The Chris Voss Show - The Chris Voss Show Podcast – Roger Williams of The Crossing It Off Podcast

Episode Date: March 8, 2022

Roger Williams of The Crossing It Off Podcast Subscribe to the podcast at: Podcasts.apple.com

You wanted the best. You've got the best podcast, the hottest podcast in the world. The Chris Voss Show, the preeminent podcast with guests so smart you may experience serious brain bleed. Get ready, get ready, strap yourself in. Keep your hands, arms and legs inside the vehicle at all times. Because you're about to go on a monster education roller coaster with your brain now here's your host chris voss hi folks it's voss here from the chris voss show.com the chris voss show.com hey we're coming here in another great podcast we certainly appreciate you tuning in thanks for being. Be sure to go to all of our channels on YouTube.com, Fortress Chris Voss, Goodreads.com, Fortress Chris Voss. See everything we're reading and reviewing over there.

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Roger Williams is on the show with us. He is a writer, podcaster, adventurer, and chief crosser-offer of his bucket list. After more than 30 years working in the youth development and teaching field, a year in quarantine and two heart attacks, Roger embarked on an adult gap year to prioritize a life which is known not by his professional work, but by the way he lives his life and the people he grows relationships with. Now he is traveling around the world to cross off his bucket list and inspiring other people to do the same. And he's here to inspire us. Welcome to the show, Roger. How are you? I'm doing great, Chris.

I appreciate the time. And buongiorno from Trieste. Italy. There you go. What a beautiful place. Give us your plug so we can find you on the interwebs. Yeah. I have a podcast called The Crossing It Off Podcast,

and it's available everywhere from all the streaming services, as well as you can now listen to it on Facebook mobile and it's available on YouTube. Awesome sauce. Awesome. And I have a pretty solid following on Instagram where you can follow my adventures and the things that I'm doing and I'm crossing off my list and you can can get there at crosser.offer. Awesome. So tell us more about what you do. Let's identify a few things. What is a gap year?

I'm not familiar with that. Okay, so a gap year is typically a European event that students take in between graduating from high school and graduating from college or going to college. And then also it can be done after college as well. And it's kind of a time to find yourself, experience the world and try to figure out what you want to do with your life. So now is that like a sabbatical or is it just different? It's just different for the, for students, for young people, it's typically planned out. They're usually doing things.

It's not like sitting on your couch and playing video games for a year. It's actually doing intentful things to better yourself as a human and prepare yourself for school or life. For me, I just decided that I was going to take an adult one and take a year off from working. So I quit my job last October. And so I'm out just doing things I enjoy doing. So what motivates you that you mentioned, you had two heart attacks, went

through some different things. What brought you to this point of, is this a new career move and stuff for you? Yeah, it's, I don't say it was a career move as much as it is. I mean, definitely not doing what I used to, but it was a couple of years ago, I had a heart attack. We were going through quarantine and a lot of people, as we've seen this great resignation, have decided that they don't want to be recognized for the work that they do. They want to be known for more than just their labor. And I was going through that same dilemma in my head. Who am I? What am I doing? How do I want to live my life? And I just decided that I want to become the head crosser from a bucket list. That's what I wanted to be known for. And so I changed my

profile on all my socials and said, this is who I am. We always ask the question, what do you do? What do you do? And typically the answer is, what do you do to earn money or what do you do to sell your labor? And I just didn't want to answer the question like that anymore. I wanted to say, this is who I am is how I live my life and who I integrate my time with as far as relationships. So I started putting everything down on a piece paper of things I wanted to do and things I wanted to cross off. And the first one I did was the Camino de Santiago in Spain. It's a 790 kilometer walk across Spain. Oh. to Santiago in Spain. It's a 790 kilometer walk across Spain. And I did that last August. It took me about 30 days. And when I came home, I had an employee, a direct reporter of mine say,

hey, I'm quitting. Like three days after I got home, I got this news dropped on me and we talked and she wasn't going to another job. She wasn't going to, she was just going to like slow down and stop for a while. Yes, exactly. And so, you know, I started thinking about it for myself. And about two weeks later, three weeks later, I decided to do the same thing. And really the impetus behind it was I got back from this amazing trip and I had made a reel on Instagram. And it was just basically a slideshow of all the people that I had met along the way and taken selfies with. And I showed it to one of the other employees that I worked with.

And I've been working with this person for about five years. And she got done watching it. And she looked at me and she goes, I've never seen you that happy. Wow. And I just thought about that. And I'm like, I've worked with you for five years and you haven't seen me that happy? I don't want anybody to know me. Five years.

Yeah. I don't want anybody to know me not like that, right? I want people to know me in that state. And so I decided that I was going to quit my job and had to raid the retirement fund and decided that I'm only going to do things that make me happy. And so that's what I've been doing for the last couple of months. And I'm currently on a three-month trek around the world to kind of write some books and, and see some friends that I met on the Camino and enjoy myself. There you go. So are you engaged in any sort

of business? You mentioned that you're in trying to influence others to do the same thing or pursue their bucket list at the very least. Yeah. That's the essence of the podcast that I started. It really, it really is just a chance for other people to share their stories of how they've crossed off items off of their bucket list. So it's very specific. Each episode is different. I've interviewed lots of different people for lots of different things.

I interviewed one person that learned to tap dance over 60 and I interviewed one person, something she always wanted to do with her life. Right. And then I interviewed someone that raised a million dollars for charity through her artwork. So yeah. So it's not just big things. It's small things. It's whatever. I don't judge the people that asked to be on the show. I don't judge their bucket list items because I don't want anybody to judge mine. So, because like I just got knuckle tattoos, cross that off my list. I hadn't, yeah, something I always wanted to do.

And it was a big step. I've had tattoos, I've been tattooing for about 25 years on my body, but I kept my knuckles clean. And so I crossed that off by putting some words across my knuckles. So it's whatever is exciting to you. And that's And for me,

it's really what's actionable, right? Because a lot of people have dreams and dreams are good starter points, but you have to be able to actuate those goals. And so one of my dreams has always been to say live from New York, it's Saturday Live on that show. That's never going to happen, right? Most likely that's never going to happen. But I Well, there's still time. Most likely that's never going to happen. But I also would like to be an extra on a Star Wars movie or a TV show. I could probably get that done, right? I can network with people and try to make that happen. But being a big enough star to say those words across that stage,

that's probably not going to happen. So I try to make things actionable as possible, that I can actually cross them off and say that. You could do. You could go to the NBC studios where they host that. You could maybe bribe a page to let you go on stage in off hours and just hit the note. Yeah.

You might try that. Hey. I want to do it. I've always thought about doing it. I love the show. I started watching it when I was seven years old. I've watched it it on the, I've always thought about doing, I've loved the show. I started watching it when I was eight, seven years old. You know,

I've watched it almost every season and it would be great to be in the skit on the show live saying those words. I just think that would be just outstanding, but it's just, you know, something probably I can't make happen. Yeah. And then you could just make your own skits on Saturday night live where

only every third one is funny. I'm just, that's right. I love, I like like you i grew up with snl so i can do that bashing because there were some years it was really bad yeah i think yeah that show you just kind of have to take it for what it is and it's definitely rooted in the context of time yeah i've never been one that's like oh it's so bad this year and it's so much better now. You're right. It's hit or miss. Certainly the original ones where everyone was doing coke in the back were the best years. That's my opinion of the first one. But we know. So how do you help people? You're part of this

great thing. And even I, during the COVID lockdowns and a lot of my friends, we were kind of what I called the little foxhole of where I had a whole mess of friends. A lot of them I developed through the app Clubhouse. And we're all sitting in line just talking about our lives and contemplating about stuff and reevaluating stuff. Because I'm like, when death is at your door and you went through two heart attacks, so I'm sure there was a mortality moment for you. When death is at your door and things can happen anytime, you really start evaluating your life. You're like, do I want to be working and just fall over one day? And a lot of men die earlier now more than ever. I mean, men, it's a weird thing that we have now where men die seven

years earlier than women. Didn't used to be that way, actually. We're working ourselves to death. And a lot of people are unhappy, miserable. And so I started looking at my life and tried to write a book for 10 years and finally sat down and said, write the damn book. Yep. And got that done. But really, I started looking, when I come out of this, what am I going to do? And I think a lot of people like yourself did that. And there was a lot of arguments that I had and debates I had with people that were like,

well, people aren't going back to work because they're getting bonuses from the government. And I'm like, no, I don't think that's why. I think there's something deeper. And I think people realize that. I think so many people realize that. They just said, hey, man, this isn't worth it what I'm doing, and I'm not doing what I want to do. And like you mentioned, I think you really nailed on the head when you said, I don't

want to be remembered by my work because usually most employers aren't going to put a plaque up. John was here and he gave his life to, I don't know, scrubbing toilets. And so I think it's commendable. Do you help people go down that path? And was it correct in my assessment? Yeah, it's more of being an example for the most part. I think that, like you said, we all have 165 hours in a week, right? And if you sell 40 of those or 50 of those, that leaves you with 125. And then if you sleep for 40, if you're lucky, and you sleep for 40 or 45, that still leaves you with almost 75, 80 hours a week. That's what I want to be known for. And I want to help other people be known for that. No, not everybody has to quit their job and take out their

retirement and take a gap year and do all those things. It's just, what do you, how are you prioritizing your life in such a way that you can look back and say, I did these things. I didn't just sit around and think about it or dream about it, but I actually did them. And that's what the show really tries to do. We try to, I try to give lots of varying options as far as guests go. And one of the great things is that at the end of the show, I tell folks, read the show notes, right? Because not only do we have, do we, do we give the guests information so that they can get in contact with them or see some of their stuff. But we also have notes that should say, if you want to do this too, this is how you do it, right? If you want

to raise money for charity, here's some of the things you can do. Here's some links you can go to. It's really trying to be a resource for people to begin to actuate them. I would love for people to listen to every single episode, but I'd also love for someone to say, I want to get this person's autograph. How do I do that? And I have a guest that his passion and his goal was to get Arnold Schwarzenegger's autograph. Wow. And listen to that. And then there's resources.

How do you do that? Right? So it's really just trying to inspire and empower people through those stories to actually go out and do stuff. And then I try to do the same thing through my Instagram account, my Facebook account, and just say, here's what I'm doing, right? And it's just a matter of taking that first step. It's like you said, your book, that writing is hard. It's not an easy thing to do. And you really need to set aside time to really do it. So when I decided I was going to take this gap year, I'm like, I have some books in my head and I need to get out. Whether they

get published, whether I make a million dollars, whether I become a New York Times bestseller, I want to get these books out of my head. And that's going to take me isolating myself at some degree away from everything else, right? I'm in this Airbnb in Trieste, Italy, and I can't watch TV. I don't know the language very well, although I'm sure after two months, I'll know it a lot better. But it's hard to go out and make relationships with people and just get distracted. So that's really why I chose to leave the States and come and actually do these things, right? And put pen to paper or type keys and, and actually get them out. Anything happens with them. Great. If not, I at least got them out

of my head. So, yeah, I gotta tell you, I, I wrote my stories, some of my stories and the fun ones, the good ones, I guess, but the top ones, I suppose is the way of saying it and put them on my book. And I didn't realize that for 35 years I've been wandering around retelling those stories. And the reason I was retelling them to everyone is I was being a historical, what they call in Africa, in the old tribesmen, a griot. And what that is, it's a verbal historian. And back in the day, they assigned a person to the tribe. You are the historian of the tribe. And so he would have to keep all those in his head and him telling those stories and repeating them and why we tell stories as a humanity, why we have movies, why we have TV, why we have books. each other and help each other and entertain each other sometimes with the happenings in life or values in life or stories of life, lessons that we can learn that are basically there.

And so even old families used to sit around and either a father or a patriarch would be the storyteller or whomever. I mean, they even had female, I forget what they're called, griots in Africa as well. It just depended on who they picked as a historian. So I didn't realize that I was repeating these stories, not so much to help other people, but to try and keep them from being lost in my memory, which some of them were. And when I wrote the book, I was like, oh shit, that happened and that happened and oh my God, I forgot about that. And they do start getting lost in the dust of your memory of time. And so it was so peaceful to finally get those stories on the paper and page.

And when I got my book published, I was able to go, screw it. I don't have to remember that stuff anymore. What's funny is now whenever the stories come up, I'm like, just go read the damn book. The story's in the book. I don't remember it. Yeah. I feel the same exact way. I spent two weeks in Pamplona, Spain before I got here to Italy.

One of the books I want to write is a memoir about my father and I's relationship. And then my comparison, contrasting that in my relationship that I have with my son, all through the lens of professional wrestling. Because we're all three fans in different generations, in different timeframes, in different historical contexts of the wrestling industry. And so it was good to sit there and think about all those stories and think about those times I had with my dad and those times that I had with my son. And if the only person that ever reads it is my son, so that he knows how important that was to me, that bond was created through that.

That's good enough for me. I would love for other people to read it and go like, yeah, wow, yeah, I want to bond with my child too. You don't have to do it through professional wrestling. That's not the point of the book. But it's what bonds do you create and the importance behind that. So let me, because there's people in the audience, I'm sure they're going to think, well, you know,

you're blowing your retirement thing. What's the mindset behind that in the trade-off and what you, in deciding to do that? Because somebody who's in the audience going, well, you're not going to retirement. What's the plan there? Well, you know, you use it or you lose it. And especially right now, a lot of people are losing in the market. So I actually was able to get more money than I would have had now. Yes, long-term, I probably could have recouped that. But like I said in the beginning, when I decided to take this year, I said, I'm only going to do things I enjoy and things I like.

And I like coming to Europe. I like being able to have the time to write a book. I like being able to visit my friends that I met as I came to Europe. Those are all wonderful things. And yeah, I'm trying to grow the podcast and write these books. And if those things become successful, fantastic. If not, I go back to work. I go back to being a teacher and we need a lot of right now. So I'm pretty secure that if I wanted a job next year, I could find one. So it's a decision of do I hold onto it and just like you said, do I want to keel over when I'm working one day and just keel over and never having enjoyed that? We're kind of the

first generation that's not going to really pass on our wealth to our children. And some of that has to do with us spending it, but some of it just has to do with the fact that there's not a lot out there. Yeah. I mean, and you probably get paid more for what's going on nowadays. I mean, certainly with everybody doing the Great Resurrection, whatever, Resignation. No, I'm caught on that. With everybody doing that, I mean, everybody's, the people, it's crazy how many people need a job and everything else. One of the things about being an entrepreneur is you find, you go search your passion and you go do your passion. And that, and when you can find something you can make money on that you really love, that is your passion, that is your bucket list. For instance, I really love my podcast. I mean, we have some of the

greatest people, researchers, historian, people's people on the show that are, you know, anchors on news channels, great journalists, Pulitzer prize winning people. We've had people on the show that have consulted with the last six administrations, worked at the White House. It's just extraordinary the people I have on my show. And I love it because there's such a richness. A richness? What the hell is going on? What is it, Thursday? A richness of people that are on my show.

It's just so wonderful. And I get front seat with them. I get front seat to history. They spend tens of thousands of hours in research, writing their books. And I get to ask all the questions. We've had people on the show that have spoken in impeachment hearings, worked for the FBI. And I never seen the questions asked on media that I get to ask. And so I finally get to sit down with them and ask them. I don't have the soundbite of what MSNBC or CBS or CNN have, where they just have a three minute soundbite that they have to ask questions. I get to ask all the good questions that hopefully everyone else wants

me to ask and stuff like that. And so it makes for extraordinary podcasts. And I love it. I love it. I'm a student of history, a student of stories. And one of the things I realized early on, I didn't realize even though I was doing it, collecting stories and being a people watcher. But one thing I really wish I would have learned early on, I didn't learn until I was 50, was that life is about story collecting. It's about the journey, not the final destination. I fought that for so long. And collecting stories is the fun part of life, being interested in people and their journeys and what they're doing. And that's the real fabric of life. Because when I'm dead or when I'm sitting on a rocking chair in an old age home, which I'm, I don't know, I'm almost there. The things that you look back on in life, I don't

look back on multimillion dollar companies I built. I look back on the experiences I had, the stories I had. And that's probably going to be my fading thought whether I die or go into Alzheimer's is those stories. And hopefully maybe I'll remember some of them. And that's the richness of your life. Like every now and then I'll remember something. I'll be like, fuck yeah, I fucking did that. That's fucking awesome.

And very few people can say that they pulled that off. So that's really the fabric of life to me. Yeah, I've been attempting over probably the last seven years of trying to figure out, okay, how do I use, everyone's using social media, everyone's using the internet to make money. How do I do that? And what's my niche in that process? And I had some starts and stops and some major failures and all those kind of things along

the way. And when I came up with this idea for this podcast, I went to a close friend and I said, hey man, because he listens to a lot of podcasts and I felt like he was probably the most authoritative person on the topic. And I said, this is what I'm thinking about doing. What do you think? He said, that's you.

He said, that's completely you. He said, he said, you meet people and get them to tell you their story, what you're going to do. You'll be successful at it, regardless of whether you try to fail or not,

you're going to be successful because you do that naturally just in life. And that, that really hit me. That's like, yeah, I do that. I do meet people and I do ask questions and I do get them to tell me their story. And so that's what it's all about. That's what the podcast is about. Tell me your story. Come on the show. Tell me your story

of how you've lived out intentionally something on your list. And it was very interesting because as I'm sure you experienced you go through this process of really fleshing out what your podcast is going to be and what the purpose is and all those kind of things and so i started off i'm like i'm gonna have the same questions for everybody i'm gonna ask everybody the same questions and the final questions that i ask are what's the next thing you're going to cross off your bucket list and what's um and what's most important on your bucket list and i didn't realize how important those questions were going to cross off your bucket list and what's most important on your bucket list. And I didn't realize how important those questions were going to be to the podcast because the people I have,

I don't have the same caliber of guests as you have on your show. I have average people and people that are trying to do something in the world, but not real well-known names. And I found that through just discussing their story of the what the item they crossed off is that listeners tell me that oh i got invested in this person and so when you got to that point where you said what's the next thing on your list and it could be completely different should be completely different than what we just talked about i wanted to know i wanted to know what this person what the next thing was that they wanted on your list and hopefully that's where the empowering and it comes in to when people listen to the show is that they wanted on your list. And hopefully that's where the empowering and it

comes in to when people listen to the show is that they see everyday people, average people have made choices and intentionality of saying, I'm going to live this out. I'm not just going to dream about it. I'm going to make it happen. Yeah. I mean, we, we all learn from each other, regardless of our experience or status in life. And we all have lessons that we can share. And, you know, I mean, that's the one thing I learned about life is that everybody has the journey. Everybody has a story. I remember watching CNN's Larry King back in the day. And he said one time in an interview that he was really interested

and curious about people and life. And so when he would meet people on a plane, when you meet people anywhere, he'd want to understand what their journey was. What motivated you to do this? Like I'm asking you, what motivated you to do what you do? And there's lessons there. So did you sit down with a scientific, any sort of study? I mean, on how do you build a bucket list? Let's kind of touch on that a little bit. How do you build a bucket list? What sort of resources you use to build it? And how do you know what you should put on it, I guess, for someone who's never gone down that road? Yeah, I think it's a different experience for everybody. I

actually have multiple bucket lists. I have a general one. I have a general one. I have place one where I want to go to places. I also have a concert list of bands that I want to see before I die. I mean, so I've got different lists and that's okay. It's the kind of thing where it's everybody's list is different. If I was suggesting to someone, one of the key factors is what are you already doing? What are you already enjoying? What do you already like? What, you know, what for me, like I said, I'm a professional wrestling fan.

So I want to, so I want to go see a Lucha Libre triple A match card in Mexico City, right? And I could go to Mexico City and only do that and I'd be good. I want ringside seats for WrestleMania. I've been to WrestleMania, which is WWE's biggest show of the year. I've been to WrestleMania. I've seen every single one since number three, either live or on TV, but I've never, I want to be ringside. I want to sit ringside. I want to sit ringside and do that, right? That's because those are things. So I could create a bucket list just about wrestling if that's what I wanted to do. And I think that's where people need to start. What is the, what am I already interested in? What do I already like? It could be cooking,

right? If somebody says, I'd like to be a better cook. Okay, great. Write down the top 10 recipes that you want to learn how to cook. I want to, I've interviewed to be a better cook. Okay, great. Write down the top 10 recipes that you want to learn how to cook. I've interviewed someone that drove Route 66. They always wanted to go on Route 66. So they did that. Very popular one is crossing off all 50 states. I've got 48 down. I got two more to go, and I'm hopefully going to get those done this year.

But really just saying, what is it that you're already interested in? I think for me, because of all that trauma that I went through, I actually sat down and forced myself to write it out. So, so that's one of the things that you have to do. You're never going to, if it's in your head, you're never going to get it out. You're never going to, you're never going to say, oh yeah. So I actually wrote out a list and put it on my mirror. So I saw it every day and said, okay, what's the next thing? What's the next thing? I like this.

Sorry, I'm going to interrupt you. No problem. I like this idea. I never thought out of the box on this where you can have multiple bucket lists. I never thought out of the box. And I was like, there's always one. I'm going to compile it somehow. But no, that's brilliant.

You can have multiple ones. How do you keep from freaking out if you're not getting towards it or do you prioritize them? Yeah, I think there's different ways to prioritize it. You can prioritize the things that don't take a lot of money and don't take a lot and start that way on your list. If you create a list like learning a recipe, that wouldn't take a lot of energy or time or finances to get the ingredients and to do a recipe. Walking the Camino takes a lot of money and a lot of time. And in the middle of a pandemic, there were times where I just told myself, I'm going, I don't care if I have to swim and get there. I'm just doing this because it'd been on

my, it'd been on my want list for about 11 years. And I just finally said, I'm doing this. Excuse me, damn the part, the pandemic, I'm going to get this done. And so every day I woke up and go, okay, what are the restrictions? What do we need to do? What documents do I need to have? What is it going to take? How are the conditions there? Is there housing? Are they going to be restaurants open? All that kind of stuff. But at the end of the day, I just was like, I'm doing this. I'm going to do this. Whatever happens, whatever the conditions are, I'm going to do it and it's going to be what it is. And so I think there is that determination of taking that first step. And for me, the Camino was buying the

plane tickets, right? I bought them almost 10 months in advance and it's like, okay, I'm going. I just spent $1,400 to go to Spain. I'm going, I can't get out of this really. So I think it's just deciding what it's going to be and take that first step. And people can take small steps, crossing things off, and don't take a lot of money, don't take a lot of time, and work your way up if that's what you need to do. Some people just need to jump right in like I did and say, I'm doing this thing. It's big and it's a hairy, audacious goal, but I'm going to do it, whatever it takes. There you go. Well, this has been an awesome discussion, man. Give us your plugs one more time so people can find you on the interwebs. Sure. You can find me on Instagram at

crosser.offer. You can find me at Facebook at the Crossing It Off podcast, which I highly recommend because you can now listen to the podcast on Facebook, on the mobile app, and anywhere that you listen to podcasts, you can download the show. And yeah. There you go. There you go you go. It's been wonderful to have you on the show. We certainly appreciate it, Roger. Thanks, Chris. I'm glad I was here. Thank you, and thanks to my audience for tuning in. Go to goodreads.com, 4chesschrisvoss, youtube.com, 4chesschrisvoss.

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