THE SYNCREATE PODCAST: EMPOWERING CREATIVITY
HOSTED BY MELINDA ROTHOUSE, PHD
WELCOME TO SYNCREATE, WHERE WE EXPLORE THE INTERSECTIONS BETWEEN CREATIVITY,
PSYCHOLOGY,AND SPIRITUALITY. OUR GOAL IS TO DEMYSTIFY THE CREATIVE PROCESS,
AND EXPAND THE BOUNDARIES OF WHAT IT MEANS TO BE CREATIVE.
SUBSCRIBE / FOLLOW US ON SPOTIFY, APPLE PODCASTS, YOUTUBE
OR WHEREVER YOU GET YOUR PODCASTS
HOSTED BY MELINDA ROTHOUSE, PHD
WELCOME TO SYNCREATE, WHERE WE EXPLORE THE INTERSECTIONS BETWEEN CREATIVITY,
PSYCHOLOGY,AND SPIRITUALITY. OUR GOAL IS TO DEMYSTIFY THE CREATIVE PROCESS,
AND EXPAND THE BOUNDARIES OF WHAT IT MEANS TO BE CREATIVE.
SUBSCRIBE / FOLLOW US ON SPOTIFY, APPLE PODCASTS, YOUTUBE
OR WHEREVER YOU GET YOUR PODCASTS
EPISODE 11: LEADERSHIP, VALUES, AND CRIMINAL JUSTICE REFORM
WITH ATTORNEY AND CRIMINAL JUSTICE REFORM ADVOCATE DYLAN HAYRE
LISTEN TO THE AUDIO EPISODE HERE:
WATCH THE FULL VIDEO VERSION HERE:
Dylan Hayre, based in New York City, is a leader in criminal justice reform focusing on supervision in probation and parole. We connected through his work and leadership, and from the start I was struck by his passion and drive, not only for criminal justice work, but in his striving for self-cultivation in leading from his core values and principles. Dylan is a highly creative thinker, bringing an innovative approach to solving the problems of a complex and highly entrenched institutional system. Our conversation in this episode focuses on the creativity in Dylan’s work, as well as the values and principles he brings to his leadership in the field.
Currently serving as Director of Criminal Justice Reform at Arnold Ventures, Dylan previously served in the ACLU’s Justice Division, where he led their advocacy work on clemency and death penalty repeal. He also supported state-level work on supervision reform and reentry, collaborating with strategists and litigators from across the organization. Prior to that, he served as the Senior Policy Advisor at JustLeadershipUSA, where he led the organization’s policy analysis and helped build, advised on, or managed justice reform campaigns in several jurisdictions alongside a diverse array of coalition partners. Dylan began his career as a prosecutor in his home state of Massachusetts and went on to manage his own criminal defense practice before joining a Boston-area firm. He has also served on or advised several candidate- and issue-based political campaigns at the local, state, and national levels.
Our Creativity Pro Tip at the end of the episode focuses on the creativity of leadership and leading from our values. We all lead in different ways in different contexts, whether explicitly or implicitly, so I encourage you to consider how you show up as a leader in your own life, whether based in formal leadership roles or positions, or in your family, community, and so on. Leadership is an exercise in creativity, and our values are the cornerstone of our leadership. So what are your core values and passions? Have you ever formally articulated them and how they guide your path and decision making? If not, today is a great time to start.
If you enjoy this episode, you might also like our conversations in Episode 6: Gratitude, Gentleness, and Generosity with Mayela Padilla Manasjan and Episode 7: The Syncreate Story with Syncreate Co-Founder Charlotte Gullick.
Currently serving as Director of Criminal Justice Reform at Arnold Ventures, Dylan previously served in the ACLU’s Justice Division, where he led their advocacy work on clemency and death penalty repeal. He also supported state-level work on supervision reform and reentry, collaborating with strategists and litigators from across the organization. Prior to that, he served as the Senior Policy Advisor at JustLeadershipUSA, where he led the organization’s policy analysis and helped build, advised on, or managed justice reform campaigns in several jurisdictions alongside a diverse array of coalition partners. Dylan began his career as a prosecutor in his home state of Massachusetts and went on to manage his own criminal defense practice before joining a Boston-area firm. He has also served on or advised several candidate- and issue-based political campaigns at the local, state, and national levels.
Our Creativity Pro Tip at the end of the episode focuses on the creativity of leadership and leading from our values. We all lead in different ways in different contexts, whether explicitly or implicitly, so I encourage you to consider how you show up as a leader in your own life, whether based in formal leadership roles or positions, or in your family, community, and so on. Leadership is an exercise in creativity, and our values are the cornerstone of our leadership. So what are your core values and passions? Have you ever formally articulated them and how they guide your path and decision making? If not, today is a great time to start.
If you enjoy this episode, you might also like our conversations in Episode 6: Gratitude, Gentleness, and Generosity with Mayela Padilla Manasjan and Episode 7: The Syncreate Story with Syncreate Co-Founder Charlotte Gullick.
EPISODE VIDEO CLIP
EPISODE-SPECIFIC HYPERLINKS
Dylan Hayre on LinkedIn
Overview of Criminal Justice Reform from the Equal Justice Initiative
History of Juneteenth from National Geographic
Overview of Sikhism
Overview of Stoicism from the Stanford Encyclopedia of Philosophy
Article/Commentary by Dylan Hayre: How To Reform Criminal Justice, When Prosecutors Hold The Power
Overview of Criminal Justice Reform from the Equal Justice Initiative
History of Juneteenth from National Geographic
Overview of Sikhism
Overview of Stoicism from the Stanford Encyclopedia of Philosophy
Article/Commentary by Dylan Hayre: How To Reform Criminal Justice, When Prosecutors Hold The Power
EPISODE TRANSCRIPT
Melinda: Welcome to Syncreate, a show where we explore the intersections between creativity, psychology, and spirituality. We view creativity broadly, and one of our primary goals is to demystify the creative process while expanding the boundaries of what it means to be creative. I'm Melinda Rothouse, and I help individuals and organizations bring their creative dreams and visions to life.
So today's episode was recorded at Mystic Oaks, my creative studio and retreat space in the beautiful Texas Hill Country. And I'm very excited to have my guest for today, Dylan Hayre in New York City. Dylan works in philanthropy. He's an attorney with a focus on criminal justice reform, specifically focusing on supervision in probation and parole. And Dylan, you were previously with the ACLU Justice Division, focusing on clemency and death penalty repeal.
And I just want to make a note, we are recording today on Juneteenth, which is a very important day celebrating the end of slavery, and freedom and liberation, and yet the criminal justice system is actually the one place where slavery still legally exists in this country. So just want to note that I think it's quite interesting timing that you and I are speaking today, so maybe we can touch back into that.
But I just want to say a little bit more about how we came to know each other. So, we connected through your leadership work in criminal justice reform, and from the start, I was really struck by your passion and drive, not only for this work, but really in striving to cultivate yourself and leading from conviction, from your values and principles, maybe more than anyone I've ever worked with.
And this also strikes me as a very creative way to be, and to exist in the world. So I also see you as a highly creative thinker with a strong degree of both self awareness and systems awareness, not to embarrass you or anything, but, you know, so this show is about creativity, right? And we might not necessarily immediately think, oh okay, somebody working in criminal just justice reform is a creative, but I absolutely see you as a creative. So I'm wondering, do you see yourself that way or how do you see the creativity in your work?
Dylan: Well, first of all, that is a very sweet and kind introduction. So you can keep going with that if you'd like to, but I'm happy to answer the question first. Uh, you know, it's funny. I, there was probably a moment in my life where creativity in the most commonly accepted form of the word was more central. I was an artist, I guess, in high school. I used to draw a lot, actually drew the cover of a couple of our high school literature magazines. And so, I think there's always been a part of me that's been drawn to that idea of using your hands and your mind to sort of put something on paper in a way that only you can. That's how I would define creativity. Paper can be metaphorical, I think, in that definition, but the idea of just using what you have, using your capabilities and your passion to do something that other people aren't doing or to try to do in a way that other people aren't doing, and to be additive to the people who are doing this work alongside you.
I actually, you know, you said I'm an attorney, but for me, I think the real start of my story, as weird as it might sound, is the fact that I was a math major in college and I bring that up because for those folks who sort of know me as a creative person, and I don't know that that's a lot of people, they understand that it really comes from my love of mathematics and I approached math differently than I think a lot of folks, but I was taught by a mentor early on that mathematics is really the art of fearless curiosity.
It's this idea that there is so little we truly know about the world around us, about the universe at large, but we know a lot, right? And in mathematics, what you're doing is starting with those sort of basic truths that you know, sort of building on them, building on them, building on them, trying to solve problems that have not yet been solved, trying to get to a place that has not yet been arrived at.
And if there's ever a moment of doubt, if there's ever a moment where you think, I'm going off course, or I'm not sure; you think about doing math homework on a piece of paper, you kind of look up a couple rows to the last sort of line where you feel pretty confident you knew what you were doing and say, okay, do I still feel good about that? Great. If I do, we can keep going, you know, and that idea, that approach is how I approach criminal justice reform work. It's how I approached everything in my life. You know, I start with what little I know, keep building, building, building, building.
There are certainly times where I think, I don't know if I'm doing this correctly. I don't know if I'm on the right path. I don't know that I have the best idea. And so you go back a couple steps, right? And you think, okay, what's the last thing I felt really confident about? Let's go back to that sort of decision point. Would I make the same choice? Okay. Would I not make the same choice? Okay, you know, but it's that idea of just sort of constant, for lack of a better word, creation, right?
You're always going back and reiterating the things you've done. You're reflecting on them. You're trying to center yourself in that work in a way; I know you mentioned how I try to ground myself in my values, my faith, things like that, and I think that's a big part of it. But, to answer your question about if I see myself as creative, I think that's probably a creative way to approach problem solving in the world in general, but it's nothing I came up with, right? It was taught to me and I've just used it in a way that I think was probably unexpected at the time.
Melinda: Yeah, that's great. So you're anticipating some things I want to talk about, but I love this for a few different reasons because we don't necessarily always think about math and creativity going together. And this is kind of a theme in this show so far, we're talking about kind of creativity and science and now creativity and math. And I love what you said about creativity is bringing something new into the world and trying to solve problems and sort of creating new knowledge and coming to understand things in a new way.
So I really love kind of looking at it through that lens and so many places we could go from here. I guess I want to ask you next: I'm really curious, you know, again, I see you as being so driven and passionate about what you do and I'm curious what motivates you to get out of bed every morning and do the work that you do?
Dylan: I will definitely answer that, but I do just want to respond quickly because I think you just said something that I hope everyone who cares about this work hears when you think about the work we do in criminal justice reform. You mentioned today is Juneteenth, the idea of recognizing ending the oppression of human beings. If there is someone out there who knows how to end oppression and discrimination and harm, they're either the biggest jerk in the world for not sharing it or they're lying.
And so the inevitable conclusion you arrive at is you are going to have to be creative, you're going to have to lean into creativity, if you want to try to solve things on this planet that other people have yet to solve. And that's kind of I hope what we all are able to contribute, is a little bit of ourselves, right, and just sort of think a little differently about these problems and the potential solutions. So I appreciate you naming that.
Melinda: Yeah, and especially with the complexity of something like an entrenched system, like the criminal justice system, right? If there's no easy answers, there's no easy fix, or somebody would have come up with it by now.
Dylan: Yeah, no, I certainly don't have the answers. I wasn't just waiting for certain people to show up so I could share it. I'm trying my best. I think we all are, but I guess that actually segues to your question because, the question about what motivates me in the mornings to get out of bed. On one hand, there's I think a very material answer to that. I like what I do, I'm very blessed to have a job that I really appreciate, and colleagues I enjoy working with, a problem I enjoy trying to solve. And so from that kind of very material, almost physical sense, that's more often than not an easy thing to get your feet on the floor for, right, and you just, I get to do it.
But I think even beyond that may be more powerful than that for me, I'm obsessed with the idea of trying. I adore the idea of efforts, both in a physical kind of work life sense, but also I think in a very hyper-personal sense. And so each day I sort of wake up and the first thing that I tend to think is, there's so much I want to improve about myself from the day before, or there's so many things I think I can do just a little bit better, or there's just a part of me that I haven't accessed yet that I could, I could keep trying, I could keep getting there.
And that idea of, there's something to do, right? There's also this sort of love of, imperfection and failure in some way because I'll never be a perfect person. None of us will be. I'll never be complete, you know, in that way. None of us will be. But that means there's always something to work on and something to do and something to strive for and a level to get to.
And even if I don't get there, I don't ever want my efforts, or lack thereof, to be a reason I don't get to a place I want to get to. And so when I wake up, as tired as I might be some days, that idea of I get to try again, that fires me up.
Melinda: Yeah, I love that, right? Because, you know, we're all a work in progress. The journey never ends. We never just get to this place of perfection. So there's always room to grow and develop ourselves.
Dylan: Actually, so I know we're probably touch on this or you might have been heading there. But yeah, you know, part of it comes from my faith.
Melinda: Yes, exactly. Tell us more.
Dylan: So I'm Sikh (or Sikh, depending on, you know, if you don't want the Americanized pronunciation of it). And in Sikhism, there are basically five core virtues. And none of them are ranked above the others, but there is one in particular that I think is seen as the overarching, kind of core virtue. And it's this idea of contentment. This idea of acceptance. Another one of my hobbies, as you know, Melinda, is I love Stoic philosophy.
Melinda: Yes.
Dylan: I love reading about it, trying to practice it, trying to put it into use in my day to day life. And there's a core idea in Stoicism that I think is also about this idea of acceptance, right? And accepting the world around you. Sikhism, being content with whatever it is you're handed in life, and the circumstances you find yourself in. And I think there's probably a lot of people, and I was one of them, who early on misperceived that as acceptance, as passivity. As not being able to do anything, right? And I think the more accurate interpretation or the one that I've arrived at is that these ideas of contentment, of acceptance, are premised on effort.
So the idea, the way you sort of attain contentment and Sikhism isn't just by sitting back and letting the world go by. It's by giving your full self to the things you're doing, the people around you, your family, your colleagues, yourself, the world, your God, whoever it might be, and then whatever happens at the end of that is the outcome you accept, right. But it is, it's really a focus on process. It's really a focus on controlling what you can control. So again, there's like a stoic sort of philosophy, that I think is brought into the Sikh faith, doing the things you can do. And then whatever happens at the end of that, I think it's a lot easier to accept if you know you've done your best
And I hear this all the time too, you know, heroes of mine, professional athletes who I really admire, I've heard them talk often about this idea of every loss is a lot easier to accept if you know you gave it your all. The games that you can't stand losing are the games where you know you didn't do a good job, you didn't practice, you didn't prepare.
But if you gave everything you had and it just wasn't your day, then okay, it's easier, it's not fun, but it's easy to walk away from that thinking, okay, I'll come back next time. And so, yeah, a lot of it really for me comes from that idea of contentment, acceptance, but having those things premised on this idea of you've got to give your all to the things you're doing. And then whatever happens, happens, and you can be okay with that.
Melinda: Yeah, so we, we talk about this a lot, you know, and kind of bringing sort of spirituality and these fundamental principles into the work, into your leadership, and it's also kind of reminiscent of the traditional Indian philosophy of karma yoga, like always do your best and then letting go the fruits of the actions. And I hear you saying that with your sports heroes as well. It's like, ultimately, you're competing against yourself and striving to become the best you can become rather than some sort of outside adversary. Right?
Dylan: Yeah. That's one of my morning, I have a, I try to do a morning and an evening reflection. And one of the two questions I ask in the morning reflection is that, when you're competing against yourself, how will you win today?
Melinda: Yeah.
Dylan: You know, so this idea of, it's just me against me. You know, we started out talking about the work I do and I think being in a space like criminal justice reform or any social justice space, I think there's this inclination to lean on the side of not focusing on yourself and focusing more on the other people, right, the people whom you are serving, the people who you do this work for, and I in no way disregard that. I certainly think that I'm accountable to the people who are impacted by the system and you that's who I work for, that's why I do this.
But I also think that anyone who does this work or any social justice work, really any work, you have to be your best self first, before you can be your best self for others. And so I think that idea of like really focusing in on you, I think it can come across as selfish or self-centered, probably the same way that the ideas of acceptance and contentment probably can when we first come across them. But my hope is that. Again, it goes back to the practice of creativity, right? My hope is that I'm able to root myself in such a way that I then give my best self to the people around me, but that starts with me trying to ground myself.
Melinda: And that's something I emphasize with everyone I work with, with clients, with students, whatever it is. You know it's like we might perceive it, as you said, to be selfish to focus on ourselves in that way, and yet the way that we treat ourselves, and the way that we work with ourselves, it ultimately ripples out, right?
You know, it's about self-compassion or self-kindness because if we're really critical and judgmental of ourselves, then that can translate out to how we interact with other people, and same thing with our self-cultivation, right? The more we cultivate ourselves, the more that can permeate and ripple out into our work.
Dylan: Yeah, I agree with that. And I think it also, it's sort of cyclically connected, I think, to the idea of confidence and self-belief as well, right?
Melinda: Yeah.
Dylan: Like, you've got to believe about yourself that you are a positive contribution to the thing you're doing. If you don't believe about yourself that you're able to make a positive contribution, I think you lose a lot of motivation and incentive to kind of focus on yourself to begin with, right?
Melinda: Yeah.
Dylan: Um, but I know that I am confident that when I do my work well, it is a positive contribution more often than not. And I think you come up with a way to do that that works for you.
Melinda: Exactly.
Dylan: I don't think the things I do for me would work for everyone else, but and I think for me, like, I try to pull a little bit from people I admire, right? So I take one thing here, one thing there, and kind of blend it all together. Maybe that's another form of creativity, right?
Melinda: Definitely. And I think another aspect of creativity is around storytelling. You know, what are the stories we tell ourselves about ourselves, about our work. And to that end, you recently told me a story and it's funny because often when we talk, you know, you're sort of a master of metaphor and analogy. I'm hearing metaphors of boats and mixed martial arts and things like this, but you recently told me about a sort of a children's parable that you came up with kind of on the fly and I thought it was so awesome. I wonder if you would share it with us. I know it's kind of a work in progress, but.
Dylan: Yeah, there's the caveat. This is a massive work in progress. Um, if you are a children's book author, please do not contact me saying this is a terrible story for kids. Don't ever share. It's, I'm trying, okay. I do, I think in metaphors and visualizations a lot. And so, this actually came up because I would just say someone very close to me was experiencing a challenge, like sort of normal run of life challenge, like we all experience from time to time.
But I think in talking it out for several hours, several days, I came to this realization that a lot of what was being experienced was being driven by internal stuff, right? Internal questions and doubts and anxieties. And I think from, for a lot of people, that's probably true of most things they're experiencing in life. And so I was like, you know what? There's like, there's a children's story here that I'm thinking of, and let me say it. So this is, this is a rough draft story.
But I said: You start out on the shore in life, very comfortable in the shade, but you know you have to get out onto the ocean at some point. That's just growing old, it's being in a job, being in a relationship, whatever it might be. You've got to get out to the ocean. Okay, you grab your boat, you're in the ocean, you're sort of rowing along as best you can, and all of a sudden, these big angry fish just start jumping out of the water. And they start hitting the boat, hitting you, disrupting the water. It's, it's really difficult to proceed under these conditions.
And so finally you grab one of these fish, right? As best you can, you grab the fish and you say, “Hey fish, come on, you got to stop. You got to stop banging into the boat. I'm trying to, I'm trying to go somewhere here.” And the fish just looks at you and says, “We're not trying to hit you or the boat. We don't even care about you. We're running from the shark. You know, there's a shark just beneath the surface. We're afraid of the shark.”
So you throw the fish back and you're like, “Oh, wow, okay. That's interesting.” So you've got to work up your courage a little bit. Cause sharks are scary. You kind of take a few deep breaths. You dive down into the water. You go deep, deep, deep, and you see the shark. There it is. You're terrified. So you get back up to the surface. That didn't work. Okay. But a few times, a few practice runs later, you're able to stay down there and meet the shark head on and confront it.
And you're able to say to the shark, “Listen, shark, you got to stop swimming where you're swimming. You're making it hard. The fish are jumping. Can you just swim a little deeper? Maybe if you just swim a little deeper, I think all our problems would be solved.” And the shark all of a sudden looks like the shark is scared. And the shark says, “I can't swim any deeper.”
“You're like, why you're a shark? The shark goes, no, no, no. There's something, there's something big down there. I don't know what it is, but it's big and scary. I can't see it, but I can feel it. I'm not going any deeper.” So now you're back up in the boat and you're wondering, wow, what's this all about, you know, something that terrifies a shark and it takes a lot of effort to get down to the bottom of the ocean.
You know, you got to practice, practice, practice, build up your lung capacity, dive, dive, dive. It takes work, right? But after days, weeks, whatever it might be of trying and practicing and getting your body and your mind fit, you get down to the bottom, and at the very bottom of the ocean you see a whale, and you look at the whale, and you're just like, “You're not a scary creature, you're just a big friendly whale.” You know, and the whale goes, “I know, I don't know why people are afraid of me. I'm very lonely. No one ever comes and visits me, but maybe that's, they misunderstand me, I don't know what it is.”
And the whale says, “Hey, you made it down here. Maybe if you come back a few times and we get to know each other, I could swim in a better direction. I could swim in such a way that I help clear your path.” And you go, “Oh yeah, that'd be great. That'd be super helpful.” You know? So you get back up into the boat, you sort of keep going down to the whale again and eventually you build this relationship. So I told this sort of visualization, this story.
At this point, the person I'm talking with was like, where is this going? This means nothing to me.
Melinda: Yeah, what about this whale?
Dylan: But I was like, let me try to sum this up now. The way I'm visualizing this, the fish that were attacking you or jumping at you in the surface, those are the problems in your life. Those are the angry boss, the delayed train, the screaming child, the bad weather, whatever it might be. Those are the sort of things that you're just confronted with time and again.
The things they're running from, the shark, that is your fears and anxieties. That's the thing that makes every problem and challenge in life that much worse. You know, because it goes from being a little bit late to work to all of a sudden, what will my colleagues think of me? What will my boss say? How can I get my work done? I'm not organized enough. What if I don't have enough time? What if this project fails? What if it's all my fault?
Melinda: All the what ifs.
Dylan: You know, that's just sort of your internal, it's all your internal dialogue, right?
But the whale, the whale is your self-confidence and your self-belief. And it takes a ton of work to get down there and see it and touch it and talk with it. But I just think that, man, if you can do that, if you can get down to the bottom and talk with that whale and become friends with it, yeah, they're still going to be, as you go through the ocean, waves and fish and things happening. Sure, I'm not saying that like all the problems will disappear, but it's going to be a hell of a lot easier. And I think you're going to feel a hell of a lot more in control. Knowing that there's that whale just beneath the surface where you can, you can't see them, but you know they're there.
And so yeah, that was the parable of the whale and I figured, oh, that's actually maybe a decent kid's book. I should write that someday, but that was the visualization that we came up with, yeah.
Melinda: I think you should. And I love that because not everyone takes the time or the kind of self reflection to go deep, in that way and sort of draw deep into themselves, but I think it's kind of a theme of what we've been talking about today. And you mentioned earlier, you know, this deep grounding that allows you to stay connected to yourself and connected to the work that you do and allows you to keep getting out of bed every morning. And I'm sure it's not easy at times, right, kind-of fighting against an unjust system. So I've got an eye on the time, but I think where I want to go here is, you know, we're talking about storytelling and I think, you know, that is part of the creativity in your work, in many people's work, right?
What is this current story we're telling ourselves and how can we begin to create a new story? And it starts with, you know, we have to envision it, anything creative, we have to envision it first and then we bring it into being. So I'm thinking part of the work you do is about creating new narratives and engaging in institutional storytelling and how could things be different?
So how, how does that land for you?
Dylan: Yeah, I think vision is really important. I think it's hard to work towards something that feels completely unrealistic. And I think if you can visualize it or tell a story about the thing you're trying to achieve in your mind, it just becomes that much more palpable in some way.
And so for me doing criminal justice reform work, I don't have a specific story in mind or a specific sort of like parable that comes to mind as I do this work. But I do sort of visualize families together. I visualize people receiving support before they're inclined to harm themselves or other people. I visualize communities that are vibrant and connected. And I don't know that there's like a specific time, place, or person that I think of when I think of these things.
There are certainly people I've worked with who come to mind as examples of what I think other people, you know, could strive to be like, there are people organizers in particular who give their hearts to their communities. And I just think, wow, if everyone got to see that or do a little bit of that, but absolutely, I think vision is critical. I've worked with people who every day, the first thing they do in the morning is they get up and they just sort of draw a picture. Grab a piece of paper, grab a pencil, draw a picture, whatever's on their minds.
Or I've worked with people, like I write every morning, right? So I wake up and I do about like 5-10 minutes of writing every morning. Just kind of whatever's on my mind, having some anchoring reflections, just sort of thinking through, okay, how do I want to approach the day? It's all sort of centered in this idea of like, I'm visualizing where this will end up for me.
Melinda: Yeah.
Dylan: Whether it's at the end of the day, end of the week, end of my life, whatever it might be. And I think without that, it becomes really hard because it feels like you're just kind of working in this sort of big vacuum of nothingness. It's already hard enough knowing that there'll never be an end to this work. You have to kind of accept that to begin with, but absolutely having a story in mind, I think is a huge piece of finding joy in what is a very challenging calling for sure.
Melinda: That's great. And I know we talk a lot about journaling. I talk with, you know, so many people about how helpful it is to just start the day with some kind of grounding practice, right? Whether it's meditation, whether it's exercise, whether it's journaling and just touching in with oneself, and setting some intentions. And that's how we make progress toward our goals, whatever they might be. So. Anything else you want to add to the conversation before we close?
Dylan: I feel like we touched on a lot of stuff. I feel like there's so much more we could talk about if we keep going. We often do. Our sessions are usually packed and we’re even over so we won't do that here. But no, I just appreciate being able to think through this out loud with you and share some of it. And I appreciate listening to the conversations you've recorded previously. I think having this space available for folks is really, really important. So I appreciate you.
Melinda: I appreciate you too. Thanks so much for taking the time today. And if people want to learn more about you and your work, what's the best way for them to find you?
Dylan: Probably just, as lame as it sounds, LinkedIn is a good place to start. I don't really do social media, but yeah, I'm on LinkedIn. Reach out, connect. I'd love to chat with people who are working in this space or any other space. So we all have a lot to learn from each other. So yeah, reach out anytime.
Melinda: Great. And we'll include your LinkedIn contact info in our show notes. Awesome. So thanks so much, Dylan, for being with us today.
Dylan: Yeah. Thank you.
Melinda: One of the things I want to emphasize here is that we all lead in different ways, in different contexts, whether explicitly or implicitly. So, for our Creativity Pro Tip today, I encourage you to consider how you show up as a leader in your own life, whether based in formal leadership roles or positions, or in your family, your community, and so on. Leadership is an exercise in creativity, and our values are the cornerstone of our leadership. So what are your core values and passions? Have you ever formally articulated them and how they guide your path and decision making? If not, Today is a great time to start.
Thanks again to Dylan Hare for the conversation. You can learn more about him and his work on LinkedIn. We'll provide a link in the show notes.
This episode was produced by Mike Osborne at 14th Street Studios in Austin, with production assistance by Christian Haigis.
Follow Syncreate on Instagram, YouTube, Facebook, and LinkedIn, where you can also find out more about all we do at Syncreate. Thanks for listening and see you next time.
So today's episode was recorded at Mystic Oaks, my creative studio and retreat space in the beautiful Texas Hill Country. And I'm very excited to have my guest for today, Dylan Hayre in New York City. Dylan works in philanthropy. He's an attorney with a focus on criminal justice reform, specifically focusing on supervision in probation and parole. And Dylan, you were previously with the ACLU Justice Division, focusing on clemency and death penalty repeal.
And I just want to make a note, we are recording today on Juneteenth, which is a very important day celebrating the end of slavery, and freedom and liberation, and yet the criminal justice system is actually the one place where slavery still legally exists in this country. So just want to note that I think it's quite interesting timing that you and I are speaking today, so maybe we can touch back into that.
But I just want to say a little bit more about how we came to know each other. So, we connected through your leadership work in criminal justice reform, and from the start, I was really struck by your passion and drive, not only for this work, but really in striving to cultivate yourself and leading from conviction, from your values and principles, maybe more than anyone I've ever worked with.
And this also strikes me as a very creative way to be, and to exist in the world. So I also see you as a highly creative thinker with a strong degree of both self awareness and systems awareness, not to embarrass you or anything, but, you know, so this show is about creativity, right? And we might not necessarily immediately think, oh okay, somebody working in criminal just justice reform is a creative, but I absolutely see you as a creative. So I'm wondering, do you see yourself that way or how do you see the creativity in your work?
Dylan: Well, first of all, that is a very sweet and kind introduction. So you can keep going with that if you'd like to, but I'm happy to answer the question first. Uh, you know, it's funny. I, there was probably a moment in my life where creativity in the most commonly accepted form of the word was more central. I was an artist, I guess, in high school. I used to draw a lot, actually drew the cover of a couple of our high school literature magazines. And so, I think there's always been a part of me that's been drawn to that idea of using your hands and your mind to sort of put something on paper in a way that only you can. That's how I would define creativity. Paper can be metaphorical, I think, in that definition, but the idea of just using what you have, using your capabilities and your passion to do something that other people aren't doing or to try to do in a way that other people aren't doing, and to be additive to the people who are doing this work alongside you.
I actually, you know, you said I'm an attorney, but for me, I think the real start of my story, as weird as it might sound, is the fact that I was a math major in college and I bring that up because for those folks who sort of know me as a creative person, and I don't know that that's a lot of people, they understand that it really comes from my love of mathematics and I approached math differently than I think a lot of folks, but I was taught by a mentor early on that mathematics is really the art of fearless curiosity.
It's this idea that there is so little we truly know about the world around us, about the universe at large, but we know a lot, right? And in mathematics, what you're doing is starting with those sort of basic truths that you know, sort of building on them, building on them, building on them, trying to solve problems that have not yet been solved, trying to get to a place that has not yet been arrived at.
And if there's ever a moment of doubt, if there's ever a moment where you think, I'm going off course, or I'm not sure; you think about doing math homework on a piece of paper, you kind of look up a couple rows to the last sort of line where you feel pretty confident you knew what you were doing and say, okay, do I still feel good about that? Great. If I do, we can keep going, you know, and that idea, that approach is how I approach criminal justice reform work. It's how I approached everything in my life. You know, I start with what little I know, keep building, building, building, building.
There are certainly times where I think, I don't know if I'm doing this correctly. I don't know if I'm on the right path. I don't know that I have the best idea. And so you go back a couple steps, right? And you think, okay, what's the last thing I felt really confident about? Let's go back to that sort of decision point. Would I make the same choice? Okay. Would I not make the same choice? Okay, you know, but it's that idea of just sort of constant, for lack of a better word, creation, right?
You're always going back and reiterating the things you've done. You're reflecting on them. You're trying to center yourself in that work in a way; I know you mentioned how I try to ground myself in my values, my faith, things like that, and I think that's a big part of it. But, to answer your question about if I see myself as creative, I think that's probably a creative way to approach problem solving in the world in general, but it's nothing I came up with, right? It was taught to me and I've just used it in a way that I think was probably unexpected at the time.
Melinda: Yeah, that's great. So you're anticipating some things I want to talk about, but I love this for a few different reasons because we don't necessarily always think about math and creativity going together. And this is kind of a theme in this show so far, we're talking about kind of creativity and science and now creativity and math. And I love what you said about creativity is bringing something new into the world and trying to solve problems and sort of creating new knowledge and coming to understand things in a new way.
So I really love kind of looking at it through that lens and so many places we could go from here. I guess I want to ask you next: I'm really curious, you know, again, I see you as being so driven and passionate about what you do and I'm curious what motivates you to get out of bed every morning and do the work that you do?
Dylan: I will definitely answer that, but I do just want to respond quickly because I think you just said something that I hope everyone who cares about this work hears when you think about the work we do in criminal justice reform. You mentioned today is Juneteenth, the idea of recognizing ending the oppression of human beings. If there is someone out there who knows how to end oppression and discrimination and harm, they're either the biggest jerk in the world for not sharing it or they're lying.
And so the inevitable conclusion you arrive at is you are going to have to be creative, you're going to have to lean into creativity, if you want to try to solve things on this planet that other people have yet to solve. And that's kind of I hope what we all are able to contribute, is a little bit of ourselves, right, and just sort of think a little differently about these problems and the potential solutions. So I appreciate you naming that.
Melinda: Yeah, and especially with the complexity of something like an entrenched system, like the criminal justice system, right? If there's no easy answers, there's no easy fix, or somebody would have come up with it by now.
Dylan: Yeah, no, I certainly don't have the answers. I wasn't just waiting for certain people to show up so I could share it. I'm trying my best. I think we all are, but I guess that actually segues to your question because, the question about what motivates me in the mornings to get out of bed. On one hand, there's I think a very material answer to that. I like what I do, I'm very blessed to have a job that I really appreciate, and colleagues I enjoy working with, a problem I enjoy trying to solve. And so from that kind of very material, almost physical sense, that's more often than not an easy thing to get your feet on the floor for, right, and you just, I get to do it.
But I think even beyond that may be more powerful than that for me, I'm obsessed with the idea of trying. I adore the idea of efforts, both in a physical kind of work life sense, but also I think in a very hyper-personal sense. And so each day I sort of wake up and the first thing that I tend to think is, there's so much I want to improve about myself from the day before, or there's so many things I think I can do just a little bit better, or there's just a part of me that I haven't accessed yet that I could, I could keep trying, I could keep getting there.
And that idea of, there's something to do, right? There's also this sort of love of, imperfection and failure in some way because I'll never be a perfect person. None of us will be. I'll never be complete, you know, in that way. None of us will be. But that means there's always something to work on and something to do and something to strive for and a level to get to.
And even if I don't get there, I don't ever want my efforts, or lack thereof, to be a reason I don't get to a place I want to get to. And so when I wake up, as tired as I might be some days, that idea of I get to try again, that fires me up.
Melinda: Yeah, I love that, right? Because, you know, we're all a work in progress. The journey never ends. We never just get to this place of perfection. So there's always room to grow and develop ourselves.
Dylan: Actually, so I know we're probably touch on this or you might have been heading there. But yeah, you know, part of it comes from my faith.
Melinda: Yes, exactly. Tell us more.
Dylan: So I'm Sikh (or Sikh, depending on, you know, if you don't want the Americanized pronunciation of it). And in Sikhism, there are basically five core virtues. And none of them are ranked above the others, but there is one in particular that I think is seen as the overarching, kind of core virtue. And it's this idea of contentment. This idea of acceptance. Another one of my hobbies, as you know, Melinda, is I love Stoic philosophy.
Melinda: Yes.
Dylan: I love reading about it, trying to practice it, trying to put it into use in my day to day life. And there's a core idea in Stoicism that I think is also about this idea of acceptance, right? And accepting the world around you. Sikhism, being content with whatever it is you're handed in life, and the circumstances you find yourself in. And I think there's probably a lot of people, and I was one of them, who early on misperceived that as acceptance, as passivity. As not being able to do anything, right? And I think the more accurate interpretation or the one that I've arrived at is that these ideas of contentment, of acceptance, are premised on effort.
So the idea, the way you sort of attain contentment and Sikhism isn't just by sitting back and letting the world go by. It's by giving your full self to the things you're doing, the people around you, your family, your colleagues, yourself, the world, your God, whoever it might be, and then whatever happens at the end of that is the outcome you accept, right. But it is, it's really a focus on process. It's really a focus on controlling what you can control. So again, there's like a stoic sort of philosophy, that I think is brought into the Sikh faith, doing the things you can do. And then whatever happens at the end of that, I think it's a lot easier to accept if you know you've done your best
And I hear this all the time too, you know, heroes of mine, professional athletes who I really admire, I've heard them talk often about this idea of every loss is a lot easier to accept if you know you gave it your all. The games that you can't stand losing are the games where you know you didn't do a good job, you didn't practice, you didn't prepare.
But if you gave everything you had and it just wasn't your day, then okay, it's easier, it's not fun, but it's easy to walk away from that thinking, okay, I'll come back next time. And so, yeah, a lot of it really for me comes from that idea of contentment, acceptance, but having those things premised on this idea of you've got to give your all to the things you're doing. And then whatever happens, happens, and you can be okay with that.
Melinda: Yeah, so we, we talk about this a lot, you know, and kind of bringing sort of spirituality and these fundamental principles into the work, into your leadership, and it's also kind of reminiscent of the traditional Indian philosophy of karma yoga, like always do your best and then letting go the fruits of the actions. And I hear you saying that with your sports heroes as well. It's like, ultimately, you're competing against yourself and striving to become the best you can become rather than some sort of outside adversary. Right?
Dylan: Yeah. That's one of my morning, I have a, I try to do a morning and an evening reflection. And one of the two questions I ask in the morning reflection is that, when you're competing against yourself, how will you win today?
Melinda: Yeah.
Dylan: You know, so this idea of, it's just me against me. You know, we started out talking about the work I do and I think being in a space like criminal justice reform or any social justice space, I think there's this inclination to lean on the side of not focusing on yourself and focusing more on the other people, right, the people whom you are serving, the people who you do this work for, and I in no way disregard that. I certainly think that I'm accountable to the people who are impacted by the system and you that's who I work for, that's why I do this.
But I also think that anyone who does this work or any social justice work, really any work, you have to be your best self first, before you can be your best self for others. And so I think that idea of like really focusing in on you, I think it can come across as selfish or self-centered, probably the same way that the ideas of acceptance and contentment probably can when we first come across them. But my hope is that. Again, it goes back to the practice of creativity, right? My hope is that I'm able to root myself in such a way that I then give my best self to the people around me, but that starts with me trying to ground myself.
Melinda: And that's something I emphasize with everyone I work with, with clients, with students, whatever it is. You know it's like we might perceive it, as you said, to be selfish to focus on ourselves in that way, and yet the way that we treat ourselves, and the way that we work with ourselves, it ultimately ripples out, right?
You know, it's about self-compassion or self-kindness because if we're really critical and judgmental of ourselves, then that can translate out to how we interact with other people, and same thing with our self-cultivation, right? The more we cultivate ourselves, the more that can permeate and ripple out into our work.
Dylan: Yeah, I agree with that. And I think it also, it's sort of cyclically connected, I think, to the idea of confidence and self-belief as well, right?
Melinda: Yeah.
Dylan: Like, you've got to believe about yourself that you are a positive contribution to the thing you're doing. If you don't believe about yourself that you're able to make a positive contribution, I think you lose a lot of motivation and incentive to kind of focus on yourself to begin with, right?
Melinda: Yeah.
Dylan: Um, but I know that I am confident that when I do my work well, it is a positive contribution more often than not. And I think you come up with a way to do that that works for you.
Melinda: Exactly.
Dylan: I don't think the things I do for me would work for everyone else, but and I think for me, like, I try to pull a little bit from people I admire, right? So I take one thing here, one thing there, and kind of blend it all together. Maybe that's another form of creativity, right?
Melinda: Definitely. And I think another aspect of creativity is around storytelling. You know, what are the stories we tell ourselves about ourselves, about our work. And to that end, you recently told me a story and it's funny because often when we talk, you know, you're sort of a master of metaphor and analogy. I'm hearing metaphors of boats and mixed martial arts and things like this, but you recently told me about a sort of a children's parable that you came up with kind of on the fly and I thought it was so awesome. I wonder if you would share it with us. I know it's kind of a work in progress, but.
Dylan: Yeah, there's the caveat. This is a massive work in progress. Um, if you are a children's book author, please do not contact me saying this is a terrible story for kids. Don't ever share. It's, I'm trying, okay. I do, I think in metaphors and visualizations a lot. And so, this actually came up because I would just say someone very close to me was experiencing a challenge, like sort of normal run of life challenge, like we all experience from time to time.
But I think in talking it out for several hours, several days, I came to this realization that a lot of what was being experienced was being driven by internal stuff, right? Internal questions and doubts and anxieties. And I think from, for a lot of people, that's probably true of most things they're experiencing in life. And so I was like, you know what? There's like, there's a children's story here that I'm thinking of, and let me say it. So this is, this is a rough draft story.
But I said: You start out on the shore in life, very comfortable in the shade, but you know you have to get out onto the ocean at some point. That's just growing old, it's being in a job, being in a relationship, whatever it might be. You've got to get out to the ocean. Okay, you grab your boat, you're in the ocean, you're sort of rowing along as best you can, and all of a sudden, these big angry fish just start jumping out of the water. And they start hitting the boat, hitting you, disrupting the water. It's, it's really difficult to proceed under these conditions.
And so finally you grab one of these fish, right? As best you can, you grab the fish and you say, “Hey fish, come on, you got to stop. You got to stop banging into the boat. I'm trying to, I'm trying to go somewhere here.” And the fish just looks at you and says, “We're not trying to hit you or the boat. We don't even care about you. We're running from the shark. You know, there's a shark just beneath the surface. We're afraid of the shark.”
So you throw the fish back and you're like, “Oh, wow, okay. That's interesting.” So you've got to work up your courage a little bit. Cause sharks are scary. You kind of take a few deep breaths. You dive down into the water. You go deep, deep, deep, and you see the shark. There it is. You're terrified. So you get back up to the surface. That didn't work. Okay. But a few times, a few practice runs later, you're able to stay down there and meet the shark head on and confront it.
And you're able to say to the shark, “Listen, shark, you got to stop swimming where you're swimming. You're making it hard. The fish are jumping. Can you just swim a little deeper? Maybe if you just swim a little deeper, I think all our problems would be solved.” And the shark all of a sudden looks like the shark is scared. And the shark says, “I can't swim any deeper.”
“You're like, why you're a shark? The shark goes, no, no, no. There's something, there's something big down there. I don't know what it is, but it's big and scary. I can't see it, but I can feel it. I'm not going any deeper.” So now you're back up in the boat and you're wondering, wow, what's this all about, you know, something that terrifies a shark and it takes a lot of effort to get down to the bottom of the ocean.
You know, you got to practice, practice, practice, build up your lung capacity, dive, dive, dive. It takes work, right? But after days, weeks, whatever it might be of trying and practicing and getting your body and your mind fit, you get down to the bottom, and at the very bottom of the ocean you see a whale, and you look at the whale, and you're just like, “You're not a scary creature, you're just a big friendly whale.” You know, and the whale goes, “I know, I don't know why people are afraid of me. I'm very lonely. No one ever comes and visits me, but maybe that's, they misunderstand me, I don't know what it is.”
And the whale says, “Hey, you made it down here. Maybe if you come back a few times and we get to know each other, I could swim in a better direction. I could swim in such a way that I help clear your path.” And you go, “Oh yeah, that'd be great. That'd be super helpful.” You know? So you get back up into the boat, you sort of keep going down to the whale again and eventually you build this relationship. So I told this sort of visualization, this story.
At this point, the person I'm talking with was like, where is this going? This means nothing to me.
Melinda: Yeah, what about this whale?
Dylan: But I was like, let me try to sum this up now. The way I'm visualizing this, the fish that were attacking you or jumping at you in the surface, those are the problems in your life. Those are the angry boss, the delayed train, the screaming child, the bad weather, whatever it might be. Those are the sort of things that you're just confronted with time and again.
The things they're running from, the shark, that is your fears and anxieties. That's the thing that makes every problem and challenge in life that much worse. You know, because it goes from being a little bit late to work to all of a sudden, what will my colleagues think of me? What will my boss say? How can I get my work done? I'm not organized enough. What if I don't have enough time? What if this project fails? What if it's all my fault?
Melinda: All the what ifs.
Dylan: You know, that's just sort of your internal, it's all your internal dialogue, right?
But the whale, the whale is your self-confidence and your self-belief. And it takes a ton of work to get down there and see it and touch it and talk with it. But I just think that, man, if you can do that, if you can get down to the bottom and talk with that whale and become friends with it, yeah, they're still going to be, as you go through the ocean, waves and fish and things happening. Sure, I'm not saying that like all the problems will disappear, but it's going to be a hell of a lot easier. And I think you're going to feel a hell of a lot more in control. Knowing that there's that whale just beneath the surface where you can, you can't see them, but you know they're there.
And so yeah, that was the parable of the whale and I figured, oh, that's actually maybe a decent kid's book. I should write that someday, but that was the visualization that we came up with, yeah.
Melinda: I think you should. And I love that because not everyone takes the time or the kind of self reflection to go deep, in that way and sort of draw deep into themselves, but I think it's kind of a theme of what we've been talking about today. And you mentioned earlier, you know, this deep grounding that allows you to stay connected to yourself and connected to the work that you do and allows you to keep getting out of bed every morning. And I'm sure it's not easy at times, right, kind-of fighting against an unjust system. So I've got an eye on the time, but I think where I want to go here is, you know, we're talking about storytelling and I think, you know, that is part of the creativity in your work, in many people's work, right?
What is this current story we're telling ourselves and how can we begin to create a new story? And it starts with, you know, we have to envision it, anything creative, we have to envision it first and then we bring it into being. So I'm thinking part of the work you do is about creating new narratives and engaging in institutional storytelling and how could things be different?
So how, how does that land for you?
Dylan: Yeah, I think vision is really important. I think it's hard to work towards something that feels completely unrealistic. And I think if you can visualize it or tell a story about the thing you're trying to achieve in your mind, it just becomes that much more palpable in some way.
And so for me doing criminal justice reform work, I don't have a specific story in mind or a specific sort of like parable that comes to mind as I do this work. But I do sort of visualize families together. I visualize people receiving support before they're inclined to harm themselves or other people. I visualize communities that are vibrant and connected. And I don't know that there's like a specific time, place, or person that I think of when I think of these things.
There are certainly people I've worked with who come to mind as examples of what I think other people, you know, could strive to be like, there are people organizers in particular who give their hearts to their communities. And I just think, wow, if everyone got to see that or do a little bit of that, but absolutely, I think vision is critical. I've worked with people who every day, the first thing they do in the morning is they get up and they just sort of draw a picture. Grab a piece of paper, grab a pencil, draw a picture, whatever's on their minds.
Or I've worked with people, like I write every morning, right? So I wake up and I do about like 5-10 minutes of writing every morning. Just kind of whatever's on my mind, having some anchoring reflections, just sort of thinking through, okay, how do I want to approach the day? It's all sort of centered in this idea of like, I'm visualizing where this will end up for me.
Melinda: Yeah.
Dylan: Whether it's at the end of the day, end of the week, end of my life, whatever it might be. And I think without that, it becomes really hard because it feels like you're just kind of working in this sort of big vacuum of nothingness. It's already hard enough knowing that there'll never be an end to this work. You have to kind of accept that to begin with, but absolutely having a story in mind, I think is a huge piece of finding joy in what is a very challenging calling for sure.
Melinda: That's great. And I know we talk a lot about journaling. I talk with, you know, so many people about how helpful it is to just start the day with some kind of grounding practice, right? Whether it's meditation, whether it's exercise, whether it's journaling and just touching in with oneself, and setting some intentions. And that's how we make progress toward our goals, whatever they might be. So. Anything else you want to add to the conversation before we close?
Dylan: I feel like we touched on a lot of stuff. I feel like there's so much more we could talk about if we keep going. We often do. Our sessions are usually packed and we’re even over so we won't do that here. But no, I just appreciate being able to think through this out loud with you and share some of it. And I appreciate listening to the conversations you've recorded previously. I think having this space available for folks is really, really important. So I appreciate you.
Melinda: I appreciate you too. Thanks so much for taking the time today. And if people want to learn more about you and your work, what's the best way for them to find you?
Dylan: Probably just, as lame as it sounds, LinkedIn is a good place to start. I don't really do social media, but yeah, I'm on LinkedIn. Reach out, connect. I'd love to chat with people who are working in this space or any other space. So we all have a lot to learn from each other. So yeah, reach out anytime.
Melinda: Great. And we'll include your LinkedIn contact info in our show notes. Awesome. So thanks so much, Dylan, for being with us today.
Dylan: Yeah. Thank you.
Melinda: One of the things I want to emphasize here is that we all lead in different ways, in different contexts, whether explicitly or implicitly. So, for our Creativity Pro Tip today, I encourage you to consider how you show up as a leader in your own life, whether based in formal leadership roles or positions, or in your family, your community, and so on. Leadership is an exercise in creativity, and our values are the cornerstone of our leadership. So what are your core values and passions? Have you ever formally articulated them and how they guide your path and decision making? If not, Today is a great time to start.
Thanks again to Dylan Hare for the conversation. You can learn more about him and his work on LinkedIn. We'll provide a link in the show notes.
This episode was produced by Mike Osborne at 14th Street Studios in Austin, with production assistance by Christian Haigis.
Follow Syncreate on Instagram, YouTube, Facebook, and LinkedIn, where you can also find out more about all we do at Syncreate. Thanks for listening and see you next time.
