Celebrating America's 250th with Michael O'Brien

[00:00:11] Welcome back to another episode of The Political Life. This is Maggie Mick with Multi-State, and today is a special episode in honor of our nation's birthday, the Big 250, coming up next week. And I actually invited a new friend who I would not put in the political box, but I think is doing some Herculean work on behalf of the country right now and wanted to talk to him about his pursuit and

[00:00:39] what drew him to this work. And so today I'm pleased to introduce you to Michael O'Brien. He is host of a new podcast called A Perfectly Imperfect Union. He and I met recently, which he can go into. But I just thought that the work that he's doing is a nice pause for us to think about how special our country is and can't wait to hear from him on how he came to this podcast and the

[00:01:08] work that he's doing. So welcome, Michael. It's an honor to have you. Oh, Maggie, thanks for having me. This is so awesome. A little bit of a flip-flop and rolls with our podcast. I can't wait to share with the world our conversation on the series, and I'm so looking forward to this one. Perfect. Well, and thank you again for the invitation. As everyone that listens to our podcast knows,

[00:01:31] James O'Brien launched it many years ago now. And when Michael O'Brien reached out, he name dropped Jim and just said that he was a brother from a different mother. So it caught my eye at his outreach. I knew it wasn't spam. But Michael, you know, this has been a passion project of yours, part of your life story. What was the road to standing up a perfectly imperfect union?

[00:01:59] Well, that's really cool that you mentioned road because it popped up during a bike ride across the country in 2022. I went from Astoria, Oregon to the Lincoln Memorial in Washington, D.C. My wife was with me. She drove our rented Cruise America van. We had our two Springer Spaniels as

[00:02:22] co-pilots. And we went through really the rural part of America. That's how the route worked. We avoided all like big cities. We went, like we kissed Pittsburgh and Eugene, Oregon. Those were probably the two largest cities that we touched. But we went through like the heartland of America, which was really cool. And there's one particular visit where I had like these wonderful conversations. And

[00:02:52] what sparked this series was all the different conversations I had with people I would never have met in a million years if it wasn't for this trip. In states I had never been to. And, you know, coming from the East Coast, I'm like, you know, wow, this is a huge country. And there's, it's so diverse and it's so interesting and so many good people. I went into a cafe because usually I would stop

[00:03:16] mid-morning for a coffee and a muffin, you know, fuel up. And I stopped into Rushville, Indiana at the Moose Cafe and Antiques. And I walked in with all my cycling gear. I looked like an outsider because I was an outsider. And there were about 12 people sitting around the table having a coffee clutch. And they looked at me and the cafe was actually quite busy. There was probably 18 to 20 people there. But the 12

[00:03:43] people were holding court talking about whatever they were talking about. And there, after I ordered, they're like, hey, biker, come over here. And they peppered me with questions. And it was so cool because, again, I would not have met them without this ride. And we probably, maybe from a political perspective, would not necessarily agree on everything. But we found like so many common interests and this,

[00:04:10] and the town was having its 200th anniversary. It was founded in 1822. And I was like, that was really cool. And as I left, they said it and everyone else in the cafe said it. They were like, God bless you, safe travels. And I'm like, okay, there's something there. That's a start. And so as we come into our 250th, I was like, let's have 102 conversations with everyday folk across the 50 states and DC,

[00:04:39] and just have not political debate, but just conversation around connecting and appreciating one another. So you structure the conversations by choosing people from every state? Yeah, two, two from every state and DC. That's the goal. I have about 47 conversations, as they say, in the can. And I plan to run the series through election day or up until election day

[00:05:08] in 2026. And I usually release about three episodes a week, although that might have to get amped up as we get closer to September, October, and the first part of November. But that's the goal. 102 across the 50 states and DC. And the people are from all walks of life, all different professional backgrounds. Yeah. So I'm using LinkedIn as my primary source. So shout out to LinkedIn. Since I'm sort of

[00:05:37] professionally in that professional genre, if you will, as an executive coach and as a speaker, I'm using LinkedIn. So I do something very simply, I go into sales navigator, I type in a state, I make sure that they're active on LinkedIn, you know, so they posted something. And then I just go through, like, who is there? Like, who are my first connections? Who are my second and third

[00:06:01] connections? I might put a particular interest, like if they're a community builder, or if they're into resilience, or if they're into kindness, or joy, or I use different keywords to, you know, with my search, sometimes I put in the word cycling to see if I get any cyclists. But the goal is, is to speak to people

[00:06:24] who are not like me. And just by random chance, I'm going to get people who are maybe similar to me, but I'm, I think I'm doing a decent job, at least reaching out to people who are not like me, they don't have my background, certainly they don't come from my own lived experience. So we're getting a good sample of like, what America looks like. Although it's not perfect, you know, some people will not respond,

[00:06:53] they think it's spam, right? So I try to personalize each note. So my hit rate isn't like fantastic, but I go into each state and I go through like who pops up. And one of the things that's most fun is to go through each, each person's profile. I don't go through everybody. I go through maybe the first three pages. So when you came up, I was like, oh wow, she's a daughter of the American revolution. I go, I bet she's got some really cool stories. I'm like, that's interesting. I don't have

[00:07:22] anyone in this series that has that type of legacy. And so I was like, I'm going to reach out to Maggie. And so there's usually something within everyone's profile that's like, oh, that's a little bit different. I'm going to talk to that person and see what they have to say as America turns 250 years old. The conversation that you had with the woman from New Mexico, I learned so much. Talk about like lived experience, just like, you know, New Mexico is such a unique space. I loved how she said,

[00:07:52] you know, our friends say that it's a unique place that we don't want to tell anybody about or something. It's so true. Like, please don't overrun and making it, make it not so, you know, such a destination, but she was just a fascinating human with whom I would never speak to or be able to cross paths with. And I loved listening to her conversation. Yeah. No, Vanessa is a special human as everyone is on the series. And, you know, she, she really helped me because one of the

[00:08:20] questions I asked is, hey, tell me about your family's origin story to America. And she is indigenous. She's native part of the Navajo tribe. And she's like, well, that's a very interesting way of wording that question because my family has been here long before it was actually known as a country. And I'm like, oh, wow. Okay. Lesson learned. Let me see how I want to adjust the wording of that

[00:08:45] question. And she was very gracious. You know, she used a lot of humor in the conversation and I think she brought a really cool perspective. So like everyone brings their own thing. And I, what I found is that we have so much more in common that we can at least start with than what divides us. But, you know, some of the powers that be want to divide us for their own wealth and status and fame

[00:09:12] and fortune and all that stuff like that. But if we get like real people talking together, I think we can find, even if we are quite different, we can find things that we can agree on. And on the first episode, you actually, I picked up from our conversation that you change your question set based on not only do you have the questions planted from the last guest, which is a

[00:09:35] really cool continuation of connectivity, even among the guests. But I picked up that you started asking questions in your question set from just things that you're learning throughout the series. Absolutely. So when I started off, I'm like, I'm going to ask these questions. And then what I'm trying to do is also role model. Like we can learn as we go. We can also change our mind.

[00:10:00] You know, I, sometimes I feel like you have to come up with a point of view and you got to stick with it. And if people, if you, if you change your perspective, then people are like, well, you're a flip flopper. And I'm like, well, I don't know. I just, I gained a little bit more knowledge and experience and I decided to do it a different way, or I've come to this realization or that realization. So when I first started off, yeah, I had a certain amount of questions and I'm like,

[00:10:26] you know what, I'm not sure if those are working well enough. Like for example, when I first started off, I didn't ask people their thoughts about AI because you can't get away from current day without having some type of interaction or conversation about AI, unless you're say off the grid. So I started inserting that, but I feel like once we get to the end, as I get closer to September or October, there might be even other questions I've popped up this morning. I thought,

[00:10:55] I could ask that question. Like I haven't asked that question yet. So I want to try to mix it up. I want to show people that nothing is static, like as a country, as people, we're not static. We're, we're fluid. We're ever changing. We're also messy and the country and democracy is messy. We like to think that our founding fathers had this come together in Philadelphia and everything worked

[00:11:23] out so perfectly. And it's just like, this is how it is. But the reality is, is that they fought vigorously. They had great debate. They disagreed. They, they found a way to have a beer or pint of ale afterwards, maybe, you know, with Ben Franklin and Thomas Jefferson or whomever, you know, it's like, but it was, it's a messy process and it's, it's a slow, messy process today. And I think in today's

[00:11:48] world, we want everything to be neat and fast and clean. And that's just not how the country was built. And I think we have to find a way to embrace, embrace the messiness of our lives and the country that we happen to call home. Yeah. I love the question on what's the misconception about your state? What do you think is the most interesting response that you've gotten out of the 47 in the can

[00:12:16] to the misconception question? Oh, it's, it's like all stereotypes, you know, depending on which region you come into, but it's all about, well, people believe that people from this state are like slow. It is from the South. It really is. They, they think we're slow. It's the Southern draw. Like we're not that intelligent. We're not that smart. We're backwards, right? Stuff like that comes up.

[00:12:44] They're like from the Northeast. It's like, well, we're cold. We're, you know, we're somewhat removed. It's hard to break through. Out West, it's a little bit of like, we're too like free spirited. We're like to like laid back or what else, you know, like, we're just going to like go bungee cord jumping. Although I don't think we do that too much in the States, but like stuff like that. So it's a little

[00:13:07] bit about, I think the conversation, we all have conversations with ourselves, right? We all talk to ourselves. And so some of the misconceptions pop up is it's the conversation that the people in the state are having about themselves sometimes. And it's just not, you know, obviously with misconceptions, there's not, there's not truth in that, but that's how people see that particular

[00:13:33] part of the country. And the thing is we, we live, as I mentioned earlier, we live in a big country and we, we don't necessarily travel to all corners of it. So we might think like, oh, the people out in California, they're all this way. And I'm like, California is a big state with a lot of different people, just like people in Kentucky are, well, they're this way or people in New York are all like this, but like a state of New York, which is my home state. When you go to New York city and

[00:14:03] Long Island, it feels completely different than if you go to say Rochester or Buffalo or up in Lake Placid, you know, when you're in Buffalo or Rochester, it feels more like Cleveland than New York city. And so for, and for us to say, well, all those people from that state, they're like this, it's just, it's too simple. It's too binary. And you shut down any possibility that you can learn from someone

[00:14:29] within that state. Yeah. My husband and I have, you know, the great fortune of traveling for work and personal, but often for work, you know, last month we've been on the road most of, of the month and, you know, we get tired and we get a little grumpy, but I always say to him, you know, we get to, we get to move around this country. There are people in Kentucky who haven't left their town to

[00:14:53] even go to Lexington once this year. There are people in the state that have never crossed the border out. It is such a privilege to be able to move, um, even when you're tired. So. Yes. It's, uh, the, the, the roadways and the trains and planes allow us to do that. And and having some appreciation, like, you know, some people they've never left their hometown.

[00:15:20] Yeah. And so that's just more common than you, than you think. Yeah. Yeah. That's what I realized as I wrote across the country is that if this is all I know, right. And this is the, my small little town in rural Wyoming or Montana or Kentucky, or even New York, if this is all I know, and then my outside world is the internet, then. Okay. I can start to understand why you might believe

[00:15:49] what you believe, but when we travel, that's when our aperture widens and opens up and says, oh, you know what? Uh, the world's a little bit more complex, as I mentioned earlier, messy. And it also helps us appreciate what we have because we can get grumpy on the things that we don't have, but a little gratitude goes a long way to say, you know, a lot's working. And if we can,

[00:16:16] we don't want to sugarcoat what may not be working and what's hurting, but we can also at the same time talk about, Hey, this is what's working. And that can, those can be building blocks to help us move forward and have some progress. I also think that's why it's so important to capture oral history, which essentially is what you're doing. My husband and I did the veterans history, oral history project

[00:16:39] about 15 years ago. It's a program, I think through the library of Congress. And we did it in our small stories and sharing them also humanizes us all and brings down barriers. So I think beyond, you know, you going across all 50 States, but essentially what you're doing is capturing oral history. I also think that that's what we do on this podcast too, is capturing people's careers. It is their oral

[00:17:06] history of their career to the benefit of others. Um, absolutely. That's what I wanted to do through, you know, podcasting allows us to do that. I remember when America turned 200, I was a young kid where my memory is whatever, whatever I've captured from it and brought through my whole life. But with podcasting, we can really do, we can hear someone's voice. You can feel the energy of their

[00:17:35] voice and also a snapshot in time. Like this is where people, you know, how they feel about a particular topic. Like, as I mentioned AI. So it'll be fun in five to 10 to 20 years, or maybe another 50 years to look back and listen to how people felt about AI in 2026 and how we feel about AI say in, uh, 2050.

[00:18:02] Yeah. So as an executive coach, I have to ask, you know, you, you study and teach and guide and coach people every day. How has that professional work kind of been informed by this kind of passion project that is the imperfect union podcast? Well, there's a lot that's happening in the country

[00:18:25] that, that bleeds into corporate life, you know, because it can't help, but not, we were all people going into the office or dialing into zoom or Microsoft teams. So whatever's happening in greater, in the greater society is also coming into our workplaces. And we can see our workplaces are trying to figure it out as well. They too are messy. There's a lot of employee disengagement.

[00:18:53] We're trying to move really quickly. Things are changing rapidly because of technology. So leaders today are trying to lead through a lot of complexity and there's always been uncertainty, but the uncertainty feels more charged, I think for a lot of leaders today. So what's coming out in the series from all the people I've chatted with is like, Hey, why don't we hit the brakes a little bit,

[00:19:19] slow down enough to listen, to understand and connect with each other as opposed to just listening to reply or to react. So I think that's a really good thing. It's a basic thing, but a good thing for leaders to understand that, that maybe the days of the sage on the stage, like the leader with all the answers, those days are over. And now we can crowdsource wisdom by being curious with our team

[00:19:46] members, asking really good questions, really good prompts as we do with AI and see and really listen to connect with the employees, bring them into shaping the culture, extending grace to one another, because we are going to make mistakes as long as the mistake isn't repeated over and over. And again, that's a different conversation, but we're going to, we're going to miss the target. And if we can learn

[00:20:14] from that experience, then we can be a bit better going forward. So yeah, there's a lot as far as like crowdsourcing wisdom, leaving the whole, like I'm the expert off to the side for a bit, also checking our ego when we do that and really tapping into the wisdom of the employees. When the employees have a chance to shape the company and shape the culture just by that, there's more skin in the game.

[00:20:41] I think that can drive overall employee satisfaction and engagement and make what is messy today, a little bit less messy. Yeah. Feels a little bit safer too, to be comfortable with the mess. Yeah. When we're, when we're safer, when we feel safer with the mess, there's greater trust. Mm-hmm. And what, I think what we're missing in today's culture, work or society, and this has

[00:21:11] popped up in the conversations is that we've, we've had some damage to the trust, you know, trusting what's real, trusting what's true, trusting good intentions. And so we, the only way to get back to trusting each other is through conversation, like really connecting and say, Hey, I see you,

[00:21:33] I hear you, I appreciate you. And with trust, and this goes back to an old guru of leadership development, Stephen Covey, he wrote a book called The Speed of Trust. Like basically companies and cultures, I'll add, move at the speed of trust. So when we have trust, we, we feel grounded, like stable, and then we can take really good action. We can be thoughtful. And I think

[00:22:02] really we could use more trust within our greater society and within corporations. And we only do that through good conversation. Yeah. And you can move faster if you have trust. Sure. Yeah. Yeah. If we don't, if we don't have trust, we're going to be a little hesitant. We're not going to necessarily lean fully into it. We're going to take like baby steps, but we're going to hold

[00:22:26] back a bit because we don't know if something scary is around the corner. But when we have trust, when we feel like people, Hey, I got your back, right? I got your back in good times. And I got your back when there's a crisis, then we feel more, more open to perform and really tap into our potential. And I hope, you know, my hope is that we can get there. I'm a very hopeful guy. I think

[00:22:53] hope with hope there's action. So we got to take some action to lean into that hope. But I, I, I think we can get there. So going back to the origin story of the bike ride, why did you choose to do the cross country bike ride in 2022? I feel like most people were doing a YOLO trip like that in like 2020. We didn't know what the world was going to continue. So why in 2022 and, and why that,

[00:23:22] why that decision to, to, to go across the country? Yeah. So my origin story with all of it starts back in 2001. I got hit head on by a speeding SUV during a bike ride during a corporate offsite meeting. So I had, I had a big, big catastrophic accident and the doctors had no clue whether I would survive. They predicted a life of a lot of

[00:23:49] suffering and pain and probably were, was going to be in a position never to ride again or really walk with a lot of trouble. So I start the whole story about riding across America from a point of like, I'm lucky to be here. I feel like I'm in bonus time and I want to show up really living life fully. So in 1976, there was the start of this thing called the trans America trail created by an

[00:24:19] organization in Missoula, Montana, a bunch of maybe back in the day, hippies, right? Like got people riding their bike across the country, right? Back when there was like different roads set up and the whole thing. And they went from Astoria, Oregon to Yorktown, Virginia. And I thought that was the coolest thing as a kid. I'm like, Oh my God, they're riding across the country. I was always into my bike. I'm like one day I'm going to do that. But when I had this big accident and my doctor said,

[00:24:47] Hey, listen, you're not going to ride your bike ever again. That dream died. But I was like, you know better. And as I got stronger, I was like, okay, that dream sort of came to life a little bit more, even though a lot of people said you shouldn't do it. There's no way you can do it. We'll still look at you. Right. And I was like, wow, you know what? It's always, it's always impossible until someone

[00:25:16] does it. And so I'm like, I'm going to keep that dream alive. When 2020 happened, you know, we had our girls, I have two daughters, they came back, they were in college. So we were trying to figure it all out. They're living at home. So the YOLO trip just from a timing perspective didn't work. We thought about doing it in 2021, but because of my accident, I needed a total knee replacement. So I got a total

[00:25:42] knee replacement in July of 2021. And then I said, okay, well, we're going to do it in 2022. It was the 21st anniversary of my accident. I was like, my accident is a full-fledged adult now. Let's do it. We were also coming out of the pandemic at that point in time. And I really wanted to show people, the country by through this bike ride, at least the people that I was connected with to say,

[00:26:10] listen, we've all gone through something unimaginable and there's goodness amongst us. There's good people. There's, there's beauty. This country is so from a natural perspective, so beautiful and beautiful people. I thought it was a good time to like, let's do this now. My wife agreed and luckily, cause she's my co-pilot and all this. I was like, let's go through

[00:26:36] the country and try to showcase what we're all about as America. The things that we're really proud of in some of our history that, you know, are blemishes on our track record and really try to embrace all of it as a way. It was my small way of saying like, we can heal and we can grow from what we've gone through in the pandemic. And let's, let's find a way to come together. Like, and so that, that was it.

[00:27:06] It was like, it was a little bit of like my initial accident back in 2001 coupled with this lifelong goal. And I just thought 2022 was a good year. Cause we were coming out of the pandemic. It was also safer to travel. And I was like, let's, let's do it now. And I'm glad I did. Like each night I got onto Instagram when I was over on Instagram, I went to a local dairy. This was the big part of the ride.

[00:27:35] And every time we landed in a, in a town, the main goal was to find the ice cream place. Yeah. The dairy barn, the dairy bar. Like I was like, okay, where's the best, where's the best ice cream in town? And I will say that not every town in America has a really good ice cream shop. My husband and I have the same pursuit with two little kids. Where's the best ice cream? Sometimes it's just the gas station. It's just the gas station. And you're getting like a nutty buddy from the freezer, the gas station.

[00:28:05] But so we would hit the local ice cream place and I would order a milkshake because I'd been riding my bike for about six hours a day and I could have a guilt-free milkshake. Right. And I would get on Instagram and I would do an Instagram live called milkshakes with Michael. And I would just share what I experienced in the day from the people to the weather, to the roads, to the traffic points of interest. And it was a really great way of just sharing the country with people. And

[00:28:34] I got a whole bunch of milkshakes in me and we even survived Dairy Queen gate, you know, because I went to Dairy Queen in one town because that's all there was. And I got a blizzard and I served it up as a milkshake and people were outraged. They were like, that's not a milkshake. A couple of people actually called Dairy Queen headquarters to determine if it was a milkshake or not. I've since learned that

[00:29:03] a blizzard is not considered a milkshake, but still it was very delicious. So fun. Yeah. So it's just, it's just, I would also realize that. Yeah. A lot of people have a lot of time on their hands. Like, you know, it's like, you know, like why are you calling Dairy Queen headquarters? But that's, you know, it's not, it's not for me to judge, but it was still a lot of, a lot of fun. And it was, again, it was such a great chance to see the country and get encouragement from complete

[00:29:32] strangers and have laughs with people and just, yeah, see, see what we're all about. Well, I'm going to close our conversation with, I think the final question that you have on your podcast. What is your wish for America at 250, knowing that this will likely run right about July

[00:29:56] 4th? Yeah. Well, so coming through my recovery, I developed like a little acronym called pause, breathe, reflect. So when my recovery was so overwhelming and there was so much I had to think about like, who was I going to become? Could I provide for my family? What kind of father or dad I would be? All of it was so overwhelming. And so what I know from my lifelong interest in

[00:30:25] sports is that sometimes when the game gets a little intense, we call a timeout and it's a chance to pause the game for the players to take a breath. And then in a moment of reflection, right up the next play, like how are we going to get back on the field or back on the court? So pause, breathe, reflect became my little mantra and also my mindfulness practice, if you will.

[00:30:48] So what I hope we can do is to hit pause from all the rushing around, take a few deep breaths and reflect on what works in this country to reflect on things in the past that haven't worked, try to heal those wounds. And then part of reflection is how do we wish to move forward?

[00:31:15] And so my hope is that we can take a moment to do just that. I do think our country would be better off. I think the world would be better off if we took one minute a day just to stop and take a few breaths and think before we go forward and not be so reactionary. Like that's the reflect piece. So yeah. So I would say, um, I hope that we can pause, breathe, reflect before we blow out the candles.

[00:31:45] Yeah. And if we do that in our day-to-day lives, maybe universally we will be better. Yeah. It just, it's a minute out of all the minutes that we have just a minute to slow it down and breathe, uh, because, you know, we're, we're not promised what I learned through my accident is that we're not guaranteed tomorrow. We have today and we get to decide how we want to show

[00:32:10] up for ourselves and each other today. And hopefully we can do that with grace and compassion, with trust. When we have trust, we can have rigorous debates like the founding fathers did and try to solve some of the complexities that are in front of us. I believe we can do it, but we're not going to be able to do it if we are rushing around like, uh, chickens with our heads cut off, just reacting to

[00:32:38] this, that, and everything. We need to be thoughtful. Um, that's what I think the world requires right now, some thoughtfulness. So I hope we can do that. Well, thank you for your leadership and your service to our country by doing this project. And I hope everyone will tune in to the series. Again, it's a perfectly imperfect union hosted by Michael O'Brien and you're going, I think to Kentucky next, but what's the state in the hopper

[00:33:07] after Kentucky? After Kentucky, I go to Missouri. Okay. So, and across the border, just this morning, I interviewed someone from the beautiful Commonwealth of Massachusetts. And then later on today, I interviewed someone from, uh, Mississippi and Connecticut. So I'm, I'm going all over the map. Yeah. Yes. I mean, what a joyful ride though.

[00:33:32] Yeah. It's really cool. It's like, we were filled with good people who want to do good things. So I hope people get that from the series. Perfect. Well, thank you, Michael. Happy for, happy for a few, Maggie. Thanks for having me on.