36. The Messy Middle of Creative Entrepreneurship

We’re back with a real, honest, and slightly emotional life + business update. This one’s going to feel a little different than our usual episodes, but these are the conversations that matter just as much as business strategy.

If you’re in a season where your calligraphy business or creative business feels a little… unclear, messy, or like you’re outgrowing things faster than you can keep up with, this episode is going to resonate.

We’re pulling back the curtain and sharing what’s actually been happening behind the scenes, why we took a break, and what this next chapter looks like for both of us. From big life changes to making those “I know this is right, but it still feels hard” decisions, this conversation is all about the real side of creative entrepreneurship—not just the highlight reel. 

We’re diving into what it really looks like to grow and evolve a creative business, including stepping into the “messy middle” where things feel unclear, uncomfortable, and uncertain—but also full of potential. The part no one really prepares you for. Tune in if you’ve ever questioned your direction, felt pulled between multiple paths, or wondered how to create a business that truly supports your life.

What we get into in this episode:

•  What calligraphy business growth actually looks like 
•  The “messy middle” of creative entrepreneurship and why it’s actually a good thing 
•  Making big CEO decisions in your creative business (even when you don’t feel ready) 
•  Letting go of things you love so you can grow 
•  Building a creative business that actually supports your life—not the other way around 
•  Why not having all the answers is… kind of the whole point 

This episode is a reminder that calligraphy business growth and creative entrepreneurship aren’t linear. Sometimes the most powerful growth happens in the quiet, uncertain moments where you’re redefining everything.

If you’ve been feeling like you’re in a season of transition in your creative business, you’re not alone - and this conversation might be exactly what you need to hear right now.

Transcript

Introduction: The Reality of Creative Entrepreneurship

alane_1_04-15-2026_154654 0:32

Hello And welcome back to Calligraphy Biz Corner. I'm Elaine.

shaochen_1_04-15-2026_134653 0:35

And I am XO Chen, and today we wanted to give you a little bit of an update on this podcast and also some exciting changes that are coming.

Behind the Scenes of Our Calligraphy Businesses

alane_1_04-15-2026_154654 0:42

some of you who have been here with us for the whole time, you'll know that we started this podcast. Back in January of 2024, which is wild. I feel like it was the fall of 2023 when we were like trying to come up with names and what we were gonna call it and figure out all of the tech stuff. But we had been friends since we probably connected what, in like 2020. And you can go back and listen to our very first episode for the history on our friendship and on this podcast and how it all came to be. But when we started it back in the beginning of 2024, I believe that it really came out of a season where there was a lot more breathing room in both of our businesses. We were both. Pretty much like well-oiled machines. I wanna say in our calligraphy services, at least I'll speak for myself there. I feel like I had my wedding calligraphy services really dialed in and my pricing and my systems and my client experience was all at a place where I was like, oh my gosh, I have free time for something fun and when Chao Chen asked if I wanted to do a podcast,'cause we had been talking about it for a while, I was like, yes, I have the time now let's do it. And so we did. Of course as things happen, life evolves, businesses evolve, and a lot has changed since then. We've both done a lot of growing and evolving, which is a really good thing in my mind. And you know, we have been on a bit of a break, and so we wanted to. Pop on record this episode, give you an honest and real update because there also wouldn't be a show without any of you listening, and we wanna make sure that we are just always keeping you in the loop about what's going on and always being very real of what's actually happening behind the scenes in our businesses, in our life, et cetera.

shaochen_1_04-15-2026_134653 2:27

So, as you probably know, as Elaine mentioned, we were on a break for a while, since last August. And I came back with a few solo episodes starting in March. In September I actually welcomed my second kid to the family. And so that was obviously like a big driver for taking a break.'cause like I wanted to. Be full, full on, checked out for maternity leave. That was my first episode back was I talked a little bit about how I was able to really fully disconnect from my business, which was so, so good for me as I was going through this new big life transition and I feel like I've been taking things a little bit more slowly as I've come back because there's been a lot of. As you can imagine, adjustment in my personal life and I feel like I'm just starting to get my feet back under me. Come, you know, coming into Q2 of 2026.

Navigating the “Messy Middle” of Business Growth

Making Big (and Kinda Scary) CEO Decisions

alane_1_04-15-2026_154654 3:15

Yeah, and so while we agreed that it was time to take a break because XO Chan was going to be going into this really exciting new life chapter, it also just felt like a good time for me too, because. In 2025, I had started adding a group coaching program to my repertoire of services. So in addition to wedding calligraphy, I was really working behind the scenes to not just create and develop this group coaching program, but then to also launch it and to build advanced rooms and to really build out the ecosystem of that. Because the more and more I did it, the more and more I fell in love with it, and so. Where we started in 2024 with like, oh, I have some breathing room. This is really great. Let's do this thing Last year. All that time very quickly got sucked up as I really was dividing my time between weddings and then coaching, and then also having the podcast. So we both agreed that taking that break was probably gonna be the best for both of us. And I think it definitely was some time that we both needed, you know, Chen for developing her family and me for developing a new side of my business. So, as we came back this year, start of 2026 and really. Thought about where do we want this podcast to go and what does our business look like and what do our lives look like? For me, you know, I've been talking about this a little bit on my Instagram and I'll share more in the coming weeks and months for sure.'cause I wanna bring you along on this ride. But this year has definitely been. I have no other way to describe it than just like a big, messy, middle kind of year for me, where I'm just reevaluating a lot of things, right? Like I'm taking the time to re-look at my offers, re-look at my services, really get clear on what I want my business to look like going forward and what I want my life to look like, and making sure that those two things still actually go hand in hand. I mean, if you've been listening to this podcast, you know that we are both big proponents of building a business that actually supports your life. And I was starting to feel some tension there. And so I knew that I needed to kind of pause, reevaluate, and figure out what does that next version actually look like? And so as I've been getting. A little bit clearer on that. Granted, I still do not have a clear picture, but a lot of that is just the beauty of the unknown, right? Like you never know what's coming around the corner. But I know that this current version is not necessarily what I want in the future. So as I've been sitting with all of that, it has required me to make some really hard and uncomfortable decisions, and usually decisions that I don't always feel. Ready to make and I'm gonna get emotional. And I knew that would happen. But I've just been reminding myself that being ready isn't a feeling Ready is a decision that we have to make. You're just gonna decide whether or not you're going to do it. And. I know that the decisions that I'm making right now, while they are really hard, while they are really uncomfortable, while that they aren't necessarily the fun decisions, I know that they are in service of whatever the future has in store for me, whatever the future business life, et cetera, that I'm building. One of those decisions that I have been faced with is this podcast, and I have made the decision to press pause and step away for the moment. For the time being, this was absolutely not an easy decision to make, and it's not one that I came to quickly. But just being really honest with myself about what fits the season that I'm currently in and what I feel like I'm building towards and following through on that, even when it's uncomfortable, is like really what I am trying to step into. So, like I said. We're coming on here to give you that update, and maybe you've guessed it, maybe you haven't because of Chen's solo episodes that she's released. But I will be stepping away for now, and this is not fun news that I wanna deliver by any means, and it's not the easy decision by any means. But I also just refuse to believe that this is goodbye forever. But I do believe that this is the right decision for me in this moment in time.

shaochen_1_04-15-2026_134653 7:38

Yeah. You know, Elaine and I had chatted, I think at the end of 2025 about this podcast and what the plan was and if we were bringing it back, what that looked like, and that's kind of where we talked about. Elaine needing a little bit of time to think through and process everything that was going through her head, which is like a lot of things kind of happening in parallel or all at once. And I am really supportive of what she's doing and I'm glad that she like took the time and the space to really think things through.'cause I think that's so important a lot of times as a business owner, I feel like we need to make decisions quickly. But in the times when we're able to take some space and really think through the things, I think that can be really powerful too. So I really commend Elaine for making this choice and this decision, not just from a place of emotion.'cause of course emotion plays into it and we both feel emotional about it. I know she loves the podcast and the community we've built through this platform, but she's really. Kind of putting on her CEO hat and thinking about what her business needs from her in this moment. I think she's making a great example of like showing how in order to evolve our businesses to the next version, sometimes we need to let go of things that we've already built. Even if those things like we care about a lot, in order to have the room to build something new. And oftentimes that's something new is something we can't even envision right now. That we can't even, it's not, it doesn't even have a shape or a form yet, but we need to have the space to figure out what that looks like. You might've heard me say before, lean into the discomfort. You're on the brink of something amazing. And I think that that's exactly where Elaine is right now. That she's on the brink and she's leading by example.

Taking Leaps of Faith in Your Calligraphy Business

alane_1_04-15-2026_154654 9:19

I feel like when we were talking about this decision, you had said exactly that to me on that call, and I was saying to you how like, I wish that I just had all the answers. Like I wish that I knew what was waiting on the other side of this kind of messy middle season that I'm in, and I could just like know that every decision that I'm making, every thing that I am, you know, stepping into or stepping away from is. Going to pay off and going to lead to that next chapter and that it will be something even better than I can imagine. But you know, then I guess that also takes away the beauty of the actual journey, right? Like if we already knew where we were going and where we would end up, there wouldn't be any of this. There would be no emotions, right? There would be no challenge. There would be nothing to actually push or work towards and. So I'm really just trying to embrace this as like this is all a part of the journey and it's what makes entrepreneurship in its highs and in its lows a really exciting path, for better or for worse. And it does require you to take a lot of leaps of faith because there is no roadmap and there is no blueprint and there is no, you know, crystal ball telling you how it's all going to work out. Like we just have to. Come to the decision that, okay, I'm ready for this next thing and I'm just going to jump into it. Because you can prepare as much as possible and still not know what's actually waiting for you once you actually jump. I'm in a season where it feels a lot like when I left my corporate job to pursue Right. Pretty for me full time, which was almost eight years ago now, which is so crazy'cause I can remember how terrifying that felt to walk out of the steady paycheck and the office. And it's funny, I was actually just talking to somebody in my group coaching program who. Was giving her notice to her job today for something else, and I was like, well, you're gonna do a better job than I did, because I walked into my boss's office and just started crying when I gave my notice. And it's literally what I'm doing on this recording today is I just want my notice and in tears again. So. Now I have hindsight of what waited for me on the other side of that leap, and I am just really rooted in the faith that the same thing will happen, right? That all of the hard decisions that I'm making right now will result in something beyond anything that I could have imagined in this moment because that's exactly what happened eight years ago. I never would've thought eight years ago, if you could hand me a crystal ball that it would be like, oh no, you'd have a really successful wedding calligraphy business, and you would start a podcast with your really good friend and you'd have a group of listeners who DM you the sweetest messages about the episode. Like I never would've thought that any of that would've happened.

shaochen_1_04-15-2026_134653 12:08

If, the future you came to you and told you all that, you probably wouldn't believe her anyway'cause you hadn't gone through the journey yourself. You were probably not ready to accept all of that in that moment. So to your point, I think that journey is really like, that's what makes it all worth it.

alane_1_04-15-2026_154654 12:23

Yep. Yeah, absolutely. So just to kind of like wrap this up and so I stop crying. I do really believe that this decision is also just rooted in, you know, the freedom for both of us to be able to find our own voices and talk to our people in our own voices and explore wherever that takes us it's really just like I see XO Chen doing so many amazing things and building her business in really incredible ways, and I'm doing the same thing, and I think it's more like. It's time for us to explore that freedom on our own and see where that takes both of us to really fully be able to expand into these exciting things that we're both building.

Friendship, Business & Navigating Change Together

shaochen_1_04-15-2026_134653 13:09

Yeah, so I think this separation is really about creating more space and more expansion for both of us to, because I think there's ways that we might be wanting to use our platforms in ways that we haven't even. Like we were saying before, I haven't imagined yet and maybe the formats are gonna look different and, you know, our podcasts or whatever platforms we have are gonna end up looking very different. And so I think we're just wanting to have some more space to play and, and use our creativity. I.

alane_1_04-15-2026_154654 13:38

Yeah. Yep. Absolutely. And I think what makes this so hard. For me was just like knowing that we are friends outside of this podcast, and this podcast did start as a friendship and I'm probably gonna start crying again, but I'm really gonna try not to. But I put, I feel like I put off making this decision that knew was probably the right one for a while, because I also knew that it wasn't gonna be an easy. Conversation to have. And I was super nervous about it, like having hard conversations with anybody in your life, whether it's a friend, a partner, a mother, a sister, is not easy. And you never really know how people are gonna take it. And you hype yourself up, making up stories in your head about what's gonna happen or how they're gonna take it. And I was really worried that I wouldn't, say it in the right way or. That, coming to this decision would make Chen take this personally or feel like I was walking away from something that we built together or walking away from our relationship or anything like that. But instead, like I mean, the way that you took it was just so incredibly supportive for you to be able to see it for what it is, which is. It was a good decision for both of us and both of our businesses. And I think how gracious and supportive you were was just such a testament to the friendship that we built. And

shaochen_1_04-15-2026_134653 15:05

Now Elaine's gonna make me cry. This is just gonna be like, a sob Fest episode.

alane_1_04-15-2026_154654 15:09

I told Brendan, I was like, we're going out for sushi after this. I'm gonna need like an emotional support meal.

shaochen_1_04-15-2026_134653 15:17

I mean, I think it's exactly what you said is like we have such a solid foundation of friendship and that doesn't change. No matter what happens with this podcast, you know, this is just like one. form that we've collaborated over time and like one way in which we've wanted to our knowledge with our community. And I'm sure there will be other ways in the future, you know, that we come together. I think because we have such a strong friendship and I feel like I know you well enough from like all these years that it was easier for me to understand like where your head is at. And I never felt like it was something personal. And honestly I just found the conversation to be really cathartic because it's, great to be able to talk to someone and be vulnerable. And I think that's always been how our relationship has been. That's how this podcast essentially even started was us talking on like, I think Voxer or just having our maybe like monthly Zoom or whatever it was we were doing at the time and being like, wish that we could bring other people along in these conversations and be on Fly on the wall because I think it would, some of these conversations benefit them too. And that's kind of where the podcast initially came from. So. It was nice to get back to that place of just like being completely open, honest, vulnerable, even though those conversations are hard or not fun to have. But it also opens up all the possibilities to like where we want our businesses to go, we took a picture when we were on that zoom call because I just know in my heart it's, it's a moment we're gonna look back on in however much time. Once you know, our businesses are kind of like where we envision them to be today. And we'll be like, remember that call when. You know, we were both crying and,

alane_1_04-15-2026_154654 17:02

Yep.

shaochen_1_04-15-2026_134653 17:03

but yeah, of course, like this change is hard and emotional, but I think it, it also feels exciting too. And I think now that we've like had some time to talk and chat about it more over the past week, like it's, I feel, I just feel more excited about the future than anything else.

alane_1_04-15-2026_154654 17:18

Yeah. I feel like when you have these big decisions kind of hanging over your head, it's almost harder because you have all of this like anxiety that you're building up around it. But once you do make that decision, then it's like, okay. It's done, it's decided. And now we can move on to wherever it is that we're going from here. It's just funny. It's like I feel like this season is just filled with like me feeling really excited. One moment and really sad the next, and really excited the next, next moment. But again, like that's just part of the ride. And I also think it's really important that we share that with you too, our listeners, because. Entrepreneurship is not easy. And like I did, I shared something on my story this morning about that and then just popped into like my broadcast channel with a couple of voice notes because it can be really lonely. And I remember we set out to create this podcast because we wanted people to feel a sense of community. And I do think that that's what we create. I mean, just based on like DMS that I'll get and I know dms that you'll get. It's like I think that we did that and. You know, part of the really hard thing of making this decision too, is like, I didn't wanna let our listeners down either, and like stepping away from it in a way does feel like I'm letting them down. But, you know, we'll go into like what you can expect next, but I know that you are gonna be in. Fantastic hands, and you're gonna also still see Chen and I in each other's worlds, like we're still showing up for each other, we're gonna be cheering each other on. This is absolutely not a goodbye by any means. Like I said, I want this to just be like more of a pause for me. But I also can't say to Chen like, I'm just gonna keep pause on the podcast for now. Like, I know that I have to make a decision about it. So that's what has brought us here, so that way she can also continue to do what it is that she wants to do.

What’s Next for the Podcast (and for Us)

shaochen_1_04-15-2026_134653 19:02

Yeah, I mean, don't be surprised if you see Elaine as a guest on our show. To be on your own show that you started. But yeah, no, I think like, you know. We talk about like our businesses like oh, the CEO like it's a some big corporation. But the reality is of it is that most of us are like one individual running these businesses. Maybe we have a small team or we work with contractors, but like. human is part of being this business. And like, I think being human is part of why I love small businesses so much because you get to be close to the person who is behind the business. I think we just wanna be transparent, be honest about like what's happening, being, be honest about the person that's behind the business, who knows what you think of us when you are. You know, looking at our Instagram accounts, maybe we look really polished, maybe we don't, who knows? But there is a real human behind this that's also messy and that has emotions. And you know, some things aren't filters and this episode's meandering, but that's the reality of it. So I mean, as listeners you're probably wondering what is, what's happening, what's coming next for this podcast. Calligraphy, this corner isn't going away. You can expect to see new content, new episodes, some guest speakers. I'm already kind of like planning and plotting, but. You know, just with the season that I'm in, I mentioned that I'm a new mom to two. I think the way that I run this podcast is gonna look a little bit different. You probably already noticed like episodes are probably not gonna drop at the same cadence as before. although I'm still aiming for Tuesdays, so maybe just. Tuesdays, you could just check your app and see if there's a new one. But it could be like every four Tuesdays or every second Tuesday. I don't know. But I'm gonna be honest with you about that is that that's just the season that I'm in. I am much more of a last minute operation than, you know, when Elaine and I were kind of like collaborating on all of these different moving pieces of podcast production together. Now it's just gonna be me. And also like the podcast Instagram that's probably going to be a little bit behind on announcing you episodes, or it won't be as like consistent with posts and things like that. But I think the most important thing to me that I wanna continue bringing you quality content and continuing to create a show that you love and a community. That you feel like you can be a part of that makes you feel like you're on this business journey with a bunch of other friends or with me. It's also. This is also a chance for me to maybe change things up, do things a little bit differently. So I'd also love to hear from you, like what topics do you wanna hear about? What season of business are you in? What are you struggling with? What are you loving? What formats of the podcast do you like? Do you like long episodes, shorter episodes? Feel free to message me directly at Monster Gold or at Calligraphy Biz Corner since I check both of those accounts.

alane_1_04-15-2026_154654 21:58

I am so thrilled that Chacha is gonna keep the podcast going because we also work really hard to build it right, like it's our baby, and I'm glad that it is going to continue to live on through you. Chen had sent me a Voxer as we were kind of talking through all of this and talking about like, okay, what are we gonna do? And talking about this episode that we wanted to record. And she shared with me, you know, I want to make sure that I just do this podcast justice. Like I'm just worried about letting people down or, I don't forget what your exact phrasing was, but it was just like about. You know, keeping it going, what people already know and love. And I immediately messaged her back and was like, I have no doubt that you're gonna do that. Like, you don't have to be worried about that at all. Like, people love this podcast and they're gonna love it with me or without me. With us together, or not together. And I think that that's just because of, you know, your personality and the space that you have created here as well. Again, hopefully I can be a guest every once in a while, but yeah. But no, I am really excited that this is going to keep going and I love that you are just also, you know, so much of this is also just about like practicing what we preach in a way. Going back to we both are very big believers in building a business that supports your life. And so for you to continue to take this on, but also just be. Fully transparent with like, hey, it might be a little like not not on a set rhythm or you know, who knows if the Instagram is gonna keep up, but like, that's okay because that's also the cadence isn't the point. The Instagram isn't the point. The point is that the, is the value that people will be getting from the episodes and from your knowledge and your experience. And that's not going to go away. Whether you're releasing every other Tuesday or the fourth Tuesday and then the third Tuesday or whatever

shaochen_1_04-15-2026_134653 23:49

Right.

alane_1_04-15-2026_154654 23:49

may be. So I think that's the, the most important thing. So I'm excited to now start to tune in as a listener and. Keep up with what's going on here. And then as for me, I am gonna be, heads down working on some things behind the scenes. I do plan on having some sort of long form content platform. I don't know exactly what that is all going to look like or feel like yet, but you know, once again, like if you've enjoyed our conversations, then I know that you're gonna enjoy Chao Chens. On her own and hopefully you'll enjoy whatever I go and do as well. But if you wanna follow along with what I'm doing and as it all kind of comes to light for me, I'll be sharing all that over on my Instagram at write Pretty for me. So, you know, I'll show you what I'm building, taking you along for the ride. So definitely don't be a stranger. Come follow me there.

A Heartfelt Thank You

shaochen_1_04-15-2026_134653 24:43

We're all gonna miss having you on the show, Elaine, but we're also. All very excited for whatever comes next for you. I think we just wanna close this episode with like a big heartfelt Thank you. It's been Elaine was saying, over two years since we started the show, we hit 10,000 downloads earlier this year, which is like a huge milestone I think just. Someone who dreamt up this podcast for so long, and again, not being able to see what it could possibly look like at the moment, I was dreaming it up. To see that email come through that we hit 10,000 downloads was just like, just felt like a really big moment. we just wanna say thank you so much for being here, for tuning in and I hope you continue to do so.

alane_1_04-15-2026_154654 25:25

Thank you for supporting us through all of our different changing seasons, and we wouldn't be where we are without you, and neither of us would be able to grow into whatever is next without you. So just a big thank you, a big hug. We really appreciate all of your support.