Scott is a compass helping advancing difference-makers lead themselves and live their legacy. He’s Creative on Purpose’s Chief Difference-Maker and author of the Amazon top-sellers Endeavor and Onward. Scott is also the head coach for Seth Godin’s Creative and Freelancer Workshops.
He crafted a brand called Creative on Purpose and a book called Endeavor. Through these enterprises, Scott helps people discover, develop, and deliver work that aligns with who they are, leverages what they’re good at, and serves those who share their values and need their talents to enhance their lives.
Scott is a husband and father, goes for a cemetery run every day, and quotes Marcus Aurelius more often than he should.
For over thirty years, Scott found and spread joy as a professional musician and guitar teacher while maintaining a happy marriage, homeschooling his sons, and taking care of business.
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Scott Perry Journey From Professional Musician to Creative On Purpose
Hello, everyone, and welcome to another episode of underdog. Today I have an amazing guest here with me, Scott. How are you?
I am doing really, really well. Even better now that I’m spending this time with you. Pamela, thanks so much for having me.
It is such an honor to have you here today. I’m so thrilled to talk about the amazing work that you do. And also your amazing book that you’re launching super soon. Which is super exciting and I always start off with the most loaded question. What inspired you on your journey to where you are today?
In a way, I think I’ve always been, even from a very young age. Very interested in what we now call personal development. Just this idea of developing my potential and delivering on my promise. I had many inspirational teachers as a young man. That made me want to always pursue better in myself. And in the circles that I moved in. I would say that a real pivot for me in my adult life. I’ve had several pivots over the ages that I’ve done many different tags. But in 2016, I took a program of South Dakotans called the ultra MBA.
And that was a moment that made me decide to switch lanes. From being a professional musician and guitar teacher and moving into the domain of coaching and community leading. It took several years for me to develop the brand and develop the traction and the audience to turn that into my full-time endeavor. But at the end of 2018, 2019, I closed down my performance career at the end of 2020. I closed on my guitar studio, this is what I do now. So it was really that very impactful program that showed me. It reacquainted me with my love of writing, my love of working with other people. And my desire to have as much impact as I’m able to have. You know, that I’m into the second half of life.
I love that. And I always ask this, it’s so interesting how they always correlate. What did you want to be when you grew up?
Well, I don’t think I had any childhood aspirations to be an astronaut. Or a cowboy or any of the usual things of my generation. Honestly, I grew up very close to where you live and my father was in the service at first. And then, he worked for the telephone company, back. When it was a monopoly and we moved around a lot. And that caused me to always be like the new kid in the class. That manifested in kind of acting up behavior. I think it would be kind to say that I was definitely a juvenile delinquent and maybe headed towards juvie. As we say, in your neck of the woods and my parents. When I was in the seventh grade, I kind of saw that if they didn’t do something. Things were not going to go well for me.
And it turned out that across the street, from where we lived. Was the headmaster of a really small little private school, that was in the town. They asked him if there’s anything that he could do to help me attend a school, where there was very small classrooms and very inspirational teachers. I got to manage, to get a scholarship, and get in that completely changed my life. Because I went from being someone who always tried their best to do the least amount possible just to get by. And to stay humble and hiding and unseen to be someone who was eager to raise his hand and eager to learn more.
One of the stories I always tell is, in seventh grade. We got introduced to several different languages and one of those languages was Latin. My Latin instructor would translate Marcus Aurelius’ quotes from Greek into Latin. And then have a stroke-like them from Latin into English and I used to love doing those, so much that I would ask him for more. Finally, he said, Listen, quit bothering me, kid. Here’s a copy of the book, just read the book that inspired me to want to be a teacher. And so when I went to college, it was actually initially to be a classicist. Or to teach classics and I ended up becoming a history major instead. When I first left college, I was a school teacher for several years.
So it’s interesting how that school kind of changed you a little bit. And was it a particular mentor or a teacher that really transformed you in that space? Because that seems like a really serious transformation. You know, from going to a kid that was headed to juvie to loving school and just kept turning it all around. So was there a particular person there?
The middle school met in a separate building and we only had two instructors, two teachers. One of them was a long-term teacher of mine. Because I pursued Latin all the way, through my four years of high school. And another was, that did not end up teaching there long term. But was my English teacher and taught some other things. There were seven kids in the classroom, there was no place to hide. That was a big deal for me because I was used to sitting in the back and keeping my head down. And to the point where at parents night, when my parents asked how I was doing, none of my teachers knew who I was.
That’s how good I was at staying humble and hiding and not being noticed. So it was just really, I mean, it was almost like the Robin Williams character and Dead Poets Society. That’s how inspiring these teachers were in my life and so it was literally just. And I had other teachers in high school and in college. Then mentors along the way beyond that Seth Godin who created the alt MBA being another one of them. And then I always had Marcus Aurelius, who has been a lifelong influence on my work. So yeah, it’s all really due to the luck of winning the teacher slash mentor lottery and having parents. That put me in a position to be with those people, for sure.
That’s incredible. I always say teachers are God’s angels on earth. Like they can be serious at the point where you were in your life. Where you it was either juvie or turn things around. Like, they have that type of influence. So powerful, especially in the middle school and high school years. That’s when your life is really defined in a way. You could really screw yourself up, or you can really line yourself up the right way. And it’s like, which route will you take and honestly the teachers and the schools are a huge part of that. I know, for me I was in public school until I was in seventh grade. Those seventh grade.
And I transitioned from a public to a private school and much, much similar to you. Got into that private school and from there, I totally turned around In public school. I was very shy, very low-key, I didn’t really want anyone to know, I was like, a really shy kid and nobody believes that now. They’re like, there’s no way you were shy ever in your life. And so, going to a private school where you like, I felt valued. Like, I felt they could see me like I’m a person.
I’m here too and my teachers really brought out the best in me. And that six months later, I’m running for class president. Going from the kid that was like hiding in the back. Transitioning into, like leadership and just building who I am today. So, which is so crazy, it’s just insane. How teachers can play that role. And you know, that you shifted into that sort of thing shortly thereafter.
I don’t know if it was like this for you. But the other thing for me, in all that was my parents, invested in me, like my parents actually had to sacrifice. I mean, I did get scholarship money, but it was not a full scholarship. And my parents were typical middle-class parents, I mean saving for college and putting their kids through six years of private school before then. Was definitely a sacrifice and a burden. And I felt that like going into the starting like, okay, I better make good on this. Because my parents are sacrificing and investing in me and I’m going to do the best I can, with this opportunity.
100% Yeah, my parents, I mean, they owned their restaurant at the time and saw, like they weren’t rich. But it was also still pretty expensive to send me to private school. Starting from seventh grade all the way through high school. So just like you six years and then college and all that. Luckily, I got almost a full scholarship to college, I actually paid less for college than I did for high school. Which is crazy, so that investment was huge. But it’s like you feel like this responsibility to your parents. I need to do well so that they make their investment worth the ROI.
The ROI on the investment, but on the intellectual side, you just can’t. What the schools can bring you, it’s just like in a smaller setting, you’re just a lot more personal, which is so cool. I love that and then you transitioned into teaching, which is remarkable, and into history too. What sparked your love for history?
One of my teachers in high school was a history teacher and he was a real inspiration. In fact, it was my very first teaching job, so this teacher moved from the school that I went to another private school in Connecticut. And when I was graduating, I connected with him and he helped me get my first teaching gig. At this other school where he was then teaching and I loved teaching. Yeah, and I still consider myself a teacher. Even though I’ve closed my guitar student, I’m teaching coaching that is just human acts. Teaching is something you do on purpose to lift people up.
And sometimes the best teachers are the ones that have a negative impact on our life. But we learned from that experience, kind of almost what not to do. Or earn resilience that I experienced, but I had a really positive experience for the most part. As a teacher, there were definitely things that made me move away from teaching in addition to spending the time in the classroom and all that. There’s just a lot of BS as there isn’t any institution organization. When it comes to hierarchy and administrative stuff and politics and that sort of thing.
And at the three-year mark, I was kind of balancing like. Okay, I like this part of it and I don’t like this part of it. If I decide now that’s kind of statistically, the three-year mark is when people either get out. Or they stay in for 30 years and I was like, I think there’s other things that I could try. So that was my primary reason for leaving teaching. But again, I was a teacher on stage as a performer in the studio as a guitar instructor. I homeschooled my two sons all the way through high school. So teaching has always been a part of who I am.
What Inspired Scott’s Music Side
I love that. And the music part, what inspired that side of you, too. That’s amazing.
So when I went to college, I had a partial scholarship, a football scholarship. And even though I was going to a division three school. Where you would think that athletics would be in its rightful place, kind of secondary to academics. There was a lot of pressure to do things that were out of alignment with who I really was. So after a season of playing football and being really miserable, like in high school. I loved playing football and I loved everything about it. At the college level, I learned to hate football and everything about it.
I had for the first time of my life, I had like these. This three-hour hole in my day was normally filled with either practice. Or the weight room and I had this guitar under my bed and I just decided. I’m gonna find, I’m gonna learn how to play this thing. I took that guitar, I took a recording that I was listening to that I really liked and I went to the music department. And I literally knocked on doors and all the instructor rooms and said, Hey. Can you teach me to play like this? And another mentor appeared, my friend, Carl Demo. Who I’m still in touch with to this day, I said. Yeah, I can teach you how to play that.
And I took lessons from him for four years in college. We remained friends to this day and still when we get together, play music together. But again, as a teacher and as a performer, he really showed me what being a musician really is about, which is not about fame and fortune. It’s about serving the song and about presenting a gift to an audience to enhance their experience. And so after my teaching career, I bumped around doing a couple different things and after my first son was born, I thought. I’m ready to give this, I’m going to try this, I had a long conversation with my wife and I said, I want to give this a go. If I don’t do it now I’ll never do it. Because we wanted to have more children.
I knew that was gonna bring more responsibility. So I said, here’s the deal, I’ll do it for a year. And if I’m making enough every day to do it again, the next day. I’ll continue to do it until I stop making enough to do it the next day and I’ll just get another teaching job. I did that for 30 years and because my family was important, I spent some time on the road doing a lot of touring. And decided that was not the life that I wanted to live. So I was able to carve out this career playing mostly locally. But playing in the best possible gigs, for the highest pay with the best players. Doing the teaching on the side earned a living, I wouldn’t say it was a great living. But we bought homes, we bought cars, we put our kids through college.
And I had an incredible career, you know. Most musicians are not going to be Bonnie Raitt and even then not very many people earn a decent living. That allows them to keep a marriage together and maintain a family and all that. So I just feel like I was incredibly lucky and I also took it really seriously as a profession and as a craft. But also I just had fun every single night that I was doing it and I did it until it stopped being fun. And then I just decided that it was time to switch gears.
I love that. And you just recently made that transition, right?
About three years ago is when I concluded my performing career. And just at the end of last year is when I shut down the studio. We had moved from the studio to online, again, very lucky. Almost all of my students moved online with me and the ones that didn’t. I was able to replace, but my coaching and community and my work with Seth Godin has, towards the end, I was working what felt like three full-time jobs. And I am capable of working really, really hard.
But three full-time jobs for a period of three years was a lot. And so it just felt like time for me to conclude the whole kind of musician phase of my life. There’s a lot of sadness, obviously, because I really had worked with wonderful students and became almost adopted by many, many families. I made a real impact on this community and at the same time. Because I had done good work and because I had given myself fully, I was able to also close that part of my career. And we all shed a few tears, but it’s not like I’m going anywhere. So we’re still friends and neighbors.
I love it. Thank you for sharing that. Because some of the hardest things to do, you know, as I know. There’s entrepreneurs listening that may be struggling with this and learning to accept when it’s time like that. Like I remember my first business, I had two restaurants before I got into real estate development. I held on to them for a while until I sold and leased them and it was just like. Holding on like it was your babies, right? And then, like you just couldn’t, I couldn’t give it up.
Like I finally it just something is I was like, Pam, you cannot advance any further and impact the world. If your cup is empty, you need to let go. So I’ve just been interested to note for you, what was that transition period like. And for any entrepreneur, anyone out there who’s listening. That might be going through something similar, holding on to something that really should be, like kind of how you walk through that.
I think what we’re talking about is sunk costs, I mean, there’s. You know, I invested fully in being the best musician I could be. And hiring the best musicians that I could afford and that were available and playing the best venues. That would give me the privilege of playing there. When young people say, how did you do it? How do I do it? I want to do that, I always remind them like two or three hours that you spend on a stage. If you’re kind of a local hero-type musician or an hour on a festival stage or showcase. You know, that’s like 1/10 of the time that you’re putting into the business of being a musician. Because there’s all the phone calls to book the gigs.
There’s all the travel, there’s all the band management, and everything that goes along with that. I tell people don’t do it if you don’t. If you can not do it, don’t do it. Do it on the side, have fun, let it be your hobby. Let it be something that you just do for the pure joy of it. For me, I just couldn’t do it every time I tried twice in my career to just put my guitars under the bed and say. Okay, I’m gonna go back and get a straight gig. On both occasions, my wife said, haha, I’ll give you two weeks. And within 10 days, I was back on the phone hustling gigs and putting things together.
I just couldn’t do it until there was a moment where I realized, I feel like I’ve written this pony. As far as it’ll take me I’ve had a blast. Yeah, I’ve got 30 years invested. That was. That’s a sunk cost, that’s a gift from my former self to my current self. And I’m going to thank my former self for the 30-year journey and I’m going to say goodbye to that for now. I’m going to pursue this other thing and just see where it takes me. So I think I was having a conversation with Jacqueline Novogratz. On my broadcast about this.
Jacqueline is the founder of the acmin fund and wrote a fantastic book called the manifesto for moral revolution. And she was talking about reinvention and I think men think about this a lot too, like. Oh, I reinvented myself from juvenile delinquent to high performing. Student to student-athlete to teacher to a restaurant manager for several years. To musician to and now, kind of coach and author. And then I thought, Oh, actually, that’s not reinvention. That’s just me becoming who I’m going to become. Because all the way through that. As you know, we’re talking about earlier, I’ve been a teacher, I’ve been a coach.
I’ve always been a person that helps people get from where they are to, where they want to be. And sometimes that’s by being a teacher. Sometimes that’s by being on a restaurant tour, sometimes that’s by being a salesperson. Or whatever it is, but it’s just this long journey and becoming. And Jacqueline is someone who’s had a similar series of adventures. That doesn’t seem very connected at first blush. But when you look at the through-line you can see. So it takes a lot of self-awareness and self-reflection, but also some courage. Because if you’re going to break something that’s been working for a long time. So that you can become a better version of yourself and do better work with better clients.
You have to break what you’ve been doing, what got you where you are. Won’t get you where you want to go and I’ve known that for a long time. Just from my musical adventures and so for me, it was not a hard thing to say, I’m done. It’s been fun. Thank you very much and now I’m going over here saying that said, I’m a freak. And for most people, sunk costs are real anxiety-ridden thing that’s very hard to let go off.
Absolutely. And this is a perfect segue into your book called onward. Tell me all about that.
So when I had my kind of that moment of transformation in the alt, MBA, and August of 2016. I knew I was ready to let go of my music career and my teaching career, I didn’t know exactly what I was going to do next. And I knew it was going to be around creativity and my lifelong study of stoic philosophy. I didn’t know what to do with it. So I literally just started blogging and broadcasting about what I was building. Even though I didn’t know what it was that I was building. And those conversations and all that writing helped reveal what is now creative on purpose. I’ve written several handbooks now.
And onward is a follow up to my previous Amazon top seller, which was called endeavor. Which was all about discovering the meaningful work that you can and should be doing. Not necessarily as your job or occupation. But it can be a passion, project, side, hustle, vocation. Whatever onward is about the mindset and posture of a difference-maker. Someone who embraces uncertainty and navigates adversity. And understands that work that’s worth it is always fraught. But you can still cultivate joy, even as you lean into the inevitable challenges and the trials and the tribulations. Because you can be unattached to outcomes beyond your control and fully invested with intention and integrity and effort.
And it’s a book about learning something that’s been part of every spiritual and philosophical tradition that I’m aware of. Which is you can’t control outcomes. Even though in the United States, we love to think that all of our success is due to our genius and hard work. There’s lots of luck and quite a bit of privilege involved in that too. But when you pay attention to the work that’s right in front of you and you put your best efforts for. Then you do the work with an intention and staying true to yourself and your values, then generally good things happen.
Even if you don’t get exactly what you want, you’ll get some great work. Because you are doing your work on purpose. With purpose for a purpose within the right people. And when you’re doing that, good things are going to happen. So onward is just a book about cultivating that kind of posture and mindset that will help anyone that’s ready to lean in or level up in an endeavor that matters. Do so with less stress and a little bit more joy.
I love that. So what would be some of your Sneak Peek top tips?
So the book is actually a retelling of three principles of stoic philosophy. The disciplines, three disciplines, the discipline of perception, the discipline of action, and the discipline of well. Book gives you a process of three, just to answer three questions, what’s now, what’s next? What’s it for now is what’s really going on. Not the stories you’re telling yourself and the lies, you’re telling yourself. About how everything is so unfair and how everybody’s conspiring against you. But like, objectively without any strong emotional attachment. Without any value judgment, what’s actually going on.
And when you can do that, then you can see the possibilities and the choice. The real choices ahead of you and leads you to the discipline of action. Which is making the best decision that you’re able to. Because you know that decisions are not attached to outcomes, that decisions are just decisions. And any decision can lead you somewhere good or somewhere bad. But it will always also lead you to an opportunity, to make another decision.
So it’s about making the best decision that you’re able, then to act on that decision. What’s it for is to understand that since the results are not guaranteed. And you’re certainly not entitled to any outcome. It’s all about the quality of your effort and the intention and integrity that you bring to the process. And if you can do that, you will always have a sense of fulfillment and prosperity in the work that you’re doing. As you continue to lean in and pursue excellence in whatever your endeavor is.
Love that. And how long has this book sort of been in the works?
I published in November of 2020. Thanksgiving Day in the United States is my favorite holiday. And it’s the second time I’ve published a book on Thanksgiving Day for no good reason other than. It’s my favorite holiday and it achieved the best new release in five or six categories. Still selling really well to this day, It’s become one of my online courses of creativity on purpose. And it’s my latest billboard. I don’t think of my books as obviously making money, but I don’t think I’m going to ever retire on my publishing income.
But each book is sort of a calling card and a business card, for what I’m doing now. And so onward has become what I talk about when I do speaking engagements. It’s become a workshop that I present online, for corporations and institutions. But also for just individuals who are interested in this idea of how I can find the intersection of who I am. What I’m good at and where I belong? And how can I craft an endeavor that will help me forge meaning? Bring full fulfillment and build identity and help me do what we call our creative on purpose life. My legacy Isn’t what you leave behind. It’s the difference you’re making right now.
I love that. Legacy is what you’re building right now. I think that that’s so impactful and profound.
So thank you, it’s been a very resonant message. And probably the most often quoted line from the book.
Really, oh, man, that is just like speaking to me, right? When you said it, because I’m like, most people think legacy is what you leave behind. And it actually can be framed, like you just said, what are you doing now? Right? What are you making now? And these are questions.
You know, as an entrepreneur, people don’t buy what you do. It’s not the features and benefit people by the way you make them feel and the experience that’s on offer. And so it’s not if you leave behind a building with your name on it. Or a statue of yourself somewhere, nobody’s going to give a rat’s behind about that. But if you have had an impact on the culture, even just within your community or neighborhood. If you’ve made a difference, you know. That was one of the reasons why when it’s teaching guitar, it was like, okay I’ve really had fun being a performing musician.
But I don’t think people are going to be pulling my CD off the shelf 20, 30, 50 years from now. And play me on the radio, but I had this opportunity where if I do it long enough. I could create hundreds, if not 1000, guitar players and that will make the world a healthier and happier place. And so for almost 20 years in this little town where we live. That’s what I did and I easily over the years, created hundreds of guitar teachers, many of whom are creating more guitar players.
And so this thing that we know, scientifically, neurologically, psychologically. Making us smarter and happier is rippling out. You are talking about return on investment. My friend and I are playing around with other options. And I’m currently playing with ripples of influence and ripples of impact and that’s what matters. Not how much you know, how much capital I’ve amassed and I’m going to leave behind, it’s about. What’s the impact? What’s the difference that I made while I was here?
I love that, but I love it so much. And I mean, what I find so amazing about that, too, is that ripple effect. Sometimes we could feel so small in this big world. But what we don’t realize is how much we’re all bonded together. How one action that you can make can truly make a difference in change. So when we’re thinking about these major life decisions, it’s your book that. I think it is really going to help people get in alignment and live a more fulfilled life.
Because if you’re thinking about all these things. And you become self-aware that like, wow, because I did this, it affected someone this way. It has this giant ripple effect, then it might change the trajectory of their career. Which you know, their life path, which is so exciting. So I’m pumped for you, my friend. Now one of my favorite questions is based on everything that you know now. What would your older self tell your younger self?
I love that question. It reminds me a little bit of another show that I was asked about. What would you do if you knew you couldn’t fail? I just thought, oh, that would be I would never want to know whether or not. If I had an opportunity to go back and I just, I don’t think that life can be reversed engineered. And I think every path that could have been is a path that can be filled with prosperity and fulfillment and joy. Even when there’s a lot of challenges and when the way is very fraught, I think if I stop beating around the bush and answer your question. And I think I would just tell my younger self, keep showing up, keep doing your best.
And just keep going onward. There you go, keep going onward. I love that. And you mentioned your book, but what else are you up to these days? You might have some digital courses and some programs that you’re offering. So what is Scott up to these days?
So right now, about a third of my day is dedicated to being head coach for a few of Seth Godin’s akimbo workshops. Akimbo workshops are now an independent B Corps. But the workshops that I’m head coaching with Seth Godin is the featured instructor. And so right now I’m head coaching the creative workshop and later next month. I’ll be head coaching a freelance workshop. I love that work, Seth Godin obviously has a much bigger platform and megaphone than I do. And so I am getting to have an impact at a scale that I would not be able to have on my own by being a coach in his programs. I really enjoy that work and I’m very grateful for the work that I get to do there.
The other two-thirds of my day, I am spending with my coaching clients in my community at creative on purpose. I’m what I call, I’m a compass for advancing difference makers, who are ready to live their legacy. So I work with a lot of freelancers and a lot of executives that are or professionals that are approaching. Or at retirement and are ready for that second act. That’s going to be where they make instead of the status and the money. They’re ready for having some influence and living their legacy.
And those two things keep me plenty busy. But I’m still finding time to blog a couple times a week and broadcast every week. And definitely have my next book kind of percolating in the back of my mind. So if anybody wants to keep up with any of my adventures, creativeonpurpose.com is the place to go. You can sign up for a free mini-course called make a bigger impact by making better decisions. It’s basically a very distilled version of what I teach onward just about how to be a more decisive and intentional change agent.
And now, Scott, where can everybody find you?
creativeonpurpose.com, all day long. I’m there all the time.
Thank you so much for sharing your story and the amazing work and everything that you’re up to Scott. Truly is an honor to have you here today. And I’m just pumped to see what comes next in your future and just all the amazing work that you’re doing. Thank you for bringing that.
I appreciate the opportunity to talk with you. You’re a great interviewer. But I also had been checking out the difference that you’re making. And I want you to know that the work that you do matters, it’s making a difference. It’s deeply appreciated. I think it’s people like you and people like me, at the grassroots level. Doing this kind of impactful work and making a difference peer to peer. With and for the people we find ourselves with. This is how we’re going to make things better. Just grateful for the way that you show up every day and make the difference that only you can make.
Tune in to the episode to hear the rest of my incredible interview with the amazing Scott Perry.
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