How to Use Creativity as a Leadership Advantage with Will Day

Ashish Kothari: Hey, it’s so lovely to finally kick off the new year by recording a podcast with you, my dear friend. Thank you for being here.

For those listening, I had an accidental run-in with Will, believe it or not. I was heading to an event at his gallery, but it turned out the event wasn’t there—though Will was. The moment I stepped into his studio, which is also his gallery, I was blown away.

What I saw wasn’t just art—flowers or landscapes—but movement, color, and life. I started talking to him about the large canvases he works on, and he described himself as the paint thrower.

It was amazing. I asked, "What’s going on here?" And he told me this incredible story, which I hope he’ll share today. It’s truly inspiring, and I know you’ll learn a lot from it.

On this podcast, we focus on helping people build resilience and flourish in life. Will embodies that spirit—he’s the definition of resilience, creativity, and passion. Of course, he’s also an incredible artist.

Will, welcome! It’s so great to have you here.

Will Day: Thanks for having me. I’ve really been looking forward to this.

Ashish Kothari: Let’s start with this—when did you first discover your passion for art?

Will Day: I’ve been thinking about that question, Ashish. I believe art has always been part of my soul, part of my spirit. From the moment I arrived on this earth, I had a creative energy within me. But the real question is—when did I awaken to being a full-fledged artist?

That happened in different stages. But I always wanted to be creative and share my ideas with the world, but I didn’t know how to do that. So, I wanted to live a purpose-driven, creative life, to inspire people through my actions. At one point, I thought I was going to be an athlete.

Ashish Kothari: When you were younger?

Will Day: Yes, but I was always creative ever since. From an early age, I had this deep hunger for painting and abstract expressionism—I just didn’t have the words for it then. Thankfully, I grew up in a family that nurtured my curiosity for art.

I was born in New York City and raised in Connecticut, where I was influenced by incredible art through museums.

When I was in middle and high school, as I started recognizing my artistic calling, my parents would take me to museums for my birthday because that’s what I wanted—a creative experience to energize my spirit.

Visiting the Guggenheim, the Museum of Modern Art, and Broadway shows was a dream come true. At the time, I didn’t fully understand what it all meant—I just knew I felt comfortable in those spaces.

Ashish Kothari: It made you feel alive. It made you happy. It filled you with joy.

Will Day: Exactly. It wasn’t about money, trophies, or winning. It was about being in the moment, embracing this creative energy that felt so natural and authentic. I wanted to immerse myself in it, to experience it fully.

Ashish Kothari: Amazing. So, you grew up surrounded by art in an environment that nurtured it. When you went to college, did you study art? What was your major?

Will Day: I think the story should go back a little earlier. I really woke up to the senses of art in high school. One of the questions is, what really inspired you? What sparked the curiosity?

I remember being in middle school, and my first art teacher asked me to do a watercolor in seventh grade. I thought, All right, cool. That was the first time I got into a flow state. The world just stopped. At 13 years old, something clicked. I created this amazing watercolor that I still have in my studio today.

Fast forward to highschool—I went away to boarding school and really connected with the art team there, especially an art professor named Bob Johnson. I remember my first day showing up and saying, “Hey, I'm interested in art. I'm pretty good.”

He said, All right, cool. Sit down at the desk. I’m going to ask you a question: What does your heart want you to create? I was like, “What do you mean? Stick figures? Landscapes?”

He said, “No, I want you to start thinking. I need to get to know you.” He did this with all the other artists, too. From that point on, I felt free to express my inner spirit of being creative. That sparked the curiosity and confidence to say, “I can do this. I can be a painter. I have something to say. I’m not going to be afraid, and I’m going to challenge myself.”

High school was my awakening. I traveled a lot overseas and embraced European art and the Impressionists—I couldn’t get enough. I even did a term abroad in Paris, surrounded by incredible artists. At the time, I didn’t know this was going to be my path, but I knew it just felt right.

Ashish Kothari: That’s so important. For those listening, we hear so much about finding purpose and meaning. Many times, we walk through life without stopping to notice what fills us up, what gets us into flow, what brings us joy. What you're highlighting through your story is that these moments—these grains, these nuggets—are always around us. If we just stop and pay attention, we can find them.

Will Day: You nailed it. But remember, when we’re younger, we’re not tuned into that.

Ashish Kothari: Right, we’re focused on external success—achievements, accomplishments, what we can conquer.

Will Day: Girlfriends, travel, good grades, teachers. I wasn’t that wise back then. I just turned 54, so now I can reflect a little. I’m on the back nine of my life.

I always say to everyone—every experience, good or bad, has meaning and purpose. It’s easy for me to say that now, because I’ve looked back and changed, and pivoted many times. But you have to be aware—God put you on this earth for a reason. It’s up to you to find your calling.

You’re given all these little signs, these experiences, to wake you up. But you have to put yourself in a place where you can say, I believe, I trust, I know I’m here for something.

Once you start compiling those interests, you begin to realize—This is my purpose. This is what I’m meant to do. And then it becomes fun. Everyone around you benefits.

Ashish Kothari: Yes. Once you discover your gifts, they’re meant to be shared in service to others.

We’ve talked about this a lot on the podcast—the hero’s journey. This notion of one day, you wake up and hear a call. Not everyone takes the journey, but those who do cross the threshold.

And then you go through the path, slaying dragons. It’s not easy. Many don’t make it. But those who do come back transformed, having discovered their gifts. A common person becomes a hero. Siddhartha becomes the Buddha. These journeys shape us into who we’re meant to be.

I want you to take us through that journey. You always had this artistic gift, but you followed a very traditional path—until something happened.

And I want you to share that story—the wake-up call that made you realize you weren’t just meant to grind it out like everyone else.

Will Day: I think the journey in the story really starts when we open our own eyes. And I’m a seeker, my journey started at a young age, and you highlight this—my parents divorced in the seventies. That was really tough. I loved them, and it all worked out great, but it put me in a place of being by myself, feeling alone.

Again, I don’t judge them—I love my parents, and it all worked out fine. But as a son, I was left figuring out, What is this?

Ashish Kothari: Yeah, you had to grow up much earlier than you wanted to.

Will Day: Exactly. And I felt alone. That was just the process, even though my parents were amazing. I love my mom and dad, and my stepparents were great. But internally, I started asking—Why am I here? What am I supposed to do? Who’s going to take care of me? What do I want to do? What’s my purpose? Where do I belong? Who loves me?

These questions started early. So I realized—I want to see the world.

At a very young age, I thought, I’m out. My family was broken, and I saw it as my time to explore. Looking back, that worked in my favor because it gave me drive and passion. I had empathy, and I wanted to see the world. So I left the comfort of home—just like in the hero’s journey. I heard the call, and for me, that call was going out into the world.

I went to Europe, studied there in high school, and started to find my voice as a human being—as Will Day. That was my call to adventure, realizing that there was more to the world than just growing up in the suburbs of New York City, even though that was amazing.

Early on, I knew I had this drive and passion to find my calling in life. I didn’t know what it was—I wasn’t thinking, I can’t wait to be an artist.

Europe to the Soviet Union in: 1989

My parents gave me the freedom to explore and to contribute in my own way. I still didn’t know my calling, but the hero’s journey is about seeking. You hear the call, you step into the adventure, and then you reach a threshold—a moment where you have to take action.

If you look at my studio, one of my paintings is called Threshold. It’s part of my latest exhibit, Relentless. That piece was a breakthrough for me. It represents that moment where we stand at the edge, hearing the call, but then ask—How do I actually step over? How do I slay my dragons and keep moving forward without being paralyzed by fear?

Once I realized I had to embrace vulnerability and cross the threshold, I said—I’m in.

So, high school was my awakening. Then college hit, and it was amazing. I studied some art, but I also studied finance and politics—it helped me appreciate the world. It was in my French class that a professor suggested I consider the Peace Corps.

I thought, That’s interesting.

I had wanted to be a diplomat, to connect with the world. That French professor sparked my curiosity, and that hunger led me to apply for the U.S. Peace Corps. I got accepted and was assigned to Tunisia, North Africa.

The journey was unfolding. I was crossing the threshold. I didn’t know exactly what it meant, but I always followed the hero’s journey—because we are all heroes in our own story.

Some journeys are bigger, some are different, but you have to find your own hero’s journey. That’s what’s so important. You can’t compare.

The human spirit allows all of us to be a hero in our own story. That’s the beauty of being human.

Ashish Kothari: Yeah, and so you go to the Peace Corps. And then what happens?

Will Day: So I get accepted into the Peace Corps, and I’m assigned to North Africa, the Sahara Desert in Tunisia. I was like, Whoa, this is interesting.

Ashish Kothari: Thats very far from the civilized world of France and the art-rich world of New York.

Will Day:

I think there are many messages here, but for me, what happened was—I got the creative bug. I didn’t have much. I didn’t have money. I lived in a small village called Spica, in the middle of the Sahara Desert. I was the only American there.

It was a reality check. It didn’t matter what I looked like or where I came from. The question was—Can I connect with people? Can I understand them? Can I speak the language? Can we get along? That was one of the greatest tests I’ve ever had, and it turned out beautifully.

I loved the culture. I loved the people.

It also gave me an opportunity to dive deep into my spirit and ask—Who am I? What am I all about? It wasn’t about where I came from or what I looked like. It was about—What is my spirit? What is my purpose?

And then I realized—I’m actually really creative.

I started painting, photographing, and writing every single day. I never knew I had that in me. But until you put yourself in a place of vulnerability—until you truly have to be relentless, open, and empathetic—you never know what your God-given talents are.

Yes, that was an extreme experience. But I wanted that. And it came to me. It opened up a whole new channel of opportunity to continue on the hero’s journey.

Ashish Kothari: And what happens after the Peace Corps? You’re in Tunisia, you’ve learned and found another part of yourself—this connection to community, the challenge of language barriers.

I found that so inspirational. So many people never leave the comfort of their homes and what they know. But at a young age, you stepped into the unknown. Unknown for you, at least—it might be a known world for them, but it was unknown for you. That kind of experience shapes us. It teaches us something.

So you went there. Then you came back. And what did you do next?

Will Day: I love that question because I was so fulfilled.

I felt great. I grew my hair out, didn’t cut it for two years. I looked like this wild guy—I was Zen. I’m joking, but honestly, I felt deeply connected to the world in a way that wasn’t about money, career status, or sales numbers.

It was about living—immersing myself in a culture that was historic, heartfelt, and deeply connected to human relationships. It was about not being judgmental.

Ashish Kothari: And slowing down, right? It’s such a slower world.

Will Day: Yes! Slowing down. I forgot about that. It was such a slower world.

I remember thinking—Where are all the activities? Where’s the TV? Where are the phones? There were none.

We had to actually reach out to people. We had to break bread together at dinner, lunch, and breakfast. We had to look people in the eyes and have real conversations. We had to be present.

That was such a beautiful time—when technology existed, but it hadn’t taken over. We still connected heart to heart.

After the Peace Corps, I wanted to go into diplomacy, to become a U.S. diplomat. But when I came home, I realized something—I’m a guy who likes extremes.

I had done something intense, I had loved it, but now I wanted to reconnect with my own culture, with the United States. I also wanted to make money. I was curious about Wall Street.

So I applied for a few jobs, got interviews, and was hired at Bloomberg Financial Markets. But before that, I’ll never forget—

I came home, and within a couple of weeks, my family was like, Okay, you’ve been here a while. Maybe it’s time to cut your hair and look for a job.

So I applied, and on a Friday, I got a call back. They said, We want to interview you Tuesday at 11 a.m. Come to our office on 59th and 9th, and we’ll have a chat.

Meanwhile, I had no suit. I still looked like Michael Bolton—long hair, full hippie mode. I had to scramble to get ready. I adapted, walked in there, and the rest was history.

I got the job. I learned so much about capital markets, finance, teamwork, competition, and sales. It was an incredible experience.

The message here is—when the call comes, whatever it is, it may not be what you expect, but you have to be open to it.

I took another call. This time, it was to enter the world of finance, sales, and competition. And I went full tilt.

Ashish Kothari: Yeah. There are so many lessons in your story, and that’s why I found it so inspiring.

This is a different kind of podcast episode for us, but it’s such a beautiful journey—these grains of wisdom throughout your life. From discovering what fills your cup, what brings you joy, to your early love for painting and creativity, to your path of self-discovery, stepping into the unknown, and learning to embrace a slower world.

We often think these journeys are linear—that it’s either this or that. But you’ve swam in different worlds.

So now, you find yourself in a traditional corporate environment. And I have a question for you.

Even in the hustle and bustle of New York—the consumer-driven, finance-heavy, cutthroat world—how were your experiences up until that point shaping how you showed up?

How was your experience different from someone who followed the traditional, linear path—growing up, going to a top school, getting straight into a job, and staying on that straight track?

Will Day: Yeah, and I think that’s a good question. I used that to my advantage.

One of the things I’ve always told people—and I even did a TED Talk about this—is that there’s no straight line in life.

Going into a highly competitive environment like finance, I had already learned to navigate the unexpected. There were so many differences—language, people, culture, and, most importantly, expectations.

I learned that once you let go of your expectations—of thinking, I’ll go to school, I’ll get a job, I’ll work at this company, and this is the path to success—you open yourself up to different opportunities. My path was different, but I had the same drive and desire for a great outcome.

So, I embraced flexibility. I lowered my expectations of what I thought success had to look like, and that opened me up to new ideas. I wasn’t one-dimensional. And I think that was refreshing for my clients and colleagues.

I also reminded myself—Hey, I was just in the Sahara Desert. I figured things out with nothing. If I could do that, I can do this on Wall Street. I can do this with my family, my friends. And I can have fun with it.

So that’s how I approached it.

Ashish Kothari: I love that.

Many people, because they’ve never had those foundational experiences—never really discovered who they are—end up constantly comparing themselves to others, always asking, Am I doing good enough?

Whereas you had this solid internal confidence—I am good enough. I’ve survived things many people never will. I am capable.

The other thing you touched on, which is so important, is expectations. Expectations come in when we’re used to an environment—when we know what’s coming. We think, I’ve been here before, so I expect this road to turn left, then right.

But in your journey, everything was new.

I was reflecting on your story, and it really speaks to the power of dropping expectations and surrendering to what is rather than clinging to what we want things to be. Because how else would you have survived in Tunisia? You had no idea what to expect from one moment to the next.

Will Day: Exactly. And it’s hard to explain that to people.

They’d ask, How’s it going? And I could’ve said, Well, it’s terrible. The food is awful. My shelter is horrible. I don’t shower. I don’t know the language.

I could’ve labeled everything as negative.

But I chose to put myself there. So, I was going to find joy in the middle of the Sahara Desert. I was going to have fun.

I was going to build friendships that would last a lifetime. And that’s what I did. That’s what a lot of volunteers do.

Ashish Kothari: And once you’ve lived there, a lot of things that seem like big problems to others—these first-world problems—start to feel insignificant, right? Because you’ve seen the world, walked in it, and truly lived in a different reality.

Will Day: Exactly. And that ties back to your earlier question.

When I was struggling in finance and sales, I reminded myself—I’ve been in the world. I may not be the best with technology or know all the latest advancements, but I understand how things truly come together on a deeper level.

At the end of the day, it all comes down to a few simple things:

1️⃣ Trust—Do people trust me?

2️⃣ Belief—Do they believe me?

3️⃣ Honesty—Am I being truthful?

4️⃣ Care—Do I genuinely care about the human being in front of me?

Those qualities stand the test of time.

Ashish Kothari: Beautiful. All along, that ember—that fire—was still burning inside you. You were out in the world doing different things, but then 9/11 happened. That was a transformative moment for you and your family.

Tell our listeners a little about that story—because that moment really plunged you into the next phase of your journey.

Will Day: So, to go back to the timeline—I was in the Peace Corps, right? Then I came back and started working in finance at Bloomberg Financial Markets.

After that stage, I was in New York City, and in August, a month before 9/11, I told my wife, Hey, I’m going to get my master’s in architecture at Pratt.

She was like, What? Why not get your MBA at Columbia? She thought, You’re in finance. You’re great at it. Go to Columbia or maybe NYU. But I said, No, I’m going to get my master’s at Pratt Institute.

I bring this up because, even before 9/11, I was already shifting. Another pivot was happening. And at the same time, my wife and I were getting married two months later, in October, at the Boathouse in Central Park.

Everything was planned. Then 9/11 happened. That morning, I didn’t have class. My wife was working at a company called Baseline, an equity research firm that was later acquired by Thomson Reuters. She worked on the 78th floor of Tower 2.

She had come home late from a business meeting the night before, so she decided to sleep in. That morning, before heading to work, she said, Hey, we need to talk about wedding plans. I was like, Great! I’m doing nothing. How can I help? Just a regular guy, joking around, completely unaware of what was about to happen.

She stayed home. We walked out of our apartment, and then the planes hit. We lived downtown, so we saw the first plane fly over the city and hit Tower 1. Then we saw the second plane circle around and go right through her conference room.

Our building faced the south side of the towers. To answer your question—it was dramatic, horrific, confusing, depressing. It was a war. That day changed everything, not just for us but for so many people.

A lot of our friends died. My wife was saved. I don’t talk about this often, but I remind myself—She could have been gone. She should have been in that building.

We were supposed to be here. If we weren’t meant to be, she would have been in that tower, and I’d be living a very different life.

Ashish Kothari: Yeah. What a stark reminder.

That story stuck with me because, in many ways, your life and journey have been shaped by both your own choices and circumstances beyond your control.

Talk about surrender—you didn’t choose that moment. Nobody would.

But what a powerful reminder that life is short. You can’t take a single day for granted. And if there was ever a moment that called you forward, it was this. I love what you just said—I’m here. I wasn’t there. I need to live into what I am here to do.

Will Day: Exactly. And I think we have to use that as a message. It was a horrible event to be a part of—I didn’t choose it. Afterward, my wife and I looked at each other and said, All right. We’re lucky. You’re alive. She was actually supposed to be at a meeting on the 110th floor at Cantor Fitzgerald that morning. She canceled it.

She could have been up there. She could have been in her conference room. There were so many strange moments that, looking back, feel like God saying, You’re not ready to go.

It’s heartbreaking. We lost so many people. And we don’t talk about this much, even with our closest friends. But it was a turning point.

We all have choices. We all have those aha moments where we decide—What are we going to do with this?

Are we going to be angry and bitter? Spend our lives fighting the people who hurt us? Or are we going to move forward and forgive?

Forgiveness is hard. It’s incredibly hard for me to forgive what happened that day, the lives lost, the pain it caused. I’m sad. I’m angry.

But I made a choice—to do something better, to honor the people who died. And right now, in this moment, I am choosing creativity. Creativity changed my life. Creativity saved my life. That’s my message. That’s my mantra.

I remember. I will never forget. But I will use creativity to move forward—to bring healing, to help others, to introduce new ideas into the world.

Ashish Kothari: You know, Will, I want to say this—what happened on 9/11 was obviously life-changing for everyone involved, but for you, it was incredibly personal. I can see the pain, and yet, you chose a different path.

But here’s the thing—9/11 wasn’t just your moment. It was a moment for the U.S., for the whole world. And these kinds of moments? They’re happening every day in some other parts of the world. It’s in the news.

Think about what’s happening right now—in L.A., in Hawaii, in Australia, the attack on Israel, the war in Ukraine. I could go on.

If you step back, you can see 9/11 as one tragic event. But the truth is, these moments are happening all the time. And yet, the majority of people live as if they’re going to live forever.

They postpone what they’re meant to do. They even postpone joy. They think, I’ll work hard today because in 10 years, I’ll finally do what I love.

But how do you know you’ll be here in 10 years? How do you know you’ll even be alive 10 minutes from now?

Everything you hold dear could be gone in an instant. I think there are these crucible moments in life. Sometimes we’re placed in them, and sometimes they just happen around us. If we choose to pay attention, they can serve as constant reminders—reminders of how fragile life is, but also how precious it is.

And with that comes responsibility—the burden, or rather, the obligation, to live in service. To become the fullest expression of who we were born to be.

You don’t have to narrowly escape 9/11 to realize you have a gift. We all have gifts. And if we really tuned into that, the world would be so much better for it.

Will Day: You nailed it.

I’m just a human being, standing here, asking the universe to let me receive all the experiences this world has to offer. I want to experience them wholeheartedly. And in doing so, I hope to be an example for others.

By asking—How can I serve this world?—instead of just focusing on myself, we open ourselves up to all of it—the good and the bad. You have to experience both.

You can’t know what joy feels like unless you’ve known sorrow. You can’t know what light feels like unless you’ve walked through darkness. That’s part of what it means to be human.

We don’t know what’s going to happen tomorrow. We could spend our lives spiraling—Oh my God, the world is falling apart. It’s over. But the truth is, you and I are still here. So what do we do with that?

We become examples—of positivity, of healing, of joy. We help people find their joy. We remind them—We’re all in this together. I’m not better than anyone. What I am is tuned in into the experiences and trying to be more present based on the circumstances that God gave me and put me to be in right now. So I’m going to take advantage of that.

Ashish Kothari: I love that. My friend, I want to fast forward to today. You’ve been a professional artist for over a decade now. And not just any artist—you’re a force.

You’ve created hundreds of paintings, each one bursting with vibrancy and meaning. Your work carries these bold names—Wonder, Dream Big, Resilience, Threshold. Every single piece captures an emotion, a way of being, an inspiration.

Talk to me about where you see yourself going in this creative journey. What’s fueling your work right now? Talk a bit about that with us.

Will Day: The journey is always evolving.

Ashish Kothari: Of course. One step, one brushstroke at a time.

Will Day: I’ve been painting full-time for almost 17 and a half years. It’s been incredible. And my work has completely transformed from day one to now.

So where am I going? I’m continuing to seek new opportunities—new galleries, new exhibitions, new places to travel. I don’t just paint in my studio.

I’m building a studio practice that connects with people. My art could be used for emotional healing campaigns, for clothing lines, for inspiration. I want my art to speak to different cultures, to different movements.

For example, let’s say a country wants to launch a massive campaign around hope. I’d say, Let’s do it. Art has the power to bring opposing sides together. It can show people what humanity is capable of.

We’ve seen this happen with music. But art? Art is still very individualistic. The art world is full of egos. And I think there’s so much room for healing. I see an opportunity to break through all this division—between political sides, between countries, between ideologies. It has to stop.

I believe artists—all artists—have the power to open people’s hearts, to get them to think differently.

Art doesn’t have to be political. It doesn’t have to be shock-and-awe. It can simply invite connection.

So where do I see myself going?

I want to travel. I want to bring my work to different corners of the world. I want to create opportunities—for kids who don’t even know they’re creative. Because remember—Creativity saved my life. And it can save others, too. Not just through painting—but through singing, poetry, business, innovation.

If we teach people how to think differently, how to embrace multiple perspectives instead of just one rigid way of thinking, we will all benefit.

I see it all the time. People step into my studio and say, I don’t know how to paint. I can’t even draw a stick figure.

But that’s not what art is about. It’s about trusting yourself. It’s about believing in yourself.

So my vision? Will Day Art is going global. I want to connect with people everywhere. Through my art. Through my message. Through the possibility of creativity.

Ashish Kothari: You know, what I love about that—there are two or three things that really stand out to me.

First, I love that you call it a practice. Most people think about art as a painting, an object—something out there. But there’s so much beauty in its practice.

In the work we do at Rewire and the programs I run, I often say—there is nothing new in what we talk about. What I do, what I teach, what I share—these are wisdom traditions that have been around for thousands of years.

I said this on an earlier podcast—there was a time when knowledge was power. But today? Knowledge is not power. Knowledge is just noise. You know what is power? Practice.

And for anyone listening—especially those who, like me, have told themselves for the longest time, I am not creative. I am not an artist—I want you to hear this: That is a myth we have to break.

If you are alive, and you have a soul, you are an artist. Because guess what? With every word you speak, you are creating something. Our words generate reality. Whether I shout at you or hug you—whether I extend kindness or hostility—I am creating different realities with each interaction.

Every single moment, we are creating the world we live in. And what is an artist if not someone who creates? You might be unconsciously creating your reality, but you are creating it nonetheless. We all have this creative spirit inside us.

Every culture has dance and song. We are moved by landscapes, by sunrises and sunsets. So the question is—are you willing to practice? And at first? It’s not going to look like anything. And that’s okay. Because this judgment—Unless it looks like this, it’s a horrible painting—who says that? Who decides what’s good or bad?

I love that you said, Creativity saved my life. If more people tapped into that, if they gave themselves permission to try, to practice—creativity would save the world.

Will Day: That’s exactly what I want to talk about. Because there are so many levels to this. Creativity really puts people in a place of 100% vulnerability. And yet, we are so afraid to show our colors. And I just want to say—Get over yourself.

We have such a short period of time in this world. Why put up walls? Imagine if we all had the chance to just be ourselves. Show your voice, and more importantly, don’t just brag about your voice.

But let’s connect with people to say—I appreciate the human journey. I appreciate the human spirit. I may not agree with you. But you know what? I’m going to listen to you and I’m going to try my best to find a way to connect.

Not to please you. But to simply be present with you, and recognize this incredible moment we all share—the chance to be alive on this earth for 70, 80, 90, maybe 100 years.

That is the most magnificent thing I could ever imagine.

Ashish Kothari: Yeah. I love that, Will. And I love how interdisciplinary and global creativity is. It doesn’t belong to just one person, one industry, or one way of thinking. It’s something that connects all of us. And frankly, even if it doesn’t connect you to others—if the practice of picking up a brush, a pen, or just moving your body… connects you to YOU? The real YOU? I think that’s great.

Will Day: Exactly. You asked me earlier—how do I show up every day? I show up not knowing what I’m going to create. I ask the universe—Let me be a conduit. Because we are conduits. We’re conduits for whatever message we’re meant to bring into the world.

Right now, for me, that message is through painting. Through art. But this practice is always evolving. Every single day, I come into my studio 100% vulnerable. I look at a blank canvas and think—What’s going to happen today?

And I can tell you—every artist feels that. Even the most famous ones. They reach a certain level of success, and then suddenly, they think—Oh my God, now what?

Do I just keep doing the same thing? But a true artist doesn’t get stuck there. They recognize when they’ve hit something meaningful, but they keep evolving. And that’s what we all have to do in any practice.

Ashish Kothari: Yes!

Will Day: We have to listen. And it’s never going to be the same. People say, “Oh, I loved Picasso’s Blue Period. I loved his geometric work. I loved his abstract phase.” But you don’t think he was struggling to figure out what’s the next big thing?

You don’t think he was asking himself—What’s next? What am I supposed to create? He pushed himself. And I know we haven’t talked much about this, but being relentless in your passion—whatever it is—is so important.

Right now, I’ve chosen painting. But it’s constantly changing. And I have to remind myself—it’s okay to fail. It’s okay to create a terrible painting. It’s okay to fail, fail, fail… and then start over. Because painting itself is a metaphor. I can paint over those emotions and then see beauty again where I was really in a dark place.

Ashish Kothari: Yeah, I love that. Talk, talk a little bit about that, Will. Talk about Relentless.

Will Day: Relentless—you know, a lot of people have different meanings for that, but my last show here in Boulder was the Relentless series based on the Hero’s Journey. We talked a little about that.

But for me, it's not about being academic. It's about doing. And so when someone says, Oh, that's terrible, that's bad, people freeze up—Oh my gosh. Okay, I’m going to stop now. But being relentless means saying, “All right, let me learn about that. Why is it so bad? Let me dig into that. Why was my work terrible? Why did no one connect to it?”

Because, maybe because I didn’t connect to it. Maybe I didn’t give my true heart and demonstrate what it really feels like to share what I want to tell the world.

So then I have to be self-reflective and constantly be relentless with myself and say, Hey, you have to look at yourself and figure out—what are you really trying to say? And is it more ego? Is it more driven by sales? Is it something else?

But when I’m relentless and very calm, I get into this beautiful flow state where I’m naturally downloading creativity and expressing it onto a canvas.

Ashish Kothari: That doesn’t happen all the time, but we can make every act we do—everything we do in the world, the work we do—whether we paint, whether we write, whether we code, whether we trade—whatever it is—it doesn’t matter.

I love that. Every action we take can be an opportunity to discover something about ourselves, and it can be a step on the path, right? Relentless is a choice. Again, it’s a practice. It’s an action. It’s not about being perfect all the time, but it’s about listening and choosing to take one step after another. I fall down, I’m going to stand up.

Will Day: Yes.

Ashish Kothari: That’s what I’m taking away.

Will Day: And that’s what I want to continue to share in my studio. I come in and there are a lot of things that don’t work. But I try to put myself in a place where I say, All right, I’m going to try to... No, I’m not going to try. I am doing this. I am going to change. I am going to make a conscious effort to evolve and shift and pivot—whatever you want to call it—because that’s what keeps us young.

I hope I have this incredible joy for life for the rest of my time here, but to do that, I have to make sure my mindset is right. I have to challenge myself. I have to put myself in different situations, through both dark and light, and know that I can never give up.

Ashish Kothari: Yeah. So on that, I want to go to the next question. As we bring this to a close, you said, “To create out there, I have to keep doing the work in here.” So my question, Will, for you is—what are some daily rituals that keep you grounded and keep your inner flame burning? How do you fill your cup? How do you continuously fuel that fire?

Will Day: I think it changes a lot, right? But number one—I show up every day.

Ashish Kothari: I show up every day.

Will Day: I show up every day. I’m present in my studio or wherever I am having an event. I have to mindfully say, Take all the noise away. Either I’m going to pray or meditate or just calm down and be one with my space. That’s super important. I’m a very hyper, ADHD guy—super impulsive. So I have to reverse that. I have to be calm. Every day, I try to find moments of stillness—stillness in my vessel, as I call it, or my studio.

Number two—exercise. I get very amped up, and I get frustrated in here a lot. But this space should be full of joy and happiness. To get that joy, I need to leave. So I have to work out, hike, ski, whatever the activity is—I have to physically sweat.

And number three—I have to remind myself that it’s okay not to always be creating. I have to spend time with my family. I have to connect with the core people who mean the most to me. If I don’t, these practices won’t grow.

Ashish Kothari: I love those. And they’re so powerful. You talk about well-being—at Rewire, we talk about three core elements: body, mind, and spirit. You talked about movement—moving your body. You talked about mindfulness—being present. And it’s so hard to do, right? So many people go through life absent. They’re physically there, but their minds are everywhere else.

When I’m here, I’m thinking about there. When I’m there, I’m thinking about here or the next place I need to go. People are never actually present. And it takes practice. Like you said—even for you, being hyper and impulsive, you have to practice being here. Because if you’re not here, nothing happens.

I love that invitation and reflection—to say, I have to be present. I have to be mindful.

And the third piece—spirit. That’s what fills you up. You said, My family fills me up. It’s about doing the things that matter to us, that we keep front and center, so we don’t lose ourselves in just work and meaning.

I love that, Will. And I can see how having a consistent practice of these things is flowing through you. My friend, you said you’re a conduit, but you’re also doing the work to keep the conduit pure.

Will Day: Thank you, I appreciate that. But remember—it’s the trifecta. We should all think in threes, right? It’s a very historical, practical way to practice. And it’s basic, but you asked me, so I have to get back to basics.

I have to remind myself—Why am I painting? Why am I here? What’s next? We’re reaching a point in the world where things are getting more chaotic, more confusing. So how do we help each other stay balanced, empathetic, creative, and inspired—especially in times of darkness?

If we have a good practice, and we have faith, I wholeheartedly believe the right people will lead, guide, and help heal the world.

Ashish Kothari: Will, my friend, I’m honored to know you. I so appreciate you taking the time to share your life’s wisdom. You truly are an embodiment of resilience and bouncing forward. And it’s beautiful. Thank you for sharing all of this. I look forward to our growing friendship and to experiencing and seeing more of your amazing work here in Boulder.

Will Day: I appreciate your time. These were great questions, and I hope some people will be inspired by our stories.

Ashish Kothari: Thank you.