138: How to Navigate the Intersection of Art and Entrepreneurship: Interview with Steph Halligan

Many people believe that if they were to make a living from their creative work, the art itself would suffer. That getting paid somehow cheapens their craft, when in reality, they have finally received validation.

138: How to Navigate the Intersection of Art and Entrepreneurship: Interview with Steph Halligan

Instead thinking of art and entrepreneurship as opposing forces, consider, perhaps, that they are two sides of the same coin. Rather than competing with one another, your creativity and career are intertwined.

Sometimes, as in the case of this week’s guest on The Portfolio Life, you might pursue a shadow career and rediscover a lost creative passion that breathes new life into your vocation, or reveals a new path entirely.

Listen in as motivational cartoonist and writer, Steph Halligan, and I talk about losing and finding your artistic self, hidden benefits of daily creative habits, and how to reconcile the tension between art and entrepreneurship.

Listen to the podcast

To listen to the show, click the player below (If you’re reading this via email, please click here).

Show highlights

In this episode, Stephanie and I discuss:

  • How drawing a student loan debt monster led to new opportunities
  • The progression of quitting your day job
  • Why self-confidence and creative frequency are interrelated
  • What it feels like to be an artist and an entrepreneur
  • Letting your fans celebrate and support you
  • Packaging your creative work into products people care about
  • The importance of environment and changing elements that influence the creative process to get unstuck

Quotes and takeaways

  • “The beauty of doing something every day is you build up a portfolio of work.” —Steph Halligan
  • “If you give, you are allowed to receive.” —Steph Halligan
  • Create products people want. Start a dialog with your audience.
  • If you help enough people there will be people lined up to give you money.
  • When money becomes the chief concern, it doesn’t always lead to the best art.


Do you think getting paid compromises your craft? How do you navigate the tension between art and entrepreneurship? Share in the comments

Click here to download a free PDF of the complete interview transcript or scroll down to read it below.


“SH: As I started adding the cartoons, it started building this confidence inside me that I had something of value to offer to the world that was beyond whatever job I had.”


[0:00:41.2] JG: Well Stephanie, welcome to the show.

[0:00:44.3] SH: Thanks for having me.

[0:00:46.7] JG: You call yourself a motivational cartoonist?

[0:00:49.5] SH: That’s right.

[0:00:50.5] JG: What does that mean?

[0:00:52.6] SH: I’m a cartoonist, and an author, and a writer, and so those are all titles I use too, but I landed on motivational cartoonist. One, because I had a motivational speaker actually tell me that’s what I do. He said, “You’re like, a motivational cartoonist.” I was like, “Yeah. That’s actually a perfect way to describe what I do.”

Why I love the phrase so much is because I’ve taken my medium of choice, my craft, which is drawing and writing, and I use it to inspire and infuse a little positivity in the world, and help people make people feel better about where they are in life. That’s where the phrase motivational cartoonist comes from.

[0:01:35.8] JG: Have you always been an artist? Have you always been drawing, or is this something you came to later in life?

[0:01:42.4] SH: Yeah, I would say that I was born to draw, and then I lost it for like 20 years, and then I came back to it. Yeah. If you would ask friends and family, and anyone who was around me as a kid, I was meant to be a cartoonist. It was something I did as a little child. I was illustrating and writing books even before I could properly write. and then I would just write scribbly words. and I wanted to grow up to be like a Looney Tunes animator or a Disney animator.

Then there was that kind of period of in between time when I was probably starting in high school, and then definitely in college, when my mind shifted over to, “Okay, what do I practically, really want to do in life and make money from?” Art just really fell by the wayside, so there was a period in my life where I maybe, I would say a year or two years in college, when I wasn’t actively drawing or creating any sort of artwork, just because I was trying to figure things out, what my career ladder was and my major. I picked up cartooning regularly, maybe about two years ago.

[0:02:52.5] JG: Really?

[0:02:53.5] SH: Yeah. It was a large piece of me that was missing for a while, and I’m really happy I got it back, that’s for sure.

[0:03:00.9] JG: I want to talk about this project, arttoself.com, but before we talk about that, this is a new thing, you know? Being this motivational cartoonist. What did life and work look like before two years ago?

[0:03:15.5] SH: Yeah, I had graduated from college. I had graduated with a lot of student debt, which is not very uncommon nowadays. I ended up going into this field of financial literacy. I was working in a nonprofit, and I was helping teach college students and low income families about ways to save money, and especially for college. My career path really looked, it was involved in this kind of personal finance field.

It was a topic I cared about a lot, because I felt very personally affected by student loans, and I even started a blog around personal finance and my own kind of student loan payoff journey. My professional life was starting to make sense after college, I was putting pieces together, and realized I was building this kind of unique skill set in putting my career ladder up against the wall of financial literacy, and personal finance, and a topic I sincerely cared about,

And as I was blogging, too, about my student loan journey and personal finance journey. I could tell maybe four years after graduating, maybe even three, that something was kind of missing, it felt really good to be able to share my story with the world, and I loved writing blog posts and being able to put them out there, know that even just friends and family were reading my point of view.

Then I had that kind of hunger for something else, and I couldn’t even name it. I think at the time I couldn’t even tell you, “It’s cartoons,” or “it’s drawing,” but it just felt like that creative piece of me didn’t have a place to go. The writing was helping, the blogging. There was something else that was not quite syncing up with what I was doing, and it was when I was still in a nine to five job that I took my personal finance blog and I actually started drawing cartoons on it, because there was something there that I thought would be interesting if I maybe drew about my student loan journey, and I started drawing this student loan debt monster.

I drew myself as a super hero that was trying to pay off student loans, and that was the first little experiment of mine to find out, “Okay, what is my creative outlet that I really want? Drawing comes naturally. What if I did the crazy thing of adding this to my personal finance website and see where it goes?”

That was the moment where that moment of experimenting kind of clicked into place, where I remembered that cartooning was that thing in my blood, and finding a place for it, and putting it out into the world, even if it was about student debt or something like that. It started exercising that muscle again when — something in me kind of came back to life that had been almost ignored and kind of atrophied for the better part of a decade and a half.

[0:06:12.1] JG: Isn’t it interesting that you didn’t realize this was the thing that you were supposed to do until you did it, and then you’re like yeah, this has been here all along.

[0:06:22.3] SH: Yeah.

[0:06:22.5] JG: I love that, that’s really interesting.

[0:06:24.5] SH: It was so funny. I remember telling my mom, I was like, “Hey mom, I’m going to start adding cartoons to my personal finance site,” and she was like, “Of course.” Excuse me? She’s like, “Yeah, that’s what you’re meant to do in life.” I was like god, I should have just asked my mom, maybe a couple of years ago, and this search would have been so much easier.

[0:06:44.6] JG: Yeah, that’s hilarious. Writing was that way for me, I wouldn’t have said, “Yeah, I was meant to be a writer” when I was 16 or 21 or whatever. In fact, I wanted to be a rock star. At whatever it was, 27, 28 when I started writing, I was like, yeah. I guess it’s like that Steve Jobs speech that everybody quotes about connecting the dots.

You look back and you go, yeah, totally makes sense. It’s fascinating. Personal finance blog. You and I ran into each other, I think we’ve seen each other twice now at FinCon, which is a financial blogging conference, and like just like the craziest party I’ve ever seen. It’s just wild.

[0:07:24.4] SH: For people, yeah.

[0:07:25.6] JG: It is. You’ve got like people that are like arguing about which credit cards give you the best cash back bonus, sort of…

[0:07:34.2] SH: That’s right, yeah.

[0:07:36.0] JG: Then there’s like a dance party, and all things in between. When you were doing this financial blogging thing, what was life like at that point? Were you a full-time blogger? Was this something that you were doing on the side while doing the nonprofit thing? Help me better understand that.

[0:07:50.8] SH: Yeah, I had my blog for about two years, and once I started adding cartoons to it, a funny thing started happening. At the time I added cartoons to my personal finance blog, which is about two years ago, I was working at a startup that was focused on financial literacy, and as I started adding the cartoons, it started building this confidence inside me that I had something of value to offer to offer to the world that was beyond whatever job I had.

I could just really — I could map out the trajectory, which is like the frequency in which Steph draws cartoons, like, the higher her self-confidence is. At that point, I started shifting mentally to really thinking about venturing out on my own. Not just from the cartoon perspective, but I had built this unique skillset around financial literacy curriculum development, and I was drawing cartoons about financial literacy and personal finance.

I took that kind of that combination of confidence and the unique kind of skillset, and I started shopping around to see what life might be like if I decided to quit my job. I asked an old employer of mine, I asked some potential freelance clients, and just to see, if I ended up stepping out on my own, what would be the appetite for some of the work that I do, and I got some responses from the nonprofit world.

They were like, “Yeah, come work on a project about personal finance with us,” and I got responses from other people who were like, “We want you to be a freelance writer, we’d love to add cartoons to our site.” It was a — the transition away from my nine to five job wasn’t jumping directly to I am a full-blown motivational cartoonist, and cartoons are what I do, and that’s everything.

It was the kind of next iteration of that, which is, “I’m now going to work for myself, but it’s still going to be around this financial literacy skillset, and at the same time, now that I have this space and time to draw more, and think about what I want to do in life, I’m going to explore my art a little bit more.”

[0:10:05.5] JG: Yeah. That’s cool. Tell me about this project arttoself.com. These are daily motivational drawings?

[0:10:15.2] SH: Yeah. Art to Self, it’s one of the best things that I’ve done with my life, which is commit to drawing cartoons every day and sharing them with the world. One side of the coin, it’s a very selfish project that holds me accountable to doing art, and then at the same time, it has just been amazing to see how people have connected with my cartoons.

Because these “cartoon notes” as I call them, they’re motivational in the sense that there is a funny doodle with a quote, something that’s inspirational, or something to help you deal with the low days, especially if you’re trying to start your own business, and something to keep you going on the high moments.

It’s also a place for me to share really vulnerably about the moments that I’m experiencing, both as an entrepreneur and as a creative person, because that self-doubt and that self-criticism comes up very frequently, and I don’t think it ever goes away. So being able to share that with the world, and do it in kind of a lighthearted way with cartoons, has been so important to me personally, but it’s also just been fantastic to see the number of people who responded, who really resonate with the same things that I’m going through, and really appreciate that I’ve turned it into something lighthearted like a cartoon.

[0:11:38.6] JG: Yeah. It’s great. I’m looking at one right now and it’s cool, there’s these little drawings, and then you’ve got these little notes associated with these drawings that are just about your process. People say, “I don’t have enough time,” you’ve got this little doodle that says you make time. Then there’s this little sort of note from yourself to yourself.

[0:11:58.9] SH: Exactly.

[0:11:59.8] JG: I love that. There’s just something powerful, it seems to me, about not being a guru. At least in this day and age, with social media, and the internet, and I saw somebody Facebook this tongue in cheek thing and it was like, “You know what Snapchat needs more of is people giving life and career advice.”

[0:12:18.9] SH: Yeah.

[0:12:19.7] JG: I was like yeah, I just wish somebody would tell me to hustle more.

[0:12:22.8] SH: Right, yeah.

[0:12:24.4] JG: I think it’s really refreshing when you’re just like sharing your own journey, and saying, “here’s where I’m at, here’s what I need right now,” and it’s just a little bit less arrogant, I think.

[0:12:34.9] SH: Yeah. That’s the reason I started Art to Self, which was it came off, it was a spin off the phrase, you know, note to self. I needed sticky notes in my room that were like, note to self, stop beating yourself up. Note to self, you’re doing okay, you’ll get there, and so yeah. It really is the messages that I need to hear, and it’s not the Instagram sunset with a person doing yoga on the beach that’s like, “keep going,” because for me, what was the two parts that are so important is, one, a cartoon and a visual lighthearted reminder that kind of makes you laugh at yourself for the situation a bit.

The second is me writing the notes, and they’re shorter notes, they’re like 150 words, but to say yeah, keep going, but here’s what I’m going through, because I hit a wall and I didn’t feel like drawing today. Here’s the kind of reality and vulnerability behind it, because like you were just saying, I don’t want to contribute to any sort of false guru-dom that’s out there, and kind of show myself as someone who has it all together.

Because every day I’m learning and growing, and there are many days when I have imposter syndrome, and don’t feel like I have it all together. I think that can be almost more valuable to people who are dealing with those kind of struggles or moments, just to be able to relate and connect on that.

[0:13:58.9] JG: Yeah, do you ever look at your own notes and go yeah, I need to remember that.

[0:14:03.8] SH: Yes, my gosh. Funny story was, a couple of months ago, last December, I came out with my first book, because the beauty of doing something every single day is halfway through the year last year, I was like, “Oh my gosh, I have so many cartoons and notes. I’m going to make this a book,” and everyone was asking for a book.

Even though the book content was done, putting together a book and putting it out on the world is still a scary process, and it was a learning process, because there’s a lot of formatting technical stuff, especially if you’re trying to self-publish. I’d be sitting in my book, editing it and working on a cartoon, the two cartoons that just kept coming up all the time to me was “love the process,” and I’d be sitting there editing the note called “love the process.”

I’m like, okay, fine, I’ll love the process. Or I have a note that — it says, “what if it’s already perfect?” and it’s a bunch of scribbles and erase marks and stuff. I would just be editing it, and my gosh, what if this note is already perfect? Okay, Art to Self, I get it. What if it’s already perfect? My notes definitely come back around to me, and I’m not alone, I’m sure, in having to like relearn the same lesson in life over and over again. I definitely revisit the old ones.

[0:15:21.1] JG: Yeah, the reason I ask that question is I was looking at your website, looking at the book, you go to arttoself.com/book, there is a picture of Steph reading her own book, looking quite amused, and I was like, “I would probably do that. I’d go back and go, yeah.” It’s interesting as a writer, I mean, I think people take for granted that you remember this stuff that you put in books, and people are always — like, not always, but occasionally saying, “Hey, I liked it when you said this thing.” I’m like what? I said that?

[0:15:50.0] SH: There we go.

[0:15:51.0] JG: That’s pretty good.

[0:15:52.8] SH: Yeah, that was pretty smart of me, yeah. The other thing, too, that’s so funny is I’ve had people read the book and tell me how much like, you know, I love the cartoon that you wrote about taking the leap to a new adventure, and I was like, “I have not written a cartoon about that. I am so happy you got the message you needed out of my book, but you’ve made something up,” and I’m glad. I love when people take the book and make it their own, and I also just have to laugh when someone tells me about a cartoon they loved that I actually haven’t drawn. They apparently got the message they needed somehow, the work that I was doing.

[0:16:28.5] JG: It’s like a subconscious thing. It’s a very Meta thing if you think about it. You’re doing these art notes to yourself, and then somebody reads it, and then they subconsciously get the message, and then they do a note to themselves, without realizing that you didn’t write that.

[0:16:43.3] SH: Exactly. Yeah, it can get like a very — it’s a very meta process sometimes, especially Art to Self. There’s so many layers.

Click here to download a free PDF of the complete interview transcript or scroll down to continue reading it below.

[0:16:50.5] JG: Yeah, I love it. I love the four sections of this book: You are Here, You’re Enough, Embrace the Messiness, and Live Bolder. Let’s fast forward to present, and we’re talking about starting these different projects, and in most recently Art to Self, and you know, talking with a real live cartoonist, I was thinking motivational cartoonist. I don’t know if you’ve ever done a cartoon about that, but I just envisioned Chris Farley, motivational speaker, living at a van down by the river.

[0:17:19.1] SH: That’s right. Yeah, how do you get your life back on the right track? Yeah, exactly.

[0:17:24.0] JG: If you haven’t done that yet, you should probably do that. Picture of a van in a river.

[0:17:27.9] SH: I love that, I love it.

[0:17:29.5] JG: Anyway, I’ll own the copyright to that, but you’re welcome. I’ll license it to you. Let’s talk about business? Let’s talk about money, and marketing, and these things that you know, a lot of artists are uncomfortable with. I recall a conversation that we were having back in Portland during World Domination Summit almost a year ago, and we were talking about this, we were talking about the tension between having an entrepreneurial mind, or awareness of the fact that if you want to work for yourself, you’ve got to pay bills and manage financial things, which I’ve never loved.

But I realize it’s kind of an important thing to being a human being. Yet, art in some ways just kind of feels like a gift. It feels like Art to Self is a gift. Every day you get up and you draw something, and you share it with people for free, it is a gift, and in fact, you could just go look at all the cartoons. Somebody doesn’t have to buy the book, and yet, I bet that many people who have read your blog and signed up for your newsletter, out of appreciation for your work, said, “I want to do this. I want to support this.”

So it’s an interesting dichotomy, and I’m just curious, where do you sit on that spectrum? Are you comfortable with the business stuff? You did the financial blogging thing. What does it feel like to be an artist and also to be an entrepreneur?

[0:18:55.5] SH: Yeah, I would say, the spectrum is starting to shift, especially in the last couple of months, and it’s this pendulum swing for sure, but for me, I think there were two specific mindsets that I needed to be okay with. It’s a very recent, let’s say in the last six months, mindset for me. One is, the idea that if you give, you are allowed to receive, and it seems so obvious but like you said, Art to Self is a very giving brand.

I’m saying, “Hey, free cartoons and motivation in your inbox every day, all you have to do is sign up, and I’m going to just give.” The first year I did it, it was really hard to monetize that or to add any sort of request with my audience on top of it, because it felt altruistic. It felt like asking for money would be out of integrity.

It was a slow process to shift over to asking for things. Like for example, I ask for donations and I say, Art to Self is an act of love, and if it resonates with you, I would love support to keep this newsletter running. A number of people who have donated, either the quantity of people has been amazing, or the monetary amount has been amazing.

People have done monthly subscriptions or one-time donations that have just blown me away, and so offering that outlet was a big step for me, and then now shifting to product mode, and now I’m creating — I have Art to Self: the Book, I just came out with a children’s book last week, and I’m going to be creating a coloring book and a cartoon mindfulness guide. I’m realizing that because I have this brand that’s giving, and I’m sharing my work all the time, people want that tangible thing they can hold onto, and whenever I release a product now, it’s like everyone’s celebrating with me, and it’s just a wonderful feeling.

That giving/receiving mindset is what I think was the first piece, and the second big mindset that I had to take on was being okay with making money in a different capacity while I built up Art to Self.

I still have a couple of financial literacy clients. I do some cartoon and animation work for them, but there is a part of me that is still 100% pure money-making business over here, while Art to Self can take the time it needs to develop products and continue to grow my audience, so we can grow into an income stream that I’m not forcing to be the end all, be all money maker at the moment.

Actually, it was very helpful to read Elizabeth Gilbert’s book, Big Magic, in which she describes, “I would go home and write, and then I would waitress. Those two lives were separate, until it didn’t have to be,” and so not putting that pressure on my brand. As impatient as I was to get Art to Self to the place where this is my full-time money maker, I don’t want to put in any sort of undue pressure on the brand while I’m still working to build it, and offer products that people love, and continue to make money.

This is the year of Art to Self, in which I’m going to do that, where it becomes that full-time thing and at the same time it’s just my job to exercise patience and make sure that I’ve got some money coming in from other things in the meantime so that I can support this growth.

[0:22:26.3] JG: Do you subscribe to the idea that if you make money off of a passion it can kill the passion? What do you think about that?

[0:22:36.7] SH: I used to think that. I think that was the first struggle I had, again, about that giving and receiving. I do remember moments of impatience and frustration. About nine months into Art to Self, I had this amazing audience that I’d built, and it had been that giving and giving brand, and I just got so angry like, “Art to Self, why are you not making money? Where is the money and why isn’t this happening?” and so for a couple of weeks, I tested out some really weird monetization strategies.

Like selling prints, and maybe t-shirts, and how about mugs, and just trying to squeeze dollars out of it is what it felt like, and I realized that I had hit a line that was my integrity line that I crossed, but also it wasn’t going to work. I knew not only did I not feel good selling that way, but it was not going to work, and it actually hadn’t made me the money I needed. So I realized that one, I needed to commit to drawing the cartoons that I need to hear and I need to read. If I can stay fast on that line, I know that the message will always resonate with people.

Then on the side, create products that people want, and always creating this dialogue between myself and my audience and saying, “Okay, this is what I am working on next, what do you guys think?” Or for example, this children’s book I came out with, it was a long story of an illustrated story I had on my blog, and I asked people what they thought. Should I make it book?

It was a resounding yes, so the integrity of my work is important, because it’s what people resonate with, so I just have to make sure that I’m not creating a cartoon because it’s going to look good on Facebook or something, and I am creating the message that I need to hear, and then separately, looking at how I can package this into products that people care about and that people are willing to buy.

[0:24:36.1] JG: Interesting. So the creative process for you isn’t commercial? Like you are creating the thing that you think people need, or that you need for yourself, and you hope other people share that need, but then once it’s made, you go into business mode. Am I hearing you right?

[0:24:51.8] SH: Yeah, that’s a great way of putting it, which is almost like the packaging and the presentation, that’s what’s the business side of things. But the cartoons themselves are the free creative outlet for me, and so I can come up with Art to Self: the Book comes out of this collection of a hundred of my best cartoons last year. So I know the cartoons have hit home, and I was creatively in line when I drew them and created them, and it took the editing formatting, business-y marketing side of me to make that book real. So yeah, it’s definitely a two-step process for me.

[0:25:30.0] JG: Yeah, it does seem like when money becomes a chief concern, how you’re going to maximize your profit, that doesn’t necessarily always lead to the best art. When you’re writing something, or drawing something, or creating something, I don’t care if it makes money. The irony is that stuff can really resonate with people, and sometimes makes the money.

[0:25:50.8] SH: Yeah, absolutely, and I am a big advocate of keeping those hats separate, so that I could put on a hat at a different time and be like, “All right CEO marketing hat needs to be on right now, but first thing in the morning, it’s like doodle hat.” It’s drawing, it’s writing, it’s creating the thing, because that is the fuel and the fire that needs to keep burning, and it’s the thing that has built this lovely audience that I care about so much.

And then separately, carving out time, like for me working on my mindfulness guide this afternoon. It was creative time, and writing and drawing, and then deciding how to package it was a separate activity.

[0:26:30.9] JG: I really hope you have a doodle hat. Like a fedora.

[0:26:33.3] SH: Oh my gosh, now I think I need one. One that’s physical.

[0:26:36.8] JG: I think that would be cool. I don’t know what’s your creative rhythms are like, but moving around and changing locations for me when I feel stuck can be really important, and I love the idea that literally you put on a doodle hat in the morning.

[0:26:51.0] SH: That’s too funny. I should have to make a cartoon out of that one too. See? The ideas keep coming, this is what’s so great about being a human and learning lessons and stuff. So yeah, I love that idea.

[0:27:02.9] JG: So if you were talking to an artist, and I don’t know if you have these conversations like I do, I live in Nashville around a lot of musicians, there’s also a lot of writers and just creatives in general, and I hear this, what I believe is a limiting belief, which is you can’t make money as a writer, or as an artist, or as a whatever, and I really appreciate, Steph, you being transparent about the diverse revenue streams, about doing client work, but also doing creative work, and then even figuring out the discipline of how do I monetize this in a way that doesn’t undermine my own values, and voice, and making peace with all of that, which I love.

That’s the idea of this show, The Portfolio Life is the life of a creative professional, and really of anybody these days. You’re going to have multiple things, lots of different gigs and stuff, whether or not you’re a freelancer or not. I mean, that’s just the way we live our lives, and I actually have been talking about this idea for a couple of years now, and basically lying about it in my heart, because what I thought I really wanted to do was just write all the time.

And just recently while working on this book, I realized, you don’t want to do that. That would be hell. You would drive yourself crazy. You like the business stuff. You like the marketing stuff, and you also like the creative stuff. It’s just that when one overtakes the other thing, it starts to feel fake and flimsy to me. Anyway, I appreciate you sharing that. I also made peace with that as of this week.

[0:28:40.1] SH: Ha, good. I’m glad I am not the only one, because I totally feel the same way with this am I being invigorated by my work, and part of that is that’s the question I just always have to ask myself, and if part of that means my revenue equation is consulting work, which I actually enjoy, and it’s using a different part of my brain, it keeps things fresh and it makes me feel appreciative for the moments I do get to sit down and write and draw.

I just have to be in charge of lighting the fire under my butt to make sure that Art to Self grows into what I want it to be, so that I am not resting on income coming in from a different source. So that, I think, is the challenge for me, at least at the moment, which is okay, even though I am feeling supported by other revenue streams, I still need to give Art to Self the love and care, and like what you were saying, if I did Art to Self full-time at this moment, I think I would go crazy.

I think the cartoons would suffer, and I think I wouldn’t be as intellectually stimulated and fulfilled. My curiosity wouldn’t be as fulfilled, I think, if I was just doing it full-time. So I am really happy that I am not the only one who feels that, and I think it is a myth of you have to do this all a 100% this way, and you should live and breathe your medium of choice. That could be exhausting, so yeah I am all for that kind of balance.

[0:30:07.1] JG: Yeah, and I think maybe it works for some people, but for a lot of us, heading towards this idealistic voice of an artist that says like, “you should be suffering and you should be doing your work 12 hours a day,” like I read this biography of Van Gogh one time, and it talked about how when Van Gogh lived in the South of France, he would get up early in the morning, he would take his easels out into a field, and he would just paint in the heat of summer until he has like a heat stroke.

And then he painted tons of paintings. He did multiple paintings in a day sometimes, and then he’d carry them home at sunset, and if you are not doing that, you’re not a real artist, and yeah, I think that what we’re seeing these days is a different kind of artist emerge, and it is exciting for me to hear folks like you give yourself permission, because if anything, it validates my own journey. I am curious. Say somebody comes to you and says, “Well, you can’t make money doing this,” or “I want to make a living as an artist,” what kind of advice would you give them?

[0:31:12.6] SH: So I would go back to two years ago when I started doing personal finance cartoons, and I got a chance to speak with an entrepreneur friend of mine, Noah Kagan. I was down in Austin, and he’s a very successful online entrepreneur, and we were talking and he asked me what my ideal day would be like. I would be like, “Oh, creating cartoons in the morning,” and I outlined all the creative stuff I would want to do. He’s like, “So it’s not writing about personal finance, and it’s not making an e-guide about how to get out of student loan debt?”

I’m like, “No, it’s not” he’s like, “It’s cartoons” I’m like, “Yes it is,” and he said, “In the next 72 hours, before you leave Austin, you have to sell a cartoon.” I stopped and said, “What?” and he was like, “You need to put up a PayPal link, email your list of personal finance like readers” who weren’t on my list, because they liked the cartoons, but they weren’t there as an artist, or like a creative who wanted to be inspired. They were there for personal finance advice.

But he challenged me to put up a “buy here” button and say, “I have three cartoon prints for sale, first come, first serve.” Now, I didn’t even have the prints printed, and I didn’t even know what I was going to do when somebody bought one. He really pushed me to test can I sell my cartoons for money, and it was the first time ever that I put that equation together. That my cartoons could equal money, and it was the first time the rubber hit the road and I actually sent a PayPal link out to my list, and people bought.

I had two prints sell, and for me, it was the first moment that I made money off of my art to a group of people that thinks of social media, even if you don’t have an email list, being able to put it out on Facebook and just say, “I have this one print or a couple of things I’m selling. First come first serve. Here’s the link.” And it worked. And from that moment on, I knew that my only job was to test the things that worked, and to create art that I cared about.

But then consistently put it out into the world in ways that it’s for sale, because if it’s not, no one is going to — well, I have a few people ask me to create things, and buy things, and offer to do that but usually, you have to just create the opportunity for somebody to actually purchase and buy your work. So doing that for the first time is the most important step, and you would just be surprised what kind of doors it will unlock for you mentally, and it was a really significant moment for me.

[0:34:02.8] JG: Yeah, so be honest about what your ideal day and schedule looks like, and if you are not doing anything associated with that that’s going to get you there, maybe change something, and then make sure you can actually sell something.

[0:34:17.5] SH: Yeah, exactly, and I think it was Amanda Palmer’s book, The Art of Asking that I read, where she said, “At least 10% of the population is looking for a way to contribute to and pay for art,” and she said that, and I was like, “Oh interesting”. People just want a way to do that, because her musical campaign is — she had one of the biggest Kickstarters ever. All of her fans really rallied around the idea of supporting her work, and she’s like, “You just need to give them the opportunity to actually give you the money.”

And that was also a big ah-ha for me, which is like okay, I just need to create those ways in which people can pay for what really resonates with them.

[0:34:58.2] JG: Yeah, I think it was Amanda Palmer, I am paraphrasing here, but I like on her TED Talk where she says something to the effect of “you don’t have to ask people to pay you, you have to let them.”

[0:35:08.8] SH: Yes.

[0:35:09.9] JG: And that is so true. If you’ve done what you’ve done, Steph, which is be generous, give more than you take, build a community, and it’s not everybody, right? But it’s enough people. If you help enough people, literally there will be people lining up, ready to give you money. It’s amazing.

[0:35:24.5] SH: Yeah, and it is, I think, that giving mentality, and then saying what’s available. Here is a book, a children’s book, a coloring book, you know, guides, things like that. It feels really authentic, and like you said, the amount of people who are either one lining up to buy and they can’t wait to buy my next thing, or people emailing me going, “I love the book, what’s next? I want to buy it,” and giving me ideas of what to sell next.

I’m like, “Well, this is a great feeling.” It feels very much like I’m going to let you buy the things that you want. There’s no pressure, but I know that if you care about the art that I do, you’ll love and you’ll be so willing to buy the things that I create.

[0:36:06.8] JG: Yeah, I love that. I totally agree, and I remember when I started my blog, and people are telling me — and I don’t know if you went through this or not — but people are telling me, “You could monetize the blog,” and I was logging into my Word Press dashboard looking for the switch. Where do I click monetize, where money starts to — yeah, and I realize oh, I have to find out what people want and then actually let them buy it. But literally, after that first year of blogging every day, and I love that you’ve done that too, people started emailing me saying, “Can I buy something? Can I support you in some way?”

It’s a really beautiful exchange when you do it right, and like you said, I think you have to be careful that you don’t get too greedy. That it doesn’t become just about “how do I make stuff so that I can make money,” but I love that your story encourages folks who have a creative gift to share with the world that you can do it in a way where you can actually make a living.

That feels generous, and at the same time you can continue to give. I love what Chris Guillebeau says. I think he does this every time he releases some sort of product. People go, “Oh, I don’t have the hundreds of dollars to spend on this course,” or even a book or whatever, and he goes, “Well, you know the blog is always free.” We forget that. Like, “Oh yeah,” like if you are paying to host something and design it, you’re spending time, that is a generous act, and it is just a fun time to be alive, where artists can be generous, but they can also make a living, and it doesn’t have to be either or.

I don’t know about you, but that’s always my fear is I’m going to come across greedy, or I am not — because it’s actually not fun. What’s fun is to make stuff, and it’s great to get paid so I can make more stuff. It’s not fun to go, “I’m going to make this thing, and I hope it makes me rich.” That’s not as fun as going, “I’m going to make this thing, and I hope it’s amazing and really cool and people like it.”

[0:38:02.9] SH: Yeah exactly, and for me, I know that by nature I swing towards the other side, where I am worried that I’ll come across greedy. Like, “Oh, I just want to create art for art’s sake and I want to give and give and give.” So I know by nature that I’m not going to be pushing that, even if it feels like I’m marketing too much. It’s probably just right, or even not enough, and so I think as an artist just being conscientious of — I had a blogger friend tell me this once.

I was worried that I felt like I was spamming people about my book. I was like, “My book’s coming out.” I was talking to her, and she was like, “You think about your book 24/7 on your end. Nobody else, people think about it maybe 30 seconds when they open their inbox.” She was like, “You’re really like, blowing up how much you think you’re bothering people by it, because by nature, you’re giving and your whole brand is giving.” For me, that is a nice reminder that even when I feel a little squishy about a marketing stuff, that by nature I’m a giving artist, and so I am usually going to be pretty safe in doing that.

[0:39:08.7] JG: And to be honest, I think that’s what has made you so successful is the giving side of it, and I have benefited from that gift. I know lots of people listening to this as well. I hope everybody listening to it goes to arttoself.com/book and picks up a copy of your book. It’s a funny, inspiring, beautiful book, and I am grateful for your time, Steph. Thanks for being here.

[0:39:31.6] SH: Great, thanks for having me.

SH: It started exercising that muscle again when something in me came back to life that had been almost ignored


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