Artistry in Entrepreneurship: Building a Creative Business

Sasha: 0:00

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So go ahead, pull up a chair, grab a notepad, and let's talk business. Welcome to Strategy for Creatives: Business Minus the Bullshit. I, of course, am your host Sasha and today, I feel like this is probably like a meta episode of what my show name actually is. Because of course, it's called Strategy for Creatives. And a lot of what I talk about relates to creatives and their businesses. But of course, it tends to be more business focused. But today I wanted to have a conversation specifically about how to have a business as a creative. What to do when you are experiencing things like burnout and you want to have a creative career and you want to do that in your business and kind of how you simplify your business so that you have the headspace to create because I know that I talked to and I've worked with a lot of creatives that just love what they do, but there's going to inevitably be a time where they don't have inspiration to design. They aren't in the headspace to design. And so to have this conversation with me, I'm talking with Jessica who is a creative and she creates stories. So she's a writer, coach, speaker and founder of the Creatives Apprentice where she spends her mornings writing everything for fantasy novels business, how to articles, and creative nonfiction, and then her afternoons are dedicated to helping creatives own their work. So she simplifies their business practices, coaches them through limiting beliefs and connects them with the support community. Her specialty is helping people become happier and more creative as they increase productivity and live their dreams, which I of course, love. So, Jessica, welcome to the show.

Jessica: 5:29

Thank you so much for having me. I'm really excited to talk to you today.

Sasha: 5:33

I'm excited too especially because you're a writer, which I had someone I did an interview last week who talked about like books and how you can use books to like help your business. But I commend anyone who is an author and like does that because being able to sit down and write, it seems challenging.

Jessica: 5:57

I think the funny thing is to me visual thing seems super challenging. Like the idea of sitting like actually taking selfies or pictures for Instagram, it stresses me out so hard. And I'm like, I would so much rather read a book, or sit down and write for an hour than like have to actually put visuals out somewhere. So I think that for some people just lean into what feels natural and run with it.

Sasha: 6:20

Yes, I 100% agree with that. I don't mind the selfies and the visuals. But the idea... I've never been... I'm a decent writer, I've never liked writing. So having to like sit down and write anything just seems... I commend anyone who does it for a living, who can actually write so. But so the one thing I wanted to start the episode on, and we talked about it briefly right before we started recording is the idea of how creatives set up their businesses and how we should be setting up businesses or not trying to pigeonhole our businesses into models that aren't meant for creative businesses. So how, like, let's start there. What are your thoughts on that? And how do you what do you think is the ideal way for creatives to set up their business so that they don't feel like they're floundering with setting up businesses in ways that just doesn't work for how they think? All the things we hate.

Jessica: 7:19

I think that's the key is to look at how you think personally and not try and force yourself into something that Exactly. And so what I say is, if it's energy draining, doesn't work for you. How I like to look at it is I look at projects or aspects of my business as how much energy is it going to take. And what I found is there's energy generating projects, there's energy neutral projects, and then there's like energy deficit projects. And so my ideal situation is everything I'm doing is giving me energy, but that's ideal, and utopia and not realistic. So what I really try and have my clients do and what I try and do is try and have all of the work that I focus on the either energy giving or energy and you hate it, don't do it. Do you need it in your business neutral. And so for me energy giving things are like doing podcast interviews, writing is an energy generative thing. Actually doing my books as an energy generator thing, I'm really weird. I just like when they balance, it's really satisfying for me. So I see that those are things that I don't mind doing. And when I get done doing them, I actually have more energy. And I'm like, oh, I could do the laundry now, or I could do the dishes, you know, I don't like get done. And I'm like, this feels so heavy. Then there's energy neutral stuff for me, which is kind of like doing emails or follow ups or reach out, like those don't really bother me. And I can kind of waste time doing it if I'm not careful and be like I'm working. But am I really being productive, you know. So it's kind of just energy neutral, because I can kill time doing it and use it as a procrastination technique. But then there's energy draining stuff. model? And if it's something you do need, like, let's say you hate balancing your books, then that's the first thing you want to look at outsourcing. And the thing is, is we all have our specialties like my time is better spent either coaching somebody or writing something, because that's my zone of genius. So it makes a lot more sense for me to outsource my taxes which may take me I don't know, six out I don't know how long they take. So it makes a lot more sense to just let an expert do that and cough up the you know, $300 or however much it is and outsource whatever drains me. And so what I recommend is you just look at your entire business day and just kind of do an audit like go through your day like you'd normally do and then just at the end when you're done of whatever task it is be like do I feel like I want to do more of something? Or am I just like mad or am I like oh my god, this is disgusting, terrible. And that's the first place to start is to look at how your energy responds to it.

Sasha: 10:05

I like that you phrase it in energy ways. I know for some people that ventures into like the woowoo category, but I think it really does help. It helps center how you feel about doing certain things in your business. Because this is something I've said all the time, like, I'm the first person who will outsource anything and everything in my business, because my time is very precious to me. And so if I don't like to do it, I'm just not going to do it, I'd rather pay someone and get it off my plate. And I never looked at it as energy draining, but that's exactly what it is, it's something that I will stare at my computer for hours, I will bounce to other things instead of doing that. And so I like that you frame it as energy wise, because we don't typically think about it like that. But those things that you do in your business that kind of light you up and that make you happy. And you want to do more of like, that's where you should be spending more time in your business and kind of focusing more in those areas.

Jessica: 11:11

Totally agree. And so, for example, I launched my business two years ago, but while that was happening, my mom was dying from cancer. So I couldn't do like a full release, launch how you would normally want to do it and go all all it and right. So I had to stop and kind of be like, okay, I have to look at this as kind of like a soft launch beta type situation. And so this is the first year where I've been able to be like, okay, I'm ready to get all in start marketing, like really look at like expanding my reach and connecting with people who need the work that I do. And so what I did is, I have two other women I work with, they're phenomenal. And I had a list of marketing things just like you know, on the internet, there's a billion lists of all the marketing things you should think you're supposed to do. So I gave us all three, the same list. And I gave us each a black sharpie, and then two colors of pens. And I was like black Sharpie out anything on here that just makes you go this is like terrible. And for me, that was anything Facebook related. Like I don't want any Facebook groups, I don't want any of that. I was just like, it's just not friendly. I don't like it. It's not my jam. And so we went through we black Sharpie and everything that we hated. And then I said go through and in one color, choose all of the things that you already know how to do, and that you enjoy doing. And so we went through and we're all writers, so we're like, oh, yeah, write blog posts, whatever. For me, podcast interviews was one of the things that came up and like. I'm used to being interviewed because I used to run a an arts magazine and a nonprofit. So but it didn't occur to me, like I was like, oh, I just talked to people, I can do that. No, the other two of them are like, oh my gosh, that sounds so scary, you know, that wasn't their jam at all. That's fine. Like, that's not where they wanted to spend their time. And then the third color, what I had us do was things that we were interested in learning about, but we hadn't yet mastered. And so those are things where you can grow your skill set, but you're not going to be as quick at it because you're learning something, and you're not going to have the confidence to walk into the situation right away and do it to the same degree. And so what I had us look at is like, where do we want to grow as a company? And so kind of look at a few of those growth things. And then what do we want to lean into, that we know we're already good at that doesn't feel super taxing or heavy, or like a lot of work for us. And that's where we're putting our focus this year. And then all of the stuff that we blackline through not touching it, like we were just saying, it's not an option. You know, that's not how we're gonna grow our company.

Sasha: 13:39

I liked that. I listened to a podcast that did something... It's "How I Built This with Guy Roz"... It's a really big business podcast. But he was interviewing someone who had started a kombucha business. And she did something similar, she had two other team members. And it wasn't necessarily what they what they would focus on. But it was how they picked their roles in the business. They literally had like, a poster board with all of these things that you know, had to be done or you know, someone needed to do in their business. And they would just take turns picking like this is what I like to do so I'll take this one. And because they were there three different people, you know, they're they're set up in different ways. They think different ways. They like different things. So they were able to really segregate their duties and their tasks and not get stuck with things they didn't like to do. Because they just you know, they've gravitated toward different things. But it's that same thing of what you're talking about. It's like that energy of what you gravitate towards and doing more of what you're like what you're good at. Because if if you do like talking to people and you don't mind being on podcast for you like it's fine for someone who hates having to show up even in audio, because the podcast is just audio so even like it could be terrifying to have to sit and have a conversation with someone and then you get off and you're done. And you're like, oh, I don't need to talk to anyone for the rest of the day.

Jessica: 15:02

And I'm a huge introvert. So like I go out, and when I used to be when I would do speaking events, I would just be drained for like a week afterwards. And I had to learn how to look at how I was going into the event energy wise, like how I was, you know, setting myself up, because I couldn't afford to lose a whole week of just like, it was like being on Kauffman Center for you. I just felt stupid and tired and lazy, because I'd put out all this energy. And I was like, no, that's not something I can afford to lose that much time. Or it's like a hangover really?

Sasha: 15:34

Yeah, I get like that sometimes. I was having this conversation with someone yesterday, my husband and I went on a trip. Two years ago, maybe we were in Colombia with some friends. And I was, we had went out to like a club that night. And while we were standing in line, my husband looked at me and he was like, you're done with people for today, aren't you? And I was like, yeah, I was like, I'll go in here. And I'll make it work for like, 15 minutes, but I'm just, it's too many people. I'm so tired of people.

Jessica: 16:06

I feel you on that. Yeah.

Sasha: 16:09

So I wanted to ask you, because of course, you are a writer. And you know that you say you spend your mornings doing that you've written books, you've worked in creative fields, for those who are listening, who have creative ideas and tendencies, and they want to kind of pursue something in the creative realm, whether it's art or writing or doing digitally, you know, art design, or music or something like that what do you say to them, when they don't think it's possible to kind of have a business in in that arena? Because a lot of people don't think that you can be successful with creative businesses, or it's harder to be successful with creative businesses. I mean, the whole reason why I have this podcast is because I know you can be creative, you can have a business, but most creatives don't know how to set up a business. So I help with, you know, that piece of it. But like, how do you what do you tell people when they're like, yeah, you know, maybe I want to do graphic design full time, or I want to paint full time or write books, but I don't know how to do that as a career, as a business.

Jessica: 17:12

I think, especially in America, one of the biggest societal misbeliefs that we've been conditioned into is the myth of the starving artist. And we have been told that our art, our creativity, whatever it is, doesn't have value. Like we've been told that you have to be you know, sleeping on a mattress without a bed frame and like with bad lighting, and a studio apartment or whatever. That's like some overly romanticized Dickensian idea of what it is supposed to be.

Sasha: 17:44

And like, that's like, if you're a true artists, like that's how you're supposed to be living your life like never successful, always starving.

Jessica: 17:52

You have to suffer for your art.

Sasha: 17:54

Yeah. And until like, until you make it. Like you're either starving or you're like successful.

Jessica: 18:02

Then you're sold out, and you're not a real artist anymore, because you're still out. These are all of the misbeliefs that I will to my dying day work to eradicate it. My goal, like my overall mission, as the Creatives Apprentice is to obliterate the myth of the starving artist. And so the first thing to do is look at what type of information you're taking in, around is that really impossible. And there there's an Audrey Hepburn quote, where she's like, it's not impossible, I impossible. It says I'm possible right there in it, you know? And so look around. Yeah, there are lots of people who make their living through creative means, you know. If you want to go super gigantic, there's like the billionaires like JK Rowling. And there's Stephen King, and there's all those people. But there's all the writers who write for Marvel movies, you know, there's a billion of those Marvel movies coming out. There's visual artists who are making their livings by, you know, creating calendars. And like, there's so many ways to do it. And so if you start changing your interior thoughts, and start looking for the successes of artists around you look at everywhere design as a part of it. Look at how many musicians or how many times you're like listening to a commercial and you hear a song and you know, the song and you're like, oh, okay, there are ways to make money doing it. And the first step is to just start seeing all of the ways there are and then it's like, once you put those glasses on, you're like, of course I can do this. If they can do it, then why can't I do it? If someone else has done this, if you have seen someone actually succeed doing it, then clearly it is possible. It may be improbable. That's okay. But I can tell you it will be impossible if you never take the chance.

Sasha: 19:50

Yes, I'm glad you said that. And I think I do think that slowly, things are shifting when it comes to creative careers. because there used to, you know, there is this idea that there isn't value in creative arts and things like that. But, but more and more people are going into creative industries or starting their own businesses and creative industries. And they're charging their worth in creative industries, which is helping to like pull all of that up, because the time it takes to be creative and to do things like art, or writing or music or design, like not everyone can do that. And so that, you know, that's valuable work that people are doing. And I'm hopeful that maybe not you know, for me, but like my son when he's old enough, like those are, those will be careers, that and people who can have businesses that they are successful. And it's not a question of like, you have to be a starving artist and anything because there's value in what's being done in those industries.

Jessica: 20:52

I'm so glad you said about there being value in owning our worth. Because I do think that's one of the biggest mindset issues that I see people struggling with. I know I've struggled with it personally, myself as well. And the first step to owning your worth is admitting out loud when someone asks, what do you do? Like if you're at a party or your Uber driver or whatever asked, what do you do? Are you answering with what you actually do? Meaning the thing that you create? The art that you make, the super awesome things you sew, the podcasts that you do, the music that you make? That is what you do. People are not asking how do you pay your bills. Which is often how we answer the question. We often answer it with like, oh, I'm in insurance. That's what I used to do. I was in insurance for a long time. And when I like, I did not want to talk about insurance when I was not there. I hated it. But people be like, what do you do, I'd be like, oh, I work in insurance. And then they tell me some stupid insurance story. And I was like, I hate this conversation. But if I would have been saying all along, I'm a writer. And this was like, oh my gosh, I love this book, I would have had real connections with those people. And so the first step to owning of your worth is not responding by how you pay your bills. It's by responding what you actually do. And that emboldens you to own the fact that I am a writer, I am a musician, I am a creative, I am an artist. And when you start owning the fact that that is your core identity, who you are, then you go out and you start realizing how much time, talent, energy you've put in, and money. You've invested in your paint supplies, you know, you've invested in a lot of stuff. And that gives you the courage and the ownership to start charging what you're worth for your projects.

Sasha: 22:34

I love that because I think so many people do exactly what you said. So many people are like, oh, like, I work at Starbucks, or, you know, like they exactly what they how they pay bills. I mean, I even had a friend who has a podcast, she's a co host on the podcast. And it wasn't like until they were so many episodes into the podcast that she actually started referring to herself like, oh, I'm a podcaster. Because in her mind, it was like she... and she has her own business. She does marketing as well. But she was just like, oh, I'm like a marketing person. Like that was what she did. And she started adding, like, oh, I have this marketing business. And I'm a podcaster. And it was a completely shift in her way that she approached her podcast, because before it was just like, oh, I'm someone who is on a podcast, like I record a podcast versus like taking ownership of like, no, I am a podcaster. And so I mean, I had to do that same shift, even with my own podcast and, and my other business, I have a podcast network like I, used to have in my Instagram bio, for the longest time, I would just say business strategist. And like, that was it. And so now it's just like business strategist, and podcaster. Because this is something that I do. And it's something that I like doing and attempt to make money from. And so like owning that it just gives you it gives it value, but also helps you see the value in it. Because if you're afraid to say like I'm an artist, then you're in your mind, you're devaluing what you do when you create art. Whereas if you constantly own like, oh, I'm an artist, then you see value in the art that you create. And therefore you when you want to sell it, you're going to sell it for money, like real money and not be willing to give it away because you see the value in it by attaching it to yourself.

Jessica: 24:20

Yeah. And I think another key point and starting to own your value in that mental shift is looking at who you are sharing with and who you're surrounding yourself with. So I teach a class called slay your dream assassins, and it's about your mental saboteurs that are holding you back. But then also I talk about external dream assassins, and those are people who have good intentions for you. But they're the people who are saying, oh, you're never gonna make it as an artist or like you need to be realistic or have a backup plan or whatever. And those are their fears. And they're misbeliefs that they're like heaping upon you. And you've got your own stuff that you're carrying around and you have thought this through a billion times harder than that person and you know every reality of what what is potentially a problem. So you don't need to carry theirs with you. But when you surround yourself with people who are also building lives and creating lives that they want to, then that's a whole different energy of support. And those people are going to lift you up, and they're going to encourage you to level up. So a good example of that is one of the women I work with is named Marie Berry. She's fantastic. She's a young writer. And so when she came on one of her roles is, as a new creative, I kind of she's my alpha test for everything. So I'm like, okay, you're just getting into the industry. Does this make sense? Is this resonating with you where you are, right? And so I had her writing her bio for our website, and she has written a full book, she hasn't sold it, right? She has, she's still in the process of querying and finding her agent. And she's like, she was, she's like, Can I, can I put I'm an author in there, can I can I do that? And I was like, did you write a book? And she goes, Yeah, and I'm like, then sounds like your author. She's like, and I was like, but what you sat down and you you wrote an entire novel. And she's like,

Sasha: 26:17

I feel like people who are writers and authors, it's not the selling of the book that makes you an author. It's the fact that you wrote a book.

Jessica: 26:30

Exactly. And so it was, she needed, people who are a little bit ahead of her in her career, just look at her and validate all of the work that she's done, and understand how much of her heart and her time and her talent went into that. And then she's like, okay, I'm gonna write it in my bio. So she writes it in the bio on the website, and then she starts going out and like, she's more comfortable doing that. So that the people you surround yourself with, I call it your accountability, or your your creative support triangle, you've got your accountability people, you've got your mentors, and then you've got like your craft and critique support. And so having some mentors or some other people who are critique support with you alongside building their careers, it just gives you a safe space to talk about the problems, but then also people who understand exactly how hard you've been working, and validate the work you do, and shine light on you when you're not ready to shine it on yourself yet.

Sasha: 27:30

Yeah, you definitely need people in a circle like that in any business, but especially when you are in creative industries. Because it can be hard for people who don't have that mindset to understand everything that it takes to just create. Like it's hard work trying to pull anything out of your head and turn it into something else. So yeah, you definitely need people like that in your circle. So before we close the show, I wanted to ask you really quick that I know you say your superpower is simplifying and demystifying business for creative minds. So could you give just a quick example of like how that works? How do you demystify business for creatives?

Jessica: 28:14

Well, I think most of us when we first start out, think I have 10 million million things I need to do. And that is true, you do have a lot of things that you need to do. But one thing I encourage you to look at is you are super lucky in the fact that you already know what you want to do, and you have a calling. A lot of people never get to that point in their lives. And your creative career is going to evolve. But you can evolve that career over 40-50-60 years. So if you feel like you have a million things to do, well, sure. But you've also got 60 years to do it in. So looking at the timeframe and realizing there is no race on this. Maybe what I'm creating the market isn't there yet. Like I'm ahead of the learning curve. And so maybe I'm this project isn't, you know, ready for launch or whatever. So, give yourself some generosity with your timeframes. But then the other thing is because there are a billion things we need to do. One of the tenants that I set up when I started the Creatives Apprentice is I'm not allowed to think more than three steps ahead at a time.

Sasha: 29:25

I like that.

Jessica: 29:25

Because you are always going to have more stuff to do. There's always going to be three more steps, but three feels really manageable. And also I've written articles about it but there's, if you're having a day where you just feel like you can't do anything and it's just like you're or maybe you've been sick and you're just getting back into it or whatever you think there's like three super easy things you could do, right? So look for like three easy's and you're like okay, I just need some momentum. Or maybe you want like a high impact thing. And so I've written about that before, but just look at three things like the next three steps and if you find yourself like okay, and then I need to do this, and then I need to do this. And then I need to do this, that's when you look at your mental dream assassins, and you're like, who pull down there, you know, like, you're really excited, the party's not going to stop. But like, let's just do the first steps. And so just look at three steps, the next three steps. And if you do three steps, every single day, year after year, 60 years from now you have this creative life that is just completely amazing, that is uniquely yours, authentic to you, and what you can bring to the world.

Sasha: 30:29

I absolutely love that. I actually have a productivity checklist on my website that it's like, write your To Do lists, but pick the three things that are like must do for today. And then only focus on those and everything else can wait. lBecause it just frees up so much headspace and makes you not as stressed or feel like you know, you have so much to do if you just focus on three things, then it's easier to check them off the list, then you keep going. And that's how you slowly just build momentum and keep going from there. So I'm glad that you mentioned that because I feel the same way. This has been such a great conversation. And I just really appreciate you coming on. If you want to learn more about Jessica, you can go to Jessicaconnelly.com/coaching. And you can actually book a free one on one coaching session with her and experience her coaching style and have a transformative breakthrough with her. I will make sure to drop that link in the show notes so that way everyone can access that. But Jessica, thank you so much for being on the show today and having this conversation with me.

Jessica: 31:38

It was a really fun.

Sasha: 31:39

Thank you. Happening next week on the Strategy for Creatives podcast - I'm talking to Kathy Walterhouse who has been named a top 20 business coach to look out for in Disruptor magazine. And we're talking about how to do sales without sounding salesy. So make sure you tune in next Tuesday to catch that episode. Thanks for tuning in to the latest episode of the Strategy for Creatives podcast. I hope you enjoyed the insightful discussion, and hopefully found valuable tips that you can put in your business today. If you found the podcast helpful, I'd love it if you take a moment to rate and review the show on your favorite podcast platform. Your feedback helps me make a better show and reach more listeners like you. And don't forget to share the podcast with your favorite business owner who could benefit from the strategies and insights I share on the show. New episodes come out every Tuesday, so make sure to subscribe and stay up to date with the latest trends and techniques for growing your creative business. If you want more don't forget to join the Strategy for Creatives Facebook group, or you can follow me on Instagram @strategybysasha. Have a topic suggestion or a question you want to hear answered? Email me at hello@strategybysasha.com Thanks for listening, and I'll see you next week with another episode of the Strategy for

Creatives: 32:53

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