How to Say Hello with Michael Pope and Elisa Pupko
About This Episode
Every ending carries within it the seed of a beginning. To leave something behind—whether it’s a beloved job, a familiar city, or the comfort of a community—requires not only courage but also an embrace of uncertainty. In this first episode of Season 11, we step directly into that tension: the sacred space between goodbye and a new hello.
Carrie Fox sits down with nonprofit leader Mike Pope and theater founder Elisa Pupko at the very edge of a new chapter. Together with their two young children, they’re leaving behind steady careers, a home in Brooklyn, and the familiarity of everyday life to embark on a yearlong journey around the world. It’s a leap that began with a fleeting thought on a run and grew into an intentional act of re-imagining what family, leadership, and community might look like.
As Mike reflects on stepping aside from his nonprofit after 15 years, he asks what it means to honor an organization by knowing when to let go. Elisa, meanwhile, navigates the delicate balance of letting her company grow stronger in her absence while choosing presence with her family. And together, they invite us to consider what it means to say yes—not when the plan is complete, but when the possibility feels alive.
Their story is not only about travel; it’s about perspective. About the way children learn to smile at strangers on playgrounds in foreign cities. About how leaders discover strength in stepping back. About how the question “what if?” can open doors we didn’t realize were waiting.
With this conversation we invite you to wonder what might happen if we—all of us—leaned into the space between goodbye and hello, and allowed it to teach us something new.
Follow along with Elisa and Mike and their whole family at https://twokidsoneworld.com/.
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This episode is supported by The Johnson Foundation at Wingspread. At their Frank Lloyd Wright–designed campus, Wingspread brings leaders and communities together to turn dialogue into action. Learn more at johnsonfdn.org or wingspread.com.
This episode is also brought to you by Positively Partners. When HR starts to slow down your mission, it’s time for a better solution. Positively HR is the fully outsourced HR partner that understands nonprofits—and acts like part of your team. Learn more at PositivelyPartners.org.
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'Carrie Fox
Have you ever thought about leaving the place, the job, the people you love in order to say hello to something new? Or feeling like you need a fresh start, having accomplished all you believe you can in the place that you've been. Maybe you're feeling the need to stay grounded planted, very firmly rooted, wanting to make the most of that space between coming and going. Well, my friends, this is what we are exploring on season 11 of the Mission Forward Podcast. It's a theme that touches every one of us. Whether we're leading an organization, guiding a team, or navigating personal change, we are talking about hellos, goodbyes, and the sacred space between. Over the course of this season, you will hear from people who have made bold decisions to leave familiar roles in search of something more aligned. You'll hear from people who have recently stepped into new opportunities with courage and curiosity and heart. And you'll hear from those who have intentionally chosen to stay, practicing presence in a world that constantly calls us to move. I'm Carrie Fox and welcome to Mission Forward. Hello's, goodbyes, and the sacred space between So here we are, episode one of season 11, and more than 150 shows into this show that I love bringing you every season. This one though, something tells me is going to be our best season yet, and I can't even imagine a better place to start us off than with this show. This idea of leaving the places, the roles, the jobs that we love, whether the choice is ours or not Whether we choose to say hello to and what we choose to say hello to is something I have seen so many of you wrestle with this year. You have asked me how to know when it's time and how to make sure you don't overstay your welcome. You've also questioned if starting something new later into a career is even possible. Those are questions I'm asking too. And while I am firmly planted right here, right now with you, I know this isn't the place I intend to be forever. So we're gonna take some inspiration at the start of the season to hear from two exceptional people. an established nonprofit executive and a brilliant business owner who have decided to say yes to what's next, even without a full picture of what that might mean. Today, we're talking with Michael Pope and Elisa Pupko. I have known Mike for a few years through his role as executive director of the New York-based nonprofit Youth Represent. And I've invited them here to help document the start of a grand adventure as Mike and Elisa prepare to leave. New York City, Mike prepares to leave his nonprofit and Lisa prepares to start running her theater company remotely as they empark with two kids on a year-long trip around the world. That, my friends, is quite a hello. So Mike and Elisa, thanks for being here. Welcome to the show on these last days in the US before you take off on a world tour.
Elisa Pupko
Thanks so much for having us.
Carrie Fox
You two have to tell me because this is like the dream that so many of us have, this idea of like, what would happen if we just left? Well, how in the world did you two get to be able to say that's what we're doing?
Mike Pope
Yeah, it's wild. First off, Carrie, thank you so much. Um It's been a pleasure to work with you over these years and it's um I'm just very excited to be here and to have this conversation with you and mission forward and just appreciate it so much. And it's actually wild that we're answering this question. Because if you would have asked us or we would have listened to this podcast a year ago, uh, we would have been like, wow, those people are crazy. What are they doing? That would never be us. Right. Like I think I think the idea is. um it's it's wild, frankly, that that this is where we are. But um but through like a number of kind of like really um intentionally stepping back and reflecting and and jumping into the unknown and um we've been able to find ourselves in this position that that yeah, we've we've kind of we're excited about this next phase and stepping into this adventure of stepping away from, you know, for me personally, stepping away from my um organization that I've been at for now 15 years and jumping in with our two little kids, three and seven years old, to travel the world for a year.
Carrie Fox
So Elisa, tell me a bit it. You you have a website, you have a you do have a plan, right? You have this incredible plan on all these places you're going. Just give us a sense of what this adventure is gonna look like.
Elisa Pupko
Yeah, I mean we do have a plan, but um As someone who is a type A planner, um, I very much want to have everything exactly planned out and laid out, but in our just regular travels as a family have taught us and travel in general has taught me you have to leave room for flexibility in your life and especially travel and absolutely especially travel with children and young children. So we have kind of our route that we plan to hit. the countries we want to visit, looking at the seasons we want to be there, the best seasons, not a rainy season, not height of tourist season. So that kind of helped us make our initial route. And we're not, you know, we don't have all of our flights booked for the year. We don't have all of our hotels and Airbnbs. We really just have the first couple months laid out, but we built in a lot of flexibility because we don't know what it's like. We don't know if we want to stay everywhere for five days or three weeks. We might fall in love with the place that we're at and we want to stay there a little longer and we want that flexibility. We might get somewhere and The kids are having a blast and they made a really good friend and we want to stay there longer. So we have our plan, but we are very much walking into this knowing we've never experienced anything like this and we need to leave room to change as needed.
Carrie Fox
I love that so much. So https://twokidsoneworld.com/
Mike Pope
Yeah, can you believe that I got that URL?
Elisa Pupko
It is
Mike Pope
I was just more proud of that than anything.
Elisa Pupko
I think that's what you're most excited about.
Mike Pope
Yeah.
Carrie Fox
So we can follow along, right? I mean, is that the hope that you've got people following along with you?
Mike Pope
Yeah, one of the things that honestly we um really wanted, we love, we we're in New York City now, we're in Brooklyn, we love our home and we love our friends and we love our community, right? And so really for us, like we wanted an opportunity to stay connected and to bring people along with us. as part of this journey. And we wanted just to document for ourselves like what this is going to look like because it'll be a year in a blink of an eye. And we'll be home again and wanting to reflect on all this. So we yeah, we created a website, twokids1world. com and we are, you know, blogging and and uh hoping to do weekly newsletters. mostly just to make sure that we're connected and with the community that we have and learning from folks on places that they're recommending that we go and and we can just continue to remain connected back here at home during the journey.
Elisa Pupko
And also I'm going to attempt as much as possible to be also sharing on social media, which is not Mike's world. I'm a little bit more at the Instagram savvy one. So just for me I love social media as a way to guess, you know, visually document what my life is like. And so I'm hoping to do that as well.
Carrie Fox
All right, so we're going to come back to that in a minute because you do have two beautiful kids who are part of this adventure with you. And I want to talk about what you hope they experience as part of this process. But first, I want to go back to that moment, right? That so many of us have these fleeting big ideas of the what if we just left everything and did this? And then something in us kind of squashes that idea and we just get back to work the next day. But there was something about, if I recall, a run you took and a conversation you had that made a fleeting idea turn into this, turn into a website and a world adventure. So tell us more about that.
Mike Pope
A quick context so that you understand how wild this is. If you know the old television show Dharma and Greg That is Elisa and I, right? In many ways, I am the planned lawyer. Uh, you know, I have the, you know, kind of the finances through the retirement plan, everything figured out. Um, and I've known what I want to do working in racial criminal justice since frankly I was in law in excuse me in middle school. Um and there was very much a plan. Elisa is an incredible musical theater actress and now founder of Treasure Trunk Theater. And um so that's the context in when we found ourselves maybe in October or November of last year and I was out on a run and I was approaching this 15 years as being at Youth Represent, you know, as kind of a significant milestone. And I was honestly, I've been executive director for the past five years. And really reflecting on how incredible of a place it is and how strong of a position the organization is. And I was really just overwhelmed with pride and excitement about where the organization was. And then it came to me that like Like you said, those those fleeting moments, I think, of sometimes clarity, where I said, well, actually, doesn't that mean it's probably time for me to step aside? Right. Like as somebody that is in this role. You know, my my job is to serve the mission and the organization and do everything I can to put that in front of um anything, right? Like as as a mission serving organization, that's our call and that's my call. And so Um, you know, this is particularly, I think, important for white folks that are leading organizations and for me, a white person leading a racial justice organization and really making sure that I'm balancing that tension between when is it time to step up into the work and when is it time to step aside. And I realized I wanted to leave this place in an amaz I wanted to step away and say like, you know what? It's in a strong place. And And the next person, this is gonna be an amazing job because that's what it is for me. And so I had this just realization that like, you know what, maybe it's time to step aside. um you know maybe it's time to do the Seinfeld and step aside when things are going so well. And so I had that. And then I was like, wait a minute. We have these kids and they're three and seven and they want to hang with us and they like us still and they like they want to be around us all the time and I kind of want to be around them all the time. And so what would this look like if we were to travel the world? And so anyway, there's a long run. Um, I get home, Elise is working, and basically I say like, hey, I had this idea. What about what about me quitting my job that gives us benefits and that I love and we, you know, travel the world for a year, take the kids out of school and homeschool them. Um, and Elisa, you wanna hop in?
Elisa Pupko
My first thought was, wait, I'm the big idea person usually, the crazy idea. I'm the one who brought us to New York, first of all. Um and but I said, go take a shower. But we'll talk about this later. Um I needed some time to process um because I was a little jealous that I didn't think of it since that would typically be my role in the relationship. Um but also for me I was in a place with my company, I had just literally just signed my third commercial lease in Brooklyn for a third studio uh which was gonna open in January. Um we'd also just started pre-production for our first ever full-scale musical for older kids, uh which was brand new to the company. So I just launched two really big new exciting projects. Um and I had this moment of like, I I'm really happy and excited about the things I'm building right now in Brooklyn. Like I don't want to leave. Um, but after reflection for me, um, travel. for me has been a way to understand that there's always something more to experience in this world. Um when I was full time um working as an actor, I was very tunnel-vident. Every I didn't want to travel, I didn't want to, you know, I missed family weddings and things because I was in a show or I didn't want to miss an audition. And so I became very tunnel-visioned. And there's a brief period in our life where my brother, who's a pilot, gave us his pilot like flying benefits. So we could fly for like $100 anywhere in the world. um on a whim. Um we didn't have kids at the time and I was the one who said, we're gonna travel, we're gonna take weekend trips to Australia, which we did um because we can right now. Um And that when I started doing that, and we had this like brief one year period where we were able to do that, it opened my eyes that I didn't need to be so hyper-focused in my career and my life rooted in New York City. And so I had this moment of like, I'm so rooted right now in Brooklyn and I'm so excited and passionate about what I'm building here. But there's this opportunity all of a sudden. And remember that time when you had that tunnel vision? and how much your world opened up literally by traveling, you have the chance to do that again and you have the chance to experience it with your kids. So I said, all right, let's do it. Why not?
Carrie Fox
I think about all the times that someone has said to me, just take a break. And that could be literally like take a 20-minute break. And I'll say, my answer is I can't. And I love that the two of you said, okay, like let's just figure this out. Um, I want to hear what you thought people were gonna say. That could be Mike, your employees. That could be Elisa, all of the people you work with in the theater. What you thought they were gonna say and what did they say? How have they reacted?
Elisa Pupko
Mine, I thought my uh my amazing team, um, I thought they would all be like, what? You're leaving? You've gotta be kidding me. Um, but every single one of them were so supportive. They were like Go, that's amazing. Like we got this. Um, and I think one thing I've learned as a leader um is to By stepping back, you empower your team to grow and learn and make your company better in that experience. I first experienced that just having kids, right? So two times I was on maternity leave. Um, I had to take a step back because you literally can't be working while you are giving birth as much as I thought I could with the first one. Um so It, you know, that taught me like, oh, I stepped back and look how much everyone on my team has grown and how much better off the company came because of their growth. And so it was amazing to see their support and for me to know, wow, we're all going to grow and my company's just going to be stronger because of that.
Carrie Fox
Oh, I love that. And you're not disappearing, right? I mean, you're gonna keep working remotely.
Elisa Pupko
No. Yeah. I'm gonna work remotely. I'm gonna check in, but I they're all amazing and I'm just kind of there to check in and just because it's my baby, I want to know, I want to know what's going on.
Carrie Fox
Amazing. Absolutely amazing. And Mike, how about you?
Mike Pope
Yeah, I think so uh it was it is different because for I think the primary reason that I am you know stepping down like we were appointing an interim executive director and um and I'm stepping away and so you know, um it was chang, you know, I it was a reminder and what it means to be a leader during change management, right? And there what I have spent five years uh leading the organization and creating systems and structures so that You know, with the vision being the less that I'm centered, the better, right? The less that it's about me and the more that it's about the work. Um, but you know, I have great relationships with staff and and um you know and I think it was it was hard, but I think the with my board and with my staff and that you think what's been really incredible honestly is the larger community. I can say without hesitation there's not anybody outside uh of or inside of either of organizations that isn't like, oh my god, that's amazing. And particularly parents, and particularly parents that have kids that are older than ours are like, yes, like do that. And so I think for me it's it is it's been really nice where we, you know, Elisa and I sometimes come up with, we many times come up with these ideas and they're kind of wild and people sometimes are like, that's wild. You shouldn't do that. And we're like, we're doing this. This is not one of those. This is one of those where people are like, I this is something I wish that I had done. And so, you know, we're deeply, deeply terrified and anxious and excited and all of those feelings, but having that group of people that are like This is the thing that I wish I would have done when my, you know, daughter was seven and my son was three, right?
Carrie Fox
Right. Right. Yeah. Cause you blink and they're gonna be in high school like mine are and and it's hard to imagine that that time just goes so fast. My hope is that we get you back here in a year and you reflect on this adventure. And so what I would love you to maybe put into the world is what you hope happens as a result of this? If you think about life through your kids' eyes for the next year, what do you hope sticks with them and with you about this process?
Elisa Pupko
For me, I think I did not travel internationally as a child. Um, and not it was not until my brother's flight benefits that I actually started going international places. Um and I think that what especially international travel does and especially in the climate and the world that we are in right now with so much angst and conflict and fear um is just showing that we all are humans. Like it really gives you that human connection and not to sound super cliche. But I find myself, you know, we frequent playgrounds everywhere we go with the age of our kids. We're always at a playground in every city and country we go to. And a lot of times my daughter will say to me, she's a very social child, and she'll be like, mommy, how am I gonna play with these kids? Like they don't speak English. And this is super corny, but I tend to quote that it's a small world uh lyric. And I say a smile means friendship in every land. And so I tell her. Just smile and wave. You can say hello in English, you know, but it's like if you smile and wave, they know that you're saying hello to them in a friendly way. And then that can start. the playing together. And it has. It's really amazing to watch. And so I love seeing the beauty and the innocence of children who just accept all, especially in a you know a playground environment. And so I really hope that that is like instilled in them and a lasting impression they have of this is just seeing how people live around the world and how we're all humans and we all can exude kindness no matter where we are and what language we speak and how we dress and you know our religion or any of those differences.
Carrie Fox
I wrote earlier this week, we're recording this in mid-August, and I wrote earlier this week about the importance of laughter. And how when we're kids, you know, we average three or four hundred laughs a day. And somehow by the time we're adults, we're lucky if we get 15 chuckles a day. It just doesn't happen, right? And Where all that joy goes, where we put it, I don't know, but we kind of forget about it. And I love that you're gonna be thinking about this through how to give them experiences that make them happy and make you happy and fulfill your life in a whole different way that you just wouldn't have known if you if you didn't take this leap.
Mike Pope
And and also hopefully, you know, we are in a fraught time in our country right now, and I hope that through seeing the world and remembering that the American history is quite short. Many other countries have managed through um similar situations that we're going through now. And so I really also hope that kind of a global view and a global lens of what's happening will help us have a better understanding of what that response looks like. How do you build community? Um, how do you build community across divide, across significant, you know, um differences? And I'm really hopeful that that's something that we'll be able to have more reflections on. So when we come back, we can bring that to you know, our our home and our community in Brooklyn.
Carrie Fox
Well, and you're gonna come back and tell me all about it. So I'm excited to hear that. We're definitely gonna be following along with you. My girls have gotten really excited about this. So we're subscribed to your newsletter and we'll be tracking along and celebrating you. And um we do have to wrap up, unfortunately, because you two have some bags to pack. So before we do, I'm gonna we're finishing every episode this season with some questions that let us just better understand you and and um have some fun in the process too so i'll throw these out you two get to decide which ones you want to take or if you both want to take them that's that's cool with me too um so do you say hello with a hug or a handshake Okay. What's your favorite language to say hello in?
Mike Pope
An easy one sweet
Elisa Pupko
French, bonjour
Carrie Fox
Nice. You can see my chow. Oh, what's one thing you never leave home without?
Elisa Pupko
My phone and my chapstick.
Mike Pope
I think that's good. Yeah.
Carrie Fox
Cool. And in this big game of life, while not why not end with a little question? In this big game of life, what's one thing you hope to leave behind?
Mike Pope
I hope that people, when that moment comes, they hold on to the what if. And they hold on to that and they don't let it go and they think, but what if, what if we did this?
Elisa Pupko
I'll let I'll let that be the answer.
Carrie Fox
Well, you too are reminding us the power of saying what if and being open to the possibilities of that answer. So Thank you for starting us. Thanks for indulging me and letting me ask questions and pretend I can come along with you and maybe someday I'll go on my own adventure like yours. But I'm so excited to watch where you go and what you experience and excited to see on the other side.
Mike Pope
Thank you, Carrie, and thank you again for everything that you do and at mission forward. I mean we we've been able to work together as you indicated and we've even won some awards together. I mean not to you know throw some uh some wonderful um credit that way. But it's been amazing and I'm really excited to to share this with you and with your audience.
Elisa Pupko
Thank you, Care. We'll talk to you in a year.
Carrie Fox
Sounds great, thank you And that brings us to the end of this first episode in season 11. Am I the only one who wants to go back and listen to that entire show again? I just loved that and love how that kicks us off on the wonderful season ahead. So for wherever you're going, for wherever you've been, and for wherever you are right now, I'll see you here next time.
