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Alignment and Art (at Any Age), with Lisa Congdon

Alignment and Art (at Any Age), with Lisa Congdon

At 39 years old, Lisa Congdon embarked on an art career that would quickly transform her into a pillar within the art community. And while her art began as a way to navigate a dark period in her life, today, her vibrant and heart-centered illustrations are celebrated worldwide because of their ability to inspire and bring people together. Listen to this episode of The Cultured Podcast to hear why Lisa ultimately thanks her brother for her pivot from a career in education to a career as a full-time artist.

Read the episode transcript below.


Michelle Khouri  0:01  
What do you get when you combine a teacher’s spirit, with a career working at a nonprofit, and a whole heaping dose of inescapable creativity? Well, you get Lisa Congdon is what you get. And that’s right. Today on The Cultured Podcast, we talk to the one and only Lisa Congdon. Leggo!

Welcome to The Cultured Podcast. I’m your host, Michelle Khouri. And together we’ll journey into the unknown reaches of the art world.

Hello my babies! How are you? Are you doing okay? Are you hanging in there? I know for me, it’s a matter of one day on one day off, doing great, not doing so great. And that’s okay. Totally fine. Feel how you feel. But how I feel right now is inspired, motivated, a full heart, because I just spoke with Lisa Congdon. If you don’t know who Lisa Congdon is, you certainly will get to know why she’s become such an incredible, beloved and well-respected member of the art industry. She is a superstar illustrator and artist who discovered her love of painting and illustration, when she was 32 years old and started her career at 39. And we have a conversation during this interview about these pressures we put on ourselves at different ages. But we also explore her creative process and what it means to be vulnerable as an artist which connects so deeply with me because I sang for you on the last episode. And I know that’s not a big deal for you, but it’s a big deal for me. And it took a lot of vulnerability. So it’s top of mind for me. But before we get into this really amazing conversation, which I am honored to have been a part of, I want to talk about my inspiration this week, which is courage. There is a tremendous need for courage right now, to express ourselves, to feel our fear, to look at ugly feelings in the face, and to remain rooted in the core of who we are. Courage is one of those things that’s really easy to talk about, like vulnerability. They’re very easy to talk about in high level ways. But the practical side of courage is that we feel things that make us feel incredibly uncomfortable. And there’s a voice in our heads. That’s sitting there waiting to convince us that the thing that we’re thinking about doing is not worth doing that it is too dangerous and that we should step away immediately. That’s what fear is right? Fear is a voice. Fear tells a story of what could possibly happen and how we could be in danger if we do something–that feels right to do by the way. That voice is wrong. That voice is absolutely wrong. Courage is the other side of the coin. Courage is what happens when we take that voice and we do it anyway. Because we know that the rewards are far greater than any risk could ever be. And I’m very inspired by it because I’m seeing a lot of people embrace courage in different ways. I’m seeing people embrace courage when it comes to opening their hearts to others, opening their hearts to themselves, pivoting their business models within weeks to survive this, protecting their communities in courageous ways. Being on the front lines as an essential worker. I mean, it’s amazing. I’m also inspired by seeing those who are not being as courageous, honestly. Like you can really find examples of like, mirrors is what they are right? looking at somebody who’s clearly being defeated by their own fears. It can be a mirror to be like, “Oh my god, I think I’m responding in the same way. And I don’t want to be that person. I don’t want to be that person. I don’t want to be ruled by fear.” I used to be very, very ruled by fear when I was younger. And I started putting myself into incredibly uncomfortable situations and situations that brought me a lot of fear, just so I could get through them. It was like a self-imposed desensitization practice, because I’m crazy. But yeah, so, courage is definitely inspiring me right now. And I think it takes a lot of courage to do something as simple as feeling your feelings and being okay with them. But it takes even more courage to express those feelings for one or 100,000 people to feel. Lisa Congdon is a master at being courageous with her expression, being courageous with her feelings. So, let’s dive in. I hope you find a reason to be courageous today. And I’m sending you lots of love. Let’s go! Let’s talk to Lisa!

Welcome Lisa. This is very exciting. 

Lisa Congdon  5:44  
Oh! Thank you! It’s eight o’clock in the morning here, so that’s a wonderful greeting for me get.

Michelle Khouri  5:50  
I will be your cup of Colombian coffee this morning. Well, not that you need it, as we were talking about to get to this point of 8am Pacific, you’ve already done like, a whole day’s worth of productive things.

Lisa Congdon  6:04  
Well, I don’t know about that. But yes, my workout is sort of my, like, my medicine, so to speak. So I went to bed extra early last night, got up at six, rode my bike 10 miles, did some sit ups, ate breakfast, had my coffee. Sometimes early meetings force me to be super productive in the morning. So…

Michelle Khouri  6:25  
Definitely, definitely. And that’s sort of on-brand for you, right? Like you’re known for being productive, but not toxically so. But let’s just level set real quick and why don’t you tell us who you are and what your art form is?

Lisa Congdon  6:40  
Yeah, so my name is Lisa Condon. And I identify mostly as an illustrator, but I also have a fine art practice, which means I make my own personal work that’s not for clients. And I also am an author and now I have published eight books and I have no 9, 10, and 11 coming your way soon.

Michelle Khouri  7:03  

Lisa Congdon  7:05  
Well, two of those are children’s books. Yeah. 

Michelle Khouri  7:07 
Okay. (laughter)

Lisa Congdon  7:09 
Those are a little simpler. And one I didn’t write, I just illustrated it. So I make my living drawing pictures and writing stuff. And I sort of got into this, I wouldn’t say on accident, but when I was in my early 30s, I’m 52 now, so when I was in my early 30s, I was experiencing a sort of early midlife crisis, I would say. I had just ended an almost decade-long relationship. I left my job as a teacher to go work at an education nonprofit. So all these things that had been consistent in most of my adult life, kind of flipped in the same month. And as a way to cope, I just started making art. And this was, of course before the internet before, you know, 100-day projects were a thing, right? And I don’t know. I was doing it as a sort of, I don’t know, way to heal and way to work through my feelings and a way to bring more joy into my life. And a way to spend my alone time. You know, I was single for the first time in 10 years.

Michelle Khouri  8:19  
That’s a scary thing, isn’t it? I don’t think people realize when you’ve been in a long-term relationship–I was in a six and a half year relationship that was a marriage by the end of it. And, you know, when I left it, I realized I had no idea how to be alone. And that’s a terrifying thing to face.

Lisa Congdon  8:37  
It really was.

Michelle Khouri  8:38  
So you really sunk into the art as…that’s really smart of you. That’s a good coping mechanism.

Lisa Congdon  8:44  
I didn’t know that I was being smart at the time actually.

Michelle Khouri  8:47  
You were surviving.

Lisa Congdon  8:48  
I was surviving. And actually, I have my brother to thank. He was also going through a breakup of a long term relationship around the same time. And he moved to San Francisco, which is where I was living at the time. And he started taking some classes to get his, like, landscape design certification. And as he needed to take an elective, and he asked me if I wanted to take this painting class with him. And it was on a Friday night. And we both kind of had no life at the time, because we had just gone through breakups. And I said, sure, that sounds amazing. And, so, we took this class together at this extension program for UC Berkeley, which was right there in our neck of the woods, and ended up like having this amazing bonding experience as brother and sister. We were both in our early 30s at the time. And also he never picked up a paintbrush again. We both enjoyed the class, but he went on to, like, do his landscape thing. And I was like, oh, art is amazing and wonderful. And so I just kind of dove in. Again, without all the resources we have access to now. No Skillshare classes. No. I just sort of, like, started making stuff and then…

Michelle Khouri  9:59  
But you know what? I would venture to say that’s almost more freeing. I think what we have now is, there’s always pros and cons of anything, right? Nothing is all good. Nothing is all bad. But you have to have a little bit more courage because there’s no safety net of information. But also there’s the freedom of no expectations of having to take certain classes or do it a certain way. Right? You find your own way through that courage.

Lisa Congdon  10:26  
I also think there’s a certain pressure now amongst certain people that if you decide you’re going to be an artist, or make art and put it on the internet, that somehow you should monetize it. And that was the farthest thing from my brain at the time. So I really could, kind of, enjoy the process and experience of making for the sake of making and for the sake of expression, versus what gets filtered in now, which is like making things for an audience.

Michelle Khouri  10:55  

Lisa Congdon  10:56  
Not that there’s anything wrong with that. It’s just a very different experience. And so, the formative part of my art-making experience was actually very free. And it wasn’t until I noticed that people were paying attention when I, you know, started sharing more on the internet, gained a following, people were reading my blog, I started getting press years later, that I got imposter syndrome or that I started feeling some sense of self-consciousness. There was none of that in the beginning. And I really, I appreciate that I got to experience that because I think a lot of people don’t anymore.

Michelle Khouri  11:28  
Not to mention, what you mentioned about monetizing, and the pressure to monetize is also because we’ve started really dispelling and you have a whole book about it, the myth of the artist as this broke, starving artist. And it’s interesting because not only is that empowering, but also it lays even more pressure on the person who kind of just wants to make art to make art and they’re okay with being a starving artist stereotype if they want to be, you know? Because now it’s like, “Alright, Run your art as business.” And I, as a business owner, am very inspired by people like you who actually do have successful businesses. I think I’m particularly inspired by you, Lisa, though, because you are a successful business person and artist, but you come at it from a very healthy, in my opinion, heart-centered approach. So the pendulum, the way I see it, doesn’t swing far in either direction for you. I think you’ve found a really nice, middle point. So why don’t we explore a little bit about your journey in monetizing your own art, which is not something you set out to do, like you said.

Lisa Congdon  12:41  
Yeah. So, you know, back in 2006 and seven when I was just starting out, you know, opened an Etsy shop, maybe how to show here or there, I was very attracted to this idea of sharing my art not because I necessarily was like had fantasies that I would make a lot of money and become famous. (laughter) Those things ended up happening.

Michelle Khouri  13:05  
That’s good. (laughter)

Lisa Congdon  13:06  
But, like, but that was really not my, my motivation was like, there is something that happens when you make a piece of art, and other people like it, that is beyond money. It’s beyond. It’s like a feeling of satisfaction that is, in my opinion, quite addictive. 

Michelle Khouri  13:26  

Lisa Congdon  13:27  
And so part of, I think the creative experience, has to be, you know, what fills me creatively what I want to make what inspires me and I listen to those things first and foremost. But when I also experience making those things, and that they resonate for other people, there is something kind of next-level about that. There’s this just magical combination of things. And so, part of why I started trying to build a business was because I got really absorbed in making work and having other people want to buy it or consume it. It just filled part of me like that I was sharing some happiness or joy with people. And as you mentioned, my work is very heart-centered and always has been, probably more so now than it was in the beginning because I think I really found my voice in that combination. But even in the beginning, it was like I was using these really bold colors and shapes in my work, and people were attracted to my aesthetic. So I started monetizing my work in very simple ways in the beginning and then continued that journey. And then started talking about I had a blog at the time, and now I have Instagram, which is like I call it my new blog, but I started talking about the process of making work. So I wasn’t just sharing pictures of what I was making, which were in many cases, either about my life or about things that were inspiring to me or that had happened to me. I was also talking about them publicly writing about them, writing about my process, writing about the experience of being an artist. And, you know, as you mentioned, I ended up writing a couple of books about being an artist and the business of art and also sort of figuring out who you are as an artist, that are sort of based on my own journey. And there is a way that being part of a community and having an audience–I’m very well suited for that. Like, I really like connecting with people around my work, whether it’s selling my work, or having a show of my work that people can view or just simply posting it on Instagram and having other people enjoy it. That’s that’s the sort of cycle that keeps me fed in a way.

Michelle Khouri  15:41  
And you were in education. You were a teacher. And so you very much to me, embody the essence of that. You have this interesting intersection of energy between that, like, the kindness and heart-centered approach of a teacher who wants you to succeed and be well, but also like you’re an absolute badass who is a warrior and a survivor and you have an absolute feminine power about you that is enrapturing, but then also comes with that kindness and and a gentility and a grace about it. And I think that that’s probably why we all want to talk to you. We all want to record you. We all want you to teach us. 

Lisa Congdon  16:23  
Thank you. You’re going to make me cry.

Michelle Khouri  16:26  
Yeah, you know, it’s interesting. My first career was teaching kids. I was an elementary school teacher. And that was a really important experience for me because I developed a sense of tuning into other people and understanding when people – when other human beings – were tuned in to me and when I was connecting, and when I was, like, able to reach people. And then from there, I went to work at this education nonprofit where I simultaneously started making art because I found elementary school teaching so creative that I was not necessarily making art outside of that experience, but the minute I went to an office job, I was like, I need something creative in my life. Even though at the time I didn’t identify as an artist at all. I just was, like, somebody wh\o, like, to make things. I started making art. I had this job where then I was working with adults. So the nonprofit where I worked, I did a lot of workshops for teachers and principals around best practices in education. So then I was sort of transferring the skills, the teaching skills I had learned, you know, teaching kids to teaching adults and connecting with adults. And I got into coaching other adults at the time as well around leadership and education practice. And so what’s really interesting is when I left that career to make art full-time, I had an enormous amount of, I don’t know, guilt about, or sort of sense of loss around that part of my life. That I was somehow giving back or engaged with other people in this really meaningful way. And the nonprofit where I worked was really all about, you know, inclusivity and equity and making a difference in the world. And somehow I felt I was leaving that behind, which makes me laugh now. 


Lisa Congdon  18:08  
But I figured out, you know, I thought, “I’m just going to be an artist, I’m just going to draw pictures all day.” I never imagined that eventually, I could get to this place where I was doing that same work in the context of art that I had been doing in the context of education reform, or, you know, making our schools better. So now I sort of have figured out a way to take my teaching skillset, my coaching skillset, and use it in the context of my creative practice. When I figured that out a few years ago, when I started teaching, when I started writing, when I started doing workshops, when I started speaking, when I started writing books, you know, I was like, oh, this is it. This marriage of that part of me and the creative part of me is like, I found it, I figured it out. And that’s really when things started to come together for me.

Michelle Khouri  19:00  
That’s so beautiful. And it’s also this is what I love about talking to anybody really is. We all go on these winding paths. And you talk about how sometimes I just wish I had found this earlier on in life. And, you know, I get that sentiment. That’s totally valid. But at the same time, what you just talked about is such a testament to how that was the perfect time. Because I think that’s why a lot of people struggle with developing a creative career as a career. And it’s because you’re having to juggle so many different aspects of that. And I think one of those aspects, and I want to hear your take on this, is the fact that a creative career when you are creating from your heart, it takes more energy. And so there’s not only the balancing act of like production, there’s the balancing act of mental and emotional health. So talk to me a little bit. Does that, first of all, does that resonate with you at all?

Lisa Congdon  19:56  
Yeah, I started making art when I was 32. I didn’t actually launch my career until I was 39. So I was, you know, much older than your average person. I think it’s not so uncommon, especially now for people to pivot in their early 30s. In fact, I think it’s very common. And then I think it’s common at, you know, sort of the beginning of, or end of any decade to really call into question like, what am I doing with my life? What is my purpose? And I went through that sort of at the beginning and end of my 30s pretty profoundly. And I have a perspective now seven, eight years later, that is so different, you know, then when I started,. Because I get now that the reason I have accomplished what I’ve accomplished, or that I have built this career, is because I started later. Not despite that fact. And I didn’t understand that back then. I get it now.

Michelle Khouri  20:52  
It’s a beautiful thing.

Lisa Congdon  20:53  
Yeah. I didn’t understand that that was a thing. And apparently it is.

Michelle Khouri  20:59  
Yes. It is a thing and it’s par for the course on all the external pressures we put on ourselves and definitions that we learn along the way that we then stick to, like, this is what it is to be an artist, this is what it is to be a business owner, this is, etc. And you could over-label yourself all day. I mean, you are a warrior. You are in the midst of surviving and you know, having come out of surviving cancer. You are a badass cyclist and a swimmer. You are an athlete, you are an artist, you are a warrior, you’re a survivor, you are a teacher. It’s like, come on, we can be all of those things. I think that’s what makes you so dynamic is you’re sort of like “yes and” to life. And that’s beautiful.

Lisa Congdon  21:46  
Thank you. That’s such a great compliment. I think that there are so many women, in particular, who feel that they have to make these sort of binary choices in their lives, that they either are this or that. I remember early on, I started writing about how I was both a creative person and athletic. And, you know, there’s a lot of talk about how we don’t actually find those, you know, people who like to be cerebral and in their body, you know that those people are rare and I actually don’t think they are. Because the minute I started writing about that other people who were in that category of person started coming out of the woodwork. And I also just think it’s part of what we’re told, like, if you’re some nerdy creative kid, you’re not necessarily encouraged also to be athletic. Or if you’re some kid who’s really into sports, you’re not necessarily encouraged to be creative. And that was certainly true for me. I was more of, like, the athletic kid and less than nerdy creative kid when I was little, I didn’t actually discover my creativity until I was much older. And I was like, I don’t have to reject one part of myself to embrace another part. I can be all these things, you know? And that has been one of the most freeing parts of getting older to me, I can be all of those things. You know, as Walt Whitman said, I, you know, “I contain multitudes,” like that’s true, not just for sort of feelings, but sort of how we identify, you know? And I went from being this person who had very rigid views about the world and about myself to somebody who really loosened up. And if I can be a role model for that for other people, and in particular for other women, that makes me happy.

Michelle Khouri  23:31  
Why do you think it is a challenge especially for women?

Lisa Congdon  23:34  
For the most part, we are raised to believe that we need to please other people, that we are supposed to put ourselves second, that there are just certain ways that the world is and we need to accept them. And that it’s not okay to complain. It’s not okay to make a fuss. I just last month finished Glennon Doyle’s new book Untamed. And it’s really like if there is a book that sort of encapsulates what I’m talking about here it is that book. And sort of breaking free from all of these ideas about who we are. And that being a messy, emotional person is bad. And that we need to, sort of, like show up in the world in a certain way. So I just think it’s like it’s what’s been ingrained in us more than it has been ingrained in men. I think there are certainly men out there who have had very unfair restrictions or ideas, you know, put on them about how they should behave. But I think for the most part, like, women have suffered the most greatly in that area. And I’ve been fighting that stuff my my entire life, and I still, I get criticized by women all the time, who if I go off on a social issue, for example, on social media, that I’m passionate about, you know, that I’m being too emotional, that I’m not being my usual graceful self, you know? I appreciate being told that I move through the world with grace, yes, but at the same time, like, I sometimes get pissed off about things that are happening in the world. And I’m sorry that upsets people to see this sort of my full humanity, but that’s just who I am. And I’m not going to stop being that. And I, even five or six years ago, would not have been sitting here having this conversation with you. This is really something I’ve come to embrace, just in the last handful of years. And who knows where I’ll be in five more years, you know? It was like a slow unfolding that included years of therapy and reading and all the things.

Michelle Khouri  25:33  
And allowing yourself to be.

Lisa Congdon  25:35  
Yes! And just not caring or worrying so much about what other people think, or how other people judge me and then also allowing people to love me and, you know, you mentioned my cancer diagnosis earlier. Like, I got diagnosed with breast cancer last at the end of 2019. And decided to go public with it because I was going to be going through this thing and the outpouring of love was unbelievable. And like, I allowed myself to hold it all to the point where I was in tears almost every day because I just felt so much love. And that’s not something I would have allowed myself either, even five or six or seven years ago. So, you know, there’s just like, hard things happen. But there’s also just ways that the stuff we take pains to avoid, if we just open ourselves up to it can be a totally beautiful enriching experience.

Michelle Khouri  26:29  
Absolutely. And it really is. Freedom is the word I mean. It’s a freedom from those shackles. We all carry them. I think patriarchy is a messed up system because it hurts everybody. And not uniformly. 

Lisa Congdon  26:44  

Michelle Khouri  26:45  
Certainly. But it does hurt everybody. You know, in a previous interview, I heard you mention how it was no coincidence that directly, like maybe a few years after discovering a true love for art, and that artist’s spirit within you, you met your now wife. 

Lisa Congdon  27:03  

Michelle Khouri  27:03  
And it got me thinking. Because you know, your love for each other radiates off the screen. It just radiates. And there’s such a support. And I think that there’s so much to be said about aligning with your purpose and aligning with your truth and then all of the things that align to you. And you become magnetic for this whole new reality that is just perfectly suited for you. My question is, how has your art evolved and your relationship with your work evolved as these different life circumstances have evolved? And, you know, you’ve faced a lot of turning points in the last decade alone. So how have you seen that relationship change?

Lisa Congdon  27:48  
Yeah. So I think that when I was first making art I was really focused on external inspiration. This other artist inspired me. This art movement in history inspires me. I was like a sponge. And I think that’s not so uncommon. That while art was very, making art, the act of sitting down and making art during a very difficult time in my life when I was first starting to make art was a very meditative experience for me, where that art came from was very external. It wasn’t necessarily coming from the fullness of my own DNA or my own life experience yet. And I don’t think that’s uncommon. I think that A, we’re terrified of what’s inside of us for the most part, so we avoid it. And B, we think being a creative person means making something that looks like something that already exists. I think there are exceptions. I think there are people out there who are so emotionally free and spiritually free, that they can sit down and start making art that is like otherworldly. But for the vast majority of us, there’s so many blocks that we’re just kind of looking at the outside and saying what can I absorb? What can I copy? What can I do? And that’s just a normal part of making art. And that’s really where I was in the beginning. Even as my work started to evolve and like, get more interesting and get more Lisa, I was still outwardly focused. There’s something that really happened for me, I think since the 2016 election, which was, like an existential crisis for me personally, and, I think, you know, collective crisis for my community. Just you know, as a woman, as a queer person,  as a person who cares about marginalized people, just sort of the unfolding that happened made me realize that my art had to be, it wasn’t even like I woke up one day and was like, I must make art about how I’m feeling about the way the world is changing. It just happened. Like I couldn’t hold that back anymore. And so part of my voice has really evolved as somebody who has something to say. And often it’s about my own experience as an artist, as a creative person, as a woman, as a queer person, as a person who was a formerly anxious and depressed person to somebody who has had a kind of profound awakening in her life. And I use that as a way to connect with other people. My audience is just as much a part of my work as I am, like I make work to help inspire other people and to let people know they’re not alone. And connection is even over the internet is really, really important to me, and is a very profound part of what I do.

Michelle Khouri  30:36  
That’s so beautiful. Lisa, I so wish we could give you hugs right now, just on behalf of the whole Cultured Crew. So if we want to buy your books, take your classes, learn more about you, follow your amazing awakening and progress. Where can we find you?

Lisa Congdon  30:53  
So my Instagram is at @LisaCongdon. And it’s just my first and last name. And then my website is

Michelle Khouri  31:01  
And then in Portland, we can visit you once this is all done. We can visit your shop in Portland, right?

Lisa Congdon  31:07  
Yes. I’m open Wednesdays, I don’t know what my hours will be once I reopen. So check my website. But typically I’m open Wednesday and Friday afternoons from one to five. And then also random weekend pop-ups and stuff. So I love meeting people who come into town.

Michelle Khouri  31:25  
Virtual hugs. Thank you so much for being on The Culture Podcast, for inspiring us so incredibly. You’re a wonderful example.

Lisa Congdon  31:34  
Thank you so much. It was really great talking to you.

Michelle Khouri  31:42  
I think it’s abundantly clear after that conversation, if it wasn’t clear for you already, why Lisa is such a pillar in the arts community and why she’s practically skyrocketed to fame in such a short time and with a relatively short, yet extremely really productive and exploratory, arts career. Alright y’all, I am going to go bask in this hopefulness and in this joy and I hope you do the same. Until next time, Keep it classy. Keep it curious, Keep it Cultured.