Artist As Leader: Caledonia Curry

While studying at the Pratt Institute in 1999, Caledonia Curry, under the moniker Swoon, started her career as a street artist, covering sides of buildings all over New York City with her “paper portraits,” ephemeral and incredibly detailed creations. Just 14 years later, she became the first living street artist to be featured in a solo exhibition at the Brooklyn Museum of Art.

Now an internationally recognized artist with works that have appeared on structures all over the world and in such prestigious institutions as the Museum of Modern Art, the Tate Modern and the São Paulo Museum of Art, Caledonia continues to honor her commitment to placing her art-making within a community context. She has founded a non-profit organization, the Heliotrope Foundation, under whose umbrella she can continue to operate three ambitious and very different community projects she’s been helming for several years in Haiti, New Orleans and Pennsylvania.

Caledonia spoke with Artist as Leader podcast producer Pier Carlo Talenti from her studio in Brooklyn about the many lessons she’s learned in her evolution as an artist leader, including when to let someone else steer the ship. The literal ship. It’s not a metaphor.

Choose a question below to begin exploring the interview:

Pier Carlo Talenti: I'd like to start this interview talking about how you lead yourself, and I thought one way to enter the topic would be to have you tell me about a current piece you're working on that you're particularly excited about. Describe it to me.

Caledonia Curry: Well, this piece is in a very baby-est stages. Essentially in the last two years, I needed a big change creatively and I started to allow myself to return to a very old dream, which was to make animations. So I started teaching myself stop-motion over the past two years. Then sort of by surprise last year I wrote a story. It was kind of a weird thing, where I was all of a sudden gripped by this need to write this story. And I'm not very good writer, so I just shelved it, like, “I don't know what that was.”

But then a year later when I was finishing up my first wave of animating and really getting into creating these characters, I was like, "Oh, I don't think that that story was an accident." I think that although I'm not a writer, I can maybe work with a team to take the core material of this story and bring it to life. And so that's what I'm about to do.

Pier Carlo: How is this new project different from your previous work? Just how much of a leap are you taking here?

Caledonia: I feel like I'm taking a very big leap actually. [She laughs.] Visually, people are very easily able to connect it. They see it and they say, “Of course that's you! You made that, and of course you would make that.” That's what people are saying. They say, “Looking at your drawing, looking at the way you build installations, of course you would make this."

But on the other hand, when I look at the last 10 years of my life and all of the kinds of projects that I was working on, from community-based architecture to different sorts of work, when I go, “OK, now all of a sudden I'm deeply fascinated with story-building and with characters and with what mythological archetypes mean and how they come to life and stories and building this and thinking about dialogue,” it really feels like I opened up this whole other chamber in my mind and I'm just running around inside of it.

Pier Carlo: You said you've been coming out of about two years of a difficult period artistically?

Caledonia: Well, no. For the last two years I've been teaching myself stop-motion.

I would say that the difficult part was probably the year before that, was the year that led me to decide to make a big leap. It was just one of those things where I was taking on so many projects, I was stacking plates on plates on plates, I wasn't eliminating anything, and I was just trying to say yes to everything and do every project that came to my mind. I eventually crashed, as happens when you're working in that way. So I needed to start to close up some things, and I really needed to just give myself a creative reboot, I guess.

Pier Carlo: Can you talk about how you created that reboot for yourself, what went into it and what it looked like?

Caledonia: Yeah. It started actually because I was doing a little yearly checkup. My boyfriend's dad gave me this funny book. It was like a leadership book, and I was like, "Oh I'll just do it because he gave it to me, because it's cute." So I went through it; it was asking all these different questions. When I got done with it I realized, "Oh, there's something that I want to do and I'm not giving myself time to do it!"

It was just one of those moments where I had written everything out on paper, and I was like, "You know, this isn't going to happen unless you make it happen. It's not going to spontaneously fit itself in. You really have to make some hard decisions, clear your calendar and make space for something new to happen." I wasn't able to clear a whole year as I would've loved to [she laughs], but I was able to clear off a month here, two months there, and to really just allow myself to dive into this.

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Pier Carlo: Could you talk about the moment when you decided that you wanted to actively lead community projects, when you transitioned into a community leader on three fronts?

Caledonia: I think it may have started all the way back in college, actually, even though the real work didn't get going for another 10 years. I have this memory of being in college. I had started doing street-pasting, and then all these low-level, low-hanging billboards started to go up all over my neighborhood. They were just covering the neighborhood and just blasting all this advertising at people. I was really interested in the dialogue around public space and whose spaces these are and who gets to talk and whether or not the community gets to talk back within the public space of the city.

I was in school; I was working with tons of painters. So I said, "You know what? I'm just going to organize a bunch of people, and we're going to go out in one day, and we're going to cover all the billboards on this whole block in one day, and we're going to create this big change." So I just started to go studio to studio and be like, "Hey, here's what I've been doing. Who wants to join me?" It was the first time I'd ever done something like that. I had been a fairly shy child actually, and so I never really thought of myself as somebody who could inspire groups of people.

I realized, "Oh, I can facilitate things that are much larger than myself. I can get people involved. We can do things bigger together."

But then I came to New York, I was waitressing, and that really broke me of my shyness. Then with this work, I just started to go person to person, and I realized, after we did the thing and we covered the block and we created this huge change — it was this euphoric project in a bunch of ways for us who had just first felt our capacity — I realized, "Oh, I can facilitate things that are much larger than myself. I can get people involved. We can do things bigger together."

So I think that that knowledge just was born at that moment and stayed with me, and then I found myself returning to it over and over again over the next few years. I founded a collective that would do street-art interventions and street parties. Then eventually I founded this raft project, where a bunch of friends and I were living together and traveling.

Then the nonprofit work started because I was living on a series of rafts with these friends of mine and we were just making the impossible happen every single day. I was like, "OK, here we are. We're making the absolute impossible happen every day, and we're doing it for joy and for outrageous creativity and all these things." But I was like, "Well, what if we did it to help when a community was in need? What if we took the same skillset and we tried to be of service with it?" And that's when Heliotrope started.

Pier Carlo: It’s amazing to think that you were once a shy child because —

Caledonia: [Laughing] Very.

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Pier Carlo: — what's coming across to me, what I'm hearing is that one of your innate talents is your ability to gain followership. Where did that come from, not only your chutzpah but the fact that people are eager and happy to follow you wherever you go?

Caledonia: Well, I think it's certainly not all people. Some people are horrified at me! They're like, “Oh, what is she talking about? I wish she would shut up. She's too naïve, and she's wants to be positive all the time, this, that, blah, blah, blah.” Certainly I drive quite a lot of people crazy, I think, with that. So, I think it's like with anything: You find your people. You find the people that vibe with you and that are like, “Oh yeah, that's totally what I've been wanting to do! I was already thinking about that. I was waiting for somebody to say it.”

You know… I wonder about the whole transition between shyness and leadership. For me, certainly it was a surprise. It was a big surprise. Because I was really quite cripplingly shy as a child. Looking back at it now, I think actually some of my crippling shyness was actually disassociation, because I was living in such an unstable and chaotic childhood environment, that I was pretty checked out. So I think some of my shyness may have actually been a deep coping strategy. When my life stabilized, I was able to blossom into maybe who I had always been. Maybe that bubbly, connected person was always there but just wasn't available to me when my life was so unstable.

Pier Carlo: From the little I've read about your rafts, speaking of leadership, it seems like you were actually captain of a flotilla [she laughs] on two continents, right? Didn't you cross the Adriatic Sea?

Caledonia: Yeah, we skirted the coast. We went into the Adriatic; we didn't go straight across, but yeah, we took our vessels into the Adriatic.

I should make one small correction. I was kind of team captain in the large sense of being like, “Hey, let's do this, and here's the designs, and here's how this is going to work, and let's raise the money and do the thing.” But I didn't actually captain the rafts. The reason that I didn't captain the rafts, I tried it for a little while, but what I found is that my leadership style is that I love to get together with a group of people and make something that feels exciting and that feels fun and wonderful. What I don't love to do is make quick decisions when a barge is coming at you and your motor starts to stall. [She laughs.]

I actually tried to captain the rafts. I did it for like two hours. We were going down the Mississippi River, our motors broke down, we were in front of an oncoming barge, and I froze like a deer in headlights. The person who was trying to train me in captaining took over and made all the decisions, did the thing, and I just knew right then, I was like, "I should not be in charge of people's lives. This is not me." That was one of those moments of stepping out of a leadership position that's just not yours, and just being able to see clearly, “Nope, this is not my role.”

Pier Carlo: That's amazing. Well, it is important to realize what you can and can't do as a leader, what your skills are.

Caledonia: Totally! And there were other people who were amazing at leading in that way. There were tons of people who were leading in small and large ways within the raft projects or within any of the community-based projects.

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Pier Carlo: How would you describe your leadership skills? And also what do you think in your artistic background helped you hone those skills?

Caledonia: I'm not sure, but I guess I would have to say … . Strangely no one's ever asked me to define my leadership style, so this is actually an interesting question for me. I think that in a way my leadership style is like that of a storyteller, meaning that what I'm good at is saying, [half-whispering] “Hey, it could be like this! What if we did this?”

That's really where my strength lies, seeing something and then involving people in such a way that they're able to see it too.

That's really where my strength lies, seeing something and then involving people in such a way that they're able to see it too. Then also involving people in such a way that they're able to bring their best selves and bring things I never would have thought of, that they're able to let the project blossom in ways that, if I were dreaming it up alone, just wouldn't happen. I think it exists in those two ways. First as a storyteller, and then second, as somebody who's really interested in the strengths that other people are bringing.

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Pier Carlo: Looking back on your previous work, can you give me a specific example of a time when you as a leader felt you and your team were really on fire and making something come to fruition that felt perfect?

Caledonia: Well gosh, one just happened recently. I had this exhibition, the exhibition of my stop-motion work. We were going to have the opening night, and I really wanted the opening night to feel special in some way. I had been working with live actors in some of the stop-motion and painting them and doing these elements. We brought together a whole group of people, but we only had three hours to build costumes, design the performance, rehearse the performance. That was it. We had to develop the whole thing from soup to nuts in three hours.

We came in, and I was like, "OK everyone, here's piles of stuff. You start on your costumes, and I'm going to run around and give input, say yes, no, give ideas, help out." So we did that and then, “OK, hour and a half? OK everyone, let's do the performance.” So then I’m like, “Well, I'm actually a visual artist, and I don't really lead performances." So I said, "Hey, some of you guys are dancers. Can you guys start, and then we'll feed back and forth?” We did that for a little bit, and then I was like, "OK, that idea is totally working." (Because I was standing outside watching.) “This idea is working, let's go with this, let's go with this.” And then, boom, boom, we got the whole thing designed. I was like, "Holy shit, I cannot believe how well this is working."

I realized that what was going on was that we had an amazing team already; every person who was involved already had quite a lot of their own artistic vision that they were able to bring; and because it was within this container of my show, they were also really quite willing to let me creatively direct. So it was this really beautiful thing where people were both willing to show up creatively and willing to take direction creatively. So I was just like, "Wow, this really worked."

It felt like it was a factor of having built community over a long time — because these were all folks I'd known for years in different capacities — just slowly building a great creative community and then knowing that it can be activated at a moment's notice.

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Pier Carlo: Tell me about leading outside of your community, for instance in Haiti, in Pennsylvania, in New Orleans, where you haven't yet built up your community and sometimes you're working across cultures.

Caledonia: The main thing I would say as a point of success — because of course there are points of success and failure in all of those projects — has been to nest my work and myself within a local structure of leadership. Because the thing is that in those situations, in Haiti, for example, which has been a very successful project, it was absolutely clear without question that I was an outsider and that my team, we were outsiders. What we did was we looked for a small, very self-driven, very positive community organization that could be our partner and we could take leadership from them and bring ideas to them and work within the framework that they had built.

That's so important on all kinds of levels, mainly being these are the folks that know what their community needs, that's already a group of folks that have built trust amongst themselves and with each other. So it becomes much easier to form that bond of trust between these two groups that already have a good thing going within themselves.

It also makes it possible to do something that's right for a community, because we're bringing our own ideas, we're bringing our own input, our own resources, but that can't just land on nothing. People always talk about the hot-air-balloon method where you just parachute in. I think that you can come in from the outside and that can be a really positive thing, and one of the ways I've seen that be a positive thing is when you land within local leadership.

Pier Carlo: Tell me about some of the points of success in those community projects of yours.

Caledonia: Well, in Haiti I'm incredibly proud of that project in a bunch of ways, including that we were able to build three homes and one community center and build these really long-term relationships with this community over 10 years. We're also able to do that because one of our really big successes early on is that we were able to be building at a time when almost no other facilitated building projects were happening, because a lot of other groups had their materials caught in customs, they were dealing with large scale bureaucracy, and we were four artists who connected with a small group of people who had its own local leadership, and it was just like bzzp. We made this decision to work with only locally sourced materials. So we found a factory, we got them to sell us the raw material rather than getting it in parts. We did all this groundwork, which meant that we weren't getting caught in any of the hang-ups that people were getting caught at when they were more large-scale and less flexible than we are.

It really felt like we had found this magic sweet spot that was about a small group of people connecting to another small group of people and working with what was available locally and we were able to make things happen. And I was really proud of that.

It really felt like we had found this magic sweet spot that was about a small group of people connecting to another small group of people and working with what was available locally and we were able to make things happen. And I was really proud of that.

Pier Carlo: What about, if you wouldn't mind, a failure in any of these projects?

Caledonia: A point of failure, a big one … and actually I just gave a talk about this one, which was pretty hard, but now that I talked about it, I can start to share about it more.

I started a project also a little over 10 years ago in a town called Braddock, PA. I purchased and took over stewardship of this church. Huge building, huge project. I worked with various collaborators to take on the repairing of this church. Each of the steps of the repair we tried to do in this very deeply community-based way, where we'd involve people, provide jobs, provide learning experiences. We had a lot of small successes within that.

But over time what I found was that there was a certain strain that kept cropping up over and over again that resulted in me not living there full-time. Somehow in certain places I've been able to really click and not live somewhere full-time, where the group that I'm working with is just like, there's such an electricity and such amount of goodwill that we're able to just get things done even with me as an outside agent. But with the group that I was working with in Braddock, it just felt like these same forms of stress kept reappearing.

Also the expense of the project, I think, was maybe the single biggest factor that started to feel ... . We threw a Kickstarter, and we raised a tremendous amount of money, almost $100,000, which feels like a tremendous amount of money. And it is. But when you're trying to fix a church with labor standards and all of the insurance and all of these things, it ended up to be a very tiny amount of money, and we ended up investing it more in the community and less in the structure. We were able to do work that we were really proud of, starting this ceramics factory and doing all this stuff, but we weren't able to repair the building.

It was one of those things where it felt like we had raised all this money but it really didn't get that far. And I think anyone who's taken on a legitimately scaled construction project knows that that's actually not that much, and that you really need to get serious.

Then I went through a bunch of life events that were quite difficult. There was a lot of death in my family, and I needed to really go inward and do a lot of healing myself, and I just found that I wasn't able to do that work that it was going to take to get the investors, to get the capital, to make the church happen.

So I've realized that I need to actually pass it on. That was a very hard decision. Because you want to do what you said you were going to do. You want to lift the load that you said you'd carry, and finding that you can't do it is can feel really defeating and can feel like, “Oh, of course. You came into this community, and you said you were going to do all the stuff, and you're leaving just like everyone else.” This is the voice in the back of my head. So the challenge that's before me right now is how to transition that structure in a way that's really beneficial, hopefully more beneficial, for the community.

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Pier Carlo: Describe yourself as a boss.

Caledonia: As a boss. Gosh, [laughing] I almost feel like somebody else should answer that question. I'm certainly somebody who asks a lot of people. I ask a lot of excellence, I think, in the same way that I ask a lot of excellence of myself. But I also consider myself pretty compassionate and pretty easy to work with. But again, I wouldn't take that from me. [Laughing] I would ask somebody else about that. Because I remember one day I was saying to a person who was managing something, and I was like, "Well this job is really not that stressful. This job is pretty easy." He just looks at me like, “Are you out of your mind?” And I was like, "Oh, is it not then?" I think all jobs —

Pier Carlo: That's such a boss thing to say!

Caledonia: Right! “Your job is easy. You just get it done.” And what I meant was he made it look pretty easy. It’s because we have a really friendly environment. The studio environment's very loving and giggly, and everybody's playing music and podcasts and eating snacks, and so it feels like this very fun place to be. But the fact is we've got projects, we've got deadlines, we're juggling lots of things, and so even if nobody's screaming at anyone else, there's still this sense of “We have to get it done, and we have to get it done.” And that's real, and those pressures are there.

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Pier Carlo: If you could go back and meet yourself when you were just starting out your artistic career, what advice would you give yourself, first of all about what kind of artist you're going to become and what kind of leader you're going to become?

Caledonia:Gosh, let me think. Honestly, I think I would say to teach myself about forgiveness earlier. I really have, through my family — because I have a difficult family, like we all do — I've had to really learn a lot about forgiveness and about compassion and self-compassion. I think that I would try to teach myself … I would say, “Hey, actively learn about this.” Having compassion and having forgiveness is a practice. It can be a disposition, but it's also work. It's also work to understand other people's point of view. It's work to get yourself into a place of being kind to yourself. I think I would just try to get myself to do a lot of that stuff earlier. Take care of myself and take things less personally.

Pier Carlo: You've also been studying Buddhism, is that right, in recent years? Is this learning about forgiveness and compassion part of your spiritual practice?

Caledonia: Yeah. I started meditating because I was having a lot of anger problems. It was funny because 99% of people in the world are like, “What?!” Because I never yell at people, I'm not... . In my studio, everyone's like, “Oh, she's just a very relaxed person.” But what was going on was that in my interpersonal life, in my love relationships, I was being kind of a nightmare. What I learned is that... . I come from a family who was addicted to heroin when I was a kid. There was a tremendous amount of instability, mental illness and just intense difficulty. What I learned through going to therapy is that when you have that instability in your familial relationships, when you fall in love later in life, it takes you right back to those first love relationships. It takes you back to all that anger and rage and instability and all that stuff.

That kind of stuff was getting reignited for me, and I couldn't do better. I couldn't will myself. I couldn't under my own power change my behavior. And I was like, “I need something.” So I started going to therapy, and then I started meditating. I think I started with like 15 minutes a day. I was doing this kind of meditation called Tonglen, which is about actually focusing on the difficult material, as taught by Pema Chödrön, who's amazing.

It was one of those things where overnight, things started to feel better for me. I think I'm really unusual in that the first day I started meditating was the day that I started meditating every single day for the last five years. I started the habit instantly because it was that powerfully helpful for me. The tool, which starts very simply, I think, opens up into this tool that can become very infinitely useful and infinitely mind-expanding and spirit-expanding. So it has become part of my spiritual practice.

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Pier Carlo: Lastly, what do you think it would take for more artists to feel like they could step up and lead in the world?

Caledonia: I think that there's something which is happening right now which is really positive for artists to step up and lead, and that's having creativity taken seriously. In the environment that I grew up in as a kid, we did have art classes and there was some kind of respect for creativity. But I really think that that has grown.

People are waking up to the knowledge that creative problem-solving can really be effective in all areas of life. And that the deeply irrational creative brain can make connections that can't otherwise be made.

I think that in the last decade, even just with folks like you asking questions like this — and obviously you're coming from a background of having respect for creativity — I've seen it happen in many other places where people are waking up to the knowledge that creative problem-solving can really be effective in all areas of life. And that the deeply irrational creative brain can make connections that can't otherwise be made. I really think that people are becoming aware of that.

So I think that as we become aware of that and deepen our respect for that process, more and more artists will feel that it's valid for them to go with those gut feelings and use their wilder, more creative intuitions to make decisions that are impacting all other parts of their lives and other people's lives.


Caledonia Curry shows us, with great humility and vulnerability, how we can always continue to evolve, change and improve ourselves. These are gifts that impact our creativity, our personal lives, and our professional and community impact. Opportunities we can take from our time with Caledonia include:

  • Manage your priorities. You can’t simply expect to “make time” for what’s important or aspirational. Work your calendar and prioritize buckets of time for your big-ticket/big-goal items.
  • Just ask. Not everyone may want to follow your idea, vision, or direction, but it can’t hurt to ask. You may be surprised by who sees what you see.
  • Be specific about whom you ask. Since not everyone will agree to follow, be thoughtful before asking. Focus first on the followers who may align with your vision and values as a more efficient way to garner support.
  • Know your strengths and context. There is an endless array of leadership styles and situations to which those styles are best suited. Get to know your strengths and where they make the best impact.
  • Be a follower. There are circumstances where it’s better to follow then lead. When others have the capacities that exceed your own, be willing to partner and support them.
  • Surprise yourself. You don’t know what you are fully capable of becoming or doing. Staying open to your own evolution and to opportunities can create unexpected wins within yourself and in your impact on others.