Father Time is Undefeated | Steve Filosa

Steve Filosa spent twenty years running Prep@Pingree, a scholarship, academic enrichment, and jobs program in Essex, Massachusetts. The program's premise was simple and counter-cultural: serve kids through long-term relational commitment rather than high-altitude, short-term intervention. Not something that scales. Something that works. By design, Steve built it to replace himself. Eventually, he did.

What came next surprised him. He expected to help other organizations build more Prep at Pingrees. He didn't expect that a significant part of his practice would turn out to be working with donors — people with resources to give and no one to think alongside them about how to give intentionally.

Six years in, Steve talks about uncertainty in a way that doesn't come from a framework. It comes from experience: starting a program in 2001 under enormous national headwinds, committing to something again at fifty with no safety net, and discovering both times that the net appeared.

In this conversation: what he didn't anticipate about building Prep@Pingree; why he thinks TFA-style interventions tend to serve their participants more than the kids they're there for; what changed in the final decade that made handing over the keys feel like relief; what the hardest thing to teach a board is; what year six looks like compared to year one; and what "peace" actually means when you've stopped needing to have all the answers.

IN THIS EPISODE

• What Prep@Pingree was — and why it was built not to scale
• The "100% admission rate" — why Steve bragged about the one number nobody bragged about
• The teaching hospital model: experienced teachers who wanted to train the next generation
• How alumni became the jet fuel
• Handing over the keys: what changed in the last decade
• From program director to consultant: the part he didn't see coming (donor clients)
• What the hardest thing to teach a board is
• Year one vs. year six: what changes when you hang a shingle
• The Goethe quote one of his first clients gave him — and whether it turned out to be true
• What "peace" actually feels like: the texture of not needing to know
• "Is Steve still talking?"

Transcript

FILOSA EPISODE — CLEAN TRANSCRIPT

"Father Time Is Undefeated"

The Principal Uncertainty

⸻

George Laufenberg (00:00) 

you and I have known each other for just about nine years. I was realizing thinking about this, right? It was it was the National Partnership for Education Access Conference and

Steve Filosa (00:04) 

you

George Laufenberg (00:10) 

April, I think of 2017 is where we met for the first — Because I had the opportunity to build a summer enrichment program at the school in Baltimore. And, you know, there was, there was no better model than what you were doing with Prep at Pingree.

Steve Filosa (00:18) 

Yeah. Let's try to remember the sequence. Had we met at NPEA

George Laufenberg (00:27) 

it's been wonderful to watch your trajectory over that period of time and how that's unfolded for you. And obviously we know each other from the land of education reform. And one of the things that I immediately respected and appreciated about the Prep at Pingree program that you built was that in many ways it's sort of the opposite of Teach for America. Well, what I mean is, right, TFA as with so many interventions in ed reform, right, is this like large scale, high altitude, short term surgical strike intervention, right, that ultimately does a lot more for its alumni network of young people who do the program than for the kiddos. And, you know, the — in some ways, the kind of polar opposite of that, right.

Steve Filosa (00:54) 

How so? Yeah. Cheap labor, no nothing labor, yep. Turn and burn, yep. Yep.

George Laufenberg (01:23) 

Is this incredible thing that you like built as a verb, but cultivated is one that I like even more in this context, right? Because it, you know, when I think about what you built, I think about it in terms of, know, this long term relational commitment to individuals, right? This thing that fundamentally doesn't scale, right? You could like, you could try to reproduce it, which is essentially what I was trying to do in Baltimore to replicate it.

Steve Filosa (01:46) 

Thank you. Yeah.

George Laufenberg (01:52) 

But it's not a matter of scale, right? Because the heart of the thing is the relationships, is the commitment to individuals, because you can't fake that and you can't scale it. And it's just so rare to see that actually.

Steve Filosa (02:01) 

Yeah. Yeah. And that's what people need. That's what people need more than anything. Especially kids. You know that. In a way, that's kind of your business model. You're doing the same thing in a different form, it seems, where you're trying to provide high-touch relationships with people so they can talk to you about what's on their mind. And you might offer something here and there but you're not going to have a thousand clients, you're not going to outsource it to AI. There's no AI tool, it's really going to — and I feel the same way about what I'm doing. I'm not looking to build an empire here. Because I don't think — I think those often, it goes cross purposes to what you're really after.

George Laufenberg (02:35) 

I hope not. Mm-hmm. Yeah. So you launched Prep at Pingree in 2001. Steve, what was the hardest thing to get right in the first five years that you didn't anticipate when you started?

Steve Filosa (03:04) 

That's a really interesting question because there's so many things we thought we saw coming that turned out to be the case. I always wished that the school itself embraced the program more fully. Meaning, the full-time teachers and staff, I always wished that they were more a part of it. Or even understood what it was really all about. And there are reasons for why that didn't happen, much as we tried to invite. But I really thought it might catch on more internally. We had a pretty good sense the kids would sign up because we asked, what do you want? And this is what they said they wanted before we did it. Same thing in the schools. What do you want? OK, we'll do that. We didn't invent this thing and here you go. It was — you know, go out and talk with some people and see what they say they want and how we can maybe help, if we can help. And we pretty much tried to do what everybody was telling us would make sense. So that wasn't surprising. The fact that kids signed up wasn't surprising. The fact that kids enjoyed it for the most part, that wasn't surprising. The fact that people wanted to work for us, even full-time, experienced teachers wanted to saddle up for a summer of teaching — when most teachers are looking to disappear, right? You know how that goes. That didn't surprise me. It didn't surprise me that people gave money. I knew funders. I think we had a pretty good sense that funders would be there for us and these kids, these communities. But I just internally, never quite — people didn't latch on to it. And they didn't even seem to want to understand what it was. And there are reasons for that I think, probably mostly that your full-time teacher, coach during the school year, you've got your hands full with your own stuff. And when the summer comes, most of them want to disappear. Understandably, rightfully so maybe even. It's a pretty rare bird to teach 12 months a year, right? And pretty rare kid to go to school 12 months a year. I always felt that. I used to say one of my standard talking points at any public event was like, who signs up to go to school in the summer voluntarily? Who signs up to work and continue to teach in the summer? Who does that? Well, these are the people who do that. And it turns out that's a pretty magical combination.

George Laufenberg (05:59) 

Yeah. Hahaha.

Steve Filosa (06:16) 

Because they always talked about how, I walk into my Prep at Pingree classroom and all the kids are there waiting. They got their books out. They did what I asked them to do the night before. And they're ready to go. Whereas I walk into my fancy prep school class — where is everybody? Can I go get my book? You know, if they show up at all and prepare, maybe, maybe not. They always talked about that fundamental difference of culture in the classroom, it's eye-opening to me. And I used to teach early on in those summer programs, I felt the same way. I'm like, wow. Hey, guys, you can take a break for 10 minutes and we'll pick it up again later. They come up to my desk to hang out. They don't go running out into the parking lot. I was like, alright, what am I going to talk about now, Mr. Filosa?

George Laufenberg (07:23) 

For folks who are not familiar with the model, can you maybe just give an overview of what Prep at Pingree is, how it plays out?

Steve Filosa (07:33) 

So at least during my 20 years, we described it as an academic enrichment, scholarship, and jobs program for kids from — and we use the language — underserved communities. Early on, we talked about just the cities of Lawrence and Lynn, because those were two gateway cities with all the issues that tend to come with those communities. And fundamentally, we used to say to the kids when we enrolled them, like, we know you're in a school with people who care about you, and we just want to keep the good times rolling. We want to keep it going through the summer. And what else are you going to do, by the way, especially in middle school? And kids would tell us, like, why'd you sign up for this? Often it was my parents told me to, or somebody at my school told me to, but often it was also — well, I'm 14, 13. I'm not old enough to get a job really. And I'm too old to go to camps and stuff like that. Kind of no man's land at that age. What are you going to do all summer long? So anyway, we described it in all kinds of ways, but those three things — academic enrichment, it wasn't remedial, which is often where people went, especially because it's this population of kids. Again, these were some of the brightest, most motivated, interesting, good kids you'd ever want to meet. So nobody was there because their probation officer told them to be there, or they were trying to repeat a grade. None of that. These were kids who wanted to learn, wanted to be around other kids who wanted to learn. And by mission, it was not about placing kids into prep schools or Catholic schools. Although that happened — about a third of the kids would go to independent school, about a third of kids would go to Catholic school, and about a third of the kids would just go back to their public school for high school. All of which were just fine with us, and we talked a lot about fit and what you want to do. We weren't making any claims about, do this program and you can go to Pingree because that's the best thing that could ever happen to you. We didn't talk that language. In fact, the kids knew it could be the worst thing that ever happened to them, to go to boarding school, to leave their friends, leave their community, leave their families even. But when kids got interested in that kind of thing, we tried to help them. We tried to be a neutral party in those high school destination conversations, which also is — like you were saying earlier about Teach for America — kind of counter-cultural. We didn't brag to donors about how many kids went to Pingree or how many kids went to prep school, just like a lot of high schools brag about how many kids go to the Ivies. We didn't want that conversation. We didn't want to make any kid feel less than or better than anybody else based on their high school destination.

George Laufenberg (10:55) 

Mm-hmm.

Steve Filosa (11:05) 

I used to walk into the Pingree board room and I'd say 100% admission rate this summer. And that's what we're shooting for, because we just think it's kind of cruel to tune kids up only so that we can reject them. I used to say that to a boardroom full of people who had just heard a presentation from our admission director bragging about how the admission rate is so low. We're at an all-time low. We're so selective. That language, again, we weren't buying that at all. In fact, we thought it was actually bad for kids to do that and have that dynamic in place — to intentionally set that up in all the ways that prep schools and colleges and employers now do set it up so that they can just say no to people for their own ego benefit, US News formula, whatever the rationale is.

George Laufenberg (12:03) 

What do you think it does to the kids?

Steve Filosa (12:06) 

I think it's ruinous for kids. I think it's awful for kids. I think kids absorb the message that no matter who they are and what they do, it's not good enough. And they are being judged all the time by everyone, especially the adults in the room, based on where they go to — wherever. College, high school, job. When the goal, I think — and you think with young kids especially — the message should be unconditional love. Like you're who you are, we love you, and we're gonna celebrate that. And if you want to grow, you want to do this, you want to do that, yeah let's do that too. But this constant comparison microscope — to be better than my classmate, my teammate — disastrous for kids. Teams no longer function as teams because this kid has to score more goals than that kid so that they can have these many goals for the college recruiting process. It never ends, George, you know that. You've seen it. I don't know if you've seen it with your kids quite in the same way I used to see it. And they — I think they repel from that. And they see the hypocrisy of when we get up and make a speech about how we're all kumbaya together, they're like, no you're not. You think that kid's better than that kid because they got into whatever school or they have some SAT score that they probably paid for one way or another.

George Laufenberg (13:45) 

No. Mm.

Steve Filosa (13:58) 

I'll never forget being at a spring athletic awards event and our son was a sophomore at the time, maybe a freshman, and he was on the lacrosse team. Of course I'm hearing all about lacrosse culture through his eyes as a kid. And someone from the school — I think the head of the board of the trustees was coaching this team — and he went on and on. He was celebrating some kid. I think the goalie of the team. In this ceremony, he was celebrating this kid. So-and-so's got such great character. What a wonderful kid. We love him. I hope my own son is like him. Blah, blah, blah. We're driving home that night, and from the back seat I hear — my wife and I hear — hey dad, you know that kid that the president of the board was going on and on about? He's the biggest drug dealer in the school. Of course I had no idea. I bet the coach had no idea. But the kids know.

George Laufenberg (15:01) 

Jesus Christ. But yeah, we never do, right?

Steve Filosa (15:10) 

And so they hear all this — and so, can I trust these adults who are charged with my well-being? Do they know who I am? Do they know who the other people are?

George Laufenberg (15:14) 

Yeah. Yeah. Yeah. Yeah. No, that's right. That's the beating heart of it. The question of trust. And do they know me? Do they see? And that — what sure as hell seemed to be working beautifully in what you were doing differently was precisely about being seen. That's what I was trying to reproduce in Baltimore. The experience of — when I would train the undergrads who were there for the summer, not as teaching assistants so much, but as the proxy for camp counselors — what I would say to them is that the most important part of your job is to be the person who can tell by the look on a kid's face what kind of night he had. Which is — I'm borrowing from expeditionary learning and outward bound stuff. Talk about the year-round and the longitudinal components of that work.

Steve Filosa (16:08) 

Absolutely. Absolutely. Yeah. So over time the program grew to be a 12-month program. It was principally, when we started, I think it was eight weeks the first summer we did it. And then it was kind of like good luck with everything. And again, because of our students, because of our staff — well why are we just doing summer drive-bys? Why don't we get together at least in the fall, check in on everybody? So that 12-month component was still summer principally — that was where most of the action was. But then it's, okay, let's get together in the fall and go for a hike. And on a hike in the mountains, let's go see a prep school while we're up there, in case anybody's interested in a boarding school. And then it turned into Thanksgiving. Let's all get together for a pizza. Because everybody's home from college or whatever. Let's get together, see how it's going. No agenda, let's just check in and eat some food together. And then maybe a tour in the winter to go see a couple of colleges. And whatever was working year-round and in summer, it was always because we asked the kids, what do you want to do? And when we started hiring — once these students started getting old enough — we'd hire alumni to work for us. These are kids in high school working with us. These are kids in college working with us who had done the program. And that's when — like, that was jet fuel. Because they'd come back with, well, this is what you got to do. This is what the kids need.

George Laufenberg (18:14) 

Yeah.

Steve Filosa (18:15) 

And they were actually teaching. So it's not Mr. Filosa in the math classroom — it's the kid who went to their middle school but is now 24 with a few years of teaching experience and had spent maybe four or five years apprentice teaching basically when he or she was in high school or even college with an experienced teacher. That was the other thing that was not TFA-like. We weren't hiring 22-year-olds and saying here's the toughest teaching assignment you can have with no teaching experience. We were hiring a mix of incredibly experienced teachers who understood everything and were amazing teachers in their own right, but also wanted to teach younger teachers. So as an apprentice model, we used to describe ourselves as a teaching hospital basically when it came to our staff. And that's what we thought of it as — and again these aren't all my ideas, by the way, these are things that I would talk about after someone said why don't we do this, we should do that. Which is — I don't think TFA, right. They gotta hire somebody for no money, chew them up for two or three years, off to business school, and it becomes party talk: I did TFA in New Orleans for a couple of years and now I'm a private equity guy.

George Laufenberg (19:38) 

Mm-hmm. It's so — I mean, you built this thing that, by design, the way I've heard you talk about it, by design was meant to outlast you.

Steve Filosa (19:47) 

We used to say to the board early on, the goal is to replace every single one of us with someone from the program. Someone as they got older — like the boardroom should be alumni. Should be parents, people running it. Shouldn't be me. And eventually — I think this is still an unmet goal — but the donor list hopefully starts to look like alumni of Prep at Pingree, rather than whoever the funders in the early days were or are. That's a tough one to get at. But yeah, we always wanted to replace — overtime for all kinds of reasons — most of which were just, Father Time is undefeated, right? No one's gonna be wrong for that.

George Laufenberg (20:23) 

Yeah. On a long enough timeline, everyone's survival rate drops to zero. What did it feel like to hand over the keys?

Steve Filosa (20:44) 

Well, by that point, I was ready to hand over the keys. I had been handing them over for about 10 years. Handed all the program, staff, community partners, families — 10 years before I left. And it was amazing. That's what made the program so much better. That's what allowed us to raise more money, because then I could go do more of that. So in a way, it wasn't hard to hand them over at all, actually. And I also had some frustrations about where I thought we were going and what it might look like in five or ten years if I had stuck around. And I didn't really want to be a part of that.

This is all happening during COVID, George Floyd, the ascent of Donald Trump. It's interesting because a very senior faculty person said to me a long time ago, pay attention to the national scene because that stuff starts to play out on campus. And sure enough — she was so on the money. Because the first 10 years of Prep at Pingree, I remember them as — everything is possible, what do you need from us, Steve? People who may not have agreed with what we were trying to do were relatively quiet about it because they felt a bigger momentum. Whereas the last 10 years — think it was the rise of Trump. And so people got a lot more comfortable saying stuff that they'd always thought, but didn't feel like they could say maybe when Obama was at his heyday. But yeah, I'm gonna say this now, because it seems okay.

George Laufenberg (22:40) 

Yeah. Yeah. Mm. Yeah, the permission structure that was deployed nationally for the kind of structural racism and inequality, I watched it play out.

Steve Filosa (23:02) 

Yeah, absolutely. And I could see diminishing commitments — subtle and not so subtle — to our students from a lot of places. Every year we would know how admission went, how financial aid went, who got money, who didn't get money, why they got money. We saw all that. And you learned from it. And kids knew. Our staff knew. So anyway, no, it wasn't hard to hand over the keys at all, as much as I loved the 20 years. I feel so lucky I got to do it. I worked with some of the most incredible people. I could never have imagined how great it was to work with some of the people I worked with. And so many of the people who were my best colleagues ever were high school and college kids who were incredibly talented, so smart. But yeah, I think by the time I left, I was ready to go. And I had begun to try on something else. I had begun to try on this life that I'm living now. And my kids were graduating and leaving. I was turning 50. There's all that stuff going on in a person's life. In a way, I probably should have left five years before I did. I think that sometimes. Mostly because I just love what I'm doing now so much. So anyway, wasn't hard.

George Laufenberg (35:11) 

I just wanted to turn to the transition that you've made to the work that you're doing now that you've been building for the last five, six years, right? Six years to the good. And you're doing both sides, right? You're working with donors and with organizations. What did you think you knew about the donor-nonprofit relationship that turned out to be either wrong or maybe insufficient once you were sitting on the consultant side of it?

Steve Filosa (35:36) 

Well, talk about the principal uncertainty. I had no idea I'd be working with donors. When I decided to do this, I thought — okay, I've been a part of this group of people that built something over 20 years. We've raised money, we've built boards, we've done programming, we've hired, we've looked at all that. And I know there are places out there calling up to say, hey, what's up with Prep at Pingree? Because we're starting Prep Collegiate. That made me think, I might want to do this, like, much more intentionally. And I was getting calls all the time from people all around the country saying, how are you guys doing? What are you doing? Because a lot of places wanted to do it and couldn't quite figure it out, or couldn't quite figure out the money, especially. And so for almost from the very beginning, I was taking calls. I was being invited to go talk with boards. I was asked to talk with the head of school, and often I would bring someone from Pingree with me — like I'd bring the CFO or I'd bring the development director. And we would just kind of give it all away for a long time because we wanted to see more places do it. At some point, it became clear — I might be able to just do this. That's what I thought my business was going to be. I would help places get more Prep at Pingrees going, maybe help more places raise money generally, nonprofits generally. That's what I thought it was going to be, and that's what it was. And then one of my first clients was a bank foundation, and they asked me to help them think about some stuff. And then all of a sudden, a couple years into it, I had a whole bunch of donor clients. Because it turns out giving away money is not so easy. I mean, it's easy to write a check, but it's not easy to do it intentionally, to know where it's going, to be involved in it. It's kind of lonely. I think a lot of people, they do it on their own, and they don't really have people to talk about it with.

George Laufenberg (37:27) 

Yeah. Yeah. Mm. Yeah.

Steve Filosa (37:42) 

So that kind of grew pretty quickly over time. But I did not see the donor side of the house coming at all. And there are days when I think instead of 50-50, which is what it is now, maybe it's more like 75-25 eventually — donors to nonprofits — for all kinds of reasons. But yeah, I did not see that part coming at the beginning, that's for sure.

George Laufenberg (38:04) 

Interesting. What's the hardest thing to teach an organization that thinks it already knows how to do fundraising?

Steve Filosa (38:21) 

A lot of boardrooms I walk into think that it's somebody else's job to raise money. That's our development director's job. That's our chief executive's job. Sometimes the chief executive thinks it's somebody else's job to raise money — that's our development director's job. And I spend a fair amount of time explaining that no, no, no — one of the primary responsibilities as a board member is to give and to raise money. And what does raising money look like? All kinds of different ways that take shape. But a lot of boards seem to think it's someone else's responsibility to financially keep things going. And that worries me. We want to do a campaign to build a new building or whatever it is they want to do — okay. Tell me about the board's role in all that. Anybody going to make a major gift in this room? Do you have 100% participation from your board at least? To say, you know, I'm in, I might be in for a hundred bucks, but I'm in. Often the answer is no. And I'll usually say, well, I don't think you're ready for a campaign. How about spending some time building your board. How about spending some time building your annual fund. Because that's where your campaign success comes from. So I think it's an easy misperception to think, for board members — no, that's not really our role. I have a client — they don't even have a fundraising committee on their board. I'm about to tell them they should. But I don't think they're going to like it. The number of board members who say to me, I love this organization, I'll do anything for this organization, just don't ask me to — quote — hit up my friends and family for money. I hear that all the time. And to which I reply, well, no one's going to ask you to hit anybody up, first of all. But you need to be engaged in the fundraising. You have to make your own gift. A personally meaningful gift. It doesn't have to be a big number if you can't do a big number. That's not the point. But if your name's on that donor list, I know my donor clients — when they get asked — one of their first questions is, tell me about the board. Do they give? Does the board vote for 100%? If you can't say yes as an executive director, my donor clients are going to say to you, why would I give if your board doesn't give? Talk to me when your board seems to care enough to make a gift. I hear that all the time from my donor clients.

George Laufenberg (41:10) 

Yeah, I sure have.

Steve Filosa (41:23) 

And some places — the healthy places, the great places — they get it. They totally get it. And they get that I've gotta make a gift. I've gotta attend events. I've gotta invite people. I've gotta put on my LinkedIn that I'm a board member, so people even know that I'm on the board. When I go to a party and someone says, how's it going? What are you up to? I might say, I just had this amazing board meeting, or I just went to this incredible function for this nonprofit that I support. There are all kinds of ways to raise money. You don't actually have to say, you give me money. But to spread the word, to be an ambassador, to tell the story — that's what you need from your board members. Making introductions and let the chief executive or the development director follow up. All that's incredibly invaluable, but a lot of boards don't think that's their thing. I'm going to tell George how to run this program. No. No, George knows how to run this program. He doesn't need your help. You sell missiles. What are you going to know about the food pantry? Have a little humility, right? But wealthy white men like me tend not to have all that humility. Sometimes.

George Laufenberg (42:36) 

Hmm. Yeah. Imagine.

Steve Filosa (42:55) 

Doesn't stop.

George Laufenberg (42:55) 

Yeah, it's not rewarded, right? I mean, it's part of it.

Steve Filosa (42:59) 

It's not — it's exactly right. That's exactly right.

George Laufenberg (43:03) 

There are so many disincentives to be humble. You can't get to that position. I mean, you've worked with organizations across a huge range of sectors at this point — independent schools, youth groups, international health, environmental work. Steve, what do they have in common that they don't know they have in common?

Steve Filosa (43:23) 

On the nonprofit side. I think they all know that their biggest challenge is the boardroom and getting the boardroom right. I don't think they all know that they have a role to play in that. Like they can be selective about who gets into the boardroom. They can ask the board for things. I mean, the board's got one employee and that's the CEO. But even the CEO should be leading the board, not thinking of themselves as concierge for the board. I think sometimes they don't know their own power. And I think sometimes they don't know that there's a lot of places dealing with what they're dealing with. I'm the only one who must have a hard time with my chair. Or I'm the only one whose board doesn't seem to want to help with this or that, and tends to meddle. What I see is that that's pretty darn common. And if you don't have that stuff going on, good for you. You're really lucky. And you probably put a lot of work into that. You probably set up some time and some procedures so that that's what happens. It's not an accident.

George Laufenberg (44:37) 

Mm-hmm. No.

Steve Filosa (44:51) 

But like any relationship, it takes time, it takes intentionality. Sometimes it takes an outsider to say stuff. That's often my role. A lot of the people who hire me, they already know what they're dealing with and how to fix it even. But they know they can't say it. I remember being executive director — I knew I couldn't say certain things to my board, because who am I? But you bring in a third party — maybe they'll hear it. And if they get upset at what they're being told, well, get upset at me, not your executive director. I know I serve that purpose sometimes. Steve, you need to say this, because I can't say it. Especially if it's a woman. A woman executive director, a male board — they're not going to hear me if I say it. Well, I can try. That's the book, Tell the Truth and Run.

George Laufenberg (45:53) 

I'm trying not to digress into a whole thing about how broken our approach to conflict is. But I take your point. Absolutely. Yeah. Well, the flip side being — so many of us are raised to, when there's something hard that has to be said, it's like, you know, here's a grenade. I'm going to lob it, goes off, everybody good, alright, cool, moving on. As opposed to — all right, this thing's going to go off and we're both going to get hit and we're both going to still be standing here. Bang. Ow. Right. Is there, have you found, Steve — is there a type of client that you can't help, that you've learned you can't — not won't, but you've learned you can't help?

Steve Filosa (46:28) 

Yeah. Yeah. Yeah. Twice I've said to a client — to two different clients — I don't think we should keep working together. You guys can keep paying me, but you don't seem to be really listening to what I'm suggesting. You seem to think you know. I don't agree. So why don't we just hit the pause button on this relationship. I've done that twice in six years. And that's not to say I always know the right thing to do. That's not to say that everything I say needs to be accepted. But if pretty consistently no-brainers from my point of view are rejected — for one reason or another, often by a board member who thinks he or she knows more than they do — that's when I say, what are we doing here? And I don't need the money that badly. And I really don't want to be associated with what you're doing because people are going to think I told you to do that. And I don't want people to think that. So that's only happened twice where I actually had to break up with a client, basically.

George Laufenberg (48:00) 

Mm. Mm.

Steve Filosa (48:04) 

I think on the way in, I'm pretty careful about who I work with. I want to make sure it's a good fit. I want to make sure I know them, or at least I know somebody who knows them. I don't advertise. And most of my work is referral basis or repeat. We did something, we took a break, we're going to do something else. I don't want to be like a drive-by hundreds-of-clients guy. Same thing with Prep at Pingree. I want those relationships to be relatively deep. Because I think you can do more for people when you really know them. And you can make better suggestions when you know what's really going on. And sometimes as you know it takes a while to figure out what's really happening. I think we've talked about the Mark Twain quote about people always having two reasons to do something.

George Laufenberg (48:36) 

Mm-hmm. Yeah.

Steve Filosa (49:00) 

They always have a good reason and the real reason. And I found out pretty quickly that my clients, they tend to have two reasons to hire me. A good reason — oh, we want to do a strategic plan, or we want to do some board development, or we want to raise some money, or we want to give some money away. But then the real reason sometimes becomes clear as we get into it. Oh, the board chair is a nightmare and you're trying to move them along without anybody getting too upset. Or your board doesn't give, and you need to ask them to make sure that they do. Like this is often the real reason for why I ultimately get hired. And that's okay. I think sometimes people are figuring it out for themselves either. It's not like they're being dishonest. It's just that it's hard to say sometimes, or it's hard to even figure out what's going on.

George Laufenberg (49:28) 

Yeah. Mm-hmm. Sure. So what's different at year six than it was at year one?

Steve Filosa (50:03) 

The phone rings more. Year one, it was like — is anybody gonna call? Does anybody want to come to this party that I'm throwing? Right? Maybe you're living that now. I remember that first year, I remember that vividly. Okay, I'm going to tell the world I want to do this. I'm going to give up a steady paycheck, by the way, during a pandemic. And I'm just going to see what happens here. But you think — maybe nobody will, nobody needs this or wants this or wants to do it with me. That was definitely year one. And now in year six, you still worry about the phone ringing to some extent, but you start the year with three or four people, clients that are either finishing or you know they're coming back for something because they've said, I'm going to call you in February, we're going to do this thing. So I wouldn't say that it's totally comfortable — and I think just the nature, as you know, like you're on your own, you're doing your own thing, there is no sure thing, there is no safety net really. But it feels a little less unknown.

George Laufenberg (51:14) 

Yeah.

Steve Filosa (51:24) 

A little less scary. And I think that scariness — this is part of what I think I sense on your website and your whole premise — like that uncertainty, that not knowing of whatever is coming next, whether it's for your business model or in your life, like that's okay. And get used to that and get next to that and kind of cherish that in a way. Because that's going to generate the good idea. That's going to get you out of bed to do the hard work. I think I always had an appreciation for that. But when you're employed by an employer for 30 years, it's not the same as hanging a shingle. And, well, maybe I won't make any money this year. It's not even the money, it's like — maybe nobody will even want to talk to me this year about anything. Maybe I've just become...

George Laufenberg (52:18) 

Yeah.

Steve Filosa (52:19) 

...irrelevant to the professional world. That scares me more than the money part at this stage of my life.

George Laufenberg (52:26) 

Mm. Well, it connects back to what you were saying earlier, I think, about being seen. If I were trying to distill core values from the way you were talking about Prep at Pingree, the experience of being seen and trust were the two things that really rang like bells to me. And it's funny, when you just said what you said about spending 30 years at an institution — picture like this is Wile E. Coyote off the edge of the cliff and then looking down and there's nothing underfoot.

How do you — I mean, you've talked a little bit about how you embraced that kind of uncertainty, right? As generative space, which — absolutely. That's my bread and butter. I've always been interested in that and how people's sense of their capacity to act meaningfully in the world, how that horizon moves. And the thing that always keeps coming up is — do you have a relationship to uncertainty such that it's a generative space, or is it something that you're seeking to avoid? Not to flatten it out or be prescriptive, but it's pretty common. And I'm wondering — and stop me if I'm projecting here — but it sounded like that was a really sort of jarring moment. The Wile E. Coyote image is probably overstating things a bit. The long way around to this question is — to whatever extent you kind of leapt off the cliff of having this robust institutional structure, with all of its challenges and difficulties, right? There's a there, there. How has your relationship to that not-knowing changed over the course of this work that you're doing now?

Steve Filosa (54:34) 

One of my first clients — I don't know, you cannot read this I'm sure — but one of my first clients gave me this — Goethe? G-O-E-T-H-E. You know his quote about commitment? I'll send it to you, but it's kind of long. But the quote is basically — jump, and the net will appear. Right? His point is something can't start until one is committed. And then he talks about how once you do commit to something, everything opens up. Just kind of naturally opens up. And you couldn't have imagined what would have come. But you can't get there until you actually commit. Jump, and the net will appear. One of my first clients gave me that quote.

That is so true these last six years. Could not have imagined. And then when I think back to the Prep at Pingree story — could not have imagined it. But we committed to something in 2001. We all did. Everybody who's involved in that. We committed to something. And then this just — so the idea of having a certain amount of trust that it's gonna work out. Can't quite say how. Can't quite say to what extent.

George Laufenberg (55:24) 

Yeah. Yeah.

Steve Filosa (55:49) 

And if it doesn't work out, then maybe it's not meant to be and you've got to figure something else out, which is also okay. But just having some level of comfort with that whole, all that risk. And I'm sure it's easy for me to say at this stage of my life. Like if my wife didn't work and I had three little kids at home and I had to make X for us to survive — that would be a whole other kind of pressure, I suspect. And I'm really glad I didn't make this move when I was in my 20s. I don't think anybody would have hired me either. What do I know in my 20s? What have I done in my 20s? But I don't know — just getting a little more — I cherish it, actually. I really like the uncertainty. I feel like that uncertainty is incredibly healthy.

George Laufenberg (56:29) 

Well, there's that. Mm. Mm.

Steve Filosa (56:45) 

It's all there is, right? Even when you think you've got certainty, it's not certain. I have a job with an employer, I'm good. No — they could come into your office tomorrow and say, it's over. Someone said that to me when I was thinking about making a move, but I thought I'd got all this security with my current job. And they were like, no you don't.

George Laufenberg (56:50) 

Yeah. Yeah. You just have a really robust fantasy structure. Yeah.

Steve Filosa (57:18) 

Nobody has security. Nobody has security. So why not just own the insecurity of it all and put your fate in your own hands and try to build something. So anyway, I don't know if that even answers the question, George, but.

George Laufenberg (57:35) 

Absolutely, man. How has the texture of the experience of commitment — how has that changed for you? What does it feel like to be Steve in the intentional movement into that?

Steve Filosa (57:54) 

I don't know. I think I'm just committed to feeling like I don't need to know everything. I don't need to have all of the answers for all of my clients. I don't need to know how this is all gonna work out from a business planning perspective. I don't need to know those things. And even if I did, I probably shouldn't, because it would be false. I would only think I knew. They're unknowable in so many ways. It is unknowable. So be good with that. And focus on what you can do. Like I know what I'm going to do with my day to day. I got a 12 o'clock call with George. I got this at 9. Like I can control that. And I can have certainty about that. And you keep doing those kinds of things and everything else hopefully works out. And if it doesn't work out, there's probably a reason for that and you figure something else out. I don't know — I feel somewhat at peace with it all in a way that I probably didn't. I definitely didn't when I started this. And as a 20-something, I didn't even know what I was thinking in my 20s. Do you remember?

George Laufenberg (59:07) 

I'm scared to even look at the journals. Say more about the peace.

Steve Filosa (59:17) 

The peace of uncertainty?

George Laufenberg (59:18) 

Yeah, that you're talking about right now. As concrete as possible, the texture of it. What's it feel like?

Steve Filosa (59:29) 

It feels a little bit akin to — take a deep breath and be nice to yourself. And take a deep breath and be nice to other people. Like, I think sometimes I'm not so nice to people or myself because I need something that maybe they can't give. I need an answer, or I need an assurance, or I need a prediction. And I can be hard on myself or people in that way. But I think the peace is more like — oh, you haven't figured that one out yet, or we haven't done something yet, it'll get done, we'll figure it out. Cause we're gonna talk about this again tomorrow. Or we've got three months together and we're going to figure this out, or at least we're going to take the best swing we can. And if someone else figures it out, good for them, please tell us. And if we're not figuring it out, there's probably a real good reason for that — like it's a hard question, or it may not have an answer, or it's a fundamental dynamic that no one in the history of mankind has figured out. Right? Like — just the peace of knowing that my life isn't going to come to an end, I'm not going to be who I think I am, because I can't come up with something. Or it's because some prospective client didn't hire me. Or because a project went sideways. Didn't see that coming, but I think I see in hindsight what happened, and maybe we'll avoid that next time. Much more fatalistic about it, I guess, than I might have been.

George Laufenberg (1:01:12) 

Hmm.

Steve Filosa (1:01:16) 

And I hope that doesn't sound uncaring or callous, but just fatalistic in the truest sense of the term. Like, I'm not in charge of everything here. I might not be in charge of anything here. And I don't think of it as a deity pulling strings. But stuff is complicated and things are interwoven and sometimes you know what's going on around that corner that's affecting something in front of you. Who does? I don't know, do you feel that way?

George Laufenberg (1:01:57) 

On a good day.

Steve Filosa (1:02:01) 

Yeah, well, good day. Good point. Talk to me tomorrow.

George Laufenberg (1:02:03) 

Yeah, on a good day. This afternoon. No, mean, it's for me, it's definitely a matter of intentional cultivation. I used to say that if I heard somebody talking to their kid in a grocery store parking lot the way I used to talk to myself in my head, I would be morally compelled to intervene. And it's been years of work as an adult — softening, getting gentler.

Steve Filosa (1:02:36) 

Yeah. Yeah.

George Laufenberg (1:02:39) 

Not having my sense of being okay be constantly stapled to — do I know exactly where I stand? Do I have approval from this person and this person and this person? And it's still like the wind can change direction and I can fall right back into it. It doesn't take anything, you know? And then it's about forgiving that, right? And then like, okay, yeah, I just did that. All right. One of the many gifts of being a parent — it's like, all right, what am I modeling right now? Right? Forget what I'm saying. What are my kids watching about how I treat myself and how I treat other people? What does trust look like in practice?

Steve Filosa (1:03:11) 

Yeah. Yeah. Well said. Well said. I think having kids in their 20s now, my mantra has sort of become — if I get the question of, what do you think of this, dad? Or what should I do about that, dad? I don't really get that question a lot, but even when I do — the rare time — my fallback is kind of like, I don't know. Like, you're 27, I haven't looked for a job in 40 years. Like, I don't know what you should do with your job search. Or, you know, pick your topic. Like, there's something incredibly freeing about that. Not having to know.

George Laufenberg (1:04:10) 

Yeah.

Steve Filosa (1:04:12) 

And when they were 10, there's a lot of stuff I felt like I knew. Like, you don't do this, you should do that. And we were probably right. Because the issues when they're 10 are a little clearer than when they're 27. So I was not hesitant to weigh in in those days. But now I'm like, I don't know, man. My kids will tell you that I say I'm sort of out of the advice business when it comes to parenting. Because how in the world would I know what you should do with that situation? You know more than me. You're living it. You have to live with whatever decision you make. We can talk about it. I'll ask you questions maybe. But I don't know. When it comes to what should I do — I don't know. And there's a certain peace that comes with that. Like, I don't have to know.

George Laufenberg (1:04:43) 

That's beautiful. Yeah. And in that moment — even with clients. Yeah.

Steve Filosa (1:05:05) 

And even with clients — just to finish — there are certain things I know your board has to give. And if they don't, that's a real liability for you. There's some easy ones. But a lot of people don't hire me to talk about the easy ones usually. They've got something they're trying to figure out too. And so, okay, let's figure this out. I don't think it's just that fundamental view of education going back to Socrates or Plato. Like — is the role of the teacher to fill up the empty head or is it to draw out what's in there already? And as you know, different teachers have different perspectives. Sit down, shut up, take out your notebook, I'm going to fill up your empty head. And others — no, what do you think about this? What do you want to learn today? What are you wondering about? Read this book. Take a look. Tell me what you think about it. And I'm definitely the latter. I know that about myself. And I know not everybody wants that, by the way. I was thinking of my clients — like, I'm drawing stuff out of them. I'm not filling up their heads. Because like my kids, they know more than I do about their immediate circumstances, what they're really dealing with — the personalities, the issues, all the dynamics that are going on. They know. So I'll ask them some questions to make them think about it. I'll ask a bunch of people what they think and try to reflect back what I'm hearing. Every now and then I'll put my finger on the scale, especially if they're asking me to. But yeah, that's what I was trying to say about the peace of it all.

George Laufenberg (1:07:02) 

Yeah, beautifully said, Steve. I'm just thinking about how — even with my kids being young — I do try hard to say and mean that I don't know. Because it's so important for them to have that as a model, I think. Like, being okay with not knowing because it's the truth, full stop. Some things — oh yeah, yeah, no.

Steve Filosa (1:07:22) 

Yeah. But at 8 and 12 you do know why. You can say to your daughter, like, nothing good's gonna happen after 11 tonight, trust me. So just be home. Right? Like, that's not a tough one. When you're an 8-year-old, know, eat this. You need to eat this. You can't just eat mac and cheese.

George Laufenberg (1:07:46) 

Yeah. Yeah. I don't mean like hot-stove level stuff. But the — navigating relationships, wanting conflicting things, not getting what you want — they're already in it.

Steve Filosa (1:07:57) 

Yeah, yeah. Yeah, yeah. A 12-year-old probably knows. She's a lot closer than I might have thought.

George Laufenberg (1:08:17) 

Sometimes. Last question.

Steve Filosa (1:08:24) 

Hit me.

George Laufenberg (1:08:26) 

Steve, what are you loyal to that you didn't choose?

Steve Filosa (1:08:31) 

Huh. What am I loyal to that I didn't choose? I don't know, George. I feel like I've been incredibly lucky to have made a lot of choices in my life. Whether that's people I associate with, what I do professionally, what I do for fun, where I live, how I live. I feel like I've had an awful lot of choice. And I think I'm loyal to those things that I've chosen. But what have I not chosen that I'm loyal to? I don't know. Has anyone ever said they don't know to that question?

George Laufenberg (1:09:38) 

Every honest answer I've encountered starts with that.

Steve Filosa (1:09:42) 

Huh. I don't know if this is — the first thing that comes to my mind is my country? Like, I feel loyal to this country. I didn't choose it. I don't like a lot of what's going on or who we are in the world in others' eyes and what we do in our name. But I want to think I have a certain amount of loyalty to my country. I don't think I owe the country nothing. But I might not have chosen to be loyal to the United States of America? I don't know. Is that even close to where you're going with that question?

George Laufenberg (1:10:32) 

I'm not going anywhere with the question.

Steve Filosa (1:10:34) 

Yeah, yeah. I wonder what kinds of things you hear in response to that question. And maybe it'll draw a thought, I don't know.

George Laufenberg (1:10:36) 

Yeah. I mean — the country one is a relief. Like I share that and it's fraught right now. I mean, it's been fraught for a long time, but man, that's a complicated relationship.

Steve Filosa (1:11:47) 

Yeah. yeah. Yeah. I think what's hard about that question for me is I feel like I have so much choice in my life, and I always have. Maybe I'm not correct about that, but I feel like I've had a ton of choice, a lot of autonomy, and I stopped doing things that I don't want to do anymore. Or I'm not loyal to things that I don't really want to be loyal to anymore. I feel like that's the fundamental architecture of my life. I don't think I set out to do it that way. In hindsight, it just seems to be the way it's gone.

George Laufenberg (1:12:29) 

Mm.

Steve Filosa (1:12:34) 

But I'll keep thinking about that. That's a very interesting question. I'm sorry I don't have a better answer.

George Laufenberg (1:12:41) 

Stop, stop. It's not about performance of anything for anybody here. Questions are either useful or they're not. Steve, I so appreciate your time and your heart and your head and who you are. And it's been really nice to get to know you a little better. I mean, we've known each other and been in orbit for most of a decade, but I feel like I know you better than I did an hour and a half ago. And I'm really grateful for that.

Steve Filosa (1:12:48) 

Yeah, yeah. Same. Same brush. Same. And I'm sorry to have been doing so much of the talking even though that was the design. I'd rather not, actually. I was going to say that one of the things about the peace conversation is — I can just say less now. Even though I've been talking at you for 90 minutes. Like generally speaking, I feel like with my clients or my kids or whoever, I can just say less. Nobody needs to hear me say more. I don't know that was how it always was. I felt like I needed to say a lot — younger days, earlier days. Right?

George Laufenberg (1:13:41) 

Mm. I can remember — there's a BC/AD moment that happened for me in that regard somewhere in grad school. The first time that I didn't yield to the automatic compulsion to fill an empty silence with my glorious presence. Right? Yeah. And another thing that's wise is — right, like — and just watching what happens when I don't. And I actually, in some ways, I kind of overcorrected in that direction and sat really quiet for probably 15 years. And I'm trying to find middle ground now. And I think most of that middle ground so far looks like genuine questions. So I appreciate you grappling honestly and openly with.

Steve Filosa (1:14:48) 

I feel like at the core of whatever I offer my clients is an ability to just ask some questions and shut up. And I don't always do that the way I should. But on a good day, I like to think I asked the right question at the right time, I took myself out of the response, and just tried to help them hear what they already think. And maybe give them a little bit of confidence to go do whatever it is that they already think. Or stand up to someone who's not letting them go forward with what they know they should do, and is best for the organization. Have a good day. Say less.

George Laufenberg (1:15:30) 

Yeah, yeah. On a really good day, I'm a clean mirror. Right? On a really good day. It's not always like that, but it can be. And that's — man, that's beautiful. That's just graceful. That's a great feeling. Like I didn't bring anything to this.

Steve Filosa (1:15:36) 

Well said, I like that. Yeah. Yeah. Yeah, no, that's it. Yeah, yeah — well you let me know how to inspire more of those days in my life. But I do — I think I do recognize more and more quickly when I'm not. Sometimes too late, but at least I see it. Whereas 15 years ago I might never have seen it. Is Steve still talking?

George Laufenberg (1:15:55) 

Honestly? Yeah.

⸻[END]