Embracing Entrepreneurial Transformation with Ryan Barton

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I am so thrilled to bring you this conversation today with Ryan Barton.

Ryan as an acquaintance for some time. He went through the Calling Course with me a little while ago and has just continued to impress me with the way that he thinks so deeply about his work and the business that he’s leading.

He thinks deeply about work.  We just could just plum the depths of work philosophy together. And this conversation is just such a blast.

We talk about really center in on this idea of the transformation that’s required in you in order for you to become the next iteration of yourself, in order for your business to continue to grow and to succeed, to lead people where you want them to go. To take an organization, to grow it to its next level, you have to embrace the transformation that comes along with it.

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Resources Mentioned:

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Software Generated Transcription:

Dan: Thank you so much for joining me. As I’ve already said, like I, I just know that this is not gonna be the, the last time that, um, folks on the podcast um, hear from you cuz I feel like there’s just so much we have to cover.

But welcome to, to The Meaning Movement Podcast. So great to have you on.

Ryan: Well, thanks Dan. I’m so happy to be here and be with you in this space and really looking forward to the convers.

Dan: I love it. The question I like to begin with is how do you begin to talk about the work that you do?

Ryan: Ooh. It depends on who’s asking, and I have a very thoughtful ask here today. So I would say that I talk about my work as a creative expression that flows out into the world that takes a few different shapes. My primary current day job is as CEO of a company that I founded. 18 years ago now called Mainstay Technologies.

We essentially serve as clients. IT department, a company that grows steadily every year, about 80, 85 staff. Today we’re primarily Northern New England focused. Um, but then I also have my own projects that are spinning up and growing. Now that I know we’re gonna, we’re gonna get into.

Dan: I love it. I listened to, um, an interview that you sent over another, another recent, um, podcast interview you, you’d been on. I’ll make sure to link, link up to it in the show notes. But one thing that, um, you know, I, I know of you that, but I, I’ve seen you in a different lens, I guess, than, than maybe you were the seat that you were in on that show, which is like, as the, you know, CEO of, of a technology company, and I feel like you really defy a lot of the.

Stereotype, at least from my experience of of of the kind of person who’s, you know, running it. Um, I don’t know. I guess I just wanna ask like, how do you think about that?

Ryan: Yeah, I, I, well, I, I think about that a fair bit. I think my journey has been non-standard and a non-standard journey gives such a wonderful lens to both grow into what maybe the standard journey is. And there have been times in my life where I’ve sort of been too proud of that non-standard journey and like, I don’t need to learn from these business people.

And then I’ve, I’ve learned the hard lessons that says No learn. Um, but it also gives a great perspective to criticize and maybe call, hire and call in different ways. And so business for me was not a planned journey. You know, it started as a teenager. I happened to be that kid who loved technology, just was always good with it.

Building computers so I could play video games when I’m nine, 10 years old. And then building websites for hire as a teenager. And then I started getting calls from organizations and I was 19, 20 years old, and these businesses and nonprofits started calling and saying, can you help us? And I happened to be at this intersection.

Good with people. I genuinely cared about them and I was good with technology, and so I would be able to fix their challenges and help guide them, and that intersection opened up all kinds of doors for me and ended up becoming a business.

Dan: I love it. And what I, um, I don’t know. Uh, well, so I’m filtering this through my experience. Um, you know, think we, we both share that we are homeschooled. I have an older, older brother, which I don’t think we’ve talked about. My brother, he’s a, he’s a CTO of a, of a tech company. And like, I, I could see it feels like, like his path is so parallel to yours.

Like I could see him in another reality. Just a, just a couple. Different and he could end up in a very similar space, um,

Ryan: Yeah.

Dan: to, to what you’re in. But like what a long, a long commitment to continuing to, um, yeah, down this, this particular path around technology. And I wonder how much of it has been intentional, how much of it has just been like, well, here’s the next step, here’s the next opportunity ahead of me.

Ryan: Yeah. You know, in the beginning it really was like, here’s the next thing, and then I think what’s so interesting is that we come to our work. So much because of our stories, right? It’s this combination of our giftings and our expression in the world, and then our stories of upbringing and what’s honored and what makes us feel good.

That’s based on that emotional patterning that comes as we grow. And then also what opportunities are in front of us, and sort of at the intersection of that is what Birth mainstay, which was that, you know, my. Emotional story as a homeschooler and, um, in my family, my job was to sort of hold everyone else’s emotions up and to take care of them and to so them and make sure everyone else was good.

And that was when I was okay and could go and do my things. And so, and then what? My things were homeschooled, very few friends. No, you know, we were not involved sort of in community stuff. So what, anyway, I went in the room and I played on my computer. And so then that, I went out and immediately began serving people.

And there technology’s a place that most people have a great deal of worry. You know, you’re business leader, your CBA firm, you’ve gotta worry about your client, and then you don’t know about security, disaster recovery, all these things. And it’s a great sense of worry. So I would go in and very directly tend to those emotions and carry that worry for them and say, let me deal.

With these skills that I was able to hone as an autodidact. You know, growing up homeschooled, learning how to teach myself, that works very well in technology. And then that just created opportunities and it was after a couple of years, I. Did technology work part-time for a while and then contracting in my own clients.

And then I kind of had this crossing the Rubicon moment where I was offered a job in the field and it was like, am I gonna do this as a business or am I gonna do this myself? And I, when I turned them down, as I drove back on the radio, foo Fighters was playing and it was the song, there’s no way Back from here.

And I remember pumping my fists and I was like, I’m doing this. Like this is a business. And so, yeah, that was a few years after, and it was like a year later. We had four, I had four team members. From the solar to the ensemble, and then it just, and you know, it’s a service business, so very low barrier to entry.

Anyone can say, Hey, I can fix your computer. Just gimme some money. Uh, it’s hard to scale a service business, and so it’s been a lot of work. Then transitioning from that into being a business leader and actually learning how to do all the structure and systems and process to, to scale a real business.

Dan: Yeah. And you’ve scaled quite a bit. Like how, how big is the team right now?

Ryan: Yeah, so it’s about 80, 85 folks. Um, we like to scale about 20% a year. That’s our goal is to fairly consistently, and some years are more consistent than others, but overall our average is 20% a year because that’s a good growth rate for us. But we can keep the culture, we can keep the quality high. We can, we can do things to make sure we’re doing really good work.

Dan: Yeah.

Ryan: It’s not a kind of business that you can have hockey stick scaling, you know, like a software.

Dan: yes, yes. Um, well, I, I think what’s just, it’s just so crazy to me to think about just that trajectory of going from you in your room with your computer to. Now, you know, 80 plus in scaling and just how many different skill sets you’ve had to acquire, uh, along the way. And I think of like how, how many different iterations of you you’ve had to

Ryan: Yeah. Well,


Dan: take the company to like the next, the next, like, cuz cuz every time, and I think you, you, I’m sure you could even name some very specific moments of like, okay.

in order to go to the like, get off this plateau and keep growing. We have to overcome these, these challenges. In order to do that, you have to like

Ryan: yes, yes. Oh.

Dan: so yeah, tell me

Ryan: so, yeah, sorry to interrupt. I’m so excited for the question. I, I’m stepping on your toes here. Yeah, I, I, I think you’ve nailed it so well and said it so well that one of the things that I have most appreciated about being able to be an entrepreneur and then I think I’ve realized that all good work done right has this, this characteristic is that work is not just transactional.

You know, we can often think that we exchange time for money and it’s transactional, but work flows out. And it connects us to the world and it roots into us and into the world in this way that then causes us that like, if we wanna see something more happen in the world, we have to grow and become something else.

And that the more open we are to the call of work, the challenge of work, the discipline, the things that’s, that’s involved, the more that we can grow into who we are to who we can become. And for me, I mean, I can’t tell you, I mean, there. Probably one of the biggest moments that stands out is we were about 35 people.

And up to this point was like, I was great at sales, I was great at recruiting. It was great at making sure we had a great culture. And it was like, let’s just go, go, go and this is wonderful and we’ll be at 200 people in five years and what’s the problem? And the wheels started falling off. I mean, it was like challenges, quality issues, people quitting people, and all the mojo left the halls right?

It was just like a. And we realized, shoot, we don’t have a lot of the process, the systems, the training, the hr, the structures and components for us to scale this well. And I had to wrestle with the fact that like, that’s cuz of me like, like the organization. Was in my image. I mean, a founder casts a very long shadow.

You can sit with any organization. And it was very much in the shadow of my strengths and weaknesses. And you know, at first I was like, well, I’ll just hire people who are strong in the areas, the where I’m weak. And it’s like that only goes so far because you really, as a leader, have to know enough to know how to hire, how to lead, how to recognize those people.

And I remember a moment very clearly where I had tried to put somebody in place to fix it, and it just got worse. And it was like the culture. Awful. And I had to let the guy go. And basically I said, okay, I’ve gotta do this. I’ve gotta grind out the things I don’t want to do, and I’ve got to actually buckle down and become some different kind of leader.

Because you know, Dan, I’d really bought into the lie that if you love, what if you. If you, um, you know, find your passion and what you’re meant to do, that you’ll never work a day in your life, right? That whole, like, you just love it. You’ll never work a day. You find that thing. And I thought, oh, great. I get to be that entrepreneur.

I’m successful enough. I got all these people like, and so then I started gravitating towards what I liked, and that got me really skewed away from what I needed to do. And it was in the discipline of what the. Called me to that. I actually grew up a level, like it wasn’t just like I grew better at that level.

I was actually able to grow up a level to see things differently, to become different and the, and I think work always has that hidden call in us to a higher level.

Dan: Oh man. That is so, so much good stuff in there. Um, and like, just, uh, just the, the. The, the work, you know, that you won’t work a day in your life. Um, that narrative, it’s such a, it’s such a, a trap in, in so many ways because, um, because we want that and, and to some, to some degree it’s true like that in the meta narrative.

Like, I’m not allowed to use that word. I have been specifically told, I can’t use that word. When you zoom out and look at the full story of, of where of that your, that your work is telling, you could say I’ve enjoyed. The places that this has taken me and, and the, the direction that it’s taking. But when you zoom in to, I don’t know, you know, whatever the question is, I don’t know how to build systems.

We don’t have a, we don’t have an onboarding process for new, for new staff or like, you know, all the, the, the dirty, whatever the dirty looks like for you. Uh, it’s hard and it’s rough. Um, and so I just really appreciate you naming that.

Ryan: Yeah. I think, I think it points to something true, which is that work is not meant to be drudgery, and so we are meant to love what we do. We are meant to have a deep. Sense of connection to it and belonging in our work, but it’s not like enjoyment. It’s not pleasure. It’s like, you know, if I want pleasure, like I’ll go sit on the dock and read a book like that, that sounds way more fun than working.

But anything good requires great work and great sacrifice and good work calls us to that kind of sacrifice. So. There is some truth to it, but it’s very poorly worded and it really got in my head for years, man, it was very much taught that kind of I, Randy and John Ga, like if you’re smarter than everybody, you can be independent and love what you do and see the game and be this strong entrepreneur.

And I see a lot of people who do that and they can warp the world around them with their money and their power. And there’s this entrepreneur’s journey that looks like that. It’s like, no, actually good work calls us to deeper connection with people, not less, to deeper belonging in the world and to to greater and greater things within us.

And those journeys are hard. They’re freaking hard, man.

Dan: Yes. I love it. I feel like you and I could so get lost in like, the philosophy of work and, um, I think that’s one thing I really love about, about, I mean about the way you, you run your business, the way you are as a leader, um, is that you are so thoughtful about all of these things. And I think that goes back to my, my comment, but like, you, you defy the stereotype of what a, a leader of a, you know, an IT company, um, should, should, should be as if there’s a should.

Um, but I. Uh, just to, to. I think I want to kind of shift the conversation just a little bit because, um, I think there’s plenty more that, we’ll, we’ll explore there, but to, to really talk about that, like talk about your, um, philosophy of work, um, your, the current iterations and, and some of what you’re wrestling with, um, and, and the choices that are on the table for you.

Cuz it, it, you’re in a, somewhat of a transitional, transitional space and you, you have been for a little while. Um, so I’d love to just, you know, have you narrate some of that and then. See where that takes us.

Ryan: Yeah. Yeah. I appreciate that invitation. You know, I. I really appreciate my work and I appreciate and love my company and there are aspects about my job that I, that very much flow with who I am. I am. I am by nature, a creative and it’s taken me a while to realize like, oh, I’m a creative, and business is a creative expression that flows out of that.

And so naturally there ares. Seasons in a company as it gets more mature where there’s sort of less need for creativity and more need for professional management. And in those seasons I go, okay, I need other outlets for this. And when I’ve not handled that pressure well, I’ve thought, okay, I just need to sell the business.

And I’ve never been able to really do that because I think, you know, to sort of hint at some of that philosophy, you know, there. So there are two aspects in a business. There’s the money and the financial aspect. There’s the mechanics of what we do, and there’s money which are objects that we manipulate and exploit and maximize.

And if you have investments, you try to maximize your return on it, and you treat them as objects. And then there are people. And people you treat in relationships. And what I have a hard time with is that we have a business world that has moved everything to objects. So humans are resources for the business.

They are means to the ends of profit. Even, um, business leaders or thought leaders who often say, you know, you should really do good and take good care of your people, you see a hook of so that you increase your long-term shareholder value. Like that everything is objectified and treated mechanistically.

And I look at, you know, I have. Promises to my staff, to my clients. There’s a brand promise in mainstay. There’s a commitment that we’ve made. There are relationships that have been forged over years. Treating those as a personal asset on my balance sheet that I could then exploit and manipulate and change that seems very wrong to me.

Now the money clearly adds something different, but there’s a difference there within a business if you can see that. And I’ve seen so many examples, especially in a service business where they sell it and everything crumbles and the team is worse off. The client’s worth off. The community’s worth off.

And the only person who seems to be better off is an entrepreneur who often regrets it and feels sad and like they’ve lost some sense of themselves than the world and their thing has that they built, has crumbled. And so I’ve really wanted to honor and build and stay connected to main state. Well, while building a.

Team that can carry this on. And so we’ve put a stake in the ground to say we wanna be a hundred year company that’s privately, internally owned, that lasts for the long haul. And then within that framework, I’m the strategic cultural leader of that, but I’m not the professional manager in all of these areas anymore.

And so that’s, that’s some of how I think about my work at Mainstay. If that makes.

Dan: Yeah. Yeah, absolutely. And it sounds like in, so the, the, the choice just to kind of, I guess put a, put a, put a bow on that the choice that you’ve made is that you’re staying, you’re, you’re staying staying at mainstay, right? Like that over the long haul. Like when you look forward 10 plus years into your career, you’re, you still will have some sort of a role in the company.

Ryan: You know, I see mainstay as something that I steward that’s bigger than me. You know, there’s 80, 85 people that, that they every day are making mainstay. What it is there are, are hundreds of clients and the thousands of people who work for them, and it’s my job to steward that well, and I have giftings that naturally work really, really well in that organization.

Now, what I am doing is saying, Hey, as. Steward this well and build this right leadership team. I’ve realized that there are creative expressions that need different expression in the world. I have things that are hungry within me, and so how do I continue to, um, you know, do multiple things? And I think ultimately being connected to the business helps me to be a better leader.

You can see, I see. I don’t want to just. You know, do something clean cut. It’s not great for main state. And then I go on to something. But have I really learned the lessons? Have I carried it? I think carrying a weight of responsibility is actually really, really healthy in our, in our personal development and growth.

And so it’s a, it’s a healthy weight, but it’s not necessarily a full time weight anymore.

Dan: Yes. Yes. I, I totally agree. I think that that’s, as I was thinking about this conversation, I think about the ways that, like, I feel like my work and your work overlap quite a bit. Um, and, and like that we could , we could get lost in the philosophy of, of work. Um, but you are so much more, like you’ve gone places that I haven’t been able to go yet as an entrepreneur.

And so like, I think that it gives you, I don’t know if I wanna use the word credibility, but, well, yeah, credibility. Um, or just, and, and maybe just the different lens of a, of a practitioner that, like you’ve done it in your business. And so it’s not just philosophy, like, I think my philosophy is very informed from one-on-one, from working with, with people, from having these, these kinds of conversations and yours is that, but then also like, very much so in like thinking organizationally and um, and about business and.

I, I just get excited about, about you bringing more of that into the world, because I think there’s a, I think there’s a gap there. I think that people need to hear what

Ryan: thank you. Uh, that’s really kind of you and I feel very honored by you saying that, and, um, while also not wanting you to, to run yourself down in any way, in any way. You said that I feel very honored by what you said and I, I, you know, that is a very stated intention of mine, which is that I believe that.

Care and performance are not at odds in the business world, and yet when we use care as a means for financial performance long term, then they necessarily are at odds, but that we can actually, we need strong performance for good care, like calling people higher and having standards and making sure. That a team who doesn’t have people who aren’t carrying their weight on it, that’s part of care, but that we can actually run business from that place.

Now, I wanna be really clear, Macy’s got a lot of problems. We mess up all the time. We’ve got cracks issues. We’re wor like there’s no, there’s no path to perfection or utopia or the promise land in this. But there is an actionable philosophy that says, no, all of this is subsidiary to virtue, to care, to doing the right thing.

And I really. Grateful that as I move into more, just like you say, I wanna expose thoughts to the world and if nobody does anything with ’em, that’s fine. But if it starts to go somewhere, then great. I just want to encourage other business leaders. Cause I meet a lot of people who are really, really good people who talk about the most fulfilling times in their career, being those times that they’ve helped somebody to develop that they’ve helped them get the next job, that they’ve mentored them and yet they operate in a business environment that ultimately sacrifices those same people.

They help to develop for the sake of the bottom line. And I say no. We don’t, we do need the bottom line, but it must be subsidiary to something more meaningful because this is, we do not find the meaning in life in hitting our numbers every quarter. That is not what we’ll be spoken about at your funeral.

It’s your quarterly financial results. We need those. We need those for care. That’s very important to generate resources and we must be financially disciplined, but all of that must be subsidiary to something higher and more.

Dan: Yes. I love that. So as you think, Um, yeah. Your, your voice in this space and this creative energy that you’re, um, finding needs an outlet or wanting, that you’re wanting to find an outlet for outside, beyond the mainstay walls. Um, maybe just narrate a little bit of how you’re thinking about, like, what, what that looks like.

What, where are the, you know, in, in whatever forms, you know, it may or may. Like, which, whatever amount of clarity that you have around that. Yeah. Where are we, where are we right now? With, with, with

Ryan: Well, you know, I, I really wanna say like I have a lot of gratitude for you because you have been really helpful in this journey for me. I mean, your work and engaging with you and your work and coaching conversations been really helpful and you ask really, really great questions.

And I remember coming to you with. This vision of this leader that I saw who, um, Gary Hogan is leader of International Justice Mission. He has this incredible high performing organization doing remarkable good in the world, fighting slavery in these really disciplined ways. He’s also writing books. He’s this incredible thought leader, and I said like, how do I get my work to be more like that?

And I had this vision that my ideal work would be the work that synthesized those different things. And you really invited me to a different mode of seeing that, which said, how do you become the integrated leader who has different gifts and mindsets that’s very integrated, and then the work flows out of that.

And that moment was an incredible revelatory moment for me that really shifted my mental model of how I was thinking about work at all and how I was thinking about this journey for me and the hunger that I have to. You know, as the great quote by Frederick Bakner that your call is that place where your deep hunger, where the world’s your deep hunger, no, I’m sorry, I’m butchering this quote where your deep gladness and the world’s great hunger meet.

Your deep gladness in the world’s deep hunger. That’s what it is. Deep gladness meets the world’s deep hunger, and it’s like that’s, I wanna see more impact in the world and I wanna do it in ways that’s more in line with deep gladness that is within me, and you are inviting me to that journey of becoming and work flowing has been really, really helpful in this process.

So I wanna thank you for that.

Dan: Mm, absolutely. I mean, I feel I, I have goosebumps like hearing you narrate that, just because like, that’s the, that’s the transformation. I, so, Want to be a part of, like, when you’re talking about the, the mental shift, like, um, it’s just so, so meaningful, special, um, just to have a small, a small play, a small part in your story is just, it’s, it’s a gift.

So thank you for that. And thank you. Thank you for saying that.

Dan: what, as you. Look at, you know, the landscape of what, what you feel like, like what, what are the options on the table? Or, or, or, and maybe we can, maybe this is kind of a choose, choose your own adventure conversation. What would be most helpful for, for you?

Like to talk about options, to talk about, like, limitations, maybe all of the above. Like

Ryan: Yeah, well let, let me outline.

Dan: for, for this part of the conversation?

Ryan: Yeah, I appreciate that. Well, I’ll outline for you, there’s three categories that I am putting my time and energy towards that feel very salient and alive for me. So one is, like I said, leading mains day to be the best damn technology services company. We can make it absolutely not compromising in any of that vision and making sure I have the right leaders in place to really walk that out in all the details and being connected in the ways that I, that I do best.

Then secondly, you know, I love the startup phase and I very much love, um, embodied brainstorming. Meaning when you are with someone in the fullness of what is alive for them, feeling and thinking your way through it and naming what has not yet been named, taking the nebulous around someone who has a desire, has a, gift that’s not walked out where they’re stuck in some way.

And then being able to bring personal and organizational. Insight to that and say, here’s I think where this is your. The work is calling you where your block is, where the organization is, how we can scale it and bring the experience of organizational scaling to that. And I want to do that in ways that most help to awaken people and draw them into the journey of becoming in life.

So I, I love what we do. Creating good jobs for people and calling them to wisdom and work and providing technology services is very meaningful to me. But I also really long to. More and more of us wake up to our, our, the feelings that we have in our body and the journey of becoming who we are meant to be and our society fractures us and dissociates us, and numbs us with Netflix and keeps us from that.

And my own journey’s been transformative with therapy and meditation and wisdom practices and insight and, and breaking from all of these shells. That kept me. So I didn’t even know what I felt. And I wanna help more people do that. So I look at my skills and I say, well, I’m not trained to be a therapist.

I am not gonna go get my masters. And like, and just one on one like that doesn’t resonate, but what is this? And so helping. What I wanna do, and I’m starting to do is bring this combination of gifts that I have and organizational scaling expertise to the thought leaders like in the therapy space, in the transformational space, and cognitive science in these spaces that are really helping people to awaken and grow in wisdom, grow in aliveness and wholeness within them.

What I find is those thought leaders, you know what, they’re not experienced in organizational scaling, thinking strategically in those kinds of ways. Like there’s very much a divide there. And so when I bring that, it’s amazing the, the life that comes out of it. And so I am really excited to start scaling and working with those.

And so I’m working with a couple of leaders now and eager to see where it, where that goes.

Dan: I love it. I love it. I see you as somewhat like the business on one side and then like, um, I don’t know, identity formation practitioners on, on the other side, and it feels like you’re kind of standing in the middle, kind of pulling, maybe inviting, inviting maybe as a bridge, inviting these two worlds to,

Ryan: Yeah. I love that visual. It is. I love that visual and it’s, it’s really cool cause it even connects from me. It’s helpful to me of the third thing that I’m doing is formulating an actionable philosophy of work that’s connected to the deepest philosophy and understanding we have of what is good for human life.

And that goes back to Christ and Plato and like, is deeply rooted, but it’s very actionable for business leaders. Say, how do you make these decisions? Think about people, how do you do this? How do you think about selling your business? How do you think about managing, what do you have to do when you do layoffs?

That’s very rooted in this philosophy and gives language to business leaders because that kind of philosophy hasn’t impacted the business world very, it hasn’t penetrated very deeply into the business world. It there’s not a lot that’s very actionable. That’s that deep and so, I what I like, what I’m trying to do is, is really be a bridge of the philosophy and the skills back and forth between the deepest of meaning and awakening and philosophy.

The ancient world, ancient meaning of the world of love for wisdom, right? The way of, of, of following away in the world that homes us into the world where we, we are connected to reality, we are connected to each other, and we are connected to our bodies that we have actually overcome. The anxiety within the alienation from others and the sense of absurdity of the world around us and that we actually, there is a way to do that.

And so I want to connect and follow that way, bridge that way into business and bridge the business skills into that way. And stand there as the bridge between those two worlds. You know, a lot of times we think of innovation as being at the end of something like, oh, you’re the scientist who takes this thing further.

Or the app developer who does something new, no one’s ever done before. It’s kinda like imagine a road and the innovators are the ones blazing new trails in the wilderness. I’m always drawn to the intersections. Intersectional innovation, to me, is fascinating and all of us stand, each of us stands at a unique intersection and to sort of say, what are the things that I know and do and I’m connected to that is unique and powerful?

And that’s the intersection for me where there’s life and I wanna stand and be that bridge. So thank you for that visual that that connects very deeply.

Dan: yes. Good, good. Um, I, I think of, and I don’t know if this is helpful, but sometimes, sometimes I find it helpful in these, um, In these spaces where you’re, you’re, it feels like things are coming into focus for you, and it’s like, what, what is this? What is this gonna be? What’s, what’s my, my voice in this space?

What’s the movement I’m gonna be, want to, want to be creating? It can be helpful to think about like, who are the people that are closest or organizations, all of the above, who’s doing this work in, in the, the most similar way to, to what? Um, what I’m seeking to create. Have you done any thought experiments around that?

Any brainstorming around that? Like have you looked at your, maybe a competitor analysis? If you, if you will, though it’s, you know, in some ways it’s, it is, it’s a new space, but I’m, I’m

Ryan: Yeah. You know, I would, I, I have, and I, I would really welcome if anything comes to mind for you or for any of the listeners of people to talk to or of models like this. You know, what I find is there’s a very trod path for someone who has my strategic thinking. Sort of building something where there is nothing, right.

Taking the unformed and forming it and it’s, you know, you go on to be an entrepreneur and you do the startup thing, or you’re on boards and you do venture capital and, and I’m someone who, who I appreciate. Wealth as a way of serving what is meaningful in life. It is a tool to serve that, and I do not see that the world needs more wealth in that way.

And I’m not saying that philanthropy isn’t important and that I don’t do that. I’m just saying like, I’m not motivated to maximize my net worth. When I look at that path, that’s what the people tend to take that path. And then those who are deeply intuitive, emotionally connected, caring about people’s personal physical transformation tend to take paths in spiritual, psychological, other kinds of career paths.

And I would like to find more, and I see coaches who try to bridge both a little bit, but I would like to find more who are at this intersection. And it’s the same with the philosophy, I mean, I’m reading Old Catholic and Cyclicals about work and theology together and philosophy, and I’m finding it in different places, but I’m not finding it in anything that I see as really, really scalable or, or, um, well connected.

But I would like to, there are a lot of, a lot of wonderful work. There’s a lot of wonderful work being done by organizations like Conscious Capitalism or Places for Business for Social Responsibility that is about work, being better, more humane, taking care of people, watching your externalities, those environmental impacts that we push outside the walls and don’t mitigate.

There’s a lot of good things in that, but all but I’m looking for those who say, And we’re gonna do that because it’s the right thing and we are subject to virtue and integrity that’s above us. The true, the good and the beautiful is above us. We serve that even in the business, not because it’s what builds long term shareholder value and trust with our clients and all of that.

I’m searching for more of an active community in that. And so if you know of one, I would love to, I would love to hear.

Dan: No, I, I, I love that. Um, yeah, hearing how you’re, how you’re thinking about it. The places that I, I was, I’ve been going as I was asking that question, is thinking, um, maybe just the, the next lane over from that. And it’s some of the, the idea of, you know, uh, Sell, sell, sell ’em what they want, but give ’em what they need.

You know, of like, who are the people who are speaking in a way that’s, um, cause I feel, I do feel like there’s a movement happening, more movement happening in the philosophy. Philosophy and work where, like, where, where there’s, there’s a, there are some voices. People that, that come to mind are, um, naval, ravikant, um, you know, some of his very philosoph, philosophical, um, his writings.

Um, Ben Horowitz also comes to mind the book, um, what you do is Who You are, but again, it’s still, it is very different than what you’re, what you’re, you’re you’re doing. But what I, I guess I’m, I’m noting is that it feels like there’s an appetite for. Philosophy of work that I would be curious if, um, approaching it first from the standpoint of what it does for your business without sacrificing, you know, without sacrificing your vision of what you’re calling people to, but using that as the entry point into this deeper conversation. To hook, to hook somebody in who might not be interested in the cap, the conscious capitalist conversation. And um, like, it’s like kind of two ends of the same tunnel, I guess you could say. Um, and I’m curious if you have thoughts about, about

Ryan: Yeah. You know, I first wanna just agree with you that I think there’s a real hunger for. for more. I mean, I think, I think most people work and are pretty disillusioned by it, and they, they don’t want to work with the kind of existential angst that they carry into their work. I think you see even in the like financial independence movement of this, like get out of the bondage of work.

And I would say to that like there’s some goodness in that, but like, And you wanna be financially disciplined, learn those things. But I have a higher view of work that doesn’t just say like, get out of work and then do whatever you want that says, connect your work to the world in the more meaningful ways.

Dan: Yes,

Ryan: It. And you know, I think that there is a lot that can be said. I agree with you that there’s sort of the philoso philosophical development and there’s the communication of it. And those are two different things. And they need to be bridged together and very intentionally treated. And I’m treating them as two different competencies to build.

And right now I’m sort of in the journey of like, I wanna get the philosophy right, talk with the philosophers, and then I want to get the communication down. And I’ll be curious how that works. And I first wanna help people who. Really see work as a beautiful thing and the way to serve people and give them language and make them not feel alone in that and make them not feel like someone’s looking at them with two heads when they talk about sacrificing something tangible and directly financial in order to serve people through their work.

I wanna give them a place in language. And then beyond that, I, we’ll see where it goes. You know, I, I do think,

Dan: Hmm.

Ryan: you know my critique. It goes all the way to our system of capitalism, which I’ll just say very briefly that Eric from was this great social psychologist, um, who, who wrote a book in the 20th century called The Haver to Be.

And he has, he identified these two modes of operating in the world. There’s the being mode and the having mode, and we have to have food. We have to have a house and shelter. You have to have clothes, and we get it and we have to have certain knowledge and you can see, like you grab things, you consume them, you manipulate them.

That’s having being. Becoming right. It’s of who you are. It’s of identity, it’s of love, it’s of place, it’s of belonging. And our capitalist society has really tried to say, all of your deep being needs you can get through having, oh, you wanna be regarded and esteemed? Drink a beer. Like, that’s what we’re gonna say very directly in the course.

You want freedom? Buy a Jeep. Like, no, no, no, no. You can’t have your way to freedom. That freedom is a place that you are, it’s a place of. And so I wanna communicate that in ways that’s very clearly understood. But we have a culture that’s kind of gone mad in the having mode where we can consume our way to happiness, to success.

We can just build and we just keep going and going and going, and not really noticing that this isn’t working. I remember Dan, I used to sit in the shower. That’s where I do a lot of my great thinking, right? Take a long shower. And it’s like, all right. And I used to always think like, all right, I caught myself in this loop of like, when I get to this point, when this debt’s paid off, when I have this kind of net worth when Maine stays this big.

Dan: Hmm.

Ryan: I’ll rest, I’ll be at peace. Everything will be wonderful. And what I noticed over time was that the milestones just kept moving. The feeling was the same, the mechanics were the same, the thought process were the same, but the milestones just kept moving. And at some point it’s like, well, we’re playing the wrong game and I don’t wanna lose that message.

Cause I think that’s the message where salvation is, is to stop and say, no, no, no, no. You can’t have your way to, to. You can’t become who you wanna be through an identity as a writer, as a, as, you know, like collect your identity. You can’t, you can’t amass your way to an identity, into peace. It’s a different fundamental journey.

Dan: Yeah. Yeah. I love it. I love it. And it feels like it’s an invitation to the idea that like, uh, you, you don’t have anything to prove like that you can already. Like, you already are enough. You already have enough. And then out of that space, if you enter your work from that space, um, it just changes the conversation rather than one of acquiring and, um, consuming to giving.

Ryan: Yes. And if, if you have something to prove, you’re never going to get enough to fill that hole, and you may have pain. That’s very real. But the path to that is, you know, meditation, transformation, transcendence, therapy, there’s a different path. To overcoming that deep need to prove that we may have, which I carried very much into work.

It was like, well, maybe if I can land on the cover of Ink Magazine, then everything will be great. And it’s like, no, I did have a lot of existential pain, a lot of deep emotional pain and angst that I took into my work, but I could never get there. I mean, I think that. You know, I, with all due respect to our former president and those who, who are huge believers of him, you know, Donald Trump is clearly somebody who, who, who keeps on trying to get there and prove that.

And, and I don’t mean to pick on a political figure, but he’s a very public figure that how much more powerful, successful, how many more billions can a person get? And yet there still seems to be some motor that’s trying to prove and, and dominate and do something. And we say, okay, if he can’t get, if the billionaire president.

Can’t get to peace in that way. I have no hope. It must be a different journey.

Dan: Yes, yes. So, so, so well said. So well said. Um, I just wanna maybe kinda circle back around to just the, the juncture that you’re, that you’re in and, um, and maybe just ask the question again, like, um, like what is it? Yeah, I guess maybe, maybe, I guess what I want you to, to what I’m, I guess the question is for you to articulate the question, like what, what are the questions that you’re asking at this moment about these next iterations?

I think we’ve kind of talked about them at a high level, have some, you know, um, some semblance of, of what they, what, what will be coming out of them. But what, how are, how are you articulating the questions that you’re seeking answers to

Ryan: Mm. That’s a great question. That’s a really thoughtful, thoughtful question. You know, I think I am really asking, you know, I, I, I, with all due respect to the books that sort of have contained one insight and. Have sort of flash of like, okay, we get this thing. I would like to offer an invitation to people of the depth of wisdom and experience that I found in the inner journey and how the inner journey connects to our work, and I want to be most. Useful in that, and as deep as I can be and as deeply connected to the deep wells of that philosophy, theology, understanding that I can be, and so I’m really asking a bit of a like how. Where, how do I develop this? Well, how do I spend time beating this up? Who are the voices, the people that I could, can get this in front of and get dialogue time with to really develop this well?

And then how do I communicate that effectively? What’s the right media? What’s the right, um, method? How do I sort of MVP this right minimum viable product? How do I get this out in different communication styles and in different, in different little products to say, is this helpful you? I really wanna be careful.

I’m also asking like, where’s my ego in this? You know, like if I start optimizing for a TED Talk or something, I know that’s vanity. It’s, it’s like, no, I know that I’m in a healthy spot when if I can find someone saying what I wanna say better than I could say it, doing what I want to see done in the world.

Would I be happy with my name? Nowhere in it, just supporting their work. And if I can say yes, then I’m serving the work. I’m serving the work and that I know is in a healthy place. So I’m also asking, where’s my ego sticking in this? Cuz I do not wanna just go write a vanity project or do something like that.

Life is too short and too sweet to waste on that.

Dan: I love

Ryan: Oh man, I’m my prone to it. Oh, do I love the idea of collecting these things? Oh, if I could be an author and a speaker and update my LinkedIn profile with all these things I’ve collected, like, ooh, there’s part of me that lights up at that idea, man.

Dan: Yeah, totally, totally. Of course, of course. I mean, like me, me too, right? Like I, I, I think, you know, your approach to it sounds very well grounded and I think that that’s, that, that question of like, would I just be happy supporting the work is, um, yeah, it’s a really healthy question. Um, and so I find that, yeah, I find that admirable.


Ryan: Thanks.

Dan: I think of, I’ve often thought of my work, and again, I feel like this is where our work, my work, and your work is parallels like, like what? What I want this podcast to be is like on being, but for work, you know, like and like Krista Tippet is a name that comes to mind who, like she, she’s someone who, um, Who, who’s thoughtful about all of this stuff.

And, and that that could be a, could be a voice, um, yeah. To, to

Ryan: Yeah.

Dan: your, some of your, um, resourcing, researching. Um, it sounds like that’s kind of the phase that you’re in, just kind of like gathering without as much yet, uh, concern of what, what the, you know, product will be is kind of how I see it at this

Ryan: I appreciate that. I’m not familiar with her work, so I look, I’ll look that up. I really appreciate that. Um, I, yeah, you know, I’m really fortunate. I count myself very, very blessed to be in a season where, You know, I don’t have a pecuniary, uh, imperative. I don’t have to go make money out of this next thing, and I can take time with it and birth it and serve it in a different way and do that while honoring the work that’s come before.

But I also get to step back and say, okay, you know, I chose my career path, or it was sort of chosen. It sort of happened when I was a teenager, you know, like that was out of all of these things and I’ve become a different person and I see the seeds of who I. Then in that, but now at a more of a fullness of time, how do I, how do I operate in the world in a more fully impactful way That’s more fully me, and that’s a really fun question to live with that I have a feeling I’ll be asking for the rest of my life because, you know, all that careers are is, is sort of like work.

Over time it’s optimized for something, right? And so what over career or vocation, if you wanna call it, it’s like, right, how do I keep optimizing to serve people well? To make a mark in the world that’s genuinely positive and not just sort of looks good on the wall, but like genuinely helpful and transformative for people.

And how do I keep optimizing for that over and. Forever and that’s work that doesn’t get old back to love what you do. Like that’s work that energizes me and keeps me up till midnight with ideas. Like that’s the kind of thing that there’s life and vitality in that I wanna sustain forever. I mean, why would you wanna retire from that?

Dan: I love that. I mean, well, I love it because it is so well, fits with my understanding of what it means to be human, which is that we are always becoming, uh, something new. And that work is at its best, a, a, uh, work at its best is an avenue or a, or a, um, a place to put, a place to put that energy to to, to actualize some of that desire.

Ryan: yes.

Dan: Yeah. And,

Ryan: I love that. You know, human beings are the only species that we know of. The only ones here that can transcend, that can fundamentally look at their wiring and their framing and transcend it and become something else. I’ve been very inspired by the work of John VivaKi. He’s a cognitive scientist who focuses on wisdom and, and this idea that is the adult.

Is to the child. So the sage is to the adult that we get to grow in wisdom and perspective, and we actually transcend ourselves. Like who you and I are now compared to who we were at 18 or at eight is there are, there’s obviously a fractal sort of unfolding, but there’s also a genuine transcendence where we go beyond our wiring, our framing.

So how do we keep doing that? And then how do we hook workups so that it’s helpful in that t. And like you say, it’s a way of actualizing the energy of that transcendence into transcending the world. And now we get transcendence within and the kingdom of heaven without, right. It’s almost like the, the growth and transcendence within and the Buddha within, if you will, and the kingdom of heaven without Right.

Or Christ, within and without, like, however, whatever you, you know, imagery is helpful. But that connection that’s, that ends up being work. That’s how we change the world and are connected in this wonderful, reciprocal back and forth wash. That is really exciting when it’s right, and of course it’s often wrong and hard and brutal and challenging, and on the best day, all kinds of bad things happen, and we can’t forget that.

Dan: Yeah, well, I, I, I mean, I totally sign off on that hopeful, romantic vision of what it can be. And then also, like, I think it also speaks to how painful, um, it also can be when it’s wrong, right? Like, because, because of the potential when it’s right. Like of course it is all the more painful when it’s, when it’s when it’s wrong.

Ryan: Oh, what a great point, Dan. I mean, that just like hit me in my chest of like, like, yes, like when we fail, when there’s issue like, oh, I’m dealing with stuff at mainstream where it’s like, this is not up to the vision that we have and it hurts my chest, like seeing someone unhappy or it’s, it hurts. And then I just think of all the.

The longing that’s trapped within so many careers and so many people who feel stuck and who, who want some path and don’t see it, and yet they, you know, we all have this desire to, to transcend and to see our work flow and be connected from who we are and it’s stuck and, and how do we just each do the work of unlocking and helping others to unlock that.

Dan: Yes, so, so well said. I think that that’s the work that’s ahead of, of us and everyone, everyone out there that’s like us, I guess, that believes in something here to, um, to offer the hope to the people who have not tasted that right, like to the, the people who have, who you know, who their work has, has only been a place of struggle and of constraint and under resource being under resourced and everything else along those lines.

Ryan: Yes.

Dan: And, and I don’t, I don’t, I don’t, I’m not making a point here other than just to say, like, I’ve, I’ve, I’ve heard those stories and I’ve seen those people, like I’ve, I’ve been in the, the conversations, I’ve been on the, the subreddits where people are talking about their jobs and like, it’s so hard to like see that and then also hold this other thing that we’ve been talking about and to try to figure out how do these two worlds collide and become

Ryan: yes. Yeah, and, and how do I not. Sort of speak from a place of like, oh, great, this is a luxury where if you happen to be so fortunate that a business starts around you and then you figure out how to make it financially successful, and you could like, like, yeah, that’s really great for you, Ryan.

It’s like, like, yeah. Like I recognize how blessed I’ve been in that, and I wanna say that. The path is always the path of wisdom that I think so much in career we can get locked into seeing that I need to figure out the binary choice of what I do or the knowledge I need or the skills, or we focus on the injustice in the world.

Not that we don’t need to grow skills or deal with the injustice in the workplace, but that I think our salvation comes from our personal transformation and our growth and wisdom. And the way that we, and that’s how we can see the opportunity, see the landscape, know ourselves, see our giftings and navigate towards this place.

And the way that I think that we do that is to help people recognize that like each of us can feel alive and that most of us work in our workday with neck down, being numb without a sense of aliveness, a sense of attunement to the environment. A. Fittedness of like the hand and glove to the world, and I get to do this and I’m connected and, and there’s life and it’s growing.

And overall with all the hardship, it’s in this spiral of growth that most of us don’t have. That I certainly, even in the middle of great entrepreneur years, I didn’t have that. It took somebody. Articulating what it can feel like to be alive and in touch with your body and have your life be coming from a place of wholeness.

For me to say, whoa, I’m missing 90% of life. How do I wake up and do this?

Dan: yes, yes. And I think therein lies so much of the power. The, the, the potential of your work and your, your perspective. And what I think you uniquely bring to this conversation is you’re leading an organization that welcomes from the neck down. Right? Like, or, or you know, like the whole, the whole person.

And to go back again, like I could go show up on those subreddits and try to try to, you know, get someone who’s working, you know, night shift at Taco Bell to try to like, You know, invite them to a bigger conversation about what’s possible with work. But unless their workplace is a place that it, it like that, where there’s space, um, it’s not gonna, it’s not gonna do much.

Right. And so, um, I guess in that, like, I just see again, so much, so much potential for you as a leader to guide other leaders. Into, and, and again, even this comes back to like talking about healers, like, and the people who are doing this work, you know, in, in the therapy setting or the coaching setting and like this one on one, it’s the leaders of the organizations.

It’s the entrepreneurs who are gonna change the way work is done. And, um, and I think, you know, for what it’s worth, I I I just want to encourage you to, um, yeah, to speak to that demographic because I think that one, you’ve got the, you’ve got the credibility. That they’ll listen to you and to, like, you’re, you’re, you, like what you’re saying, needs to be said to that, to that specific demographic.

Ryan: Well, thanks Dan. I really appreciate that and that makes me. Just all the more motivated to keep doing my own work, because the only way you can create an actual safe place where people’s bodies, their creativity, their depth, their vulnerability is welcome is if you’re actually there yourself. And if you know how to create the safe and then not allow the stuff that does need to stay outside of work.

It’s a professional environment. There’s certain boundaries, but to actually be someone. Who can hold that and who can, who can lead the way. Because the only way to do that is to do the work. And so hearing you say that in the opportunity, I feel it. I want to be worthy of that opportunity. And so that just is so much more motivation to keep doing my own work.

Cause man, I’m broken and I need, I need, I need to keep becoming and transcending, that’s for sure.

Dan: Yes, yes, yes. We all, we all are. And, um, this has just been so fun, Ryan. I know we’ve gone way over, way over, you know, the time I said we would be recording, but it’s just, I, I knew, I knew as soon as I hit this record button, I’m like, I’m gonna have a hard time stopping this conversation. Um, and so thank you for, you know, just who you are, for the work that you’re doing, for the organization you’re leading, and, um, just really appreciate, you know, everything that you’ve shared with us here today.

Ryan: Well, thank you, Dan. This has been an absolute.

Dan: If folks wanna follow along, connect with you, is there anything you’d like to invite them to?

Ryan: Yeah, I would say, you know, I would, I always love connections on LinkedIn, Ryan Barton. It’s easy, easy to find. Um, and then I also have ryan barton.com. There’s not a lot of content up there now, but it’s a place to connect. I would love to receive messages through that. Uh, you know, a lot of what we’ve talked about, I don’t have much public in terms of content or streams or official ways to connect, um, at the moment.

But I would really, if you know any listeners. Resonated with anything. It would be very helpful for me to know what and why and what they were, are curious about what they would wanna know more. That would be really helpful. Or anyone who wants to dialogue deeply about these subjects, I would. I would love to be reached out to on, on one of those platforms.

Dan: I love it. Well, I’ll make sure to link up to those in the show notes and, um, just thank you again for your time.

Ryan: Thanks, Dan.

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