6 Figure Creative Icon

Quitting Her Day Job To Become A 6 Figure Illustrator | Lisa Congdon’s Success Story

Episode art redo 2
If you're stuck in a dead-end job, about to turn 30, and thinking, “I wish I could open my own business… But I'm too old to start…” then listen up.
You're not too old – it's never too late to start your freelance career or open a business.
World-renowned designer Lisa Congdon didn't even start designing until her late 20s, and she didn't even start gaining traction until she was nearly 40. In the decade and a half since starting her business, Lisa has grown it to multiple six figures.
Listen now to hear about Lisa's journey from struggles and setbacks, to ultimate success as a creative.
In this episode you’ll discover:
  • Why it's not too late to jump into a freelance career
  • How Lisa began her creative journey
  • Giving yourself permission to be alone and its effects on your mental health
  • Why it's important to have diverse income streams (but still stay on-brand)
  • Selling physical products as a creative
  • Building your team: don't start too soon
  • Growth and mental health in a creative field

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[00:00:00] Welcome back to another episode of the six figure creative podcast. I'm your host Brian Hood. I'm here with my big bald beautiful co-host and his

nice lavender purple pinky hoodie. Christopher J. Graham. How are you doing today, Chris?

I'm really good because we have unexceptional

interview today. So exceptional, in fact that you are visibly nervous and I'm excited about that. I've never seen you nervous before.

Yeah, I I'm, I'm a little, I'm a little out of my league today, to really quickly intro the guests. We have Lisa Congdon on the interview say, Hey to everyone, Lisa.

Hey, everyone.

Yeah. So let me, the reason I'm a little bit nervous is because we found Lisa on a blue

was the creative elements podcast, who was the host of that is one of our past guests on the show friend of yours, Chris.

and we found you on the pocket and we had to get you on. And then I started actually doing research into what you, what you've accomplished, what all you've done it. And I'm, I have prepared the longest intro I've ever had for a guest right now, just to give our audience some context, because if you're not in the illustrator design space, you may not know Lisa.

My background is in music production. So I was not fully aware of [00:01:00] everything that she's done. it's terrifying. I'm just going to read it really quick. So she is first and foremost, an illustrator or designer she's worked with target, Amazon crate and barrel REI, Martha Stewart living. So that's just the tip of the iceberg for everyone.

So she's also the author of a least 10 books that at least that I could find some of which are named whatever you are, be a good one, amazing book, title art incorporated, the essential guide to building your career as an artist. So she's got the business acumen to talk about that stuff. A book called a glorious freedom, Older women leading extraordinary lives. Love that book title as well. finding artistic voice, the essential guide to working your creative magic that these book titles just get better and better with everyone. You're a podcaster. As of last April, you have a podcast called the Lisa Congdon sessions.

So everyone go open the app and listen to that and subscribe to that. And you've got an online. Selling physical products, everything from my book, prints, books, puzzles, journals, desk, accessories, houseware items, stickers, and tattoos like so many, just physical products. And you have online classes, you sell as well.

top it off, you are named one of the 50 most inspiring people in companies, but people, according to.[00:02:00] Industry creative's published by ad week. So all of this, by the way, and this is the coolest thing that I saw was you didn't actually even start seeing success and, and start getting traction until you're almost 40 years old.

So anyone listening right now, that's, that's just intuitive, almost 40 years old. She's accomplished all that since then. So. Lisa now anyone can see why I'm kind of nervous now because I, it was hard to, it's hard to, I don't know. I can't put you in a box. He said, there's no box to put you in. So we're going to try to like unpack you and focusing on a couple major things that I think you can help our audience achieve.

But now welcome to the show that people know exactly what they're getting themselves into.

Thank you. That was the most brilliant introduction I've ever had.


That was my goal. That was my goal. All right. So. When I, when we bring guests on the show, I always, as a host, I was trying to think of superpowers, like what is their superpower? when I found you, I immediately spotted the superpower is like, it's pretty obvious. Like you have found this way to take this incredible skill that you, as you have created, which is illustration design.

[00:03:00] And monetized it in ways that most people don't even dream of doing. And I want to dive into this, this transition you made you, you started in illustration. It was more of a, I believe a passion and you were just trying to learn the skill of design and it slowly but surely flourished into an actual business.

But can we first just talk about the thing that everyone starts with, which is a passion, when did you find that design passion or the illustration.

So when I was in my Twenties. I got into a relationship with somebody who was a graphic designer, art director, and I'd never had exposure to that world at all. Growing up, I mean, my parents, I grew up in a typical middle-class family. Like we went to a K a museums occasionally and, and my mom was super creative, but I didn't, I didn't know that.

You like being a creative person was a career you could actually have until I was in my twenties. And by that point I had gone to school to become an [00:04:00] elementary school teacher. That's my dog um, taking it out. So, you know, I was really creative on a regular basis with the kids that I taught. I taught first and second grade for the most part.

But then I was sort of like watching my partner, like do all the things and I got really absorbed in not into being an artist, but more into like consuming illustration and design and art. And I started reading books and like looking at all of her books and like, I don't know, I just started loving art and design and really, very much as an observer for a very long time.

And then you know, fast forward we actually broke up. Then I was like, I need something to kind of like fill this space in my life. Cause we had been together for about 10 years. And so at this point, I'm in my early thirties and I started taking art classes and I started painting and again with no aspiration to become a professional artist.

couple of years [00:05:00] later, I'm still kind of on this creative path and like the DIY movie. Starts happening on the internet. This is like 2003, 2004. I started a blog. I joined flicker, which was a photo sharing


I remember flicker.

Yup. Every everyone over the age of, I don't know, 33 probably remembers flicker.

and you know, I, I started meeting people and I started seeing pictures of what. Like living a creative life could look like there's photographers and illustrators and fine artists like posting their work. And, you know, the internet was becoming a space for creative people to share what they were doing.

And I was like, oh, maybe I can do this. You know? so I started kind of making more stuff and falling in love with the process of, of creativity and like, So excited by it every day that I didn't even want to go to my job. I just wanted to, to like sit around and make stuff. And I, I didn't make stuff that looks anything like what I make [00:06:00] now.

I was very much a beginner. It was all crap. I didn't know that at the time, but looking back, I can, I can see that now it was all crap, but like I had that passion, I loved doing it. And then I was like, okay, I'm going to figure out how to make this my life. I see other people doing it. I know it's possible.

I don't know what I'm doing. I have zero, education. I have like had no mentors. I had nothing really at the time, but I was like, I'm going to figure this out and little did I know nobody really knew, knows what they're doing. Even people who have gone to art school which is why I ended up writing a book on kind of how to make a living as an artist.

Cause I, I ended up kind of figuring it out. Um, It started with me just loving to create stuff and also loving to see people's reaction to what I created and this, and, you know, the fact that social media was

becoming a space for, for sharing kind of help. I think prod my career along.

Yeah. And if you, if you Google Lisa's name, you will find her art style. It is very well-defined now. And it took you, I guess it took you a number of years to [00:07:00] get to that design style that you now like own today. And like what your brand is behind.

Like everything about you do, what you do is just unique and cool and colorful and fun.

And you've probably seen it and didn't realize it.

I get that all the time from people.

Yeah. And so you started the way that so many people, I think

are our listeners right now can resonate with, because it was that passion first approach. Like you found something you just love to do it. You like, you like doing it more than going to your day job. But the disconnect that people have is when they, they just stop there.

There's, it's like, I'm passionate about it. Maybe I want to make money doing it, but there is more skills. It takes the skills beyond just the creative skills. And you found a way to do that. Can you talk about that transition from like your passion first, you are developing the skill. Now we're going to learn to monetize it your very first time.

What did that transition look like and what skills we forced to develop during that?

Yeah. So I was really lucky in that because this is a second career for me. I, and so for any of you listening, who, you know, have an office job or have had another career. And your mind, it's [00:08:00] not related to, you know, the creative endeavor that you are wanting to embark on or, or are embarking on. Like, it is, you have skills that you don't even know that you have that are going to contribute to that.

And I, of course didn't realize that either. Like I was like, oh, you know, cause by the time I left my job to go do this, I was working at a non-education nonprofit and had been there for about eight years. I had project management skills. I had. Client skills, I had relationship skills and all of those things are really important in building your business.

You can be the greatest artists in the world and have all the best like technical skills. But if you don't know how to talk to people, you don't have to put yourself out there. You know, you're not going to succeed um, or at least succeed very quickly. So I. Tapped into all of that stuff. And just sort of understood because I had all of this work experience that I needed to start building relationships with people who were in the industry.

I didn't know anyone. [00:09:00] I had to start networking. I had to get myself on social media, even though at the time it was at its infancy. so I just started doing all of these things and continually putting my very, at the time crappy work into the world. Like I think it was helpful that I didn't know how crappy it was.

Partly. And then also, maybe even when I did, I was like, I just, you know, I'm not there yet. And I know I'm not there yet, but I'm going to keep, putting it out there. And slowly I started building an audience for my work and I feel like, you know, there's never been a better time to be an artist because we have all these platforms that didn't exist 15, 20 twenty-five years ago.

And you had to know a gatekeeper at the time, you had to know somebody who owned a gallery or somebody owned a recording studio or a publisher or an agent. You had to know someone who could help you break through. And today you can break through yourself just by putting your work into the world. so that's what I started doing.

And I started, you know, making friends, people started inquiring, like, how can I work with [00:10:00] you? And I also started putting into place. Kind of time management and organizational skills that I had learned in the workplace. You know, I got to the point where I was, you know, wanting to get more work and so I would make a daily schedule for myself.

And you know, at first I worked part time. I didn't leave my day job immediately. I kind of did a lot of things in orders to pay my bills, like worked part-time at my day, job, opened a store with my friends. And then made work at night and on the weekends, eventually I quit. The job only had the store with my friend and, you know, made art maybe two days a week and on the weekend.

And then eventually I sold, we sold the store and then I started making art full-time. So I did it gradually. I really kind of used a lot of the skills that I learned at my job for how to manage my time and like, you know, chunk out. All the projects that I wanted to do in order to put into the world so that I might get future work, client work that I [00:11:00] was starting to get and, you know, all the other basic stuff, like having a website and updating my portfolio and like keeping myself current.

So a lot of what I did was like using a lot of the stuff that I had learned in my previous career. And I actually think. Second career creatives are sometimes the most, amazing because we know, like we know a lot of stuff that, you know, 22 year olds fresh out of school don't know about. We'll have


I love that approach so much because like so many people leave, they feel like they're stuck at this day job. That's serving them in no way, shape or form, but they don't realize that they're in what I call your Rocky montage, montage phase of life. It's like, everyone knows, like in Rocky, you see the movie, he does all these things where it's like in the woods and he's running upstairs and he's throwing his arms up and he's celebrating.

And it's like this long slog of work he's putting in condensed down into this like 32nd, like music fed montage that you see on screen to kind of represent the journey he's gone. And so many people are on that [00:12:00] journey right now, they're in the day job that sucks, but it's helping them develop these skills that they need so that they can finally succeed when they finally jump all in.

And people ignore that. And I look back sometimes with a little bit of jealousy on some of my friends that had that more formal training in a day job or corporate structure, where they learned a lot of skills that I just lack as a self-taught no college bootstrap, DIY business owner. Like I didn't learn a lot of things and I've had to learn the hard way.

And I continued to pay the price of having to learn the hard way. Bring it all back that Rocky montage scene that a lot of people are living right now is such a good way of looking at these, these hard, long slogs of your

life. That you're not necessarily loving because it's serving you in other ways, it will help down the road.

Well, and I think that I have, I have a. Question Lisa.

So I'm in a montage in my own life right now. I'm on third divorce my life is just, there's a lot going on. And, you know, I had one of these experiences where, you know, my marriage fell apart. I got into therapy. I'm looking at this love of, you know, love of my life.

I'm losing this relationship, [00:13:00] but that spurred me towards growth. And I'm wondering, Lisa, you know, you mentioned, you know, you're in this relationship for 10 years, you kinda got into art through that. Were there any sort of like a or like things that drove you to personal growth or he got into therapy or what were those things that got you on the journey?

That's clearly gotten you to where you are.

I love that question. Well, one of the things I realized when that relationship ended was that I had been a sort of serial monogamous

for my, since I was like, you know, had my first relationship.

That resonates with me.

I mean, aside from my college years where I like dated, but wasn't really in a long-term relationship.

Like I had always been in a long-term relationship and like no more than six months to nine months had passed before I met the next person. And that I didn't really know who I was. I didn't know what made me happy. I didn't know what lit me up. My life would always become about the other person fixing the other [00:14:00] person living vicariously through the other person.

No, it was perfectly happy in some of those relationships while the relationship was going well. But I didn't kind of honor, or even think about like, what did I want from my life? And when this, that relationship ended, I started really thinking about like, I, I dove into therapy and started thinking about like, what is it that I want out of my life?

What makes me happy? And I had no idea. So the therapy helped me figure that out. We did a lot of talking about that and one of the things that immediately started happening for me was like, I started making stuff and it was like kind of how I found joy, but also how I kind of started work out a lot of the inks that I was having in something that felt purposeful and, like forward moving leaning into that, like ended up becoming a career, but it's so weird to me to think, like if I hadn't leaned into that, I might be [00:15:00] like an elementary school principal or something now.

And I'd probably be a great one. And, you know, I, I don't know that it was inevitable that this happened. It's just that I like leaned into my urges. Like I let myself, I was kind of at rock bottom and I let myself just. I don't know try something that I wasn't going to be competing in, or, you know, I was also a competitive swimmer at the time.

And I was like in this kind of worked in a nonprofit organization that was like filled with a bunch of PhDs. And I was the only one who didn't have one. And so I had to always prove myself. It was like the one thing that I was doing just for fun now, of course my career's changed. And like now there's all kinds of pressure attached to what I do.

But at the time it was just this joyful thing that was like, no one had to see it. There was no social media yet. There was no sharing on the internet and it really just opened me up. and I think therapy ultimately got me. To art and that breakup got me to therapy. So like thank you relationship.

Also that person also, as I mentioned, happened to be a [00:16:00] creative person. And so like, I think I was like, well, why not me? Like, why is she the one who it's like, she's the maker. Like I could do that too. I have ideas. And I allowed myself permission to, I was, I grew up in a family.

I was like the not gifted or not creative one.

And so it was a big turn from after that breakup to be like, Hey, well maybe I love all, I love art and design now. I love looking at it. Maybe I should try to make some, and so I'm going to start taking some classes and like, I gave myself permission to do that in a way that,

That I never had before.

And and it all led to this amazing life.

I want to

I love like this is such a good conversation and I know our listeners are like uh, resonating with us. Cause this is like every, everyone can, can put some sort of similarity, like similar story that ties to what you're doing, but there's, there's something you did differently than I think everyone else that we're going to talk about, which is you took all these skills.

You've developed these soft skills, hard skills, design skills, And you've found [00:17:00] clever fun ways to monetize these skills. And I want to get into that because I think that's the best thing. That's your super power is like taking these skills and then just multiplying them in ways that people are not seeing the, the paths that you see.

You know, it's like you, you have this weird sixth sense where you're able to see the, all the past, you could go with your, with your skills. But before we even get into that, I want to talk about something that I think holds so many people back of perfectionism or a fear of. You could have easily taken the skill and just kept developing it forever and ever, and ever, and getting better and getting better and never actually doing anything with it.

How did you actually break from that? Is that, did you struggle with it or was it just like natural for you to just say I've got the skill, I'm going to go monetize it now.

I think there's definitely people in between, but there's mostly two kinds of people in the world. There are people who are perfectionists and feel really uncomfortable, putting anything out into the world until they like it or feel that they've sort of like arrived at this place where it's ready for consumption monetary or otherwise.

And then there's people like me who are not perfectionists and Are ready to put stuff out into the [00:18:00] world actually, potentially before it's even ready. And I get that from my mom. My mom is like this amazing creative person and she could give a shit what people think she's like, does something sometimes, you know, it's not perfect.

She just puts it out there. and I got that from her. People will often say to me, oh, you're so fearless. And I'm like, no, I'm not like, I feel fear just like the, the next person I have anxiety. I get paranoid that people aren't going to like something. I just feel the fear. And I do in any way.

Like, and I do think that's part of. Came with age, since I embarked on this path in my thirties and really came into my own voice in my forties, like I was ready to just be like, the world's not going to come crashing down. If I put something out that nobody likes or that gets criticized, right. Like I will live.

But I'm never going to make progress unless I keep taking these. so, yeah, I think that I'm just, I'm that person who's on that end of the spectrum where I have good, I [00:19:00] have like a particular point of view and I've developed a certain style and I have a voice. And all of that took me a while. even before it was fully formed, I was still understood that I was heading somewhere, including having my work become better.

But. If I sat on it for too long, I was going to fall behind. and I'm so glad that I had the courage to put my workout. Even though now I look back at work this on flicker or that like it's cause it's still lives there. Or, you know, or like even early work that I was doing in the illustration world, you know, eight years ago when I first, you know, signed with an agent or whatever, that, that was actually more than way more than eight years ago.

14 years ago, whatever. I cringe, right? Like, oh, I can't believe that like that, that, you know, sometimes people will post my old work and I get, you know, but I, at the time I understood like this isn't perfect. I know that I have a long way to go, but I need to keep, keep this [00:20:00] cycle and, you know, going of making work and putting out into the world, making work and putting out into the world.

And I'm so glad I did that because I got to where I am and now I'm actually really proud of my work.

And really comfortable with it for a long time. I wasn't, but I still did it

Do you feel like that courage to put yourself out there to do things that might be criticized? The healing that you did in therapy.

100%. I think that, like, one of the things I learned was that like, when you go through a really big breakup of somebody's. That you either adored or continue to adore and that you was such a big part of your life. You have to come to the realization that nothing is permanent.

You may actually have a relationship forever, but this idea of impermanence or of not getting attached, so attached to, to anything being a certain way was such important. I dunno, spiritual and emotional growth for me. Also this idea that I had [00:21:00] agency. So I really started to believe that if I could create kind of miserable circumstances for myself, even though I'm a very privileged person, I also have the power to like create a sense of happiness in myself and that creating a sense of happiness.

Was going to require risk um, risk in falling in love with somebody who might dump me someday risk in putting work out into the world that might, that might be rejected, you know, but that no risk, no gain, right. And even though nothing lasts forever, or at least exists in the same way that it did even five minutes ago, even when you're in a relationship forever, it's always changing.

Um, So this idea of. I know that nobody can do anything perfectly. No one can put any, anything into the world that is perfect. And I've got to start somewhere, so I'm going to put my imperfection into the world. And actually what I found was. That that's what made people relate to me. [00:22:00] That's what helped build my audience was just that I was a regular person, not putting perfect stuff into the world and people were relating to not just my artwork, but also like what I had to say about it.

And that, that was part of my voice. And that all started in, in therapy, I think, and like really understanding That there was no, I think that, like when we grow up, we imagine that we're going to arrive at some place sometime when we're in our twenties or thirties, where we'll have everything figured out and everything will be easy and we'll have a perfect life and a perfect partner and a perfect career.

If we could only just figure that out, we'd be set. And that is the biggest law. If you can embrace like imperfection and messiness and impermanence and all of that stuff, you're actually going to end up being a happier person. If you can kind of relax into all of that. I mean, at least that's what I found and that was so help.

That's such a helpful mindset for like putting your, putting your work into the world, even

when you're, you know, it's not it's there's it's, it's not there yet.

Yeah, [00:23:00] well, so Brian, let me add one more kind of

thought to this, to bring it back to the conversation that you mentioned, Brian, about, you know, monetizing and figuring out how to turn this into a business. I'm so into this conversation and I'm so excited about it because I feel. For creatives there is a resistance to therapy.

There's a resistance to that type of growth that often it creates a lot of arrested development and a lot of stunting and, and just unhappiness. And that was

Oh, I feel it right now. I'm like, I'm like uncomfortable with the conversation being too like. Emotional. I'm like, let's get to the business stuff. Y'all and I know a lot of our listeners are feeling the same way, but you're touching a good topic,

Chris, which is just like having good mental health is an important part of, of

growing as a

Let me

frame this in a way that Brian, you're going to

love Lisa, would you say that your success is a lagging indicator of the work that you did to yourself in therapy?

Oh 100%. Yeah, cause so much of how I have [00:24:00] become a six-figure creative is like trying things and risk-taking, and a lot of that is like, you have to get comfortable taking risks and in order to take financial risks or emotional risks or whatever risk you're struggling with you have to accept the fact that you might fail So that's like, there is no way potentially.

I mean, that's not true. I mean, there are probably some things that feel some ways that people make money or become quote successful or well-known or whatever that have been sort of handed to them. But 99% of the time, people have to go through all kinds of trial and error and like, messiness and.

Failure in order to eventually arrive at a place where things are actually happening for them. Not that you ever stay in one place for very long as I mentioned, but yes. I mean, I got comfortable taking kind of creative risks, which made me more comfortable taking financial risks or [00:25:00] creative risks, or also find out, you know, I was putting work out into the world and then eventually art director.

And creative directors at big brands started contacting me saying, we want to work with you. We love your style. I never would have gotten there had I not put the workout and had I not continued to kind of like plod through the uncomfortable part of like practicing my skill, my art skills over and over and, you know, and then continuing to share, you know, the best of that work.

So, so much connection between

my emotional work and, and my like financial success, I think.

And I would a hundred percent agree. I think the journey is clear on that. And I think so many of our listeners, they struggle with that fear of failure. And I love that. You said you still have. You're not a psycho is that you had the fear, it was all there. But then courage is literally having the fear.

And despite the fear you're still taking action. And that's what courage is. And I think the work you put in is what helped give you the courage in order to keep pushing forward, even though you were uncomfortable, even though it might've been facing failure, even though it might've been doing something that you, you were not unsure, you were not sure of the outcome.[00:26:00]

And I think the work was a huge part of that. So just to talk about this, going back to the soft skills or the hard skills, the things you were learning around creativity and becoming a better creator. Really just to can bring this back to business. Cause that's I love talking business. What was the, like what, what was the first way you started to turn those skills into actual money?

Like that's what we talk about in the podcast is six figure creative. It's like, how do you turn these creative skills into something that is actually putting money in the bank while not violating our creative.

Right. So, I mean, the first thing was like, I'm going to try to sell my work. Right. So that gives me the opportunity to make stuff. And then also monetize it. And I came onto the scene like around the time I'm not on Etsy anymore, but Etsy is like a giant platform now that you don't even have to be, you know, somebody who makes things by hand to be on there.

But like at the time it was in its infancy and it was like the first platform for creatives to sell work. And so I got an Etsy account within a few years. I became uh, top seller, but in those first few years I was like [00:27:00] scrambling to get one order a month. Right. But I just kept making work testing, like, okay, these people follow me on flicker.

Will they like this thing? You know, will the 300 people who liked me on flicker want to buy this set of cards that I had printed, you know? And I just, you know, oh, that didn't go very well. So now I'm going to try a print. And I would like outsource my printing and, you know, gamble that if I printed 30, they would all sell, you know, it was just like little, little stuff, like.

I also was really lucky in the very beginning. I knew somebody, I met somebody in San Francisco where I lived at the time who was a professional illustrator. She's like, you should try to find an agent. And I was like, I don't even have anything in my portfolio yet. Really. And you know, I ended up signing with this woman who saw something in me that.

I didn't even see, I had an art show in San Francisco at a little tiny shop that sold clothes, and they put my art on the wall. Somebody from Chronicle books, who's been my [00:28:00] publisher ever since walked in and was like, oh, that painting. We want to put it on the cover of a journal. And it ended up on the cover of their catalog.

I mean, these were some of the first things that happened for me. There was a com there's company called poquito who's based in LA. They saw some of my work on flicker, ended up licensing it for some of their products. That stuff is like such small potatoes for me now, but at the time it was like such a big deal.

I cold emailed a couple of like really tiny galleries and asked if I could have a show. You know, I just continued to say yes to every opportunity, even if it felt off-brand for me, I was like, I'm doing it all. Um, One of the things that I highly recommend people do. Keep making the songs, keep writing the books, keep making the art, even though you don't have a deal for it yet.

And just keep sharing it because you'll never know who might want to acquire it eventually, even if it means you have to have a day job in the beginning. And so once I started, you know, getting steady sales on.[00:29:00] Etsy. And I started kind of showing my work and selling it and I had an agent and I started getting illustration jobs.

I remember, I think the very first year I was self-employed, I might've made like $45,000, which by the way is not bad. I hustled my butt off. And I think every year for like another five or six years, that was like still, You know, pretty low. And then all of a sudden, everything kind of changed for me.

And I think the important lesson there is that you can't expect it to happen overnight. Some times it does, especially now that the internet. Kind of goes viral around certain things. Some people have pretty instantaneous success, but it took me about five years to get to the place where I began. I began to be come known.

My work was sought after I started to be paid, you know, more money. And I have such diverse income streams, like from, as you mentioned, making books to [00:30:00] doing illustration and design jobs to teaching to Uh, you know, all, all the things. And I really recommend that creatives try to figure out different ways that they can monetize their work, because if one dries up, you've got another one.

Or if one is slow for a while, you've got another one. And then ultimately I still do all of them. And I just have

employees who helped me execute. cause I

can afford.

you. So you've . Gone from like someone that you would just consider yourself an illustrator or designer to. Now you were like, you were a business mogul, Lisa.

I mean, it's really weird. That probably happened a while ago, but I did not start to think of myself as a CEO, a business owner, like a boss until the last year. and I was so conservative about hiring. Now I'm like, how did I go so long without having. You know, I have two full-time employee, salaried employees, and I have one part-time freelancer who does my strategy.

I think, gosh, I should have done this a long time ago. So it certainly had enough money to pay staff, but I was so [00:31:00] nervous and I actually think the return on investment has been amazing. Like I actually can make more money now that I have people working for me. and there's a whole other conversation we could have about that.

But yes, I went from somebody who could barely pay her bills, who couldn't even pay her quarterly taxes. I make, I pay more in quarterly taxes now, a quarter than I made, you know, that first year. So, my life has, has completely evolved. And I'm really glad it evolved as slowly as it did, because I think if it had happened quickly, I wouldn't have been able to handle it.

And every it's been incremental and I've learned so much along the way, and I've been ready for the next step every single time, because it's happened so organically. And so. Relatively slowly like, I'm great.

you mentioned, Etsy and selling kind of the physical products thing. And I think that's an area. A lot of designers would like to do, they have their eye on that. They have the skill of like creating cool things. But, but bringing that over to the physical world, I think is a world that a lot of.

Uncomfortable with, they don't understand. Etsy [00:32:00] seems like the safe bet, but you still recommend people doing Etsy first or did you, I know you transitioned to your own store. I think even have a physical store now, right? Like an actual retail location for your art, which is


So can you talk about that transition from just having the skills of illustration to bringing it

into like the physical.

Yeah. So well, first of all, I think I do recommend that people Etsy's great. Because it's like a shopping mall. people don't have to know who you are to find you so they can go in and you know, let's say you specialize in screening. And you know, animals and somebody types in elephant screenprint cause they're decorating their children's room with it, you know, an elephant theme, they might find you.

Right. And they would never have found you if they'd done an SEO search or a Google search, right. Because nobody knows who you are. I also think Etsy Etsy now takes very high fees and that's ultimately why I left and started a Shopify shop and I can afford to pay those fees and, you know, Integrated shipping and all of that, but as he's still, I think a really viable option for a lot of people.

And then I actually one of the transitional things I did [00:33:00] before I became full-time artist was one of my early, early, early shows was at this little shop in New York city called rare device. And This woman, it was in New York city and she emailed me and was like, I would love for you to do a window display in my shop as like a show.

so I did, and it was really successful and I sold everything in the show and we had a little opening party and then this woman and I became really good friends. And she was like, Hey, my husband and I are moving back to San Francisco. They had used, they used to live there. I didn't know her then.

And she's like, would you. Like to open a shop with me there. cause I had been talking about how I really wanted to leave my job, but I didn't feel like I had was earning enough as an artist. And so I did this transitional thing where I opened this storefront with her in San Francisco when she moved back and we owned that store together.

For about five years and then we sold it to a woman named Roselle who still owns it to this day. In fact, before I came on this call, we have the [00:34:00] same business coach and we we're like on a call together. So it full circle. Anyway. So I learned from Rina, my former business partner at rare device, I learned how to run a storefront, like how to sell physical products.

It was such a great education. And kind of how wholesale works um, which I, at the time wasn't doing yet with my own stuff. So that was such a great education. And so we ended up selling the business because my art career started to take off. She had a baby and she wanted to try something else. So when I moved to Portland, you know, from San Francisco, I was like, oh man, like here, you can get a bigger studio.

You can like afford, you know, San Francisco is so expensive and Portland is getting more expensive, but it's definitely relatively inexpensive. And so I just ended up eventually getting a really big studio and was like, okay, I'm going to, I'm going to do it. I'm going to open a storefront in the front of my studio because I have enough space.

I did that about four years ago I love it. And now I actually have somebody, a retail and product development director who like [00:35:00] basically handled. All of my retail. She used to run other retail shops and she's a great merchandiser. And, I don't really even touch it anymore, but I love having a storefront.

We're only even open like one or

two days a

week, but like people can come in and touch things and look at things.

How are you making me want to have a storefront right now? So fun.

it is fun. It's great.

I love it so much. And now I have enough product to fill an entire store.

so speaking of the product, how do you decide what you're going to create? What you're going to print on? Like, do you, do you have like a testing area? Do you do like, are you the nerdy split test person where you want to optimize and figure out what's going to sell before you print it on a, like, how do you, how do you go about the decision process for what

you're going to create?

Her name is Amy. She is my head of retail and product development. In the old days when I was by myself, I would, you know, a test paper. I bought a printer so that I could print on demand because I realized that that was going to be more cost-effective for me than sending a file to a printer and saying, print print a [00:36:00] hundred of this, not knowing whether I was going to be able to sell all of it.

So we print everything, almost everything in-house not the cards and other products, but the actual, like art prints that we do. And sometimes I do screen, I hire a screen printer to do some limited additions. And so much of my work is licensed by other companies, similar to publishing a book, you can license your artwork on a journal cover, or a mug or a.

So I work with a lot of companies who. Licensed my work. And so I get royalties from, from that. I can also buy that stuff back wholesale to sell in my own shops. So about half the stuff in my shop is, is puzzles and stuff that I've, that I've purchased that have my own work on it from companies that have licensed for me about the other half is like products that we, we make ourselves.

So we do like Our own scarves and blankets. And pretty soon we're gonna have a line of ceramics and, you know, so Amy, goes through the process of like finding vendors, [00:37:00] getting samples of materials, getting test prints. You know, we just had our first line of trucker hats and we like, you know, picked out the thread.

it's really fun. and then, you know, sometimes things sell out and we're like, that was a great idea. And sometimes you order 300 blankets and you only sell a hundred and I'm like, I make enough money now doing all the things that I can experiment a little bit and take some, take some risks.

But yeah, it's, it's a process and I, and I'm really grateful to have a person on my team who is a great designer. As a very like advanced skill in discerning quality of, of potential like materials for products and and does all of the backend stuff for me so that I can create more of my own stuff.

We don't ever want to be so big that we have to have a warehouse, you know, cause we ship everything ourselves. It's really important to me to stay. Small enough that we can, every, we can touch everything. I don't, I'm not ready to give that over. I don't, I'm not saying I'll never do it, [00:38:00] but I like having everything in house and we have a really, we took over the space next door, and now we have a

fulfillment center and all the things, so

what I want to ask about though, is I hear, I hear people. They, they hear the story or I'm sure they're thinking like, okay, so this sounds like a lot. I have to get an Amy on my team. So someone who can do all of the, like the, the grunt work. Right. And so they're going to hold off on doing anything until you do that.

They're going to get a fulfillment center built out. So now there's a huge upfront cost on Capitol to even before they can start this. Like, what would you say to someone who's like hearing the story and thinking like, they're trying to compare Lisa who's like on chapter a hundred of her book with like someone who's a chapter one, right?

As I mentioned earlier, like I let's see I've been doing this since. I quit my job in 2008. And what is it? We're at 2022.

So I mean, how many years is that?


14, 16, something like that on time. And I just promoted Amy to that position a year ago. So that's another thing, you know, and I just hired Erica.

Who's my new head of [00:39:00] operations. In October, like

I just took over that other space a year ago. Um, We just literally moved my shipping out of my garage a year ago, so I really am good at pushing the envelope to the point where I'm not going to spend the money until I'm sure it's going to pay off. I mean, it's still a big financial risk. I I'm better at taking risks on smaller amounts, but like paying salaries and like paying rent on another space.

this a little bit trickier for me. And so while I'm a risk taker, I'm also like, I'm pretty conservative because uh, don't want my business to fail. And so it is this balance of like risk and like smart decisions, risk. I mean, how many startups? I'm not a startup cause I'm totally self-funded but like how many startups have failed because they spent too much money on a fancy office space or whatever too soon.


And countless, and I didn't want to be that person. And I'm so glad I didn't cause pandemic happened and you know, the world completely changed. So I [00:40:00] would say to those people, like take this one step at a time and that might mean for a period of time, you're going to be working your freaking ass off or asking your partner for help or just limiting what you can do and provide to your customers.

Because you just don't have the band. And then you hit this sort of tipping point, or kind of critical mass, and then you go to the next step and it's really about figuring out when the tipping point happens and like when to, when to make the big move. So, yeah, I mean, I think that's important thing to remember is like comparing yourself to me.

If you're in year two or three is silly. Cause I'm in year 14 or 15 or 16, right? Like, It can't, it probably could have happened sooner, but even the soonest this could have happened is probably maybe two or three years ago. I just put it off a little bit. That's still, you know, there's still a long

trajectory for most people.

Some people can do it way

faster than I did, you know,

but it just takes time.

one of the things that I

keep thinking about,

As you're telling us your story is the other day, my mom printed [00:41:00] out the first chapter of a book uh, by Glennon Doyle. And she's trying to get me to read this. My mom has never, ever, ever printed out like photocopied a book. And I was like, oh my gosh, that's adorable.

She staple all


pages together. It is illegal, but.

that's just, that's totally on my mom thing to do. And.

Glennon has popularized this phrase. You can do hard things. And as I'm listening to your story, this phrase just keeps coming back into my mind again and again and again of, okay. Well, what if you decide to do the hard things, you'll be able to do harder things and then harder things, and then harder things you just seem like that's your story.

You had to do the hard things and The profit of doing hard things is the ability to do harder things. That's so cool.

It is. And I think that like, granted, you know, that is, that is in, and it's in and of itself a risk, right? Like doing hard things. we live in a grind culture, you know [00:42:00] where you're supposed to like, you know, put your head down and like not complain and do all the things. And I definitely have that, like the grit and the, like the stealth kind of beaten into me probably when I was a kid, not literally.

But, I am one of those people who can kind of like suck it up and do the hard thing. I'm a gravel cyclist and gravel cycling is like one of the hardest sports you can do, especially endurance, gravel cycling. And like, there is part of me that like likes the cha likes any challenge. Even when I'm not very good at something there's something very satisfying about that.

I also love Glennon and I love that sentiment because. Especially in the last couple of years, like we all feel very downtrodden. We all feel like, if there was any chance that I was going to be successful before, like now it's really, you know, diminished because the economies, you know, who knows what's going on in the country's divided and like all the things and everybody feels really hopeless.

And. I think one of the things that I like to lend to the [00:43:00] conversation is something similar to that. Like, you have to keep putting one foot in front of the other, you have to keep going, keep going, keep going, keep going. but not at the expense of your mental health and I'm sure Lennon would agree with me.

Like One of the things that I've had to balance is this determination to do hard things, but also to take care of not at the expense of taking care of myself and getting enough sleep at night and eating well and having a healthy relationship with my partner, those are all really important to and sometimes taking care of yourself is the hard thing to do.

Sometimes it's easier to just go


than it is to pay attention to your needs.

Oh, that's my story. A hundred percent. Yeah, I did. I did all the other hard things other than taking care of myself and then paid for it. but, you know, thank God it got me into therapy and it got me into this pattern that you are setting, setting the bar, setting an example for of like, okay, I got into therapy, did the hard thing.

What's the next hard thing. What's the next scary thing that I can [00:44:00] do to, to self-actualize to figure out. Who am I And what am I supposed to be doing here?

yeah, difficult things can be such a gift if you like, if you like have the attitude of, I'm going to learn everything I can about myself through this experience and how to, you know, evolve or become a better person or versus kind of like focusing on all the mistakes I made that led to this thing, this hard thing happening.

How I'm unlovable or whatever, right? Like focusing on how I can turn this into something that's gonna be helpful in the world or be helpful to myself. And, I sometimes think of people, if we all had more of an attitude of like agency

versus being a victim, the world

would be a much better.


Yeah, well, I think this is a good place to kind of wrap this episode up. I think your story is inspiring. I feel like anyone who's listening right now can, can look at what you've done and what you've accomplished and look at it as fuel to the fire, to get them to that next [00:45:00] scary thing through the hard work and hopefully out the other side to experience the success overwhelming success that Lisa has experienced.

So, Lisa, is there a place that you would like to send our audience to learn more about you or to experience what you're doing or anything like, where do you want them to go to, to find.

there are

three main places. My website, which is just my name, Lisa congdon.com. It has

links to


much. Everything that I'm about to mention. But also has, you know, that's where people buy things. That's where my shop is. And, you know, the link to my podcast, which is the next place.

The first episode of my podcast is basically a more fleshed out version of the story. A lot of the story that I told today, and then I, I kind of balance monologue episodes with interviews, with people who I think are really inspiring and amazing, and the creative world, and actually just like the world writ large, I've interviewed plenty of non-artists.

And Instagram is kind of the place where I spend my most time,

like interacting with people and kind of sharing what I'm up to.

Perfect. We'll have links to all those places on [00:46:00] our show notes for anyone to listen to. And if you're in a podcast app right now, what are you

listening on? Just look up the Lisa Congdon sessions and you'll find her podcast on there. So thank you so much

for coming on

the podcast.

Oh my gosh, Brian and Chris,

this has

been so much fun. Thank you so much for having me.

Thank you for coming on this, I'm not just gushing here. That's my favorite interview we've ever done. That was, as we're doing it, I'm thinking like this is, this is what our podcast is supposed to be this balance of, of doing the work, the mental health and the creative success and, you know, actually using good business practices. so Thank you so much

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