly, keep finding joy in the process, even in the messy middle.
