A Perfectly Imperfect Union: Reflecting on America 250 with Jack Wilson

In the latest episode of A Perfectly Imperfect Union, I travel to the Vacationland State to visit with Jack Wilson.

We talk about how you only really understand freedom once you've lived outside this country and come back.

Jack doesn't think the divide we're in is unfixable. He thinks it's a communication problem, not a values problem. We've got more ways to talk to each other than any generation before us, and somehow we're worse at it. He pushes back on the idea that disagreement has to mean disrespect, and he means it.

His challenge lands hard: stop being an armchair quarterback and start having the honest, in-person conversation instead.

Discover more about him and his unbreakable mindset on this website.

His question for you and our next guest is:

What's one thing you could do today, just one, that benefits more than yourself?

Share your thoughts in the comments and share this episode with someone you love.

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Hey there, it's Michael. Welcome to Whole Again, the show that's here in support of you creating a meaningful life and the person you're becoming. And I'm excited to share a new series with you that will air this summer as America turns 250 years old, which is still pretty young relative to many other countries across this big blue marble that we all share.

The series is called A Perfectly Imperfect Union. In 2022, I rode my bike across America from Astoria, Oregon to the Lincoln Memorial. My wife drove our RV and she had two co-pilots, Jester and Hope, two springer spaniels And when we did it, America was coming out of the pandemic and we were hurting.

Hurting from things that had happened prior to the pandemic, of course, going through what we all went through. And at that time, and this is something I still believe today, is that we were entering an inflection point. An inflection point for us to hopefully pause, breathe, and reflect on who we wish to become as individuals, as communities, and as a country.

As I pedaled across America, I wanted to share America's beauty with others, her natural beauty and the beauty of her people. And I also wanted to share where we were hurting As America turns 250, I believe Kintsugi, which is something we use as a metaphor here at Whole Again, is a perfect metaphor for where we are as a country.

There's so much beauty to celebrate, and we can also acknowledge that parts of us feel broken or are broken, but we can find a way to come back together, just like Kintsugi teaches us. And when we do, we don't try to erase or cover up where we have scars or blemishes. We highlight them in gold, and we celebrate them as symbols of our strength and resilience.

Kintsugi is called the golden repair, and in essence, we can see beauty in something that's perfectly imperfect. During this series, I plan to speak to at least two people in each state and the District of Columbia, so 102 conversations with real folk, as I like to say. We're gonna let the celebrities and the big influencers have their day somewhere else.

But here, I wanna reach out and talk to real people and listen to their reflections as they think about America turning 250 years old. And my hope is, is that you'll tune in to at least one, if not all 102, 'cause my theory going into this is that you'll hear different perspectives. Some may be aligned with yours, others may not.

But my hope is that you hear the goodness in your fellow citizens and realize, as Maya Angelou shared with us, "We are more alike, my friends, than we are unalike." We are more alike, my friends, than we are unalike. I've had the privilege of traveling all over the world and all over this country, and this belief is something that I hold deep inside of me.

So yes, I do believe that we are more alike, my friends, than we are unalike. So if you're ready to meet one of your neighbors who is perfectly imperfect like all of us, take a healthy breath in and a slow releasing breath out and get to know Jack Wilson

Jack, my friend, thanks for joining me here on A Perfectly Imperfect Union. I wanna first say thank you for accepting a random outreach by some dude on LinkedIn, and I've had the great privilege of getting to know you, and I can't wait to dive into it. But let's start here. How are you doing today? 

Man, I am, I am so great this morning.

Looking forward to spending a little time with you, and I think that, uh, you've got a wonderful topic as well. 

Absolutely. Well, we live in a great country, and we have great people in the country. You're one of them, and again, I've had a chance to read up on your endurance mindset and all your accomplishments from your professional life.

It's just endurance sports, and I'm an endurance sports addict. So, uh, we, uh, we, we come from the same mindset on that. So- I love it ... but, but for those that don't know you, uh, can you take a moment to introduce who the heck are you, and where are you calling in from? 

Yeah. So, so, um, again, my name is Jack Wilson, and I am the, the owner founder of Jack Wilson Mindset, where I am a professional, uh, inspirational speaker.

I, I go all around the world talking about the importance of mindset, and I take my professional career where I've had six exits and one IPO, and all, all the time, uh, I've been running all of these years. I ran my first marathon at the age of 16. And so I just kind of combine those together and tell people that the, the journey, wherever you're at, wherever you're going, it's a, it's a journey, and it's supposed to be difficult.

You know, if, if life was easy, uh, it would be, it would be a completely different feel for everyone. So I really spend a lot of time just educating people that you're, you're doing the right thing, and that in this, in this journey that we're all in, you know, the word success is oftentimes thrown out.

Everyone loves that word, you know, success. I want success. I wanna be successful. And I'm... And there's absolutely nothing wrong with that, but I think what we forget in that journey is that failure is a very, very critical piece of, of whatever we do, and if we're honest with ourself, we fail way more than we ever succeed.

So, and in, and the culture we live in, you know, failure is this embarrassment, your head's down low, never to be talked about again. But I, you know, I wanna really challenge people to go back to wherever you are today and wherever you're at in your journey, to go back and really embrace the failure that you've had because in my opinion, the failure i- or there's keys in that failure that's gonna get you to the success.

So that's what I actually talk about now for a living. 

I love that. I love that. Well, there's so, there's so much

But we, uh, we tend to catastrophize, uh, our failures, and then once we have successes, we c- we tend to skip past them, uh, moving on to the next thing. So I think there's some good- there's goodness in both- Yeah ... experiences, and as humans, we can hold both experiences, uh, at the same time. So where, where are you based?

Well, what great state of this union are you in? 

I am based on an island in Maine, uh- All right ... called Har- Harpswell, Maine. Uh, I came up five years ago. This, this accent's not from the Northeast. I was born and raised in Memphis, Tennessee, and spent most of my life in the South, and came up during COVID, like many people looking for a different location.

Fell in love with Maine, and I said, "You know what? Uh, I'm gonna sell everything I own, and I'm gonna, I'm gonna live in Maine." So it's been five years. 

That's so cool. 

An amazing journey and an amazing state, for sure. 

Yeah, so I've been asking people as we've gone throughout the country, 'cause we live in a big country.

You've traveled a lot, though, in your life, but not everyone's been to every state. If we did word association with people on the state of Maine, people would probably think of lobsters or, you know, uh- 

Moose ... 

or the co- yeah, moose or the coastline. So for those that haven't been to Maine, what's a, what's a something really cool about it?

You know, I, I, I think that, that Maine, uh, just physically, um, it is such a rugged, beautiful state. Um, the, the interior of the state, of course, the coastline that everyone knows. But m- more importantly to me, you know, I've really gotten to know the, the people up here in Maine. You know, I'm from the South, where everyone's friendly and, you know, waves at you.

Mainers are a little different, you know? They're, they're not as, they're not as opening to outsiders in the beginning. Um, but they are some of the most gracious people I've ever met in my life. You know, I think when you live in a, in a state like Maine that is still pretty wild, especially, you know, when you get out of the populated areas, uh, community is something that, that these people really count on.

So, uh, the community up here in Maine is as strong as I've ever seen anywhere. People taking care of people. People wanting to help their neighbors. Uh, you know, it's really the way I grew up in the South, but, uh, I've not experienced this type of hospitality in a long time, and I think that, uh, that Maine, that, that's the thing that really surprised me is just the overwhelming hospitality to your neighbor.

Yeah. I love it. I love it. That, that connection piece. I've spent some time up in New England- At one time in my corporate career, I had a territory that included Maine, New Hampshire, and Vermont. Oh, wow. And to your point, like Trying to break in as a newbie, a little hard, but once you, once they're like, "Okay, you're gonna stay a little bit, like you're, you're rugged- Right

enough to get through the winters. All right, then we'll, we'll bring you in," and once you're in, you're in, baby. Like, it's like, you know, now we're gonna, we're gonna help each other, yeah. 

And I do think that might be the, the sniff test is, you know, 'cause people love to come ... You know, Maine, our, our, our tagline is, uh, you know, the way life should be, the vacation state.

Yeah. 

So, you know, in this three months of summer where the rest of the country's literally on fire or, you know, in 100 degree temperature, you know, Maine is always in that 70s, 80s. So this time of year we get a, we get an influx of people, tourists, but I think the real sniff test is if you can make it through two winters in Maine, then, then you're embraced by 

others.

Yeah , yeah. Then you, you are part of h- uh, hearty folk and so- Right ... yeah. We'll ac- we'll accept you as a Mainer at that point in time. Yeah. So during the, the series I've been asking people if, you know, for them to define what America means to them and, you know, w- we share this conversation through audio, not video.

So you are dressed for this interview. You got your red, white, and blue on. Uh, so I would love to hear your thoughts, Jack, on what does America mean to you? 

You know, um, what America means to, to me, I, I grew up in a very patriotic family, number, number one. Uh, my, my father served in the military and always had that military presence in our, in our household.

And, you know, I can remember going to school and, you know, saying pledge allegiance to the flag, um, which, which I'm still very much whenever I hear. You know, it, it's, it's who we are. It's part of our DNA. And I have had the, the privilege of living outside of the United States many times. I've lived in Europe and I've lived in Asia and I've traveled the world, and my curiosity of, of other cultures, um, and really comparing back to the way I was raised and, and what this country has given me and others.

And I believe, if I had to paraphrase what does the United States of America mean to Jack Wilson, you know, I, I don't wanna be coy with it, but, but it, it is the overwhelming freedom. You know, you hear the word freedom wherever you go, but it's not until you actually go outside of this country and you realize that, um, that we are very unique in our approach to freedom of speech, freedom of ideals, um, you know, freedom to be able to, to make as much money as you want.

You know- A- as you travel the world, other countries don't have what we have in place, and I absolutely believe that we are the greatest country, um, in the world 

Thanks for sharing that, man. I appreciate that. A lot of, a lot of freedom ha- the, the concept of freedom and possibilities have, have come up from others I've interviewed in the series, and we've also explored our relationship with the country or at least our family's, um, origin story.

Because in this country, uh, some people were here before it was known as the United States of America. Some families, the indigenous people were here before it was a, a country, per se. Uh, some were forced here through slavery, and of course we have a ton of immigration stories in this country. Uh, so do you know much about your family's origin story w- with America and, and this land?

Yeah, yeah. Act- actually, so my m- the, the history of, of where we came from, we were, um, the, the majority Scottish- Okay ... but we've got a bunch of other, other pieces inside of us. And, and my great-grandparents, they landed outside of Memphis, Tennessee. Um, and, and that's really where we were raised. Some of, some of the folks were across the bridge in Arkansas, but the majority were...

So we're, we are Tennesseans is where the, the Wilson clan kind of, um- All right ... put, put the stake in- The, 

the volunteers of America ... 

the Volunteer State. That is, that is correct. 

Very cool. I love it. So, um, yeah, we, my family is a little bit of a mixed breed as well, uh, mainly s- you know, Irish and whatnot.

And so, uh, we, uh, we landed here in, uh, like, upstate New York, and that's where we sort of made our M- made our, um, landing be known. So, uh, I always love hearing other people's stories about, like, what br- what brought them to the country and where did they end up being, so. 

You know, it, it's, it's very interesting now that as an adult, because as, as a, as a kid, you know, you're pretty much in your, in your state.

You don't travel a lot. But as, as an adult, when you travel, especially, you know, the whole Northeast where I live now was ... That was just the wild, the wildness of America, you know? I knew nothing about it as, as a kid. 

Sure. 

And now, now as an adult and being able to rationalize where people live and how they live, you know, it is, it is a different culture in the Northeast because I think the Northeast is pretty much where, you know, it started from the immigrants coming into New York and then spreading across the country.

Sure, yeah. Yeah. So I, I find it very, very, uh, very amazing that we're as, uh, that we're a country as large as we are and, you know, and a, and a young country that we've been able to accomplish so much really in a very short amount of time. I think it's just amazing. 

It ... That is a really great point that you bring up, just the how big the country is.

That really hit home for me when I rode my bike across the country back in 2022. And when you think about it through today's lens, okay, through the phones and the web and stuff, you can communicate out to people Right? So this is, hey, this is where we are, where we're, where we're at, and this is what's happening, right, in the world.

But back in the day when our country was being founded and shaped and going through revolutions and evolutions and all that jazz, communication was much harder, and it was harder to reach people. And still, somehow we found a way to, like, come together in local communities and make this thing happen, and in a very, as you mentioned, we're a young country, a very short period of time.

We have done a lot of remarkable, remarkable things. So I, I love the fact that you brought our size into play because back in the day, it made communication really challenging, so we don't... I don't know if we necessarily appreciate that through today's lens. 

I, I, I don't... You know what, the, what a, what a great, uh, you know, I'm gonna try not to go down the rabbit hole, but when you talk about the size of our country and, and the youth of this nation, um, leading up to, to this conversation today, uh, because I've always been a history buff of all history, not necessarily US history.

But I wanted to, I wanted to test my thoughts on what I thought I knew about our country. So I went back to the History Channel, and I've watched a couple of documentaries where I thought I knew the story, and, and apparently I didn't. So I think, you know, as, as Americans, anyone listening to this, I, you know, I would, I would challenge you to go back to the beliefs that maybe you thought you had as a youth and, and go back and really dig in.

And the, and two things that, uh, just blew my mind. I watched the Theodore Roosevelt, um, on the History Channel, about a two-hour documentary, and it just blew my mind at the, at the integrity, the curiosity that Theodore Roosevelt had about this country and the amount of, of work that he put in to opening up the country all the way to the West.

Yeah. 

Um, and he would be gone, you know, and the, and the only way they communicated back then was a letter to somebody that could then go and take that letter, you know, across country. So there, there was no immediate, you know, uh, "I need help," you know, "Send me money." What- You know, you had to go out and figure it out on your own.

But the most amazing thing when you talk about this country and really- how we got here is if you go back and you look at the Civil War, and I watched this amazing documentary on Ulysses S. Grant where I thought I knew a lot about the Civil War, and I was completely misinformed, or I, I thought things that I never was in my head correctly.

But if you only realize how close we were to the Union completely fragmenting, I mean, we, we were a nanosecond away from this country going two different ways. And when you think about what could have happened that thank God it didn't, you know, the South would have been its own country and the North would have been its own country.

You know, it never would have worked the way it does today. So I think it's, it's just amazing that we live in the country that we all recognize today. And if you go back in history and see the way it was formed, I think it would just really amaze any American that lives here. 

I love that. Love the fact that you brought that in, and, and great, great on you for all the prep leading into our conversation.

So, uh, as you know, I'm using the Japanese art form of, of Kintsugi as a metaphor for this series. It's actually a metaphor for my podcast in general, knowing that, you know, we can have breaks, uh, we can chip apart, but we can find a way to come back together, and then those golden, golden lines of our fracture can be great symbols of our resilience and strength.

So when you think about us as a nation, we're young, we're big, we're perfectly imperfect So is there one thing, Jack, that you would like to work on that could help us find a way to connect better, to perhaps heal, even grow from that healing, uh, that could help us, uh, become that more perfectly in perfect union?

You know, uh, it's, it's, it's, it's a great question, and I don't have the, the silver bullet or the magic answers, but, but I, I will say that in my opinion, anything in life, anything, a bad marriage, I don't like my job, um, you know, you c- you can't throw it out where I would say open and honest communication, um, it, it heals m- many things.

You know, take politics, 'cause we're not talking a- we're not talking politics or, or political at all. We're human beings. We all live on the same patch of, of Earth here, and we do live in the United, United States of America, which means we, we have to be united as a country. It's completely fine to have different opinions, um, a different viewpoint on where we're going, but this complete divisiveness of, of us versus them, them versus us, I, you know, it's not scalable at all, and, and if anything, it's holding this great nation back from, from the greatness that, that we could be.

Um, so I encourage everyone, you know, have open and honest conversations, and if someone's talking about something that you don't agree with, it's, it's absolutely fine to disagree, but we don't have to be nasty to, to others in those disagreements, you know? I mean, it's fine to have a different viewpoint, but other than talking, you know, y- you're gonna have to go out and do your social activity too, you know?

I mean, you know, it, what, what good is having opinions if you're, if you're completely against whatever the, the other opinion is? Then that, that's the call to action. You know, we have to do better at being able to verbalize our differences and then figure out a way to work together to bring us back to one country, you know, under God, indivisible, with liberty and freedom for all.

You know, somehow this message has gotten a little sideways over the years and, and I believe open and honest communication is the key to getting us through this. 

Love it, Jack. Yeah, there are too many people out there that are, uh, full of courage behind a keyboard and, uh, just throwing, um, throwing crap at each other and, and maybe some of those people aren't real people, they're bots or what have you.

But I love the fact of just trying to see each other in each other and have Better conversations where we can disagree without being disagreeable. So now you're a, you're a history buff, of course, so this question I've been asking people before you, like, "Hey, do you have a question for our next guest?"

And in turn, you get to ask a question of the next person I chat with later today. So this question comes from Nelson. And so as a history buff, and you're watching the History Channel, of course, we... Most people know Ken Burns, the great documentarian. So if you could whisper to Ken and say, "Hey, Ken, for your next project, I want you to focus on this topic, this, this piece of history," what would it be?

Man, I love being put on the spot. If, if, if I could whisper to Ken I would, I would go back to, um, to, to the way that we ... A- and a lot of this has come from me watching this History Channel, and it's just been amazing to me at how just rudimentary we were just 50 years ago. 

Sure. 

Right? The way, the way ... Just 50 years ago, none of this technology that we all have, you know, the, the ability to do what we're doing now, the, the, the freedom to send a text and to get immediate gratification.

You know, I, I would say if we could go back at history and look at just how fast the technology craze has hit this country and, and then anybody that would look at how fast this has happened would look at it say, "You know what, guys? This probably is not a sustainable way for this nation," uh, because it- it's, it's causing us

And, and you said it, Michael, you know, it, it's easy to be an armchair quarterback, um, when things are, are going wrong, right? So people weigh in on topics. I think people stir the topic. And, and these, these wonderful devices that we all have, I believe if you go back in history, there's gonna be a time of reckoning that the amount of information that we're consuming on a daily basis is

It's not, it's not good for any of us. It's not good for, for our mindset. It certainly is not good at bringing people together, and that was the whole premise in the beginning anyway, right, is this communication layer was supposed to bring people together. I think we've completely overreached with that, and it would be to anyone looking at history w- where, how has communication affected the union up until 50 years ago, and then what has happened in the, in the past 50 years with the way that we communicate?

I think it would be a fascinating study of what we thought we were doing right. And at the end of the day, I, I believe that the communication layer that we've implemented has given people the freedom to say whatever they want, whether it's right or wrong, and, and there's no checks and balances. And I, and I think that it's, i- it's, it's not, um, it's not a good thing for us long term.

Yeah. I will sign up to watch that documentary. So Ken, if you're listening- 

Ken, get on it. 

Yeah, get on it, Ken. I think Jack has a great idea. So Jack, what question do you have for the next person I chat with? It could be about really anything. Doesn't have to be about America per se or America turning 250 Anything un- under the sun is fair play.

Yeah. I mean, you know, I, I'm, I'm a, a- again, I'm a big believer in this mindset thing that I've been, I've been preaching, and I'm a big believer that, that our human capacity is way bigger than, than any one person. You know, we're, we're, we're all individuals, but if we do not come together, um, as a, as a team, as, you know, more than one for a, for a better cause, we're gonna continue to be fragment.

So my question for the next guest would be, what is one thing that you, we, can do in our everyday life, just one, that is for the betterment of everybody? Not, not just me, you know, 'cause I could think of a thousand things that selfishly benefits me. But what's one thing that, that we can do, or your next guest can do, that, that can start this process of, of its betterment for, for the better good of everyone?

Yeah. And it doesn't ma- it, d- you know, white, Black, whatever your race, your creed, wherever you live, it's, it's everyone gets to benefit. What's that one thing? Because I'm a believer the ... and I preach 1% better every day. You know, it's very easy to get sidetracked with how fast life is going and how overwhelmed people can be.

But if you just look at it and say, "Hey, listen, if I can just be 1% better," I'm not asking for, you know, for big leaps and bounds, 1% better, and then at the end of the year, you're 365% better. So you think about it, just 1%. What is that one thing that we can start today, that we can start our movement, that's, that everyone can jump on board with?

It's a big ask, and I don't know the answer to it, so whoever's after me has to figure it out. But that, that's the question that I would throw out. 

Yeah. Well, I'll serve up that question to our next guest. And Jack, again, thanks for joining me here. Thanks for the ripple effect you're putting into the world and helping us become a more perfectly imperfect union.

I appreciate you, brother. So again, thanks for being here. 

I appreciate the opportunity. And, uh, no, no matter where we are in our journey, I am a believer that we are a, a perfectly imperfect union, but we are the best country, the best place to live, the best place to raise your family, to make a living, is right here in the United States of America.

And if we all come together, we can continue to grow this imperfect union. But I think having open and honest conversations with your family and with your neighbors is where it starts. 

We'll end there, man. Be well. Peace. 

Thank you.

I love Jack's energy, and this was an interview where I wish I did video along with audio for this podcast because Jack looked the part. He was all done up in red, white, and blue. He had all his medals in his background. It was really awesome to see, and I love his question. So what's the one thing you think you can do today that could benefit more than just yourself?

Maybe those in your immediate circle or the circle beyond that. In essence, what can you do to create a powerful ripple effect today? Let me know in the comments, and ask your friends what they could do. And as always, thanks for being here. Thanks for listening as we celebrate America at 250 years old.

And remember to celebrate your scars as golden symbols of your strength and resilience, and don't forget to have fun storming the castle.

And if you wish to learn more about creating beautiful ripples and how to prevent a bad moment from turning into a bad day, please visit my website, michaelobrienshift.com, and sign up for my newsletter called The Ripple Effect. And join us each Monday, Wednesday, and Friday here at Whole Again, and discover how you can heal, grow, and become more resilient, and celebrate our scars as golden symbols of strength and resilience.

Until then, remember, you can always come back to your breath. You've got this, and we've got you.

Key Takeaways

Jack Wilson believes the current divide in America is a communication problem rather than a values problem, and that disagreement does not have to mean disrespect.

Understanding freedom comes from living outside the United States and returning, according to Wilson.

Despite having more communication tools than any previous generation, current society is worse at communicating with each other.

Wilson challenges people to have honest, in-person conversations instead of being armchair quarterbacks.

Frequently Asked Questions

What does Jack Wilson think is the main problem dividing America?

He believes it is a communication problem, not a values problem.

What is Jack Wilson's challenge to listeners?

Stop being an armchair quarterback and start having honest, in-person conversations instead.

What question does Jack Wilson pose to the audience?

What's one thing you could do today, just one, that benefits more than yourself?