UAC 114 | Building Strong Character


Life is inevitably filled with tensions, and the best way to live in the midst of the tensions is with intentionality, that is, infusing intention into all we do. Someone living with intentionality so well is Houston Kraft. Houston is a speaker, curriculum developer, and kindness advocate who has spoken at over 600 events internationally. In 2016, he cofounded CharacterStrong, a curriculum and training that transforms the way schools teach the whole child through social-emotional learning, character education, and equipping educators with practical tools to create a compassionate culture on their campus daily. Today, Houston focuses on how they’re building strong character and sustainable growth in education. We also dive into various topics that include challenging our paradigms, empathy and building it through play, the current challenges facing education and the next generation, being helpful versus being right, the power of human connection, mentorship and fellowship, priorities and how boundaries help create compassion, listening and asking good questions, and so much more!

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Serving The Work: A Speakers Journey To Sustainable Growth By Being CharacterStrong with Houston Kraft

This is a show all about learning how to live a good life. We believe that it takes living with intention in the tension. Life is inevitably filled with tensions and we believe the best way to live in the midst of those tensions is with intentionality, infusing intention into all we do. That’s what we’re about. We impact that through topical episodes, fellowship episodes, which are peer-to-peer conversations and deep dive, long-form interviews to unpack someone’s life and story. This episode is one of those unpackings. I’d love to encourage you and remind you that we can’t do this without your help. The best, easiest, simplest way to help us is leaving us a rating and review on iTunes.

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This episode is with Houston Kraft. Houston is a speaker, curriculum developer and kindness advocate who has spoken at over 600 schools and events internationally. He was inspired to do this work at a summer camp in Washington State in 2006 and has served on the camp staff ever since. In 2016, he cofounded CharacterStrong, which is a curriculum and training that transforms the way schools teach the whole child through social-emotional learning. Character education and equipping educators with practical tools to create a compassionate culture on their campus daily. They have worked with over 1,200 schools globally serving over one million students. In 2019, he cofounded the Good Work House, a community focused on meaningful conversations, intentional programming and connecting people with nonprofit organizations.

He found out he likes black licorice and was once invited to play on the JV National Lasertag Team. His mom is his hero and her best life lesson is to hug like you mean it. Houston is an amazing storyteller and an amazing guy. He lives out intentionality so well and I’ve been blessed and I’ve benefited from getting to know him. I’m helping as a speaker on CharacterStrong. This episode is amazing. The topics include challenging our paradigms, the way we see the world, empathy and building it through play. The current challenges that we face in education and with the upcoming generation. The difference between being helpful versus being right and the power of human connection. We talked about mentorship and fellowship and that importance. We talk about priorities and how boundaries help create compassion. We talk about listening and asking good questions.

He is an incredibly gifted speaker. There are a lot of things that we didn’t get to, but I would encourage you to look at the other interviews he’s done to know more of his stories on kindness and why kindness is so important. We didn’t get to dive into much of that. You can find more about CharacterStrong at You can find him on the socials, @HoustonKraft. You can find more about the Good Work House, @GoodWorkHouse on Instagram. Definitely, check those out. Send him a shout out. Let us know what you thought. You can send us an email at

speechlessly Houston Kraft , welcome to the show.

It’s been a long time up and coming. I would love to begin by knowing about an excursion you went on which involve your 30th birthday. What happened to celebrate and bring in the 30th year of your life?

I believe in celebrating any occasion possible because the days in between the traditional holidays and celebrations are too long. This was my 30th birthday. When you do have a formal occasion to celebrate, you got to do it well and I only get one of the 30th, so I wanted to do it pretty well. A group of friends and I went out to the woods in Big Bear, California. We got a beautiful space that slept about 35 people on 40 acres. The theme of my birthday was Survivor Summer Camp. The premise was roughly four tribes of about eight people competing for the honor of being the survivor of the weekend, by combining summer camp-style games, connection, building exercises and true Survivor-esque activities. There are about 30 activities over the course of three days. We arrived at one winter and it was the best weekend of my whole life.

Who was the winner?

The winner was my cousin, Karena, a dark horse of the competition. She played it thoughtfully and kindly with the occasional competitive edge. I have traveled quite a bit for work over many years. The prize was to go anywhere in the world with me. Your flight and hotel were taken care of because I have lots of points that I don’t know what else to use it on besides sharing an adventure with one of my closest friends. She and I are going to Japan.

I love the idea itself, but the winner and the prize make it twice as cool.

[bctt tweet=”The valleys and the mountains sometimes exist on top of each other. There’s good and bad that live in every moment.” username=”upandcomersshow”]

There are some good stakes involved, which people would have been bought in anyway because I think we crave simple, goofy play and competition that feels not too contrived, but competition in a way that allows us to play with friends. People took it very seriously. Anytime we explained an activity, people have twelve questions about the rules, “Can we do this?” I’m like, “Play Tug of War. It’s not that complicated.” It was truly brilliant and bringing people together from a lot of walks of life. From different areas of my life as I’m sure lots of people have the opportunity from one occasion or another, whenever you get a chance to coalesce the groups in your life. There are few greater gifts than seeing people being in love with people you love.

That is truly one of the greatest gifts. It’s so special. The other thing that is an incredible life goal that most people would hardly agree with is finding your face on potato chip bags across the country. Tell me how this happened?

It’s been a big year thing in a lot of weird ways. I was one of the 30-some odd smilers that has the lower half of their face on Lay’s potato chips bags as part of their spreading smile campaign. It came about in a funny, beautiful way that I ended up meeting a friend here in Venice, California at an event. We talked for 30 minutes. I told him about what I did in school and the work I did around kindness. It must’ve stuck with him because his partner works at a marketing firm that I believe Lay’s worked with to create this campaign. They did the campaign and they did it with professional models and people called Lay’s was like, “Who are these people?” They were like, “They’re good-looking mouths.”

They had this beautiful idea, in partnership with Operation Smile, to raise over $1 million for that organization and to still do that smile campaign, but they found people around the country who did work that helps spread smiles. This person was in charged with helping find some of these people. Because her partner had told her about me, I get this random text messages like, “Can I submit you for this thing to have your face on chip bags? It’s truly a dream I didn’t know I had. It wasn’t something I was planning on the vision board or anything like that.” It’s been a cool and humbling experience to have some people reach out.

I think anytime you get widespread exposure like that, people come out of the woodwork maybe who have passively supported the work, but now that there’s this public-facing thing, all of a sudden there’s an excuse to be like, “I wanted to tell you that I saw this and I think what you’re doing is awesome.” I’ve had so many people over many years who I haven’t talked to in a decade being like, “I saw this and this is so neat.” That’s been a beautiful part of it. Lay’s credit has been an awesome way to spread smiles. I smile every time someone sends a picture of me. They’re smiling when they see my silly face on barbecue and jalapeno chips.

Are those the two flavors you got or are you on all flavors?

No, barbecue, jalapeño and spicy habanero. I don’t know what spiciness they saw in me, but I’ll take it.

UAC 114 | Building Strong Character

Building Strong Character: A motivational speaker only last as long as the good feelings last, unless there are practical tools to keep it alive.


Speaking of the work of spreading smiles, how would you describe that work that you do?

I’ve worked some capacity in schools. For many years it was pretty much exclusively doing assemblies, workshops, and training mainly to students talking about kindness, compassion and love. From around 2010 until 2016, I was on my own being an assembly speaker, motivational speaker and conference speaker. I had a chance to work with about 600 schools over that time telling stories to hopefully help change some paradigms and offer new ways of thinking or being around what it means to live a life of love or kindness. In 2016, I came together with one of my longtime heroes and one of the initial inspirations for why I started speaking in the first place. A guy named John Norlin, we came together and we formed CharacterStrong, which is our answer to the sustainability part of the motivation.

It’s like a motivational speaker only last as long as the good feelings last, unless there are practical tools to keep it alive. I’ve always wanted to be a part of the work and change that has created impact that was long-term. John and I came together to create CharacterStrong, which is focused on developing curriculum and training for schools and educators to implement content that effectively teaches social, emotional skills, character connection, community building. Along the way, it helps equip educators with the tools to weave that stuff into their daily practices and pedagogy.

I’m excited to dive into a lot of that because we got connected and it’s been a blast to learn more about that work and to see the impact it’s having and to participate a little bit which has been cool. For the people, I encourage you to check out more about Houston and what he shares. They have a podcast called CharacterStrong. He’s also been on quite a few interviews that tell some amazing stories. They’re very much worth listening, but the goal is to tell some different stories. That’s why I’m interested to know a little bit more about some of where this comes from, some of your background but also some of what you’re experiencing in that process.

One thing you mentioned that I love is finding a sustainable solution to motivational speaking. Because it can seem like there is a lot of good, encouraging and challenging people to take ownership of different ideas and to be internally motivated and to spread kindness. It’s hard on a daily level to do that. What was that process like for you in that nine to ten years of voyaging through that? What was that process of finding that frustration and not seeing the sustained impact necessarily and then trying to find a solution and then putting that solution into action? That is a long road and you’ve come a long way down that road and there’s still a long way to go inevitably. Can you speak a little bit to the different seasons and phases of that process?

I studied English and Theater in college for a long time and thought that that road was going to take me down the path of acting or production. In fact, I took my junior year off of college to pursue acting. Shortly before I was finalizing some details to move to Los Angeles from Seattle, a friend of mine who I met at a leadership camp messaged me about an internship he was doing with this company that helps set up mentorship programs in schools. I ended up showing up to hang out with him. Along the way, I found that I loved what he was doing with students. It was like summer camp playing games. The whole purpose at least intentional programming and summer camps are empathy-building and experiential learning that helps you unpack complicated and meaningful things about your life through play, experience, challenge or group struggle.

I’ve always loved being a part of and I’ve always loved leading those. I went to this orientation day and I started leading some activities. The people from the company were like, “You should come back.” I did and I ended up working with them for a year, traveling a little bit around the country. My primary role was to teach upperclassmen kids how to be role models for incoming younger underclassmen. I loved that work and I realized that it combined some of the things that I loved about acting right like storytelling, having a message, being on stage and presenting with the things that I’d loved and learned about leadership over many years. What does it mean to be influential in the world, to cultivate influence and to use that influence for good?

[bctt tweet=”Character is not what we do when no one’s watching because there’s nothing at stake; it’s what we do when everyone’s watching.” username=”upandcomersshow”]

I went back to school and doubled down on education and thinking about theater through that way. To make a long story a tiny bit longer, shortly after finishing college, that first year was interesting. I was doing freelance graphic design and ended up meeting a woman who I would later be in a long-term relationship with. Spending a lot of time on that and then dipping my toe into trying to speak and tapping into those relationships I’d built in other areas of my life to see if I could go talk to their leadership class, their conference or maybe even in assembly. That first year, I did thirteen engagements and every one of them was a different speech because at the beginning I was like, “I’ll talk about anything.” They’d be like, “This is the theme and these are the five things.” I’m like, “I’ll write a speech about it,” which is a ton of work to come up with an hour plus of material around these different content areas.

Every one of them was exciting and my goal was always to try to provide value beyond the stage with different tools and resources. I made some videos using some of my acting background and production background. That second year after getting a bit of traction, it was 35 engagements. The next was 77, and then the year after that, it started getting up into the 100, 2,000 and 3,000 marks, along the way developing more and more serious relationship with this person. We ended up getting married and two weeks before the wedding, I spoke at a National Student Leadership Conference. I would describe that conference as one of the big turning points in my career.

Maybe the simplest way to say it was two weeks before I got married is when I was about to get busier than I’ve ever gotten. I was starting to speak on a national level, which had already dabbled in, but I was exposed to 50 states simultaneously and passionate kids were motivated to bring you to their different states. That next couple of years were a tremendous amount of travel. When you talk about the seasons of this work, there’s great enthusiasm leading up to that and you find yourself presented with an opportunity that is in many ways career and life-changing and everything you’ve been working towards. I don’t know how long it was into after that moment when you start to realize like, be careful what you wish for sensation because I’m on a flight every other day, staying at a Hampton in somewhere

I’m taking a lot of rental car shuttles I didn’t want to be taking. I’m spending a lot of time away from people I cared about, including a pretty new relationship and feeling a tremendous amount of excitement and exhaustion at the same time. There was probably two years of a lot of that before making a decision to move to Los Angeles. The week before I moved to Los Angeles, I got a call from my mom that she had been diagnosed with stage IV colon cancer and she lives in Maine. I’m navigating the dynamic of moving my mom being across the country, struggling with a terrifying battle and still navigating a growing list of people and organizations I’m speaking to. That year was hard.

I’d love to know how you faced that because that is the definition of the decks being stacked against you. When you think about a low point, I can imagine knowing all of the factors in that and putting myself in your shoes, I don’t know how to keep moving forward in the season. What was that experience like for you?

I got the news about my mom the morning I was heading to speak at a school. I drove down and I talked to the school and at the end, I told them what had happened that morning. One of the pathways that you navigate valleys to valleys is to not do it alone. I don’t know who granted me with that information or how I arrived with some of the tools in that toolbox. I’ve been listening to a lot of people share about it and I suppose talked about it a lot myself as an own version of teaching. That day I went to this school and I was like, “I need your help.” I found that to some degree, a part of the healing and the comfort as I would travel from engagement to engagement.

I would film students at the end of every assembly saying my message and wishing my mom to kick cancer’s butt. I have a video of thousands of kids all across the country in different areas, different venues, saying, “Choose love and kick cancer’s butt.” I gave it to my mom for Mother’s Day. Simply the sheer energy behind that is a piece of the puzzle. Maybe to expand on the fact that I don’t think I had all the tools to navigate some of these things was what came next was a lot more time away from home, away from a relationship, were our love languages look different. Mine’s acts of service, hers are more quality time. I remember along the way starting to take up therapy.

UAC 114 | Building Strong Character

Building Strong Character: CharacterStrong’s work is touching students’ lives in some capacity across a million humans.


At some point, my therapist said, “Houston, you can’t be a ten at everything.” I said, “Don’t tell me that. Can I be a ten at therapy? What do I have to do to get a ten here?” It’s unpacking some of the perceived and felt needs to try to win at everything. Not in a competitive way, but in a desire to be lovable because of what I’m achieving. Having to wrestle with what my priorities were and what success looked like to me. All that to say over the course of roughly a year and a half, my mom went through her own whole battle. She’s two and a half years cancer-free, which is amazing. On the far side of that, my partner and friend of many years, her and I separated back in 2017.

The valleys and the mountains sometimes they exist on top of each other. It’s not like you necessarily get to have, “I’m at the top of the mountain.” It’s like, “I’m in a valley mountain.” Recognizing that the simultaneity of work exploding, being beautiful, finding so much traction and talk for a living about kindness is ridiculous. My friend, Esteban, who has been on your show, jokes about me. He goes, “Houston hugged someone in middle school,” and said, “How can I monetize this?” This is not how I’ve thought about it, but I’ve made a career out of kindness, which is ridiculous. The fact that that exists and my mom is healed, a relationship had to come to an end. With all of those, there are goods and bads that live in every moment of that.

To have a long-form answer to that question, the ten years that it takes into build what we’ve created with CharacterStrong and the work I’ve done in schools has had a thousand little mini-chapters along the way. Some of them are fun that has looked like travel and excitement. Some of them have looked like holding my mom’s hand at Mass General Hospital. Some of them have looked like an extended hug that my partner and I have the time acknowledged was the last time we were going to be in the same space as this together. Some of them have looked like 5,000 middle school kids who walk away thinking about kindness in a different way.

The visual of all those things is important to freight success with. Success is so loaded with so many yeses, noes and sacrifices along the way that those traditional definitions of success, if you don’t spend time clarifying for yourself will definitely mess with your head a bit. My friend Kyle Scheele, one of the people I admire for the way he lives his life. He’s a speaker and a creator. I remember a casual conversation with him one time where he said, “I define success by the number of times I come home smelling like campfire.” I’m like, “That’s such a cool number to put next to the number of gigs on your calendar or to put next to the money in your bank account.” He’s like, “The traditional models of success, add a couple of your own columns and erase the other ones if you want. You can do whatever you want.” That conversation is important whenever you’re like, “How’d you get here?” Here means a lot of different things. Even though we might’ve had the best week ever for CharacterStrong monetarily, it doesn’t guarantee it’s the best week ever for CharacterStrong in the context of my life.

I’m curious, what are a few of those line items for you of what success looks like?

The number of nights would be a good example where I get to sit my backyard with friends who are meeting new friends. We are laughing for no other reason than we’ve found something to laugh about. Anytime I can gather with friends and introduce new friends, that’s a successful night for me. The number of times over the course of a week, I jump in the ocean. I live close enough to it that if I were to not do it on any given day. It is only because I have made a decision consciously or unconsciously not to. The number of days I get to experience the ocean. The fewness of days in between when I talked to my family. I talked to my mom or dad almost every day. I think that’s success.

We don’t always have the stuff to talk about. I don’t always necessarily want to share. Sometimes I’m exhausted and would rather go into myself, but I value that connection. We have cool metrics and the scalability of CharacterStrong and what it means. We’ve served about 1,200 schools in some capacity, which means our work in some way as reached over a million students. I like numbers like that, where you can start to draw a line. It doesn’t guarantee tangible or necessarily long-term impact. This work is touching students’ lives in some capacity across a million humans, which I think is rad.

[bctt tweet=”The only way you’re going to make a difference is to be different.” username=”upandcomersshow”]

That has got to be one of the coolest numbers to see for you. I can imagine after spending those years and to be able to come to a place where you realize that when you pause and consider that a million students’ lives have probably been impacted in a positive way through your efforts. We are both threes from what I know. Have you gotten better at pausing and celebrating those wins? What is it like with achievements or “wins” or accomplishments along the way for you?

The struggle to accept what we’re doing is good at the moment without thinking about what the next thing is. I love those things in concept, the anecdotal stuff where you get a direct message from a person and having worked in a lot of schools over the years. There’s only been truly a handful of those moments that I’ve gotten lots of cool messages. Sometimes teachers will have their whole class write a thank you note and all that stuff’s neat, but to your point, I have a hard time may be receiving that in bulk or truly pausing to appreciate the gravity of whatever that work looks like. Over the years, I have probably five moments with teachers or students that I can hang on to that I was able for one reason or another, truly able to sit with the gratitude of this “Is important.”

Would you be able to share one of those?

I’ll share three mini examples that speak to a couple of different angles of the work. One of them was an assembly I spoke at. The morning assembly, off to the left there was a senior section. I got this email after the assembly was over that was very long and incredibly well-written from a high school student who spent her life as a military kid moving around quite a bit. Having in her own words oftentimes have displaced the sense of home. She has been in communities long enough where she makes friends and then they get ripped out on repeat. Over the course of this note, she talked about sitting in an assembly as a senior and not even knowing where it was.

It’s like a mini piece of evidence of like, “I don’t even know where to go here.” After the assembly was over, she was crying and she said she’s good at hiding a lot of this stuff. The assembly and that whole experience were emotional enough for her that she started crying passively in the back of the room. It sounds like prompted in some capacity by the conversations we were having stopped and had a conversation with her and they ended up getting lunch. At the end of the day, she sends me this long email. At the end of the email, she references the school as her school. In parentheses, it’s that little note that gets me every time I read it. She goes, “See my school.”

The encouragement for me to understand like the things I was talking about, I have the capacity to give kids like her hope. It is one of the most finely written notes I’ve ever received. The premise of it is very simple but so profound. I can’t read it without crying every time because of how poignantly she describes that experience of loneliness and feeling out of place. The simplicity with which she all of a sudden felt in place. I think about her often. I think about a teacher around the time that I was having the hardest time with some of the things going on in my life. I remember it was pretty early on in CharacterStrong’s growth walking into a room where we are going to do a workshop after an assembly. All the students walked in wearing CharacterStrong shirts, which is the first time that had happened because they were going to be the ones helping lead lessons, which isn’t how it always works, but this is how the school wanted to do it.

Immediately, I was humbled. There are 100 kids who are wearing this thing that I helped create. The teacher pulled me aside at the end is like, “I studied X, Y and Z. I studied History and that’s what I’ve been teaching for ten years.” She starts to tear up as she’s talking to me. She goes, “This is everything that I want to teach students and you’ve given me the tools to do it. She thanks me. I remember the authenticity of that moment feeling profound to me. It was one of those days where I was tired. It was December right before the break. I didn’t want to do the gig and showing up and being like, “I’m doing something that is empowering other people to do things they love.” That gets me excited.

UAC 114 | Building Strong Character

Building Strong Character: The most beautiful profound truths are incredibly simple but deeply complicated when it comes to implementing them in your life.


The final one is from a kid who I went to high school with who we did not get along. I got mocked by him quite a bit and we weren’t in the same social circles. I knew he didn’t like me, which in some ways meant I didn’t like him. I got a message from this guy on Facebook and it was like, “I want to let you know that I respect what you’re doing. I was watching some videos of you and show my girlfriend and we were both crying. I’m sorry I didn’t understand in high school.” That last line is so powerful to me of many things, especially when it comes to, “Doing good in the world,” or things that people were like, “Being kind.” Even pursuing ideas that aren’t normal that we get so much feedback because anytime we depart from normal we’re going to get funny looks, we’re going to get judgments, rejections and criticisms. Especially when you’re younger and you take those things. It’s hard to walk through that. One of the things I challenge often in our work is I hate the idea of characters what we do and no one’s watching. I’m like, “I’m a good person when I’m alone.” There’s nothing at stake, especially the young people, the characters that we do when everyone’s watching.

When the pressure’s on, people are saying “This is a stupid idea. What are you doing? That’s weird.” All of those reactions that people might have. For me, it was in high school. I started a club about kindness and this kid mocked me for it. What a beautiful example of his own maturity to say, “I want to let you know I respect it. I’m sorry because I don’t think I understood.” Isn’t that a great evidence of so much of what we do in life that we get judged or laughed at for? Some people don’t like us and don’t believe in the idea. They don’t have the tools, context or perspective to understand. Impacting a million kids sounds cool in concept, but as a three it’s always going to be those personal narratives that I’m going to hang on to. Those are a couple of them that keep me keeping rocking.

On what you said, there are two quotes I heard that are thought-provoking. One was by Susan Sontag and she said, “The only interesting ideas are heresies,” which is fascinating. John Cage said, “If my work is accepted, I must move on to the point where it is not.” Both of those speak to that if you’re doing work that is going to create change, it’s often not going to be initially accepted a lot of times. That’s one thing I’ve been thinking about a lot too. Our job isn’t to change people. Our job as humans is to create an environment and where they want to create themselves. If you’re trying to get me to change and I know you’re trying to get me to change, I’m not going to want to change. If you make it an attractive and incentivize for me to believe in it myself, that’s how I want to change.

I think that’s a beautiful example of that. I’ve been thinking a lot and I want to know your thoughts on this. This is something that a lot of people in your community wanted to know from you on. This idea of civic duty and responsibility and what we can bring to create more unity in or country. I put a post about it and the very thing that I was trying to talk about, I had someone messaged me illustrating I was trying to avoid. It was like, “It isn’t clicking.” That’s okay because my job isn’t to necessarily have it be clicked. I’m more of planting a seed in some ways. Before we get to some of that, I love to know a little bit about how you came to these refined truths that you believe in. I got to witness and a lot of people gotten to witness.

You’re an incredible storyteller and incredible speaker. It doesn’t happen overnight. You put in the reps. With that, you have refined truths that also doesn’t happen by chance. In developing a lot of this material that I’ve personally benefited from, it’s a process to develop. What is making kindness normal look like? What is choosing love look like and how do you get to the place where you understand it well enough to communicate it to others? I’d love to know what that process of refinement was like for you in the material that you helped create and also that you’ve been speaking through and from for the last several years.

First of all, I love both of those quotes a lot. Just the premise that the only way we change normally is to not be it. That’s for sure. That’s the premise of a lot of what I talk about in schools, particularly middle school kids or high school kids. The only way you’re going to make a difference is to be different. You need to know that that comes with inherent risk. One of the things I love challenging kids on is I think there’s a cultural narrative may be at large, but particularly with young people that it’s cool not to care. I love going right at them. I’m like, “Let’s be honest. It’s not that it’s cool not to care. It’s scary to care.” You and I have conspired to make it seem like it’s cool not to care so that we don’t have to risk the actual byproduct of caring because the deeper we care about a thing, the more we risk failing at it and the hurt that comes from that failure. The more we care about a thing, the more we were getting rejected. Every time someone laughs at us or humiliates us around that, the deeper that hurt is. It’s a direct relationship to each other. Precisely to the depth you care is what you’re risking with hurt. We got to stop thinking that narrative is true. We can keep the narrative going, but we have to stop pretending that it means what we think it means.

It’s not cool not to care. In fact, the people that we remember and hold as influential people in the world are the people that have dared as Brené Brown and Roosevelt talks about standing in the arena. “Dare to stand in the arena and be mocked. They’re the ones doing the work.” I love both of those quotes and all of those messages. Even a quote like that to the things that I talk about. My speaking mentor, a guy named Tyler Durman, he talks about great storytelling. Holding up these gemstones to the audience. He would describe it as a gemstone. It’s this thing of value, this profound truth that in your storytelling you’re trying to reveal or show to whatever that audience is, which I’ve always loved that visual. A great message is this gemstone that the person out on the stage from the perspective that you’re sitting therefrom, they’re holding up this diamond and they’re turning it very slowly. Through it all, the light starts to refract and you get to see all the facets of this truth.

[bctt tweet=”The more repetition we put into the conversations we have, the clearer they start to reveal themselves.” username=”upandcomersshow”]

Because the most beautiful profound truths are simultaneously incredibly simple but deeply complicated when it comes to implementing them in your life. There are so many things that you and I know to be true and yet we’re terrible at, which is a frustrating rub that exists in our life all the time. At least me, I’ve arrived at some of the truths through, A) A lot of listening. I love listening to other people share their wisdom, which is the hold podcasting industry thrives because of conversations like this. If you have never met me, you don’t know me, but I’m going to offer some stuff from my life and maybe something in it resonates with yours. The intersection of those stories is how we learn, “This person went through something similar, but they handled it this way. I’ve never even thought about that. I have another tool in my toolbox.”

B) A lot of the practice of the thing. It’s only when the rubber meets the road do we know if this thing works. We can talk in philosophy or abstract all we like, but my favorite thing to do at CharacterStrong is we provide practical ways to put abstract ideas into real-life action. If we can talk about humility and we can make powerful videos about it and we can have good questions about it and good quotes. Until you challenge a student, a staff, adult or yourself to put humility into action in your real-life relationships, then the stories that you get to tell about humility by thinking about it versus living it are two very different things. Listening to a lot and putting it into action.

I used to love rocks and gemstones growing up. I would collect them. I remember at one point getting the gift of a tumbler from my parents. You put it in and all the grit and grain and it grinds against the rocks until they become polished and they come out from dirty and covered to these stones. The repetition of the attempt to describe these things is the sandpaper with which gemstones are revealed. I have talked about three ideas for ten years, over a thousand times to 600 different audiences. Every time I talk about them, sometimes they get muddier when I talk about them, which is an interesting process of like, “I thought I had it.” I set it this time and that doesn’t make as much sense as I thought it did because of whatever new perspectives are being offered in my own life.

It gets muddier and then it gets clearer as you go. The arc of understanding when practiced bends towards clarity, which is to say, the more repetition we put into the conversations we have, the speaking of this thing, the practice of this thing, they start to reveal themselves in clearer ways. I love that idea that if you picture this idea, the profound truth as a gemstone. The words that I’m speaking, if you can visualize those words moving past that gemstone and rubbing off on it, eventually you strike the right word that fits it. I love the idea of repetition of these words is been the grit along the way. Every time I talk it feels a little bit closer to the clarity of that truth in my own life. It has been one of the most rewarding parts of this work. The brutal repetition of some of these messages.

The clarity that I’ve found in doing that onstage has rippled into so many more “casual moments in my life.” The event we held, I got up and I was able to speak for ten minutes about something I was passionate about. I had three ideas written down and the amount of clarity I felt speaking about what I shared and my ability to execute on it, I felt so proud of myself. I’ll never arrive at full mastery, but I feel like I’m good at my craft to the point where I can pull out of this thing. I’ve done a thousand times to do something I’ve never done before and had it come across this clear. That’s been the journey for me of uncovering some of these truths, listening to a lot of people who are brilliant, trying to live it and stumble my way through that humbly. Ultimately, saying it over and over again until it starts to make a little more sense.

I love that because it’s bringing things to the light too. Once you bring it out into the open, we refined things. That’s probably one of my favorite reasons for writing or speaking, in general. It refines your thinking so much. It’s like getting out there and then interacting with it, having others interact with it, and hearing their perspective that’s inevitably different than yours. It’s an amazing development process. I think oftentimes until we get into it and even when we’re into it, it never makes full sense at the moment. We don’t always think that this is exactly what I want to do to and get this refine. No, sometimes I don’t want to do this, but I’m going to do this because I need to and I’m committed to. On the other side, I’m like, “I’m so grateful I did that because I see it better. I can provide more benefit,” which is counterintuitive a lot of times.

It’s a great visual of bringing it to the light. It’s like developing a photo. The premise that’s already there is something I love. I had a chance to sit down with Justin Baldoni and do an interview talking about empathy. He’s a thoughtful and lovely human being. One of the things we shared right off the bat is the word human in Arabic means to forget, which is a pretty profound concept. The conversation we had is most of life then is about trying to remember. We are born with everything that we need and all of these truths are self-evident. All of these things are in preexistence and life is simply of bringing them to the light in your own life. That comes to fruition in individual lives in a million different ways. To me, it’s a great reminder that I already have everything I need and I already have all the truths accessible in my life. If I learn how to uncover them, polish them or bring them into the light.

UAC 114 | Building Strong Character

Building Strong Character: There are very few greater gifts that you could give someone than saying, “You’re not alone.”


It is interesting because then it makes your job easy. It’s all about how we remember well or how do we create space to practice enough to bring those truths to light. I think that is probably one of the most important and helpful conversations in society because the majority of things in our world are designed to not allow us to remember well or to bring those out. It’s designed to distract and to grab our attention versus us controlling where we’re putting that in. I want to talk a little bit about what the modern dilemma, especially high schoolers and kids growing up in society and what your experiences with that. I’d love to hear a little bit more about empathy. I heard you describe it once on another interview did as intentional imagination. How do you think about empathy? I know it’s come up a couple of times and I love you and what you talked about being human and remembering. In regards to empathy itself, how do you define it and what does that practice look like?

In culture to your point that thrives on distraction, I think empathy more and more of the evidence and the anecdotes would tell us that empathy is perhaps the most important skill we can cultivate as a world because it’s our number one pathway towards understanding. Understanding is our number one pathway towards healing. A world that most people could fundamentally agree needs healing and hope. Our number of skill or resources is going to be our ability to understand the hard part. In order to understand people, you need to have space and time to pay attention, to listen and to take a perspective. When you pair that with a culture of distraction, that’s moving a thousand miles a minute.

There are a couple of things about our culture. It’s a culture of distraction and a culture of productivity, which means we’re always moving towards something. We always have something to do and someone’s always begging for your attention. The things that are begging for your attention aren’t necessarily people, it’s products, to-do list and productivity. Empathy is, in many ways, the antithesis of the current programming of our whole culture, which is what makes it hard. In fact, one of the things we talk about a lot at CharacterStrong is there’s research that would suggest that the average student has as much anxiety as the average psychiatric patient from the 1950s. My friend, Dr. Michele Borba, wrote this great book called UnSelfie. She says that in our culture, we’re experiencing an empathy gap. Why? Because the more that anxiety increases in our world, the more that empathy naturally decreases.

If you think about distraction, productivity and the stress that comes along with all of those things and you realize that collectively as a culture, we are more anxious and stressed-out than ever before. Neurologically, it makes sense. The more worried I am about everything that’s going on in my life and on my to-do list, the harder time I have worrying about what’s going on in your life. Empathy would fundamentally be on the simplest level understanding of what’s going on with you. If I don’t have room, even to think about what’s going on with me, there’s not going to be space for another human, let alone another ten people, let alone a whole region of the world that’s suffering or struggling. That’s why I think the challenge of cultivating empathy is complicated.

We do have access to a lot of cool tools that allow for easier communication of some of those things. The easier we have access, the risk is also easier we’re going to have interference. Access to data doesn’t mean we know how to curate that data. We are overwhelmed with data. Do we have any tools personally or collectively that allow us to parse through all that information to take out something useful from it? Empathy to me is this key ingredient in healing that we don’t make time for. We don’t necessarily have a lot of tools to know what to do with. For me over the years, spending a lot of time thinking and talking about it. I’ve clarified a bit of my understanding around what I think it means, at least in my own life.

One of those paradigm shifts is I thought in order to have empathy for someone I would have had to have lived their story. I would have to have lived it to give it is how I think about it. I think it’s quite the opposite. In fact, powerful empathy is the experiences that I’ve never lived personally, but I can understand perhaps the way that you might feel as a result of them. Empathy isn’t an experiential intelligence. It’s emotional intelligence, meaning you and I, over the course of X number of years, we’re going to live a lot of human emotions. Those human emotions fascinatingly, most of them operate very similarly in our bodies and in our minds.

We might have different thought patterns associated with them. We might have different experiences attached to them, but joy for me and joy for you even on a physiological sense looks very similar. From a facial expression perspective from the chemicals that are being triggered in our body. The most profound in my favorite example of this is what Victor Frankl would say in Man’s Search for Meaning. He says, “Suffering is like a gas, which means it expands to fill the container it’s in.” You think about him navigating the Holocaust and my mom going through cancer and an eighth-grader watching her parents get divorced. All of those you could say are suffering. From the most high-level objective sense, you’re like, “One of these is going to suffer a lot more than the other.” From an individual perspective, if I haven’t gone through the Holocaust and if my mom hasn’t had cancer and I’m that eighth-grade girl and the most challenging that’s happened in my life so far is my parents going through a divorce. That suffering feels just as profound to me because I have nothing to compare and contrast too.

[bctt tweet=”Empathy is a key ingredient in healing that we don’t make time for.” username=”upandcomersshow”]

That visual to me is so profound that it allows me to remove so much of the judgment away from people’s life experience. They only know what they know and I only know what I know. At the end of the day, we might arrive at the exact same place through wildly different experiences, but I can still have empathy for you because I know what it feels like to hurt. I know what it feels like to be surprised. I know what it feels like to be taken aback. I know what it feels like to feel deeply accepted. Because I have those categories in my brain, even though I haven’t lived your story, I can maybe understand the way you felt along the way. That’s the profound gift that we’re able to give people because the opposite of empathy is loneliness. It’s feeling like we’re the only ones who have navigated this path. We’re the only ones who are feeling this way. There are very few greater gifts that you could give someone than saying, “You’re not alone.”

That is a powerful gift. It’s so funny because the whole time I’m seeing myself in these loops that we find ourselves in our minds. One of the things I’ve been thinking about a lot even in the process of developing and our ability to understand each other, it probably always starts with our ability to understand herself because we can’t understand ourselves while there’s very little chance we’ll be able to understand someone else or in a helpful way for them and for us. It’s probably more attainable sometimes or maybe not. I do think they go hand in hand. For me, I’ve gotten good at understanding myself through goals and through the development process. I see a big gap in my ability to actively understand other people.

Because the thing that we all tend to do naturally in our minds is how can I categorize as quickly as possible and then discard because then the brain doesn’t have to work on it. It doesn’t have to keep going on. It’s used for other things. Once I find what box you fit in, I’m going to put you in the box and move the box side so I don’t have to think about that anymore. That shuts off our ability to be with someone else or understand them in a true way versus around perception way. It’s a lot harder to approach someone knowing that you don’t know their full perspective. You want to find out, you want to learn and you want to try. What you mentioned too about you don’t have to live their life to be empathetic. That’s such an important part of it because it’s so easy for us to be like, I can’t relate because I’ve never been there. I don’t know what that feels like. It’s an easy out a lot of times. The reality is we still can emotionally put ourselves in that place and it is very much the same experience as you pointed out, which makes it a lot more attainable for all of us.

Speaking of the students, as you mentioned with the anxiety being as high as it probably has ever been, correlated with that is depression. The easy way to think about the two that I would think about is anxiety is about the future and depression is about the past, but they’re both very similar emotional reality. Both of those are prevalent in students and adults lives more than ever before. What have you seen in working with students in the direction within the younger generations as a whole? It could spread beyond that. What have you seen as the shift or momentum and how do you think about where we’re at?

The more you talk about a thing, the more accepted it becomes to talk about a thing. For the better we’re talking about anxiety, depression and mental health more than ever before. Did we have to walk through a lot of tragedy to get there? Yes. It’s the cultural narrative always, but here we are. We’ve arrived at a place where we’re talking about it more. I’ve found certainly kids are way more willing to talk about it. I don’t think in the equal step have we been more willing to hear it or have we been effectively preparing to navigate it or be helpful in it but one step at a time. The willingness that students have and the vocabulary they have around their own emotional capacity, where they’re at, when they’re feeling overwhelmed, why is huge. There could be some arguments made that has anxiety increased or are we better at talking about it?

Has there always been anxiety and we didn’t know what to say. There are some silly judgments passed on young people like that whole idea of being a snowflake or toughen up, like in my day X, Y, and Z. You look at that generation who might be critical of this generation. For many of those people that they “toughed it out,” it’d be interesting to ask the partners in their relationship, how seen or heard they felt in those relationships. It’d be interesting to know how lonely those people ended up feeling later in their life. There’s probably so much interesting data. You toughed it out back then or you still are toughing it out “now,” but what does that do to you, your body, your relationships, your community or this world? One of the people we work at CharacterStrong, a guy named Dr. Clay Cook. He says, “How many of you know an adult who is capable at math or science or holding down a consistent job but not good at managing their emotions?” Every person had their hand goes up for that.

That’s a deviation from the question, but something I feel passionate about is we cannot look at young people talking about this stuff as weak, fragile or not hard workers or they’re not tough enough. All those like narratives that we want to put on them diminishes the courage of their voice to talk about things that are complicated and vulnerable for many of them. Not even have ever been taught or yet equipped with a vocabulary to know how to do it effectively, so they’re making it up as they go. There’s been no blueprint or history of people doing it in the past so they’re the first ones forging ahead for the first time doing it. I had a chance to see this girl named Dora speak. She was incredible. She is such a gifted speaker. She gives a TED Talk when she was eleven about what adults can learn from kids. She published her first book six or seven. We’ll dig into her more because she says a lot of beautiful things.

UAC 114 | Building Strong Character

Building Strong Character: We need to be constructors instead of critics. Young people simply need mentors and role models.


Among them, I remember she closed her talk by saying, “So much of school and the conversations around the school are about making you career-ready.” Life-ready is a big term in education. She’s like, “That’s nonsense.” Why are we waiting to be ready to fix a broken world? She goes, “You’re ready right now.” Ready is what the world is trying to tell you to be programmed to exist in a system that’s currently broken. She’s like, “Why are we waiting to be ready to be in a system that’s busted?” You’re ready. The things you’re doing right now indicate the readiness that you want to change the systems that are messed up. I love that about this generation and I’ve seen it more and more.

It’s indicated in a lot of ways that these kids are desperate for real conversations. They’re desperate to enter into challenging paradigm shifts. In schools you see the question of like, “Are these kids lazy? They don’t want to work very hard.” Work ethic is a big concern among educators, which I would say is like, “No, they’re done with busy work.” They’re done doing things that they don’t know why they’re doing it. They’re done engaging in a system that they know is dated, antiquated and not preparing them to do things that matter in the world. Don’t give me this worksheet. I got other more interesting, more challenging things to take on. My challenge to anyone reading, educators perhaps especially is when you help them wrestle with their purpose in a meaningful way, these kids will work harder than ever. The things that they’ll do, get behind, rally and the things they’ll create and go after when they’re clear on why they’re doing it and you help them wrestle with that. This generation is ready to change things in ways that are unprecedented.

I love that insight because it gets to the layer that’s not seen. What’s beneath the surface? One of the things I’ve been thinking about a lot is one of my favorite questions I want to ask more in conversation is, is that helpful or what’s helpful about that? Because that hopefully always steer the conversation towards that because the goal is what is helpful and how can we be helpful? In conversation, we start talking about what’s right, what we believe or what we disagree with. My idea that I’ve been thinking about more is that so many of those conversations aren’t helpful. Instead of opposing, which produces more entrenchment, how do we mutually look at what’s helpful? I was talking to someone. It’s very much like talking about politics like, I hear you. I see that. What’s about that? How can we be helpful in that? Even for you, as you think about this generation, you mentioned finding purpose. What are other things are even more on that that you think is helpful? How do we foster this in a helpful way?

That’s a great humbling question to ask ourselves, “Do I want to be helpful or do I want to be right?” Many of us, myself included, it’s easy to confuse who you are with what you believe. The challenge of that is anytime someone’s attacking something that we believe and saying that this “Isn’t right” it means that you’re not right. There are tons of research to back this up, particularly when it comes to religion or politics. Our beliefs are so entrenched with our identity that when we get into those conversations, we’re not having an ideological debate. We’re having an identity debate. Those don’t tend to go well very quickly. I think that’s a great framework though to think about it. Can I in every conversation I have free myself enough from my own desire to be right in order to be helpful or to be understanding which is helpful?

In regards to even the students of this generation, what is helpful? Because you mentioned the purpose side, which is helpful. What other things are even deeper on that purpose side? Can we be helpful versus it’s so easy to be unhelpful just putting in a box categorizing and saying that it’s helpless or hopeless or whatever it may be. That’s the easier path for sure? How do we take the harder path, the path that’s going to be helpful? What does that look like in your opinion being engaged with so many students in this generation?

It would be nice if we didn’t critique and hold down out of them. After the shooting in Florida at Stoneman Douglas and the advocacy that came out of that and the critiques that these kids had about being advocates from adults who are ultimately scared to do their own individual self-reflection is not helpful. It’s an indication that we’re pushing against something that’s scary and hard. The people that I’ve seen be champions for kids, for the next generation and for our future are those educators, those people, those adults that engage in mentorship.

I think about people like BC, a friend of mine who is the biggest goofball that you’ll ever meet. I’m humbled by his willingness to make time for mentorship in his life. I know it’s important to him and he talks about it a lot. You see the power of that because it’s one human to another human being, giving time and energy to say, “I’ve walked a couple of things, I have a few understandings and I would love to share them and support you in what you’re doing next.” Offering mentorship is a big deal. Offering fellowship, which is to say I’m in this with you is a big deal. To toss your hat in the ring and say, “I’ll stand up here with you.” Even against criticism, slurs or the garbage being thrown at you. Rita Pierson in her TED Talk, she says, “Every kid needs a champion,” which I’ve talked to lots of educators who their philosophy is when a kid comes to them with an idea, it’s the improv method of yes and.

[bctt tweet=”The opposite of empathy is loneliness.” username=”upandcomersshow”]

It’s yes and bring me a proposal on how we’re going to do that. I know educators who their rule of thumb is never a no. You’re going to figure this out, student. This is not my job to do all the work, but it is my job to be an encourager for you. If you’re coming to me with an idea that breaks the boundaries or it doesn’t quite fit in the box or doesn’t meet the “standards” or whatever the heck we took a long time to put into writing. Let the kids be passionate. Let the kids go after these things and be a voice that’s a champion for them. Sometimes the worst thing that happens is that they can’t get it done, or they try it and it’s a huge “failure” in their mind and you’re there to be like, “What if we tried something else?”

There are so many things we can do to be helpful to young people. We need to be constructors instead of critics. We need to be advocates and champions in their lives. Young people simply need mentors and role models, which is what I love so much about the area I’m in. I find that young people doing work around me. The content that they’re creating and the things that they’re thinking about are tremendous role models for what it means to use your success and influence for good. Which is some of the work that we’re trying to get at locally in the communities that we’re trying to build is creating a space where collectively we can do better good.

Mentorship and fellowship, I love that idea. I love constructors instead of critics, being advocates and this idea of encouragement and empowerment. How do we foster a culture of encouragement and empowerment, of highlighting what’s good and empowering others to start taking action on that? You never can be superman. A lot of our tenancies is trying to be that. That hurts you and others, so stop it. Multiple people in your community were interested to hear from you and I’m also very interested on what does it look like to have healthy conversations that involve the political sphere? As I’ve been framing it more, it’s a solo episode that I did. It was all about our civic duty and our civic responsibility.

As an individual part of a greater whole, each of us who live here in America is we have a civic responsibility. The way I’ve been thinking about it is a lot more healthy or helpful way than talking about “Politics” I’m curious how you’ve thought about this because you inevitably have been working with students, schools and people on the gamut all over the map on every area of ideology, view, belief or perspective in any realm. What’s your perspective on what a healthy conversation in that realm looks like or what is helpful in that even with the role that you play?

I think about a lot of this in the long-term that the work I’m trying to do in teaching social, emotional and soft skills, teaching conflict resolution and civil discourse. The work that I’m trying to do, I hope empowered more meaningful and productive, helpful conversations in the future. That’s part of my work and I try to hold on to that perhaps because I am so deeply frustrated with the way that we have conversations. I truly believe so much of it is simply a skill gap. Perhaps the best thing we can do when it comes to these conversations and our willingness to enter into them is to wade through them in a pool of empathy.

One of my favorite quotes by Dr. Ross Greene is, “Kids do well when they can.” His premise is this, the only reason someone might behave in a way that you “Don’t want them to” is for one of two primary reasons. Number one, they’re emotionally overwhelmed. When any of us feel emotionally overwhelmed, our actions tend to be different. Number two, the other reason someone might not behaving in the way you want them to is that there’s a skill gap. I don’t know how to respond to X with Y, so I’m only going to respond to how I know how. When the only tool in our toolkit is a hammer, everything looks like a nail. My adaptation of Dr. Greene’s quote would be people do well when they can, not just kids. We all do what can. The reason any of us behave in ways that aren’t ideal is number one, we’re emotionally overwhelmed. Number two, we don’t have the tools.

UAC 114 | Building Strong Character

Building Strong Character: The only people that change the world are people that are unreasonable.


His framework as educators, if those are the two things, the number one, our job as teachers, number one, is to help them navigate or be patient or listen to their emotions to help them bring back to a place where they’re able to engage in a more healthy, less emotionally charged way with the world. Two, our job as teachers is to teach, help fill those competency gaps to give them the skills they need. That doesn’t always play out in different power dynamics when you and your peers talking to each other. Conceptually they’re sound, which is to say if you’re entering into a challenging conversation and someone’s not responding in the way you want them to, the number one thing we can do is start with an empathy statement out loud or even in our own mind of this person is doing the best they can.

This person might be emotionally overwhelmed. It might be a lot of emotions attached to this issue for this person for a thousand reasons that I may or may not understand. When someone’s emotionally overwhelmed, the worst thing I can do is to continue to prod those emotions and to amplify them. The best thing I can do is listen to understand, listen to develop my empathy for this person. Number two, if it’s a skill gap, meaning they don’t know how to have the conversation when it’s a peer or someone like it, the best thing we can do to teach it is to role model what effective conflict resolution or effective civil discourse looks like. Which looks like starting with a lot of I statements. Brené Brown’s, “The story I’m telling myself in my head is blank. How I’ve heard it or how I’ve thought about it is this.”

It’s never attacking an ideology. It’s starting with me. It’s de-escalating by reiterating what that person’s saying and clarifying to see if like, “Is this what you mean by this?” It’s asking more questions to dig into the root of the matter. It’s navigating conflict in ways that understand that you’re not in every conversation. Are you going to walk out on the other side in collaboration with each other? Sometimes the best thing you can do is a compromise, which is agree to disagree. When it comes to conversations like this, sometimes that’s a very healthy outcome. For always fighting to win versus fighting to understand or fighting to be helpful, then you don’t get to arrive at that. You don’t get to agree to disagree because that doesn’t create a winner.

Knowing those things as you enter into those conversations and doing your best to practice those, even when you’re feeling emotionally frustrated is the best way we’re going to teach it. It’s a two-part thing for me. One is the long play of I want to teach these skills so that we get better in the near future. In the short-term, my own practice is to do my best, which doesn’t always look very effective with some of the conversations I’ve had with family and friends. I will do my best to show up from a place of empathy and to teach by example the conversations I want to have in the way that I want to have them.

The quote I’ve been saying so much is that “You teach what you know, you reproduce who you are.” We put something we believe in. You want to live it so that you can have a chance of reproducing it. I think people will do well to go back to that because it’s something that never happens by chance. We won’t default to that. We have to intentionally choose it and practice it over and over again. One of the things I’ve heard a lot is the competition. Even talking to some of your community, that’s something that they said, “Some people may not know about you. You’re a highly competitive person.” Outwardly you wouldn’t assume that as much about you, but you definitely can see it in what you’ve done. One of the things you’ve talked about a lot is healthy competition. I’d love to know your perspective on what healthy competition is and maybe how it’s different than most people think about it. Somebody said that they’re still loving the fact that you can’t beat them in cornhole.

It’s funny that people would describe me in that way. I have a competitive spirit, but I think I’ve done some work that I’m proud of about releasing myself from the competitive result. I love what competition can do for ourselves and for others. The only way that we bring out our best is to put it in contrast with other people’s best and duke it out, fight it out. There are the great stories of people like Roger Bannister who before the four-minute mile was thought possible. Here’s this guy that shows up and does it. Simply because someone else has done it, it gives permission for other people to enter into that space and do the same.

That’s the brilliant part of the competition. Watching other people exceed their best, it drives you to say, “Maybe I could do that a little bit more.” I had an amazing game of spike ball where we were down twelve to two and we came back and won it sixteen to fourteen. The amount of adrenaline, I was on that beach flexing covered in sand. There are a few feelings quite as lovely as a hard-fought victory. I think that to me, so much of the spirit of that, whether it’s on the spike ball court or the cornhole court, so much of that translates nicely to what I believe about purpose, which is one of the core beliefs we have at CharacterStrong that we share with educators and with students. We believe that we need to stop living for happiness and start living for purpose.

Because happiness is this fleeting transactional thing that you’re never going to be all the time versus purpose, where if you can wrestle with that, people that live purposeful lives are going to suffer. They’re going to be okay with suffering. It’s one of my favorite conversations we have with students at a leadership camp. It’s a camp I’ve been a part of for thirteen years. Clearly than ever, we articulated the young people this paradigm shift around happiness, which is the cultural narrative, would tell us that life owes us something. The alternative paradigm perhaps more challenging one to wrestle with is that we owe life something. When we think about it through that lens that means we have to do something bigger than us.

[bctt tweet=”When educators help kids wrestle with their purpose in a meaningful way, they will work harder than ever.” username=”upandcomersshow”]

Life isn’t handing us something. We have to pursue something challenging in life. Whenever we figure out the purpose, we become okay with suffering because we know exactly to what end we’re doing it. When I work with teachers and it’s a great example. It’s like, “You teach and you know along the way you’re going to suffer. You have bad days where you suffer for this work.” For many people, it’s deeply satisfying work. The difference between happiness and purpose is a big deal. When I say a hard-fought victory, I’m diving all over the sand. I’m sweating, I’m exhausted, I’m sore, I’ve sprained my wrist playing spike ball because I fight for it out there. I’m a diver partially because I like style points, but also because I won’t give up on a ball.

Much of that translates beautifully to the idea of purpose. When you know why you’re doing a thing, you’re going to dive all over the place for it. You’re going to skin your knee, you’re going to sweat, you’re going to be sore the next day. On the other side of that sixteen, fourteen victory, the hard-fought win is always more beautiful than the non-fought hand it to your thing. I find that funny that people would say that I’m competitive and I think I am when it comes to stuff like that. One of the things that have happened as I’ve gotten older, as I’ve been around this work and as I’ve watched other people pursue stuff like it. One of the byproducts to me is I’ve removed some of the egos from it where I can be competitive and I could have lost that game and still been like, “That was fun.” I’m not mad and I’m not throwing a fit most of the time. The same thing’s true about the purposeful work that I want to pursue my life. Sometimes it’s not going to go right and sometimes things are going to be frustrating, but it’s all part of the work. Sometimes it shows me there’s more work to do.

I love the idea that forward progress is not a finished process. There’s always work to be done. I think what you said in regard to the competition is so profound that there’s a huge difference between the competitive spirit versus the competitive result. These ties back to what you were saying about even the debate between the ideological versus the identity debate because it’s what it is. The ideology of competition is good, but the identity of the result isn’t. We have to separate that. The key of that is the ego. That’s always going to be there but how do we express our self in a healthy, not in an unhealthy way or how do we remove as much of it as possible to make way for the spirit and not the result? I think it’s a testament to the work you’ve put in because that people that know you best see that, but the people that don’t, don’t necessarily see that. I wouldn’t have described you as a competitive person but getting to know you more I can see once people say, “That makes perfect sense.” I want to affirm you and it does take a lot of work to get there. It is important to work.

I would describe myself more like a relentless person.

One of the things I like to ask people in your community is how they’d describe you in two words. Some of the words they said were relentlessly thoughtful, genuine, vibrant eyebrows, playful, authentic and remarkably unreasonable. I’d love to know a little bit about what remarkably unreasonable means to you.

It’s a compliment that has stuck with me from Kelby. I remember driving one day and it was a paradigm that he had learned from another space. The only people that changed the world are people that are unreasonable. He worked with me for three years, so he saw me very intimately in my work, traveled places with me and booked all my work. There were oftentimes where he would share what you’re doing is unreasonable. The schedule that you’re maintaining, the hours, the workload, the ideas, the things that you’re trying to do and the directions you’re heading are unreasonable. I know it was one of the reasons that we had fun together and one of the reasons that on some level respected the work that I did was like, “This shouldn’t be possible.” There’s such a learning process in that. I have so many thoughts in my brain around what that’s meant for my life because of the relentless pursuit of anything is you can’t be attended everything. I remember when I was doing some deep self-reflection around the time when that relationship was coming to an end. It was something I stumbled upon called the Four Burner Theory. The premise of this article was about traditional in the business world. Picture your life with four burners, work, family, friends and health.

The premise of it was if you wanted to be traditionally successful at work, you had to turn off one of the burners that weren’t work. If you wanted to be successful, you had to turn off two. It’s an oversimplification of a much more complicated thing, but it’s also those simple visuals provides you a lot of insight to do the more complicated work, which was that humbling moment of I have been relentless. The burner in my work, in particular, has been relentless, which meant things had to have been sacrificed. Just that simple framework of like, “What are the burdens if I turned off?” It was an interesting and challenging thought process and something that I still think about quite often as I try to hold all these things in balance. There are so many things that I want to be unreasonable about when it comes to changing education and changing the way we think about and talk about kindness, compassion or love when it comes to community building. There are also so many unreasonable things I want to do when it comes to playing “silly games” with my friends in the woods.

UAC 114 | Building Strong Character

Building Strong Character: The best way to create a more loving world is through education.


When you can’t be attended to all of those things, then you have to be reasonable about what you want to be unreasonable with for better or for worse. It’s a great compliment from a dear friend who knows intimately that it’s also been one of my most challenging curses because it’s put me into situations where I’ve sacrificed. I don’t think you have to do anything because you have to, if your definition of blank is blank. If you redefined some of those narratives, if you redefine success for yourself, if you redefine what reasonable is, if you redefine where your energy is and how you get it, life is just a matter of priorities and paradigms. Those things have shaken out for me in a lot of ways. All that to say, one of the only reasons CharacterStrong is successful is because I’ve been unreasonable. My cofounder, John and his wife Lindsay, who works with us and all the people on the team, I know a few people more unreasonable than John in lots of beautiful ways. Here’s this guy that says, “This is what it’s about.” I’m going to do the work. It’s a loaded compliment.

I’m curious, what paradigm is most interesting to you right now?

I got to hear Brené Brown speak. She is one of my favorite writers. I’ve worked with her daughter and had a chance to interact with her a little bit in person. She’s profound and very good at what she does. One of the things she shared from her research, she discovered that the most compassionate people are the most boundaried. As someone that I pursued kindness for a long time in my life hearing that was humbling because it was a paradigm shift of if I want to be truly kind, I have to say no to a lot more things in my life. Because the people that are the most kind have made specific room for the practice. If we don’t have space to prioritize empathy or kindness and we try to say yes to everything, then we’re going to end up doing nothing very well.

That one’s been a big deal in my life to help me set more effective boundaries. That in combination with what happened with my mom and what happened with my relationship and what happened with my own health. I’ve lost track of boundaries. I’m seeing the byproduct with changing a lot way I do my work and what I say yes and no to, to create a lot more time for myself, my community and for my family. A paradigm perhaps changed was the second year I went to Burning Man. The paradigm that this whole thing is a grand experiment and that community is precisely what we make of it and precisely that what we decide we’re going to do with it. The most powerful thing of Burning Man in contrary to so many people’s opinion or idea of it if they haven’t lifted or experienced it, myself included is that we infinitely more than it is a music or an art festival, it is a massive experiment and community for seven to twelve days in the desert. Where people for a brief amount of time agree on ten principles.

Between that and some of the work we’re trying to do here with this thing called the Good Work House in Venice, it’s a reminder that the way our culture is simply determined by our daily behaviors. Those things are determined by our paradigms. It’s back to paradigms and priorities. Many of our paradigms are shaped passively. We get told what blank is and we accept it at face value simply because I don’t know if anyone’s offered us something else or the room to think about it differently or the tools to unpack that in a more meaningful way. If we get told that success is blank, then a lot of stuff we do in our life gets determined by that blank. It’s wild when you think about it. When our culture is convinced this is success looks like, the prestige of your job, how much money you make, where you live or how many followers you have on whatever platform it is. Think about how that changes your priorities on your life basis, so much that it’s determined by like, “Success is this. I need to get a job. I’ve got to do this thing.”

Your whole life, every priority of your time and energy, is determined by those paradigms. Burning Man is a fascinating example of what happens when you momentarily break all of those things. You get born into the desert in many ways, like the fresh start that doesn’t operate based on almost any of the rules that have been traditionally given to us. It says like, “Try it this way.” I’m fascinated by the premise of what that means in our day-to-day lives. I’m fascinated personally by what that does to confront my paradigms to say, “Why do I do the things that I do? Where did I get this from? Do I have any filters in my brain for all this incoming data and all the things that people say I’m supposed to be or do in my life? I don’t have any of those filters, what have I led in unintentionally that shapes every day of my life and what I prioritize?” I don’t know if that’s a paradigm shift or a paradigm revelation to me or it’s a blank slate of paradigms. The word paradigm has been coming up a lot often in my own life, in the work we do with CharacterStrong, simply because the paradigm with which we operate with shapes just about all of our behaviors. Our behaviors determine our individual life and it determines the culture of whatever organization or community we’re a part of. They’re a big deal.

I’ve been talking a lot about perspective as well and it feels like there are two different perspectives. There’s a perspective of the moment or the situation, but there’s also the underlying worldview or larger perspective all are synonymous. That one is the one that if we don’t have conscious control of our situation, we default always to that worldview that we’re operating out of. Which is why that is so crucial because the majority of times we default because we can’t be consciously aware of every perspective throughout the day. I don’t think that’s often anyways. For all of us, it developed from our inherited tendencies and our life experiences. That’s where we can have empathy. Other people are like, “They haven’t shared these experiences or born with these tendencies. There will be a difference and it’s okay. How do we find what’s helpful?”

[bctt tweet=”People do well when they can. The reason we behave in ways that aren’t ideal is we’re emotionally overwhelmed and we don’t have the tools.” username=”upandcomersshow”]

One of the things that I want to talk about is with CharacterStrong. One of the things that have been so impressive for me from the outside looking in and a little bit on the inside is what seems like a very sustainable scaling process. I think that’s rare for any company, unfortunately. From an entrepreneurial business standpoint, because from my knowledge don’t have an MBA or business school. It’s like a foreign world. It doesn’t make sense for you to be scaling a business, yet you guys have done an effective job. Can you give a little insight on what you’ve learned from trying to scale a business? What that process given you or even speak a little bit to that process?

One of the joys of working with John and the whole team at CharacterStrong is while we certainly measure a lot of metrics including numbers, profit and revenue. It is such a secondary pursuit for us. I literally don’t even understand most of the stuff. I can say this because we don’t have any investors or anything. We’re just doing it. It’s fun to celebrate the “wins” but one of our mottos at CharacterStrong is a chapter in the book, The Road to Character, by David Brooks where he talks about the story of this woman who coined this term serve the work. Serve the work is different than serving people because serving people is oftentimes driven by pity or a sense of like, “I have to do this,” versus served the work, which is the idea that we have work to do. The byproduct or the expectation of someone being grateful or getting a paycheck as a result of it is way secondary to the purpose of the thing.

One of the things that have ultimately made us effective in an industry that is incredibly relational is all we care about is the work. The work is equipping more teachers in schools with the tools, curriculum, content and resources they need to more effectively teach kindness. Our simplest, most high-level goal is to create a more loving world. We believe the best way to do that is through education. Just from a philosophical scaling process, we certainly have to think about the logistics of a growing organization, but we’re not attached to the physical results of it, which is so freeing.

It’s like, “Just do the work.” The work for us sometimes looks like a lot of weird travel days, showing up to conferences, flight delays and getting trapped in places. We show up and we’d do our best everywhere we go and try to build authentic relationships and be helpful or as Conan would say, “Be kind, work hard and amazing things will happen.” I think that’s part of the ingredient for us. I deferred it to John even more so. This guy truly serves the work and I get to witness that and try to live into that alongside him. The scaling of the message has been an interesting and fun process as well because for so long, I was a solo entity speaking and John was doing his own teaching and training himself.

He was an in-classroom teacher and an administrator and he was hosting local training. One of the scary parts of work like that is you are your brand. For me, I was the brand. There’s a level of ego removal in the natural process of transitioning out of that, that people aren’t booking Houston anymore. They’re booking CharacterStrong. That was an intentional and long process that I’m still navigating. Schools will email me like, “We want you to speak.” I’m like, “I think the better choice is for you to have this person come in because, A) I have things that I want to work on over here that look more like content creation. B) Maybe because I’ve done it a lot of times, it doesn’t necessarily mean I’m the best person to show up and serve your students or your staff.”

That’s been a beautiful part for me is working with people like yourself and other people who are part of the speaker squad to say, “You’ve lived incredible stories.” I have experienced telling stories. Maybe I can help you formulate that in a way that’s going to help or inspire kids. Myself and John building professional development models, we’re building content that educators get to go and deliver themselves. I’m good at storytelling and selling it on stage. I can articulate the why and I’m very passionate about it. I think there’s something powerful about having in-classroom teachers go and teach other teachers. We have over 40 people on that roster who in August of 2019 alone gave 120 presentations across 30 something states. That’s profound to me.

UAC 114 | Building Strong Character

The Servant: A Simple Story About the True Essence of Leadership

That’s beautiful that these teachers who feel passionate about this message have done the work to prepare for six hours of content or willing to hop on planes while also being teachers and go and deliver this content elsewhere has been neat. We’ve gotten cool feedback about how some of the best professional development people have ever received. I think it’s born out of serving the work and coming up in a world that’s incredibly based in experiential education and practical tools. That’s what John and I have both always been about. When we show up, it’s not philosophy or abstract. This is why but then here are the most practical ways to integrate this into what you do. We’ve kept it simple. We churn out content relentlessly. What we know about educators is they’re desperate for more tools in the toolbox. That’s all we’re doing and perfect is the enemy of good. We turn out stuff all the time that are experiments.

We’ve started a podcast for CharacterStrong and it is one of my favorite things we do. We have 60 episodes in a couple of months. John’s recording fourteen because they’re ten minutes or less and they’re not crazy highly produced. They’re not overly scripted. Some people have been world-class authors in their field and some of them are our classroom teachers at a small middle school. Both of those people have incredibly valuable insights to offer. We’re not afraid to just churn out stuff like that. I think that’s what’s allowed us to scale. It’s exposure therapy in some ways. People see a lot of our stuff and a lot of ways. I think we move fast and we’ve created models that resonate with people deeply enough and are simple enough to grasp, execute and make personal that the delivery of it was gone way better than I would’ve anticipated, which has been awesome. Our curriculum is all digital. We were constantly updating that as well. It’s been a humbling journey and a super exciting thing to watch from 0 to 100.

On the content side, how much do you do specifically within the content creation? Do you have a process that you’ve honed in on that’s helpful for you in creating and churning out that content for others?

I’ve realized that I think one of my gifts is the thing that I feel most drawn to. One of the best compliments I received from a peer in this work, he asked an interesting question. He came to one of our training and he sat with us at dinner. He goes, “In your niche, what do you think you’re the best in the world at?” which is a cool question to ask people. He’s like, “I have my answer. I’m interested to know if yours matches mine.” The compliment he gave us, he says, “In this business, I think you’re the best amalgamators. You take disparate information and you pull it together in a way that is super easy to digest and feels fun, engaging and relevant. You’re the best in the world at this.” I think that people like John turn out more like straight-up content than I do. I think my gift is creating the frameworks for that content to live in.

I’ve discovered I enjoy. My brain operates in a way that it’s like, “How do we take these complicated ideas or this pile of information and put it into both visually and conceptually an experience that people can understand and enjoy?” I’ve discovered I’m a bit more of a systems builder in that way, which I didn’t always think I was. I was a designer for a while and I was less good at the actual drawing of an icon versus knowing how those icons are plug-in. It’s more of user experience and user design. That’s what I’ve been working on. I helped lead the building of our elementary curriculum. Some of our characters dare, the ways that we put people into action, both students and adults, creating systems for people to process those in a way that it’s a little bit more accessible. Even our professional development models and building out new keynotes and workshops. All that stuff is I’m passionate about being a creator with.

I can affirm you’ve got a lot of gifting in ads. It’s impressive to see. As someone who is very good at asking questions, I’m curious what the question that you’ve been or that you’ve been asking others?

At a wedding, we got into the conversation of, “What’s the moment you felt closest to death?” It’s paired with, “What’s the moment you feel most alive or what are the moments that make you feel less alive?” is a nice contrasty question. My favorite question is, “What’s something that you want to do but know you never will?”

What would be your answer to the last one?

Perform a bank heist like an Oceans’ Eleven type heist or Italian Job. I’m not going to be robbing anyone, but I love the premise of tricky teamwork meets creative systems thinking, hanging out with a bunch of cool people that are all good at the things that they do. Bringing the best of the world together to do a thing, which I suppose we’re doing that with CharacterStrong with weird risk on the other side.

One of my favorite questions, a challenging one, but that I can see you enjoying, what’s a belief that you hold that you most likely to change your mind on or that isn’t true or right?

I think the thing that I will grow a lot on in the next few years is navigating faith.

What is your perspective on faith?

My perspective on faith is that it is the set of beliefs that we hold towards the things that we don’t yet understand or maybe never will understand. It is a source of hope. I grew up vaguely Christian in the Christian Church. My mom spent some time exploring Buddhism and then I grew out of the pursuit of faith myself. I probably held an unreasonably staunch perspective against Christianity in some ways, not explicitly against, but held some judgments around people that believe that way. I have found myself interested in the practice of faithfulness in my life. I’ve always been someone that doesn’t like to operate inside the boundaries of whatever box society is presented, organized religion I struggle with. Without organized something, you lose some accountability to the practice of a thing. Just trying to find more opportunities in my life to be held accountable to belief and to end do experience moments of humility that I think is only available to us when we acknowledge that things have more power than us.

That’s so important. I think we all thrive when we realize we’re part of something bigger than ourselves. That’s largely what faith is. Being a part of something that’s beyond yourself. It can take a lot of different forms. Even we were talking about with purpose. Is it bigger than yourself because that’s what’s going to help us endure through the inevitable hardships that we’re going to face? We didn’t get a chance to talk about a lot of things, but I’d be remiss if we didn’t talk a little bit about what you’re doing with the Good Work House and what your heart and passion is for Haiti.

This is a bit of that spiritual conversation to me in some ways. My dad met a guy named Jesse, a few years ago on an airplane. We’ve remained friends. Fast forward many years, he invited me to come to Haiti to see his brother’s organization, Haiti Partners in action. They had finished building the first floor of a school in a very poor area of Haiti called Bourjois. I got to go take photos and videos of these three and four-year-olds experiencing school for the first time without the perspective to know that they might not have otherwise had the opportunity to. They’re showing up because this is what they think is normal. The whole premise of Haiti Partners, its primary focus and its philosophy is helping Haitians change Haiti through education, which identifies so much with what I believe that education is the best way that we change the world and education is a human right that people need access to.

There are a lot of issues with the educational system in Haiti that is super broken. The real goal of the Children’s Academy, which is this school that Haiti Partners has built and is continuing to build, is to be a beacon of hope for what education can look like in Haiti. Because if we can’t see it locally, we’re never going to become that thing. They have some tremendous ways that they look about education and community involvement and family involvement. The way that they operate is so intentional and beautiful. Fast forward a few years later, Jesse invited me to be on the board of Haiti Partners, which is like, “I don’t know how to do that.” He’s like, “Just show up.” I have and it’s been humbling and beautiful to listen to these people speak into this nonprofit and the challenges associated with it.

Fast forward shortly after I joined the board, there’s a travel ban on Haiti because of some of the violent unrest happening there. For Haiti Partners, most of their long-term and most significant donors come from people that go and experience being there and getting to see the school. You get this challenge of how do you bring Haiti to people if we can’t go to Haiti. Jesse and his brilliance send me a link to this space in Venice, California where I live. He goes, “What if we rented this through Haiti Partners and tried to use it as a space to build awareness and advocates for the work?” I didn’t understand it at first, but I trust people and I’m like, “Let’s give it a try.”

In order to make it more accessible to people from an understanding perspective, we shifted it away from calling it Haiti Partners. We were like, “What do we want this to be about?” We want it to be about doing good in the world. We arrived at this name, the Good Work House. Our whole function is to try to be a source or a force for good in what we’d say is the creator economy, the people who live in this area who are making things and who are influencing the world in big ways. It’s evolved in an exciting way to be what I would call social houses that are more and more prominent. This is like a socially good house concept. Instead of just signing up to be a part of this thing so that you have access to network there and beautiful workspaces that some of these houses are, which I love. I’ve been a part of many of them.

How do we pair that with philanthropic pursuits? How do we pair that with not just self-serving endeavors, but how do we have that be a win-win? The premise is that if you join as a member of the Good Work House we have ongoing programming where we get together and all that programming, the only rule is it has to be good for you or good for the world. It’s wellness series, yoga, meditation and breathe work. It’s also documentaries and conversation series that point us towards doing good in the world at communal dinners, communal eating and intentional eating. You get access to programming, but your membership fee also pays for a student in Haiti to go to school at the Children’s Academy. It’s that one for one model that a lot of organizations have been using in the product space but we’re trying to do it for experience experiences. Building community around doing good while also giving student access to a community that they wouldn’t otherwise get.

That’s such a sweet model. And we talked about a little bit before, but I think that is such a missing piece in highlighting and utilizing incentives. Incentives are so powerful and they’re always present. Usually, they aren’t designed to be as helpful. They’re more designed to be profitable. How do we make them more helpful and less profitable, but we don’t need to eliminate the profitability side? That’s part of the process. How do we steer it towards more good and more impact? It’s sweet to see you pioneering a piece of that. I’m excited to see what the next season of that looks like for you and I can’t wait to see the impact you have. I always love books. What book or books have had the biggest impact on you?

The Servant by James Hunter. A simple story of leadership and a paradigm shift around servant leadership. Daring Greatly by Brené Brown. The way she talks about empathy and vulnerability I think is she’s the best in the world at it. I read a lot of fantasy and my brain operates through everything through leadership perspective. I love fantasy for pleasure reading, but I also find a lot of fantasy books like Oathbringer Series by Brandon Sanderson or Patrick Rothfuss’ The Wise Man’s Fear. Books like that beautifully articulate a whole new world, which is incredible. That sense of wonder and imagination is a beautiful thing. No matter what world you’re in and no matter what ingredients, races or make-belief things you put into it. All these worlds there are people that show up and are trying to break things and there are people trying to fix things. I read those things and I always think to myself, “I want to be someone that helps.”

Imagining your 50-year-old self, what advice do you think you’d give your current self?

You’ve got time.

If you could send a morning text reminder to every up and comer out there that get this every morning on their phone, what would you say and why?

Only because it’s played a role in my life, I have seen it in an important moment is you’re exactly where you need to be.

Houston, thank you for taking some time. This has been awesome. This has been meaningful to be able to throw us down finally. Where’s the best place for people to reach out and learn more about what you’re up to?

CharacterStrong is where I’d love you to look and explore first to see what we’re up to in schools. If that resonates with you at all, that’s or @CharacterStrong on Instagram or on all the social media you can find us. Me personally is @HoustonKraft and the Good Work House. The best place for that is probably Instagram where we share a lot of the stuff that we’re up to. If you’re interested in learning more about that community, you don’t have to live here to be a part of the community or sponsor a kid to go to school. You can learn more about that at @GoodWorkHouse on Instagram. It’s a cool thing. You should be a part of it.

Until next time, this has been such a blast. Thanks again for sharing so much to think about and to hopefully take home.

Thanks, Thane. I love you all.

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About Houston Kraft

UAC 114 | Building Strong CharacterHouston is a speaker, curriculum developer, and kindness advocate who has spoken at over 600 schools or events internationally. He was inspired to do this work at a summer camp in Washington State in 2006 and has served on the camp staff ever since. In 2016, he co-founded CharacterStrong – curriculum and trainings that transform the way schools teach the Whole Child through social-emotional learning, character education, and equipping educators with practical tools to create a compassionate culture on their campus daily. To date, they have worked with over 1200 schools globally, serving over 1 million students. In 2019, he co-founded the Good Work House – a community focused on meaningful conversations, intentional programming, and connecting people with non-profit organizations. He recently found out he likes black licorice and was once invited to play on the JV National Lasertag Team. His mom is his hero and her best life lesson is to “hug like you mean it.”

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