321 Roger Williams - Stop Putting Your Dreams on Hold & Change Your Life Now

:: 00:00

Roger Williams, host of the Crossing it Off podcast. Thank you for joining me on podcast junkies.

:: 00:05

Hey Harry, Thank you so much for having me.

:: 00:09

Where's home for you? I say dialing in, but I'm probably aging myself with that reference, I guess calling in from.

:: 00:17

Yeah, I am in the Seattle Washington area. Okay, put that way, have you always been there? No, I've lived several different places, but hometown is Indianapolis, indiana.

:: 00:30

Okay, how'd you end up in this Seattle?

:: 00:32

area. I got a divorce and my youngest decided that he wanted to come out here to go to college and I said, okay, I will go with you and we'll cut some costs and we will hang out and be together and I'll support and yeah. So I just took a leap and said, hey, probably someplace I've wanted to go, never been, and decided that I would uproot myself and move out here.

:: 00:58

How would you describe the experience of living there?

:: 01:01

Seattle area is different, especially coming from the Midwest. Social, political it's a lot different, which is good for me in that sense. But there's also this thing they call the Seattle freeze, which is this cultural thing where it takes a long time for people to warm up to you if you're from out of town. Interesting, and it's been here seven years and finally kind of starting to feel like I fit in. I live with my life partner and she accepted me pretty quickly, so that's good. We've been together about five years. Oh, very cool.

Yeah so you know it has its ups and downs. I love being next to the water and the mountains at the same time. That's a fantastic thing and I love it here. I love being in the mountains and I love the type of people that live out here and, yeah, it's been a good time.

:: 01:53

Yeah, I was recently out there. We were just briefly chatting before we started recording. I was out there for a men's retreat and it was in Brinnon, which is a little further west from Seattle. It's actually a two hour drive. As the crow flies, it's probably 30 minutes but because it's traversing all these waterways, which is no complaints at all.

I picked up one of the attendees in Seattle with another guy that met us there, so three of us drove from Seattle to the event and it was just spectacular the trees, lots of big tree energy, lots of waterways and stuff like that. So I really loved the vibe and engine. I did get to spend a day in Seattle, which I hadn't been, so I definitely loved the vibe Fresh seafood, which is always a plus.

:: 02:36

Yes, yes, yeah, I love how green it is. They call it the Evergreen State for a reason, which is fantastic. I lived in San Diego for a couple of years and that's Ever Brown, so being an Evergreen is a great contrast.

:: 02:53

We got. According to one of the guys that attended with me, stefan, we got what he said was unusually nice weather. It was sunny and about 60 to 80, the three days we were there. He said that never happens. Usually it's gray, usually it's raining overcast.

:: 03:11

Yeah, he's a local, right? Yeah, he's a local. See, it's a big lie, right? It's this huge conspiracy from locals to tell everybody that Seattle weather is just absolutely horrible to keep everybody from moving out here. But once you get out here, you find out oh, this is pretty nice.

:: 03:24

Yeah, yeah, and so it was a great experience. It was a I mentioned it, I think, on the show I've dropped, hence what I was doing so it was a really great experience, for it's a group called Sacred Sons which I connected with, so that was a really great experience for me, so with you and I, as far as us crossing paths, you mentioned that we connected via an email that you had sent over, which I appreciate you being a listener of the show. But maybe talk a little bit about how you found this show and what your experience has been with it so far. I'm always curious. It's always fascinated me how people listen, when and if, and so I'm always I want to know as much as possible.

:: 04:00

So another podcaster friend of mine, cake and chelo, cake Cheroncello yeah, cake Cheroncello was on the show, so that's how I found it. I started listening because she was a guest and so it was just enjoyable for me. I love how conversational you are. It's not necessarily with my show, it's like, okay, we've got an agenda, and so to be here with you and not have an agenda that's kind of the way I felt when I listened to your shows is that okay, we're just going to hang out and talk and that that's okay.

I also love the fact that you kind of give you I think you give yourself some room as far as your drop schedule, that you're not pressured. You know I dropped twice a week, two episodes a week, so you know 104 episodes a year and it's. I don't have time to take to do a whole lot of research on my guests and prepare for, you know, hang out with them and being able to ask all the really good questions. So I like how you have that ability with your drop schedule to kind of be more casual about it.

:: 05:04

Yeah, it's interesting because, you know, and what I love about this format is that it's a podcast about podcasting and the world of podcasters and all the things that happen behind the microphone the good, the bad, the ups and the downs, the perfect and the mostly imperfect stuff that happens that people don't tend to see, depending how tight people are with the quality and making sure what they're showing is the front facing experience for their listeners. And I've gone back and forth over the years. I started in 2014. I wanted to learn about podcasting so I figured the best ways to interview podcasters. You know, I was a fan and I studied acting, so I was a fan of that show inside the actor studio and I was like kind of that vibe.

:: 05:45

Sure.

:: 05:46

Let's get folks to kick back their heels and chat about what's on their minds. And as far as the the just the posting frequency, you know sometimes I'm consistent and it's every Friday going out, sometimes it's a Thursday, sometimes it's two or three weeks because I'm traveling and I've tried not to beat myself up about it and I think it gives me some flexibility. I don't want to go too far because at a site out of mind you know, people have got a limited queue of podcasts that they listen to consistently and you never want to make them seem like you're not publishing, because your podcast listeners are pretty finicky and fickle. I don't know what the right word there is, but it just in terms of like you're deciding okay, like let's see, should I be listening to someone else, should I be experimenting with a podcast, and always things you worry about.

:: 06:32

Yeah, actually I have two shows, and so my main show is the Crossing it Off podcast, where I interview people that cross things off their bucket list. But I have a second show that I started about five months ago with my partner where we it's just her and I and we talk about what we've benched watch on TV, so a whole season. We'll do an episode of the whole season of whatever it is. We just and we drop once a month, but we drop like four or five episodes a month. So that's been a real interesting process for us of saying, okay, well, yeah, we're gonna, it's, it's a long tail game for us, right?

So we've heard good things about people like yeah, I'm a binge watcher TV, so this works out real well for me. So I just binge your, binge your episodes, your podcast, and wait till the next one drops. They're very custom to that, so it kind of works. And at the same time, I'm sitting there going where I drop two episodes a week with my other show. It's like is there enough content out there? What are we doing?

:: 07:26

Are we doing this Right.

:: 07:27

You know. So we're just going to give it time and see how it works, and I think that's the really great thing about podcasting is there is no set rules or set ways to do it. You know, I think there's some good practices that you can take on, but at the same time, however it is you see it fit to make it happen, you can make it happen.

:: 07:49

And I think part of that challenge as a podcaster is feeling like you have carte blanche to do whatever you want, but also realizing that the other day, we do have three people in this conversation you and I and the listener and always remembering that we want to keep it engaging for them. We want them to be excited, entertained, they want to laugh or, you know, learn something new or be inspired or motivated. Maybe shed a tear sometimes if we get, depending how far we get in terms of, you know, getting personal, but I just love the fact that I just let it go where it wants to go and almost has a life of its own, and I'm curious for you how often you get a chance to talk about yourself in the context of being a podcaster.

:: 08:29

So I'm doing it more and more. I think that when I first started, like you, I had no idea what this was Like. I had never listened to a podcast before I dropped my first episode, I had just never done it, and so for me, it was this huge learning curve that I had to deal with. As far as you know, it's almost like that imposter syndrome, right, like you feel like, am I really doing this? Do I know what I'm doing? And now I'm at the point, after 106 episodes of the Crossing Off podcast and 30 or so episodes of Call the Binge Wife, I'm now meeting podcasters and people are going how do you do this? How do you do that? You know, and that's been fun for me to realize that I'm doing this.

I am maybe not making a little money, but I am a professional at this at some level, and so that's fun. That transition from oh my gosh, I have no idea what I'm doing to oh, somebody wants my opinion, and that's been joyful for me. And affirming too that I'm doing something right, at least that somebody says hey, I know you've done X, y and Z, how'd you do that? And so that's rewarding as much as just doing the podcast is. That also has been rewarding, and I've started doing more interviews, being a guest on folks show talking about podcasting, especially now that I have two shows, that's a little unique and so and they're very different and so I'm getting a lot more traction as far as people want to say okay, tell us what you're doing.

:: 10:03

Which of those experiences is one that's been memorable for you in terms of a show you've been on, where you had a great conversation?

:: 10:10

Oh, the really weird one was I was on not weird, but weird for me. I got approached to be on All Years English.

:: 10:18

Okay.

:: 10:18

Do you know? You're familiar with that show? No, no, no, it's this massive show that I think it's like 0.05% on Listen Notes, and they approached me to be on their show and it's basically for English learners. That's what the show is designed for. And so I was like, well, okay, I'll try, and they really wanted me to break down crossing it off as an idiom and a bucket list as idioms and explain that to our audience. What are these things? And so that was a lot of fun and it was just super weird. At the same time, I think she sent me an email two days or three days after the episode dropped. She goes yeah, I just want to let you know your episode's been listed to 58,000 times. Who's the host? Her name is Michelle. I think. They have a couple of different hosts that go back and forth and they but yeah, they're just massive and I had a huge spike in listeners after that, which has generated this whole international feel for the show. I have a lot of international guests. I like to reach out to folks that are from other places and hear their stories, but currently, after 106 episodes the show's been listed to in like 77 countries. My percentage of American listeners in total is only like 52%, which most independent American podcasters. That numbers in the high 80s, low 90s range. And here I am I'm getting close to having a thousand downloads in Japan right after a year and a half. So that's blown my mind. But at the same time it's been a saving grace for me because, like most initial podcasters, you go to your analytics every couple of days and look for it every hour or whatever it is. Has it changed? Has it changed? Has it changed? And I caught myself doing that the first, you know, six, seven months, and I transferred that manicness to going to the analytics and looking at the global map first, like that's the one I want to know, do I have a new country? And I can't control that number. So I think that's a little bit of why I like going to it, because it's like, okay, I really can't control. If it happens, that's amazing. And I think that was it. You know, just thinking about you know, somebody in Aburajan, somebody in Kazakhstan, you know, listens to the show.

I recently had my 100th episode and I tried to do a whole bunch of marketing for the show to kind of promote it, and one of the things I did was. I went through that analytic and looked at every single city where the show had been downloaded. Oh well, I got a big map on my wall and I put pushpins in every single city. It's like 611 cities, you know. So that's really exciting for me to know that I have a lot of room to grow. I had a friend challenge me on some stuff one time about podcasting that I was doing and I was like, look, I don't have to please everybody, I don't want to please everybody. So there's 8 billion people in the world. I just need to find about 100,000 of them. Like, if I get 100,000?

:: 13:25

of them, I'd be set.

:: 13:27

You know that'd be a great audience to have. So it's fun to look at that map and see all the places around the world where folks have downloaded the episodes and it kind of takes away from that constant worry about the actual download numbers.

:: 13:42

Yeah, I think it's interesting because I've waxed and waned in terms of looking at the stats and obviously in the beginning, like you mentioned, you're really riveted by everything that's happening, and what I've been leaning towards lately is just appreciating the fact that I have a platform and a stage and I can pick and choose who I have conversations with at the frequency that I want as well, and so I really like look forward to these conversations because there are people that reached out and, you know, looks, I can just tell it's going to be an engaging conversation and it just makes my day brighter and it just it feels like, you know, naturally as a podcast.

Once people know you have a podcast, you start getting pitched like crazy. So I've actually created a form letter already that says hey, in case you haven't noticed, this is a podcast, where I have to have a podcast first if I'm going to speak to you. So but I've already have it built in I think it's in Gmail as one of those auto replies, so I've kind of configured it already. I said here's the show, here's what it's about, here's what we do, and you know, I always try to like it's a way for me to practice my patience as well, because I'm always nice to them and just be like clearly you've not done any research. Your finance guru or tax prep specialist is prepping me to come on the show, or something like that.

:: 14:50

And that's the amazing thing that when you niche down, like you and I have with this thing, the people just don't get it For some reason. People don't get it. So you have to have crossed an item off your bucket list to come on my show. So if you haven't done that, I'm not changing my format so that you can come and hawk your business model or you can hawk your service. You know, if you have something else, if you jumped out of a plane or you've been to somewhere country, sure, come on, let's go, and I'll give you a chance to share what you're into and promote your stuff at the end of the show. But you got to have that basis and I run into it all the time with the fact that I don't.

I try my best not to repeat the items people have crossed off. I want my listeners to have the most variety of things, but I'm constantly hey, I wrote this book. Hey, I'm a life coach. Hey, I've got this system, and it's just like okay, yeah, I know that's great and it's like you, it's. How do you be? You know, I really struggled with the beginning. How do you be nice about it? And it's hard because you don't want to turn anybody away, but at the same time, it's like you know, I'm not going to sacrifice this thing, that I'm building, whether you understand it or not, so that you can hawk product, and I love, I love, I love getting people that don't have anything to sell.

:: 16:09

That's my.

:: 16:10

Those are my favorite interviews to do and I edit all my episodes myself. So when I go back in those episodes like they're almost perfect because I want to make them sound absolutely stunning, I want them. You know, no aunt, no us, no butts, no coughing. You know it's like I want to make sure they sound great so that when they share it with their family, friends because those are really potential listeners to say, okay, you know, this is something I may want to engage with where you're dealing with somebody that's selling a product and you ask everybody, yeah, will you share this out to your people? But at the same time, how many? You know, like even for me, I have to admit. You know I've done 60, some podcast episodes for other people as a guest. There's only so many times my following is going to want to hear my story. That's true, you know some.

:: 16:58

There's only some of the different ways you can tell that story.

:: 17:00

That's right. I mean it's evolved some over the last year and a half, but at the same time it's like, oh my gosh, roger's, you know showing his stuff again. So you know, I want them to be able to share it out with people that are excited about hearing their story, because it may be somebody close to them it's never heard that story before. So I get excited when I have people that don't have anything to sell at the end of the episode that makes a lot of sense.

:: 17:26

So talk a little bit about the journey, because you mentioned that you weren't listening to podcasts when you started. So normally that's how a lot of people get inspired to start a podcast, but you had, I think, some life experiences happen to you which shifted your perspective, I think, in a way that inspired you to start the show. So I'm curious if you could tell that story.

:: 17:44

Yeah, it's easy to start in 2020. It was my 50th birthday year, might as well. Yeah, awesome. So you know my pain. So I had, like most Americans you know, 95% of Americans would say they have a bucket list, but only 40% actually have what written down or doing anything about it.

it to them, and at the end of: 2020

Every time you meet somebody new I'm sure that this happened to you on your men's retreat, maybe not so much, but when you go out and you're in an environment where you meet new people, the first question is what do you do and who do you work for? Right? And I wanted to be able to answer that question in a different way. I wanted to be able to say I cross items off my bucket list. That's what I do.

My side gig is this other thing teaching and helping students, but my main focus is doing that, and so something that I had on my bucket list when I went to go write it down finally and become a part of that 40% the top of the list was to do the Camino de Santiago, which people don't know about it.

It's a 500 mile trek across Northern Spain.

It takes like 32 days to accomplish, and I just knew, being an Aquarius and kind of a scatterbrained, that I had to do something like really big and accomplish something kind of major to be able to say okay, anything else I've said to put on my list I can do. And so, in the middle of the pandemic, with Europe still closed, I bought airline tickets and made some arrangement, a few arrangements, bought some equipment I didn't have, and I was set to go so scary as all get out, because every morning I'm waking up going, all right, it's spaying going to open, it's spaying going to open, it's spaying going to open. And I think it was like 45 days before my plane left that Europe finally opened up and we could actually get permission to go. So that's awesome. So, yeah, it was a big deal for me. It's really crossed that off. I've been thinking about it for almost 11 years, and so it was something I'm like okay, I gotta go do this, I gotta commit to finding my own joy, and so that's what I did.

:: 22:09

That resonates with me because that's on my list as well. So my partner, I've been talking about it seriously because it's on her list. So the Camino, camino, yeah, yeah.

:: 22:19

So, yeah, I don't recommend it for everybody. I think that you do have to be kind of a special person, but if it's already on your list, oh yeah, yeah, we know what we're signing up for and yeah you gotta do it.

:: 22:28

Definitely that type of experience for that period of time is something that would definitely like be great for us. So I think we're just hopefully making that happen sooner rather than later, and I'll probably want to pick your brain about all the prep work you did for that, because I'm the type of person that has a challenge with planning stuff and you know you can just ask my ex as well because I was never a really good planner with the events and I struggle with it sometimes in my current relationship and I think I get lost in the details. So sometimes there's so many details and so many moving parts and I'm just like I get like deer headlights kind of happening. So sometimes for me it's it's figuring out old things that need to get done. But I have been to Burning man for a week and that took a lot of prep as well.

:: 23:10

Because, yeah, I think there's a big difference between Burning man and the Camino, because it's actually on the Camino, you can just show up and start walking and you'll be totally fine. You don't have to like have tons and tons of plans. But because it's very straightforward, we're all walking west, we're all following the yellow arrows, and when you get there, you get there. So it does make it a little bit easier to kind of go by the sea of your pants, so to speak.

Probably most important choice is that your footwear I wouldn't mention it, yes, and it's worth spending a couple hundred dollars to make that right.

:: 23:45

So obviously a lot of planning to get that done. It was something that you've had on your list for a while. Talk a little bit about what you felt when you got back from a sense of like, accomplishment and this you mentioned or alluded to it this idea of, well, if I did that, then, like now, the world is opened up. And so how did that feel for you when you got back in terms of like, what?

:: 24:06

was possible. So, taking it back a step, I had started the podcast before I left, I had dropped two episodes and some of my attention was oh, I'm going on this amazing journey for 32 days and I'm going to meet lots of people that have a bucket list, so I'll just interview all these people on the Camino and that got shoved down on like the first day and a half, like I was just like nope, this is my journey and it's these people's journeys and we don't have to inject this thing into the hat. And so I just kind of put it on the back burner.

And reentry from the Camino because it is such a different social and cultural experience than what you're used to in your regular life that most people have reentry problems. If you go to a foreign country and you spend a little bit of time and you come home, there's always kind of that reverse culture shock, right, like you went without something for a long time and now you've got it. I remember coming back from Thailand and seeing my first McDonald's and being like oh, that's gross.

But the Camino is kind of the same way, except it's more on like an emotional level, after walking that distance, meeting all these new friends and people and creating this family that you depend on as you walk and just people constantly being kind to you as you're visiting, as you're walking through these villages, and eating and staying, and it's just a very, very alternate reality to what most people experience in their lives, especially if you're coming from America. So everybody kind of has this reentry shock. And for me, I got hit in the face with one of my direct reports at my job told me she was quitting that week when I came back and it wasn't a complete surprise but at the same time it was like oh, this is happening and I've got to deal with this. And her reasoning was so solid like she wasn't happy and it was not with me and not with the work she was doing, but with some of the other situations inside the institution and that kind of stuff. And she's like I got to do something different. I'm moving from Seattle back to Maryland and she's like made these major life changes and through watching her do that, after about a month of being back home, I kind of had to look at myself and say, okay, well, what are you doing? Why are you doing this? And it really hit me.

I went back into the office after the Camino and I showed a friend who's co-worker had been close for about four and a half years. She said how'd your trip go? And I said, oh, it was really great. Let me show you this reel. And I made this 32nd Instagram reel of selfies of all the people that I've met along the way and she watched it and she handed me back my phone and she said I've never seen you that happy. And it hit two ways right. I mean, the first one was like oh, I'm so glad that she sees that right, because I was. I was extremely happy. It was extremely in my element, very content with what was going on around me and just super excited about it.

:: 27:11

When was the last time you had had that?

:: 27:12

feeling Wow that's a great question Probably when my kids were really young. All my kids are grown, they're all. I have three children. They're all over 25. So probably 20 years ago, when they were all under five and under, those were the best times that I remember and being really happy and having a lot of joy because of just being able to be their parent. There's such awesome kids that it was just. I think that's probably the last time, probably about 20 years before, and hearing that at the same time I was just like, oh my gosh, I don't want anyone to ever not meet me and see me in that state. I've been working with her for four and a half years and she had never seen me at that level of joy and happiness and contentment. There's a problem.

And so about a month later, I quit my job, quit my career, and decided that I was going to take a career break, get an adult gap year, whatever you want to call it, and decided I was just going to go and do things that made me happy and brought me joy and centered that around my bucket list. So I picked the show back up and just, you know that was part of it. For me was that there's got to be other people out there that are kind of feeling this or seeing this, and so I want to go out there and find them and start telling their stories. And so that's what I did. I made a commitment to 52 straight weeks of episodes and along with doing some other things for myself, so I started crossing a lot of items off my own bucket list and spent three months traveling through Costa Rica, spain, italy, israel and the United Kingdom and just came back from that and just felt this overwhelming sense that, okay, I want to share this with people, and not just through the podcast.

But I wound up writing a book about it as well, and a lot of that was because what I had found in my journey and my attempt to embrace this bucket list lifestyle was that the piece that I felt like was missing for most people was setting that intention for that list. So often people have a list where it's oh, I saw this on Instagram, so all these people are doing it, so I want to go do it Right. So I think about what I try to do with my show, my book, my coaching, whatever it is. I don't want to instill FOMO in other people. That is not the intent. The intent is how do I empower, inspire people to go out and figure out what should be on their list and help them accomplish that?

:: 29:50

How do you distinguish between creating what some people would say is FOMO content versus sharing an experience in a way that inspires people and motivates them to do the same?

:: 30:04

So with the podcast, we really start off each episode. There's one guest, one item that they've crossed off and we really start off. Where were you? What was going on in your life before you did this thing? And then, why did you want to put this on your list? How did you put it on your list? And after, what was it like crossing it off and what changed in you, what transformation happened in you by doing that thing? So it really focuses in on the experience instead of the thing, and that's really what I try to do in my storytelling, even in the editing and the asking the questions of really being intentional about how did this impact you?

We're not just doing things so that we can post a picture to Instagram.

I saw this horrifying statistic a couple of months ago where it said 67% of millennials or something like that and somebody will fact check me, that's fine, but like 60-some percent of millennials would not go to a foreign location if they could not post the pictures on Instagram, and so for me it's like, oh my gosh, yes, it's fun to do that, but at the same time, that's not the intent, and so, to answer your question honestly, I feel like I'm very held back in my space, of being a thought leader in this space, because I don't have all those images of me in a hot air balloon over Cappadocia, or hiking up the hill of Machu Picchu, or standing at sunrise at Inc or what.

I don't have those pictures, some of those things I'd like to do, but, at the same time, if that's what you're looking for, then what I have to offer probably isn't going to hit, because what I'm talking about is what's your? Why? Why are you doing this For me? My intention overall, for my list, is to create community, whether that's enhance existing community or foster new community.

that's what my bucket list items kind of focus on. And so in my book that's the first chapter let's set your intention. What is your attention, what are possibilities of what could be your intention? Because if you set your intention then you can use it to create the list.

:: 32:32

Where did this sort of this way of thinking, this way of seeing the world, this importance on community, this curiosity to find your why. Where does that drive come from in you, like inspired by someone? Or is it your life experiences, like, how did that start to come alive for you?

:: 32:52

If we're focusing on the community aspect, I think that that's driven by my parents a little bit. My mom would have been considered back in the 70s, 80s as the preeminent hostess. Like they would have big parties and my mom would go all out, the house had to be completely clean and she created community through those parties. My dad was a salesman, traveled a lot, but he was really good and not because he was shawarmy or slimy as a salesperson, but he really invested time into listening to people and hearing them and so not to use that against them but to use that to enhance the relationships. So when we lived in New York for three years, when my dad left the territory there to come back to Indiana because my mom told him that she and the kids were moving back to Indiana If he wanted to take the job, that was fine, if he didn't, that was okay too.

But when my dad left that territory within a year, they had to hire four people to cover all the ground that my dad covered. I mean, he was just really good at what he did and that was in most part because I think he created a community amongst his dealers and the people that he dealt with and those relationships were strong and people stuck with him and because he was good at building that community, building relationships. So I think that's a large part of it. I think my whole adult life I've always been in the community, building community, whether that's when I worked for churches or when I started a nonprofit on my own or went into education full-time. I mean, I've always looked at it as though if we don't have some kind of relationship that's built on authenticity, then it's not going to produce the fruit that we want, well, both sides of the aisle.

So to me, community is really strong. Like for you, when you and your partner go on the Camino, you're going to meet tons of people, right. You're going to meet people from all over the world and that's a great feeling, and I met some people when I did this as well, and some of them, quite frankly, were like, well, I'm good here and we can be friends here, but when we all go home, it's ethereal, right, this experience on the Camino is ethereal and for me, I couldn't accept that. I mean, I can't accept it from other people, but I can't accept it for myself.

So that was three months that I spent in Europe. The itinerary for where I went, where I stayed, the places that I visited, all centered around reconnecting with people that I had met on the Camino. I think I that's great Like 24, 26 people in those three months that I went back and visited with. They were like 10 in Costa Rica, like we, my partner, I went to Costa Rica together and then she flew home and I flew to Spain, but we went so that I could crash a wedding because that was on my bucket list.

:: 35:59

Oh yeah, so that on your site yeah.

:: 36:01

And it just happens that that that wedding was a destination wedding. And so friends that we met on the Camino that were engaged at the time, six months later getting married, and they were having this destination wedding. And, yeah, there's two episodes about it on my podcast. One is one is them talking about hosting a destination wedding. And then we turned the tables for the second episode and they interviewed me about crashing their wedding. Oh, that's fun.

And so the real story goes. We were on the Camino walking and they were talking about their wedding and how it's going to be, this small 50 person you know event. And I said, well, it'd be funny if we all just showed up and crashed the wedding. And the bride was like, oh, that's silly. And it happened that that group of people finished in Santiago a couple of days before me. They had a party, she got a little tipsy and she made invitations to everybody to come to the wedding. Oh, wow, I was not there to get my invitation. So a couple of months we get back from the Camino and I start messaging folks and saying, hey, we're going to crash this wedding, and crickets like nobody said anything. And someone finally said, yeah, we all got invited.

And I was like oh, oh, it's all in now. I'm crashing that way. So so, yeah, we went down there. My partner and I spent a week together before I went off for three months and enjoyed each other and time and did some things in Costa Rica together that were fun and amazing. And then we, the Saturday before we left, we crashed that wedding, and so cool.

The bride and groom absolutely, just absolutely, were stunned and elated. The bride told me she said that was the best gift we got all weekend was to show it up. And so you know, that to me is what's valuable right, even on the Camino. Keep going back to it. But it was very foundational. Like I, there were almost a week where I had to like some days I took a taxi from one city to the next. Okay, some days I walked some and then took a taxi and for traditionalists that's like a no, no, like you didn't really do the Camino and towards the end I was talking to some people and they were asking me about it and I said you know what I said? What those taxis have allowed me to do is to maintain these relationships. Because if I stayed and didn't walk, you know, and healed you all would be five stages ahead of me and you'd been gone. I wouldn't have been able to maintain those relationships. So I'll sacrifice the being able to say I walked the full Camino, although if you walk 100 kilometers you get a certificate. So I did. I walked the last seven days straight, so I got the certificate and said I completed it. But yeah, so when I talk about it.

I don't say I walked the Camino. I said I did the Camino, right, yeah, so that traditionalists don't like freak out, throw exapme and stuff, but yeah, for me it was super important to maintain those relationships and so, yeah, I'll take taxi. You know, I had tendonitis, you know bad knee twist, and I was just like, yeah, I'll do that. And it was great because I would sit in the town square, right where the Camino would come into town, and I would be there to greet everybody and have coax ready and you know and say, hey, there's an olbergi over here, there's an olbergi over there, you know, I mean it wasn't a lot of fun for me. I was still a part of the community and that's what mattered most.

:: 39:22

Has that always been something that's been top of mind for you? Because this theme and this thread of authenticity, authentic relationships, maintaining connections, is something you know, you've continuously talked about, and I'm curious if that's always been something that's important for you.

:: 39:36

I would say yes and yes, I always haven't been the best at it. I mean, I'd be the first person. Yeah, just because I can talk about it real nice doesn't mean I'm always the best at doing it. I'm a human and I fail sure.

Yeah so, but I think that goes back to my dad and you can also throw storytelling into that month. Yeah, so when I was younger it was about 10 or 11 years old my dad would be gone for like a week or two weeks at a time, because he would leave New York, drive up to Maine and then drive back, and you know. So he was gone a lot, and so whenever he would come home, I would always try to find ways to connect with them. It was very hard to connect with my dad and, and One of the ways I tried to do that was say hey, dad, you want to go see this movie like ETs out, let's go see ET. Yeah, empires out, let's go see Empire, or whatever it is.

And Very commonly his responses Well, I saw that last week while I was traveling and I would be super disappointed. We know a lot of money, so it wasn't like you know, he'd say oh, let's go see it again, right, you know it would be just like, yeah, I've already seen that. And that was super disappointing to me later on life, you know, I got very close and Before he passed and I asked him one time, I said you know, let's kind of really hurt my feelings that you would do this and he said well, you're old enough now I can tell you, he said. He said I, I worked in the construction industry and when those people got done with the end of the day, they wanted to go to a bar, they wanted to go to a strip club, they wanted to go to these places that I didn't really want to be in, or situations I didn't really want to be in because I love your mom so much. I never wanted to put myself in a place where something you know I can make a mistake, holy crud, did I feel like a jerk? You know? I mean and that's who my dad was. He wasn't perfect by any stretch of the imagination and he had a lot of flaws and he had a, but he also had a rough childhood. But he was pretty honest guy for the most part and very authentic, and when he said something he meant it and when he did something he did it, and so that's always been a Good goals for me to try to achieve. I haven't always met them, for sure, but but that was definitely a good model of being real.

Same thing with his friendships. He had a friend from elementary school but he had known, you know, practically his whole entire life and they were good friends and his friend always wasn't the best friend back to him. And For me, that was something that I aspire to. I wanted to have friends. So I have a friend that I've known nearly 40 years now but we're still in contact, that we still I mean Real contact, like we call each other two or three times a week, like his daughter One time said you guys are like, you know, teenage girls just talking the phone all the time, but but it's, you know. I mean that relationship's all night. I mean we're very two different people but we have invested in each other in such a way that we Love and empathize with each other and that relationship matters and so we'll do what it takes to maintain it, even when, you know, I was in California and he was in Germany or you know Whatever it was, and we maintain that. And so being authentic and having that community Was always been very important to me.

:: 42:54

Yeah, thank you for sharing that. This is a very touching story and I think a lot of the folks listening or the listener can relate, especially the males listening because I Relate directly to that, because I think about this connection I have with my dad and how strict he was growing up and even this recent experience I had with the men's I wouldn't even call a retreat, it was like a men's gathering, because it wasn't. It wasn't like we're all sitting there getting massages, it was. We were doing some serious work there and I think some of the things that came up for me is my relationship with my father. And so I'm gonna make another conscious effort as when I go back for I'm going there for a conference back to New York at the end Of this month in June, and then gonna go see my folks and Yonkers After the conference. So I'm gonna spend time like going off her walk holding my mom's hand and you know let's like she used to do for me when I was younger and and really focused one-on-one time and I'm do the same with my dad he's probably gonna want to go on a bike ride or something that we used to do in the past. You know dad's always find that way to connect in a way that they're comfortable with.

And he's an immigrant. So you know, I I'm technically an immigrant as well. I came to the States when I was a year old from El Salvador, but you know. So some of that is, you know, challenging from a cultural perspective. But I think there's something and I applaud you for taking the initiative to ask a tough question, especially as you get older, I think you sort of want to not rock the boat and you know, if you have a relationship, you don't want to put any strains on it. So, you know, kudos to you for just, you know, going maybe outside of your comfort zone to ask a tough question like that to your father, and you never want to, never want to see your father or a father figure in an uncomfortable Situation where they're forced to answer a question that may be uncomfortable for them. So that was great to hear. That turned out well.

:: 44:36

Well, we had a rough ride the first 32 years, so, and there was a specific occasion where all that kind of came through ahead and we dealt with it and I think the biggest thing for me was to be able to have that kind of relationship with my father was I had to learn how to have empathy for my dad. That's awesome and it's very, very difficult to do, because the person you want to teach you to have empathy is your parent and they can't really say, hey, could you have empathy for me? You know it doesn't really fly when you're 10, or it doesn't really fly when you're 18, or it doesn't really fly when you're 25, and but so you have to figure that out. How do I have empathy? You know, my dad had a rough childhood and that was one of the reasons why it was very hard for him to connect With me as a child or even as a teenager in my 20s. And when I started understanding that and having that empathy which I think her whole entire planet needs, a whole lot more of that that when I understood that, when I understood the empathy that I had for my dad, that our relationship completely changed.

You know, I'm very lucky as a guy to have lots of really solid male friendships. A lot of men don't have that, and my dad really Not. That he went out and hung out with us and did the things that we did together, but he was a part of that group in a way, from the fact that he was in my top five of men that I would want to go to To say and we had a very honest relationship and you know, kudos to him for For you know, because it was, yes, I showed him empathy but, man, the bravery that it took for him to, you know, be able to say this is where I messed up and this is where I felt short or this is what you don't understand, and to be able to say those things to me as another adult, took a lot of bravery on his part and I appreciated that.

:: 46:23

This is related to something I was gonna offer up as a bucket list item that I've accomplished, which is sitting in an ayahuasca session several times, and one of the experiences that I had was very profound is I, you get messages and I don't ask to describe them from source or wherever you think they're from, but but essentially the message was I saw the moment when I selected my parents. Wow, and I saw that I selected my mother and my father in this specific incarnation so that I could work through a specific set of challenges in this incarnation as a human, which has, I've come to just affirm, through other experiences that I've had. So it's really powerful. And then, right after that, I saw my dad and I saw him Almost like a teenager and I kind of envisioned him walking the streets a little Salvador. And then the message, the second message, came through, said you and your father, you've always been connected. Sometimes you're the father, sometimes he's the father, sometimes your brother, sometimes your cousins, and you always have this dance, you know, in lifetimes.

And that hit me like like a gut punch, but in a way that I just it. This was like a empathy gut punch because I was like, whoa, I get it now and I was bawling for like 15 minutes, like just with understanding, and everything just kind of clicked in and made sense and I just saw my father you know something you just alluded to just completely different light, and I just Seeing him as a, as a teenager, seeing him understanding, you know, as a child, you know, and understanding like the decisions he's had to make and you know, some good, some bad, some challenging that affected our family and you know, it was just, it's been helpful for me and it's been, you know, healing for me to understand, you know, some of the things that have happened and and also to motivate me to continue to work on that relationship. You know, because I do want to, you know, get him to talk more because he's, you know, as a lot of dads of that generation are just really reserved and quiet, keep to themselves, and so it takes more work, but it's inspiring to know that there are opportunities to break through, which is something I'm motivated to keep on trying. It's awesome. Yeah, so much to cover. I'm trying to figure out how deep I want to go.

I'm just curious you mentioned this work you do with youth development. I'm wondering how you came across that work and why that's important for you.

:: 48:34

Yeah, I actually still substitute teacher a couple of days. I just to help out and to be still hanging out with students, but also to help teachers because their job really sucks right now. So For me I think a lot of it had to do with that. I was a really bad student but I was smart, okay, like I could have done the work had I been motivated properly or had somebody that was Kind or understanding or encouraging. I just never really had that Growing up my dad was always gone, so it wasn't like he was there to support me and when he was there it's like it's been three hours doing homework, like that'll help.

It was funny because I graduated from high school with a 1.96 GPA average, okay, and then I went to college for a semester and then quit and then I didn't go back till I was 40.

Oh, and when I went back my first semester out of straight A's and my dad said, look at that, you doubled your GPA, it was a joke.

I knew it was a joke, but it hurt a little bit, but at the same time I knew it was joke, but he was proud of me, but, but yeah, but I think a lot of it had to do with not having those kind of good influences of people that Could see me, for me and help me, you know, be who I needed to be, instead of being in some kind of box, and so I just I wanted to be able to provide that for other people and for other young people, and so that's kind of where, you know, a lot of it hit was that I Want to do better for this generation than was done for me, which I think we should always want to do absolutely. And so and I've had hiccups, and you know, there was a huge learning curve coming from Indianapolis to Seattle, I was, like you know, I had to learn to use people's preferred pronouns, which was very difficult for me, not because I didn't want to, but just because I just wasn't a custom to it and yeah, it's new.

Yeah, and so there's a lot of things like that that I had to relearn or learn our nail to be able to Do the same kind of work in this environment that I was doing before, but it was worth it. I enjoyed the fact that I have several young people that I worked with over the years that now have their own families and have their own careers and their own jobs and we still keep in contact and you know it's like you were talking about your dad. You know I've had one relationship where we've gone from being mentors to you know me being his boss to you know us being friends, you know, and peers, and you know we kind of. You know, even though there's probably a 15, 16 year difference between our ages, it's been nice to watch that relationship grow. It doesn't happen with every single student that I work with but if I'm lucky, if I, you know, keep one or two of those relationships over time and that's been super special for me that I have been able to speak in the young people's lives make a difference, and Now I'm just trying to transfer a lot of those skills from that into what I'm doing now. So storytelling has always been a big part of the work that I've done with young people, whether it was Working at a church telling stories or working in a school yeah, telling history stories or whatever it was. Storytelling is important and helping people find when they are in that story, even though it's not about them. It was a real skill that I think is important when you're trying to mentor and teach, and so I've just been Transferring a lot of those skills to this new job or this new career that I've taken on as far as being a podcaster, and that's been a lot of fun.

You know that's part of the reason I wrote the book. It's called live out your list finding joy through a bucket list lifestyle, and you know I never intend. I have some books I want to write. That was not one of them, and after I came back for my three months, I'm like there's something here that this thing about intentional, having intention for your bucket list that was something I hadn't seen in the space before. So I'm like I think I have something new, so I'll write this, and it was super easy to write. The other things that I'm writing are not super easy to write, but that was like, oh, I just put on my teacher's hat and I go Break it all down and make it easy for people understand and give them steps to follow and it'll be fine. So a lot of those things that I super enjoyed about working with young people have transferred Into this new adventure.

:: 52:54

That's great.

I mean that Young men need as many role models as they can possibly find, and I think what was been apparent to me For myself on my own journey and also through some of the personal work I've done Events like the retreat we've spoken about is this idea of you know, there is no right of passage anymore for young men and you know, and it's really what's missing, and this idea of just moving from a boy into a man in a ceremonial fashion and in a way that embraces, you know, the changes happening for them to become men and the added Responsibility and what that means and how you show up in the world for the people in your life, the partners in your life, your family.

As a man, and I think you know a lot of that has been lost over the decades and it's nice to see Programs and conversations like this, you know, that are happening to make that more apparent, and it's something that I'm gonna be conscious of, for, you know, hopefully I'm looking to start a family with my partner and also my the relationships I have with my nephews. If I can impart any of that wisdom, it's definitely something that I'm gonna be trying to do. So it's good to see and it's just it's more of that is needed. So I really applaud all the work you've done in that field as well. Thanks. A couple of questions as we wrap up. What's something you've changed your mind about recently?

:: 54:12

Using Instagram to grow my show. I think I'm gonna be a little bit more confident about that. I think there's just a general sense that you know you have to. You have to be on social media, you have to be on all the platforms you have to do. You do all this, that, and the reality is, unless you're doing the rock Johnson have 40 million followers. You know there's not a lot you can do to help yourself out, and people put so much time and energy into it, especially as an independent pocket pocket. I don't have, you know, a team of folks doing all my social media.

So really deciding. You know, yes, I'll still post there when I have new episodes and that kind of stuff, but there isn't a good transfer of ROI, you know, into putting a lot of time and space there. I've had videos. I've had a real good hit 3.2 million views.

You know I have 6,000 followers on Instagram and you know, all the metrics show that Nobody leaves there and goes to a podcast, right? Well, I think what it boils down to is that people stay on the platform that they're on and we don't switch in the middle. You know you're scrolling through stories. You're screw. You're there to scroll through stories. You're not there to like, find some content and click on a link and go someplace else. That's not what you're there. It goes. Spend an hour listening to a podcast, that's right. You're there to scroll through your stories. You have a mission to scroll through your story. So even you know stories is the only place you can put a link if you're not Verified. So you know. And if they're scrolling through stories, they're not gonna click on that link. I mean, I have all the evidence in the world it says I do not click get. Click through is where I put links on there and that's the only place I can put links on Instagram with less than 10,000 followers.

So you know yeah and also the other fact that the reality is is that they Admit the throttling back. You know how many people get to see your content.

:: 56:07

Yeah, of course.

:: 56:08

So why do I? You know, I said to somebody the other day I am no longer gonna chase the dragon and I don't want to belittle heroin addiction at any level, but at the same time, I think that's kind of what it feels like I'm always chasing the dragon, I'm always, oh sure, the dopamine head. Yeah, well, not. But on the creator side it's more of what's the algorithm gonna do today? How's the algorithm gonna work now? Because every four to six months they change how the algorithm works. Of course, they change what you're able to do. They, you know. Today, you know, the big thing is everybody's putting a broadcast channel out on Instagram.

And it's like, okay, one more thing I have to go try to do to get this to work and it just feels like I'm constantly, sorry, chasing the dragon and I'm kind of tired of that. You know, there are much better ways to grow a podcast and what I'm doing right now is one of them. Honestly, and getting people to leave reviews so that you rank higher in the algorithm of the streamers those are the two best things to do. Yeah, absolutely and see my little spending time doing those instead of chasing the dragon.

:: 57:09

That makes a lot of sense. What do you think is the most misunderstood thing about you?

:: 57:14

I think the biggest misperception is that I'm a loof. I think sometimes people I know I was actually named in New York Times bestseller last month as being somebody that's a loof, that wasn't understanding of their surroundings, and that was very, very revealing to me, because I don't necessarily think I'm a loof or don't know what's going on. I think I'm spending less time talking and more time observing. I'm a huge Ted Lasso fan yeah, me too. And so the be curious, not judgmental, walt Whitman thing, I mean it is stuck with me from that day. It's like constantly, you know, I look at my partner going. Are you being judgmental or are you being curious?

:: 58:00

Yeah, they can't exist in the same space, which is great. They really can't.

:: 58:05

So I think I'm trying to be curious more than being a loof or not understanding of what's going on, and so that's probably one of the bigger ones. Because, yeah, just you know, it's weird to say that, because we're here talking for an hour plus and there's very few lags in the conversation, but when I'm out and about or meeting new people, I do.

You know, I think it's one of the reasons why, for me, I enjoy podcasting so much is because I am a naturally curious person. Yeah, we go back to the very beginning. I didn't know anything about podcasting. So I went to a good friend of mine who does listen to you know 12, 13 podcasts if that few a week. And I said here's my idea. What do you think? And he said, oh, that'll work. And I said why? He said because I've actually been in your presence when you've met new people and gotten them to tell you their story. Oh, nice, he said, as long as you keep doing that, you'll be, it's going to work. And so my hope is is that I project that all the time. It's not about me, it's about other people, and I'm like my dad, I'm listening real close and trying to know what to remember about folks so I can be able to, you know, assure them later on that I was listening and that I care. And so, yeah, I think that would be the biggest thing.

:: 59:29

That's important, and I think anyone has been paying attention throughout this conversation, and I think we'll get that impression from you that you're someone that has lived a long and meaningful life and has taken a hard look at what the important things are and what you want the memory of your life to look like, and not only thinking about those things but also actively doing stuff to make a change.

And I think that's where a lot of people fall short, because they do have all these hopes and dreams.

And you know, I heard recently someone that I know their father passed away and he was getting ready for a quote, unquote retirement, you know, and he had a heart attack and passed away and he mentioned this as like on his deathbed.

And I think that happens all too often, and so I really applaud the energy of you know what's happening with your show and probably how it's inspiring people to take a closer look at that bucket list. It's doing that for me, so it's already, you know, reminding me of things that we just keep putting off. And I've had a lot of amazing experiences in my life and traveled a lot, and but there's still more things to do, and so I'm inspired by this conversation and inspired by your show and definitely going to be recommending it to folks as something to listen to. So I really appreciate you reaching out Roger which is my younger brother's name as well, by the way so, and I really enjoyed this conversation, had a feeling it was going to be a good one, and I really love the fact that you shared your story with us today.

:: 00:52

Oh, harry, I greatly appreciate the opportunity to be here with you and I hope people are inspired. That's. You know. That's the main reason I do everything I do so if this conversation does it listen to the podcast, whatever it is, I just want folks to get out there and find their own joy. That's awesome Where's?

:: 01:08

the best place for folks to connect with you.

:: 01:10

Yeah, it's crossing it off. Podcastcom Real simple. You can see all the shows, you can get to know me, you can find my mentoring services, you can find the links to the book, everything there. So it's super simple.

:: 01:24

Okay, I'll make sure all those links are included in the show as well. Thanks again for your time, roger. I really appreciate it.

:: 01:29

Thank you.