Systems Hold The Vision

In this episode, Don reflects on the difference between having a vision and building the systems that can actually sustain it.

He also explores the personal side of that work: how we begin to close the gap between who we say we want to become and how we actually live.

He is joined by Barrett Takesian, founder of Portland Community Squash, for a conversation about founder energy, organizational growth, the discipline of sustainability, and what it takes to build something strong enough to carry a mission beyond one person’s passion.

To learn more about Don's work, upcoming offerings, and leadership resources, visit carpentercompanyconsulting.com

 If something in today’s episode spoke to you, I hope you’ll subscribe and continue the journey with me — because leadership begins within. 

Transcript

SPEAKER_01 0:12

Welcome to Meditations on Leadership. I'm Don Carpenter. Let me ask you, what happens when our vision for ourselves, our vision for our teams, or our organizations is no longer enough? What happens when the dream we once carried with passion, urgency, and belief begins to require something less glamorous but more sustaining? That question brings us into this week's meditation on systems. And the way they hold vision long after the first wave of inspiration is passed. Exploring leadership tensions like these is at the heart of this podcast. Each week begins with a meditation, followed by a personal reflection, and then a conversation with a guest whose lived experience helps bring the theme to life all in the service of the information that leadership asks of us. And today I'm grateful to have this conversation with my guest, Barrett Takesian. Barrett is the founder and executive director of the Portland Community Squash, better known by many as the PCS, a nonprofit in Portland, Maine, that uses squash as a vehicle for youth development, community building and belonging. Barrett grew up near Acadia National Park, found his way to squash in the Boston area, and after graduating Bowden in 2012, made the decision to leave the private sector and pursue his dream of working in the area of youth development. What began as a small youth clinic at the YMCA eventually grew into Portland Community Squash, which really is a multicultural and multi-generational community center located on Noyle Street that opened its doors in 2017. Over the past 15 years, Barrett has become a deeply respected leader in the out-of-school time and community squash world. He has served as senior advisor for community squash at USA Squash, Maine's after-school ambassador, chair of Portland's Out of School Time Network, and as he describes it, a general enthusiast for community centers. I first met Barrett years ago at a conference, and I remember being struck by the story told about having 100 coffees with people as part of raising a million dollars to continue to bring Portland Community Squash to life. I related to that immediately because so much of my own work had been built in coffee shops, sitting with young people, parents, donors, school leaders, business owners, and community members, just trying to understand what was possible if enough people began to care together. Barrett is a big thinker, a visionary, an analytical mind, and a true community bridge builder. He's the kind of leader who absorbs the mission deeply, invites others into it generously, and helps people see that they have something valuable to contribute. And for all those reasons, he feels like the perfect person to join me for our conversations about systems, growth, and what it takes to build something strong enough to carry a vision over time. I'm really, really grateful to have him with me here today. Barrett, welcome to the show.

SPEAKER_00 3:57

Thank you, Don. Best opener I've ever had.

SPEAKER_01 4:03

Well, just the latest one, I'm sure. So uh I'm really glad you're here.

SPEAKER_00 4:08

That was great. I took some notes from that opener. I can't wait to get into it with you.

SPEAKER_01 4:13

All right. Well, uh, before we jump in, let me share meditation 46 from my forthcoming book. The meditation is titled Systems Hold the Vision, which for you, the listening audience, should know that Barrett picked it for our conversation today. Here it goes. This is the quote I wrote down a few years ago by James Clear in a book called Atomic Habits. Quote You do not rise to the level of your goals. You fall to the level of your systems. I'll repeat, you do not rise to the level of your goals, you fall to the level of your systems. There was a time I thought vision was enough. If I could inspire people, build trust, and stay aligned with the mission, I believed everything else would follow. But what I didn't understand was this vision without systems is like planting seeds without soil. There's beautiful intent there, but no way to grow. For as long as I can remember, I've been gifted with the ability to build relationships, to see people, to connect deeply, to move with passion and energy. But when it came to systems, organizational growth, long-term planning, I struggled. My passion often outpaced my planning. My instinct was to focus on people, not process. And for a while that worked. Of course, until it didn't. Eventually I had to face the truth. No matter how inspiring my goals were, if I didn't build the systems to support them, it wouldn't progress. It would stall. Or worse, it would burn out the very people carrying the work, including myself. And the truth is that systems don't have to be complicated. Sometimes they are just simple structures to hold your values in place. A weekly rhythm that creates clarity before confusion takes over. A decision-making process that keeps everything from running through one person, an onboarding practice that helps young uh new people inherit the culture, not just the tasks, a supervision structure where people are supported, challenged, and developed. A budget process that reveals what the organization truly values not just shows its constraints. All of these are systems and they matter. Later in my career, when I began doing executive coaching, especially with founders, I started to see this pattern everywhere. They had vision, they had drive, they had heart, but they lack systems. And I get it. Having founded more than one social enterprise, I know how hard it is to move from creation mode to infrastructure mode, to trade the adrenaline of launching for the discipline of sustaining, to shift from what's the dream here to what will carry this dream over time. But once I saw this gap in myself, I went all in. I got help. I built what I didn't yet have. I listened to people who were more operationally gifted than I was. And slowly I began to understand that systems don't stifle passion, they support it. Systems give your team a way to succeed without relying on you alone. They make your vision transferable. And most of all, they make your leadership sustainable. So of course, we have to dream big, set bold goals, let our hearts lead. But we can't forget this that our vision can only rise as high as the systems beneath it. Because in the end, the dream is not sustained by how deeply we believe in it. It's sustained by what you build to hold it. So I just want to offer a quick real-time reflection as I prepared for this time with Bear today. And as I think about this meditation, I recognize that James Clear's words are not only true for organizations. The idea that we do not rise to the level of our goals, we fall to the level of our systems. Well, that is also true in our own lives. Because I can speak pretty passionately about the kind of person I want to become. I want to be stronger physically, I want to be more self-regulated emotionally, I want to be more grounded spiritually, I want to stay more connected socially, and I want to be sounder financially. I know how to name those things. I can talk about them with conviction, but naming a vision for my life is not the same as building a life that can actually hold the vision. I remember having conversations all the time with my mentor Bill about these things. And no matter what part of my life I was talking about, he would eventually bring me back to the same question. Because the truth is, I have often had more clarity about what I want than the structure to help me get there. I can lean into aspir into the aspiration, but avoid the discipline of making room to make it happen. And if the pat if past behaviors one of the strongest predictions of future behavior, then hope alone will not change the pattern. I need more than desire. I needed a system, something I intentionally build into my life that helps me practice the behavior I say I want until it becomes part of the life I'm actually living. Because the vision we have for ourselves will not be sustained by longing alone. It has to be held by what we are willing to build around it through time, energy, effort, and vision. Barrett, as you listen to the meditation and this reflection, what resonated with you? What stirred in you? What's staying with you?

SPEAKER_00 11:03

Yeah, a few things. First, I'm at a really you're catching me at a really interesting time because I always led with my vision, or in other words, my theory of change. I thought the country needed a new wave of community centers. And we've really thought deeply and innovated deeply and shared widely what we think a community center can be in this day and age. But more and more I find myself sharing our systems or our operating system and actually making room for other people's visions. And so I find myself at this crossroads. Do I double down on my narrative that organizations should embrace this theory of change and become multi-generational community centers? Or do I share my learnings about building systems and help any vision come true and become more agnostic about the actual programs that are being delivered? So I'm going through that right now, and I'll I'll just give a little context in reflection as well. We have, and I think the viewers will acknowledge that our organization is a bit unusual. Portland Community Squash, you know, what uh what does where does Portland Community Squash fit in the landscape of main organizations? I was 22 years old bringing an obscure sport uh to a city that was um, you know, trying to find more opportunities for youth, so on and so forth. I was met with a healthy dose of skepticism that squash was going to be a tool to get the city moving in in the right direction. And skepticism led to transparency. I had to be very transparent about the way we do things, the way we spend our money, the data we track, our you know, the academic theory behind our work, uh the culture we were building. And so this transition from being a visionary to being a transparent operator led me to become, I suppose, uh gave me a bit of a superpower for being an implementer and to build systems that were uh transparent. And so through that process, I ended up being a pretty good consultant. We did 13 community squash centers around the US. I I gained a real enthusiasm for helping other arts and sports organizations around Maine. And here I am still facing facing this uh decision where I could lie to myself that I can do both, or I'm going to have to make space to uh to either continue to be a talking head for community centers or to roll up my sleeves and be a system builder with organizations of all types around me. Uh so it's it's a topic that's a top of mind for me right now. And I uh I suppose for the purposes of our conversation today, let's assume I'm going the systems route and uh say farewell to the theory of change um just for this conversation, unless you have conversation questions that point us in that direction.

SPEAKER_01 14:40

Well, so I really appreciate you naming all of that because I think it'll be a great uh context for where we go. So let's let's get into it. So, like when you hear the phrase systems hold the vision, what does that bring up for you personally? Like, do you does it feel true to your own leadership journey?

SPEAKER_00 15:02

Yeah. I used to talk about human capital a lot. And we're really proud, you know, we've built our our list to 14,000 individuals around Greater Portland. And in the early days, you know, it was all about inspiring people to uh align and and come along for the ride. But over time, it's really been how do workflows and technology and data unlock the unique contributions of every person in our community? And that means getting them in the right program, in the right volunteer opportunity, aligned with the right fundraising campaign. And I asked myself that question with every person that I come across in our community. But at a certain point, the individual, you know, I can't be asking that question when I run into Don. I need systems to unlock Don. I need I need ways for Don to plug into the right programs, to the right volunteer opportunities, to the right campaigns. And it needs to be seamless and frictionless. And doing that across thousands of community members is a pretty sophisticated undertaking. And I credit um all the success here at Portland Community Squash to the people that have shaped our systems over the years and allowed people to contribute in in a myriad of ways. So that's uh yeah, it's my whole ethos these days.

SPEAKER_01 16:32

Yeah, well, so I mentioned in the um in the meditation about my own my own trajectory of growth in this area. And I'm wondering whether or not you had a similar one in terms of the early days of PCS, meaning what carried the work before the systems were fully in place? Like, was it belief? Was it discipline? Was it urgency? Or did you immediately have this theory of change and already have the system built in? Like, where where are you on the founder scale?

SPEAKER_00 17:07

Of course. I was very fortunate to have plenty of time. Uh, I was getting out of my day job pretty early in the afternoon, allowed me to volunteer with a lot of nonprofits around the city, eventually really focused on Portland Community Squash, driving vans, taking meetings. Um, and then when I eventually went full-time and tried to uh rally the community to buy and develop our community center, it was definitely hundred-hour weeks for two years. Um, when you're young, you have to promise a lot for people to notice you. So I promised the world, but I didn't have any systems. And I was pretty determined to follow through on my word. Uh, and I just did that by working myself into the ground, which uh was I'm very grateful for those years and and to uh to have the freedom to chase something like that. But it was really me seeing um my role models burning out in nonprofits, especially around development, where I started become skeptical of my how sustainable it, you know, nonprofits can be as a field. And then I started spending my time with people in the private sector a lot more to understand how they operate their businesses. And I would growth hack uh any technology or any systems that I could find to give myself a better shot at having a better quality of life in the nonprofit sector, truthfully. And so it sustainability and also the enjoyment of the role became a real, a real priority on my for my path.

SPEAKER_01 18:51

Yeah, that's great. I I love the idea of the growth hack as a way to better grow the organization uh in any way possible. I I've spoken uh a lot on the podcast about this moment that I had in you know, maybe year 10 of my 18-year career, Trekkers, where something just hit me. Maybe the burnout, maybe the hundred-hour weeks, whatever it might be. But I realized that less dawn was more for kids, less dawn was more for the community, less dawn. So if I could begin to take myself off the front lines and train other people and build the systems, then more kids, more families, more neighbors, more community members could be impacted by this work. I'm curious, was there a uh a particular moment when you had that aha moment, like a uh a real thing that sticks in your mind? Like, yeah, I was I was driving down the road and X, or you know, I came into the office and Y. Was there a moment or was this just kind of gradual over time?

SPEAKER_00 20:07

Yeah, there were a few moments. I don't drink coffee, but I take a shower every morning, and pretty much every every one of them came during my morning shower. You know, one of them, one of them around let's see, let's take development for example, an example. The annual fund is an absolute bear to climb the mountain every year. So one morning I was, you know, doing my morning routine and I asked myself, the kids are making a seven-year commitment to this organization. Why, why are our supporters not making an equal commitment? So I said, you know, I'm gonna go work in, I'm gonna completely change the way we do development. We're going to start a scholarship campaign, and we're gonna get groups of friends and families to make a non-binding seven-year commitment to back families as they make their way through our organization. And so year one, we set up 20, and then guess what? When year two came around, we already had 20, we added another 20, and now we've got about 130 recurring scholarships that make up about 75% of our total annual fund and it rolls and it and it operates um pretty sustainably. You know, taking that further, obviously we've all been made aware of the advances in technology, um, for better or worse. And you know, the other day I came to work uh with an idea in my head that technology and volunteers alone can run our entire annual fund. It used to be a lot of work to manage volunteers, but with better data and the advent of AI, I can have what used to be difficult to manage two to three volunteers. I can build automated workflows that could manage 50 to 100 volunteers and really change the complexion of uh Who those volunteers might be, you know, get some more kids in the mix, um, people that may might not ever be in a position to write a check, but doesn't mean they can't sit down and make a new friend and tell them what's going on at the organization. So, you know, the constant improvement never stops. And it's typically it's typically those like morning moments where these initiatives haunt me and uh set me on fire and watch out uh when I get to the office.

SPEAKER_01 22:31

Yeah, you know, it's so funny. Uh I was just thinking that was going to be my next question, which was, uh as I said in my opener, quite the analytical thinker. I think all the listening audience uh can already feel that from you, which is a beautiful gift you have. I'm wondering about the toll that that analytical mind of yours has taken on your uh executive team or your directors of team uh in terms of the idea, um, the ideas that you present and which then ultimately I'm assuming change workflows.

SPEAKER_00 23:05

Yep.

SPEAKER_01 23:05

Just just as your team probably is getting used to another one. So I'm curious, is like how how uh how does that land?

SPEAKER_00 23:13

Yeah, I I honestly think at this stage of our organization, our our systems are really the architecture of the organization. And as long as the systems and workflows are documented, the tools become uh less relevant. Uh you can swap them in or out, but you need to know how you do work. So I actually just built a tool called Orlock and sold it to um a consulting firm called RoboPartners, which is a really well-intentioned uh group of executives later in their careers that want to help nonprofits around Maine operate a little bit more efficiently. And what this tool does is it it does use AI to take your strategic plan and to map it down to uh the task level. And all those tasks and their standard operating procedures map to personnel on your team, and there's an audit trail all the way back to the outcomes and programs that they support. But the reason documentation is so powerful is that it gives uh it just gives total context and visibility into your organization. Um, and it also allows you to operate uh or manage your staff at the scorecard level as well. So, you know, particular staff members, they can see their entire role. Uh, they can see their scorecard, which kind of has the key metrics that uh that's the accountability layer to make sure those tasks are actually being done. And I'll give you an example. You know, we very early on we saw that we were um spending a lot of time on financial administration and development, right? So the organization made a $50,000 investment to bring in a co-op from Northeastern University to help with some of these automated development workflows and uh engage to create a committee to support the finance function of the organization as well. And so when I was, you know, when I was reflecting about how we were gonna become more efficient in those areas, it's because the alarm had already tripped that a lot of organizational resources were going into that area and we were actually missing some of our scorecards and targets. So the bell rung, and then we came up with the solution rather than just coming up with solutions left and right. So, or I'll give you another example. We had we had uh an amazing community member here that we were thinking about extending or creating a role for them. And you know, old Barrett would have probably made that offer uh instantaneously, but I had to ask myself, where where in our data or where in our scorecards are we missing that justifies you know this augmentation to our program delivery? And ultimately putting it in front of the board, we couldn't point to an area. So the question became are there are there outcomes that you'd like to add to our scorecards that you think that this person could enable? But I'm asking you to change my score, the organization's scorecard before you ask me to come up with the solution. Because right now, if I'm looking like if I'm looking at our, if I'm looking at our performance, we're we're performing above target. So I'm I've it's honestly a uh maybe a less personal. And you did say something earlier about, you know, passing down the tasks. Well, how do you pass down the culture? I will say operating the way that I have been operating the last couple of years, it's sometimes it does feel a little more task or metric first over culture first. You know, and I've I've learned you actually have to like build culture into your scorecards. Now, like, how corporate is that? That's brutal. That's like what I have to have, like a go for schedule a staff team walk in order for us to gel. But the upside has been so great that I um I'm actually enjoying corporate life more than I thought I would. Of course, getting into nonprofits too, uh, you know, I was running away from corporate America when I got through this work. So, you know, choose your own adventure. Um, but like you said, operating this way allows you to unlock so much to distribute leadership. When you give a staff member a scorecard and a clear understanding of their role, you don't need to micromanage them. And I've seen leadership be distributed much broader. I've seen community engagement blossom. Um, our our visits into the center almost tripled year over year. Now that was in part due to expanding our building, but you know, alongside our physical expansion, we were really improving our digital systems as well. So I know it can sound a bit daunting, but it's as simple as the weekly cadence of your uh of doing your work. I have a task that hits me every week to document one thing that I do that week. And so I go into Orlock and I document one process that might not be documented. And if everyone on our team is just adding one piece once a week, you'd be amazed at how good your documentation gets within six months. And then you download your architecture into a tool like Claude. And now all of a sudden, you have a genius looking in and doing a gap analysis between your organization and best practices in the field and highlighting areas that you can strengthen as an organization, um, just getting systematically better every day. So we're I don't know. I'm I carry I also carry a flip phone. So it's like, I don't know, can you have can you have it both ways? Can we can we be Luddites and deepen relationship with each other and also you know, walking hand in hand with the computer all day?

SPEAKER_01 29:28

Um well let me press on that a little bit because I I uh I was thinking as you were talking about in essence, you left the corporate world and you followed your passion from from that world into youth development, and then found yourself in this incredibly exhilarating opportunity to build an organization around your passion and the passions of the city and the passions of the people that you were around. And uh yet you also brought in this maybe too strong of a word, but a corporate mindset around building systems using technology and other systems to not just uh grow, but also to hold accountable to people, people accountable for their roles. And as you build those systems, how is it that you leave room for uh things like uh humanity, relationships, and the com messiness of community life? Like how do you keep uh the structure from becoming sterile?

SPEAKER_00 30:32

Yeah. I think it's about putting together a team. I used to be a pretty good culture builder. You know, I was running opening circle with the kids, I was giving the pump-up speech at the staff meetings. I have had to, you know, getting leaning into my system's mind has come at the cost of being a great culture builder. You know, fortunately, uh one of our staff members, a Ryundai Krueger, joined our team and a former executive director and someone that I consider to be uh a champion, a champion culture builder. And if you, you know, so I've had to, I've had to uh maybe fill those gaps where I used to be able to fill that role and I'm no longer I'm no longer as effective in that capacity. You know, I've had to find a teammate that can pick up the Slack and complement my skill set. So uh it's interesting, you know. I was always a visionary and I was always supported by implementers, and then I became an implementer, and I need to be complimented by visionaries now, and uh, and so it goes. So it's it's putting together a great team. And uh so it's it's really great. Well, let me great to be able to rely on the strengths of others.

SPEAKER_01 31:49

So let me ask you a more personal question around this, Barrett. So, what has been the hardest part for you personally about moving from building something originally to letting go of a number of things like you just mentioned as a way to sustain the organization over time.

SPEAKER_00 32:16

Like I think uh it's that that is a personal question because it's really it's really been like the creation, you know, I'm building a family now for the first time. And so I would uh I would enjoy to be more community-facing in my role, but I do feel like financial pressure now, and I do feel like I owe it to my family to serve in my best and highest use as like a you know piece of the capitalist machine that we all live in, uh, which means I sit in my office all day. So I don't know, hopefully, hopefully, um hopefully I'll be able to balance that equation a little bit more in my next chapter. But right now, it it really feels like I have to put my you know my family and the organization first. And a lot of those considerations are financial, as I'm sure they are for many of our listeners. So obviously, yeah, that that comes at the cost of like um doing what I love. But I'm very I'm so fortunate that my office is in a community center. So anytime I need to be uh uplifted, I just go for a little stroll around the building and seeing everybody playing and listening to music and having fun, and then I get right back to it.

SPEAKER_01 33:37

Yeah, I appreciate that context. And uh obviously uh we were talking before we got on about the family that you're building, and I'm just so happy for you. And I uh talked in the meditation about this idea of building systems that could um empower the vision that we have. And then in the personal reflection, I kind of I kind of shifted it to really reflect on the type of person I want to become. What am I doing to make room? What am I making uh what am I doing to uh build some sort of system in order to bridge the gap between who I say I want to be and actually live the person I want to be. So I'm wondering about whether or not you could name where you have had to build systems in your own life to help support the kind of person or leader that you want to be as a way to kind of shift it a little bit from the organizational corporate space to yeah.

SPEAKER_00 34:46

Personally, I mean, aside from health and wellness, sometimes I hit my max and I have to sit on the floor and put meditation back into my life or exercise better or eat better, et cetera. So health is health is a system, obviously. Yeah, but the one that is always been most important to me is having a personal mission statement that uh it's almost like a personal theory of change. Um, so at work, I use my theory of change to make yes or no decisions. Yes, this is something that fits within our theory of change. No, this is not something that fits in our theory of change. And then at home, you know, call it a theory of change, call it a mission statement. But for a while, uh it was to support a thousand families in Portland and help build other community centers around Maine and the US. And if it was in that mission, I would say yes. And if it was out, I would say no. Uh, I I definitely um it was probably too broad of a mission. I said yes a lot. And right now I've I've made a commitment to my family to refine my mission statement for my next chapter. And I I haven't published it to uh to myself yet, so I'm not I'm not entirely sure what's gonna be in or out of it. But that's always been the most important. And people, people that I really look up to and understand most fully all have like personal mission statements as well. And then also, I don't know, in terms of what's in, what do we make space for? There's kind of three paths ahead of me where I feel like I could have a positive impact on Maine that are uh really inspiring to me. And I'm I'm not necessarily gonna go into those right now because I'm still reflecting on them. But something that I am taking a lot of uh inspiration from are the next wave of community leaders in Maine and beyond. And I I love creating opportunities for I'm just getting to the point in my career where I get the most satisfaction seeing people empowered to pick up the torch and do things. And actually, when I used to do consulting more, I always looked for three things when we were building a community center. I looked for location and capital, the boring ones. Um, and then leadership was the third piece. But, you know, more and more I'm just totally inspired when I meet community leaders that are, you know, on fire to make a difference in their respective communities, uh, however, however they define that. So the more, you know, and that's why we love youth development. Like if you can catch a student and you can give them a passion early in their life, they just become such a powerful instrument for good. So when we underinvest in education or we underinvest in our youth, we pay that price tremendously. And it and it leads to this terrible um ideology that one individual has to put everything on their back and move mountains. When in reality, many hands make light work, and and if people have a sense of belonging and they care about the community they live in, we would be crushing it. So anyway, I'd like, you know, I'm always trying to refine my personal mission statement, and I probably would like to narrow mine and make sure that part of that is empowering others to you know form their own mission statements. And that's the who, not how, that's the like collective impact. Um, that's kind of James Clear and and his friends would all probably agree that uh that kind of collective impact goes a lot further than one person carrying a lot of water.

SPEAKER_01 38:35

There's no doubt about that, my friend. Well, I I was thinking about your opening salvo around the difference the the um inflection point that you find yourself in in terms of you know, do you continue to uh lead in organization or do you continue to inspire others to think about the things that you've created as a way to better their organizations? And I I might not be I might be in the fruit bowls, but so I'm gonna uh share a quote with you and just kind of get your uh thoughts on it. But but I was having a conversation and it might have been a topic of uh an earlier podcast, uh, but the quote was something to the effect of uh I was having coffee with this um uh uh guy by the name of Bob Rowe, he's in our community, and um and he said, you know, Don, I never wanted to be uh a leader of an institution. I wanted to be an evangelist of an idea. And so I'm curious as to like, is that the crossroads in some ways that you're at where you you can spread uh these ideas that you have uh to so many other people that could uh do community change and inspire the next generation of leaders and and and young people and that sort of thing? Or do you hold on to the institution that you've created?

SPEAKER_00 40:10

Yeah. And I think I think our our organization has to answer that for themselves as well. What is scale? Because uh we could be a multi-city organization, or we could really lean into collaboration, or we could keep things simple, uh, which is a beautiful thing as well. Um and then personally, yeah, you know, I I can't say yes to every initiative. Um, and so I've just got to define where I where I put my where I put my hours and how I support my family. But um I think Maine, I am in a kind of a pro-growth for Maine phase right now, which I wasn't always the case. But you know, the hospitals around my hometown aren't doing so well. And just I'm a little bit concerned about the infrastructure in our state. And I want young people to believe in Maine and um to want to uh to shape and improve and live and thrive here. So that I don't know. I don't know why that's kind of been calling me, but I just you know personally want to be um a champion for Maine. And I just haven't defined uh what that looks like yet.

SPEAKER_01 41:32

Yeah. Well, I appreciate you uh engaging me on that particular um quote that just came to mind. Um I'm uh let me flip the script here for a second. I'm wondering whether or not you might have a question for me on this topic or any other uh along this theme.

SPEAKER_00 41:51

Oh, sorry.

SPEAKER_01 41:52

Yeah, whether or not you have a question from me on this theme or topic.

SPEAKER_00 41:56

Yeah, where we get to flip the table a little bit. Yeah. Yeah, absolutely. I mean, Don, you are such a teacher and of uh of ideas and also the softer skills as well, which I think is um what's made you such a great leader in youth development. But I remember, you know, you connected us with the, you know, the Pear Institute uh and some of the evaluation tools early in our days here at Portland Community Squash and done collective impact and field building work. Uh so you must have had a personal mission statement along the way here because you said yes to a lot of things. And I'm curious what your filter was.

SPEAKER_01 42:43

Yeah, well, at first it was um, I appreciate the question. At first it was for a very long time what was in the best interest of the organization. Well, first it was what was in the best interest of kids, because I was on the front line.

SPEAKER_00 43:01

Totally.

SPEAKER_01 43:02

Then it shifted to what was in the best interest of the organization, which is what uh I talked about that uh evolution and pain points of uh you know having to let go of focusing on that and some of the things that you've talked about, having to do the same. And then it became what was in the best interest of rural youth. But at the same time, while I was making the transition from being on the front lines to building the infrastructure to support the overall vision, I made a lot of room. I wasn't doing a hundred-hour uh weeks anymore, which was great. Not that I wasn't doing a uh a lot of work, but it did open up a space for me, much like you're talking about, which uh allowed me to meet my wife. And uh that was, you know, about 13 years ago. And so then it became what's in the best interest of rural youth. And the larger picture, but also what was in the best interest of my family. And having to figure out how to do that. Well, that led to me letting go of Trekkers and turning it over to new leadership while I went after the idea, which was, you know, I really resonated with Bob Rowe's comment because it hit me at a time when I was saying, like, do I really, you know, there's so much of me invested in this organization? My identity is there. Who am I without it? All those questions that, you know, founders have to deal with. And at the same time, I was like, but what's in the best interest of my family? What's in the best interest of Maine for rural youth? Is there a way for me to take not the practice of trekkers, but the principle, philosophical principles behind the model? That if I could codify them in the way that you talked about documentation, could I take those and introduce them to other leaders in other communities and see what they could do with them as a way to iterate in a way of almost open source of saying, like, listen, take these, these work, they've been proven, but your community's different, your leadership's different, your your challenges are different from where we were implementing this. But let's see what we can do. And at the same time, that meant that I wasn't having to build the organization anymore, I wasn't having to uh raise money anymore, but I was in a position to give money as a way to help implement some of these ideas to see if they worked. And then we had enough money to bring a third-party evaluator to just review it all and see what things stuck and what didn't, and um, as a way to kind of level up the field in terms of those who were doing work in the rural spaces. So I that's a probably a long-winded answer, but that was part of my own. I'm so glad you brought up the piece around the personal mission statement. You know, every year at Trekkers, we would do a rites of passage for kids who went through the six-year model at the very end. And and the idea was to mark the end of one uh particular stage of life of adolescence and the beginning of something else, which was adulthood. And we began to say, like, listen, who is it that you want to be as you go there to become an adult? What do you need to let go of in your adolescence? And we want you to build a mission statement. We want you to write a mission statement for your life. And then we want you to come back from that and we'll do a ceremony where you read it in front of your peers as a way to kind of help you say out loud and as a way to kind of hold yourself accountable to manifest this in your life. And then we'll do all everything we can to help you build systems in order to get there. So I really love that you brought it up, and it it is something that's guided me throughout my career, but also my personal life that that I've always had a desire to really do what was in the best century for kids, and that's taken a lot of different scaling, but also different perspectives of how I might do that.

SPEAKER_00 47:12

Yeah, that's great. I got two more for you. Sure. Next one. I was never the best student, and I've been so empowered by uh the AI tools that have become available to feel like I can learn and move into new areas um and understand problems at a deeper level. I'm curious if you have leaned into the tools um to expand your skill set. Yeah. Just a timely question as we're all wrestling with this stuff.

SPEAKER_01 47:50

Yes. Well, here I was just having this conversation on my way to this con our interview uh with a with a really good uh one of my best friends, and he is in the steel industry, and he was asking me the same question like, how are you using AI to to to help you do your work? He said, You do a lot of writing. How how is it that you you know how you use it without it becoming AI voice and and keep it in Don's voice? I said, Well, I write everything out, and then just being totally transparent, I've had a hard time at times when it comes to my writing to get critical feedback on that, because I take it personally. And the greatest thing that AI has done is that I can put it in there and to and say, like, don't sugarcoat this. I really need you to tell me where this isn't landing, how it could be better, what what are some ideas that could get me there? That curiosity of just allowing that mirror, even though it's this strange thing of, as you said, a genius helping put that out there, it does never come back brutally honest, but it also I never take it personally and I can just keep moving on. And I can consider those ideas or not consider those ideas. But nonetheless, uh, it is one way because I I I do a ton of writing now as part of this podcast and the books I write and things like that. And when I get stuck within a particular uh loop or ruminate on something, it allows me to say, ah, I've got something that can be a mirror for me out of a space of wonder, awe, and and curiosity to help me critically think about it. Um, that's at my fingertips rather than having to go and find somebody else. So I do a lot of uh asking it for critical feedback.

SPEAKER_00 49:51

Yeah, no, that's great. You know, just back to the personal mission statement. I I feel like if you can, if you can envision it, you can you can create it. I mean, I find I sound like I'm a knowledgeable person with tech and workflows and I'm building web apps. Um, but I've just been I've been learning. I've been asked, you know, I've been um I feel like I've had a coach that I could never access before that's allowed me to build a more mature organization with the same limited resources that all of us operate in the nonprofit sector. Uh and I'm not exactly sure where it goes, but I have been grateful for the ability to learn and grow. So anyway, whether that, you know, whether it's remodeling your kitchen or or writing your first web application, I'm believing you're done. Um which brings me to my last my last one, which was uh, you know, you the the trekkers model uh and the cohort model is totally profound. And it's funny, I've I've gone against a couple of the core principles or just tried a different direction. Uh you know, our goals here are to give those high-touch uh resources to families for as little of time as possible so that families can lean in in their own authentic ways into like a broader uh community. And next time we get together, we'll have to, we talked about systems all day, but theories of change, we've both been really wrestling with the ways to unlock, unlock the power of community and young people. So I look forward to uh we'll have to have a healthy debate on another meditation sometime in the future.

SPEAKER_01 51:38

I look forward to it. I look forward to it. And I do think context matters and just in general, because I think that we have just for the listening audience, when Barrett talks about uh cohort model, meaning taking a small cohort of students and putting them in the learning community, but following them over time. Uh, the difference between um building a cohort model in an urban environment and context versus in a rural community where a small cohort can be almost 35% of the class. Yeah. You know, so all of a sudden that just does change the game a bit in a small community. So, anyway, but I look forward to that. I've got one final question for you uh before we move on, uh before we end this. It really gets at what you have personally learned about the difference between control and stewardship, meaning when does a leader need to hold on, and when does a leader need to build something strong enough to be held by others? And you know, you as a founder have gone through every probably uh developmental stage of an organization. So you know this piece around holding control over the standard versus stewarding enough of a culture and system to uh allow this thing to thrive well beyond you, which you've done, but could be even more in the future.

SPEAKER_00 53:15

Yeah, I think the way I've managed that over the years, I've always believed that the correct answer is in the collective and use the board for you know the purposes that the board was created, which is to give direction in those moments. You know, this is when we're iterating and experimenting, this is when we're codifying, this is when we're centralizing leadership, this is when we're distributing leadership. The next step has always been pretty apparent to me, and I think that's because it's being held by a broader group of people and not just one individual. The only time, you know, there's only one time that I went against the board, and I think I was right, and that was uh the color of one of our courts. I wanted to go with like a splashy color, and we went with with white, and uh anyway, we ended up repainted or something of the of the 2000 decisions that have been made. Uh I've I've pretty much always believed in in the collective on that one. So yeah, it's nice to be in uh in good company as you as you go through all the life stages of an organization, um which can be trying if one person's holding too much.

SPEAKER_01 54:34

Yeah. Well, um what I take away from your answer is that if the correct answer is always in the collective, it means you've had to build a team that believes it is the collective. And so that's big kudos to you because uh leaders uh or institutions and organizations that get stuck or don't thrive or aren't growing is usually the answer to that has to do with that there isn't a collective that's that's trusting the person leading.

SPEAKER_00 55:16

Yeah, and the theory of change is the foundation of all the systems are built on top of that. So if you're gonna change your theory of change, you should get a bunch of community input because that's gonna ripple through every corner of your organization. And for a long time we didn't even have one. And I don't think, you know, a lot of us don't. So yeah, if theory of change is a new term, whether you're private or public sector, um, worth looking into it. I'm a fan now.

SPEAKER_01 55:44

Yeah, well, uh, if you want to see an incredibly well detailed idea or model of what Barrett means by theory of change, you can go to his website at Portland Community Squash.org.

SPEAKER_00 56:00

Uh, it's pcsquash.com or Portland CommunitySquash.com, either of okay, yeah, but it's on there because I saw it and uh I was super blown away by it.

SPEAKER_01 56:10

Well, Barrett, listen, thank you for joining me today. I really appreciate it. If you could um stick with me for a couple more minutes, I'll close this out and I get to say goodbye to you. So I just want to offer a couple of things that I'm taking away from my time with Barrett. And the first thing that really struck me was that he continues to ask the question about how does he, how does the organization position the person that could be a person within the community center that comes there looking for a program, could be a person that wants to that they need to join the board, could be a staff member that comes to join their team, but how does he position the person to thrive? It's a fundamental question that he asks. And I really loved it because if you're it means that he's thinking all the time about the very mechanism that he's putting out into the world, it assumes that if people are positioned right, they're gonna thrive by that mechanism. In this case, is uh a community center where people feel like they belong, they're valued, they're heard, they're seen. So I really love that piece. I also love the fact that he said that, you know, when I was young, I had to promise the world. And at first it was through his own efforts, hundred-hour weeks, things like that. And um, but then he realized that that was leading to burnout. So he had to build systems in order to delegate some of that work and uh as a way to for the organization to grow. I love the fact that he mentioned always looking for growth hacks as a way to help him and the organization um get to where they want to be faster, stronger, uh, and more clear. And then he mentioned this idea about constant improvement never ceases. That there is this idea that you know we're growing or we're dying. And in this case, he's saying, like, I'm always looking for constant improvement. And if if you as you listen today, I'm sure that backs up by everything he was talking about and how he's thinking about it from a really deep analytical mind and how to use technology and other things to get there. And then uh two more things. One is is that this is one of the pieces that I think is so important, especially for those of you who are listening who lead organizations, which is it's really, really hard to hold people in your organization accountable if they're not clear as to what they're being held accountable for. And that means that you have to document the systems, you have to codify systems in a way that is super clear. Brene Brown talks about the idea that clarity is kindness. Clarity is kindness. And you can only be clear if you're able to codify and write down so that people can read, talk about, beat up the very systems that are holding them accountable. If it's all in your mind, it's very hard for someone to interpret what you're thinking. And then finally, I don't know how many of you in the listening audience actually have a personal mission statement, but I really encourage you to think about it. And maybe you could even use AI to say, I want to build a mission statement, what's included in that, and begin to do a reflective exercise on what that might mean. It's changed the way I did my work with kids. It's also changed the way I try to manifest things in the world, whether or not something's aligned with my mission statement or unaligned. And that gets to gets me real fast to a yes or a no. As always, I want to leave you, the listener, with two questions for your own reflection on this particular theme. First is where is something I care deeply about being held together more by my energy than by a sustainable structure? Where is something I care deeply about in my life being held together more by my energy than a sustainable structure? And two, what is one system I need to build, build, strengthen or trust so the work no longer depends so heavily on me? What is one system I need to build, strengthen or trust so the work no longer depends heavily on me? In closing, again, I just want to thank Barrett for joining me today on the podcast. It was a pleasure to see you and uh be in your presence again. So thank you. My thanks as always to Omar for producing this episode. I appreciate so much your incredible hands and mind and ability to do this so so well. You're really, really uh magical. If you found something meaningful here today and would consider sharing this episode with somebody else, that simple act really does help grow the community. So please share just one. And if you have a reflection or thought you'd like to share with me, I'd love to hear from you. You can reach me at any time, Don at Carpenter Company Consulting.com. Thanks for listening. And please remember the journey of leadership begins within the microphone.