Teaching Transformations Podcast Episode 6: Bucket List: Authors on a Train

Teaching Transformations

Bucket List: Authors on a Train

Let’s talk about bucket lists! Tim and Ryan discuss their participation in writing workshops as well as hosting them. The two friends converse about how to immerse attendees in the experiences of a workshop and what sets Tim’s aside from the rest.

The Teaching Transformations Podcast. Join Tim Desmond Ryan Wooley as they help teachers in their late forties or fifties to design a post-academic life.

Seize the Day!


Ryan  0:00  

So, are you looking forward to spring break?

Tim  0:05  

No, I had another win this week I thought you might find interesting, though. It doesn’t have anything to do with vacation.

Ryan  0:10  


Tim Desmond  0:11  

Yeah, the Spotify win.

Ryan  0:13  

What’s that?

Tim  0:13  

Well, do you have Spotify?

Ryan  0:16  

My son uses it. I use Apple Music.

Tim Desmond  0:19  

Okay, so you use some sort of streaming though, right?

Ryan  0:22  


Tim  0:22  

Alright. Well, I think people our age will appreciate this. I look to my left here, I have, I don’t know, 1200 or 1300 CDs. I started collecting when I was, you know, twelve or thirteen or whatever it was, and in the early 2000s, I remember I had like five desktop computers in my classroom. One summer, I would take a box at a time and for a few hours, I would drive to the school, I would put my disks in all the trays, rip them to mp3, transfer them to a hard drive. This took me weeks, and I digitized my entire collection, right. Then fast forward, iTunes comes out, and I’m like, I’m not paying 99 cents for music I already own. Then fast forward another ten years, and we get to Spotify. I’m like, I’m not paying Spotify. It’s not fair to the artists. They get paid like a fraction of a cent per listen. Then, I finally came to the realization that I’ve already purchased this music, so whether I listened to it on my CD player, which I don’t have anymore, or on Spotify, it’s the same thing. Now what I’m paying for is the convenience of paying it to Spotify to be able to listen on my device. Over the past few months, I’ve followed all the artists from all the CDs I own and started making playlists, and I think now, I’m finally to the place where I’ve accepted the fact that I’m consuming my music on Spotify.

Ryan  1:55  


Tim  1:57  

I guess it’s a win in a way, but now I’m looking and I’m like, what am I gonna do with those CDs? My kids don’t want them. I don’t know what to do with them.

Ryan  2:09  

So, I’ve had my own similar project, but mine’s been more recent. I have a similar number of CDs, and I would say about a year and a half ago, I went through this process of ripping them all, but I’m really particular about sound quality. In particular, the sound quality that CDs bring to the table here, so I ripped them all to flak. Then, I still wanted that convenience, so I converted them all in batch to Apple’s lossless format, and that way I could put them into the iTunes library. Now, I have my whole collection in iTunes as my library, but I also pay for Apple Music for the other side of things that you were just talking about, so I feel like it sort of combines both of those worlds together for me.

Tim Desmond  3:08  

Interesting. Yeah, I remember having that issue. I think at the time, I was ripping mp3s at like 128K, and you know, it was more about convenience and quality. I was never into vinyl, I know some people love vinyl, but for me, I thought the CD quality was always the best of any commercially produced medium by far. I really preferred listening to that, but you know, the convenience factor. That’s pretty interesting that you ripped the flak and still have those physical files.

Ryan  3:42  

I have all the CDs stored in bins in the basement now, but my son’s kind of getting into that. He’s going to like The Exchange and buying $1 and $2 CDs.

Tim Desmond  3:55  

My son is eighteen, and he said the same thing to me. I was like, well, should I sell them? Should I give them away? Should I take them to the library? He’s like, just hold on to them. CDs will probably come back the way vinyl did you know, people might start collecting CDs again, so I’m gonna do the same thing. I’m gonna sit on them for now.

Ryan  4:15  

Yeah. Well, you dodged my spring break question. The reason I asked that is because since you’ve been out of education, spring break doesn’t mean what it used to. I mean, you still have two children that are in school, but you don’t look forward to it as a teacher would, so I’m curious.

Tim  4:41  

No, it’s totally meaningless now.

Ryan  4:46  

There’s probably a lot of things like that.

Tim Desmond  4:48  

Weekends, evenings. It’s an interesting question, and I’m not being cheeky, I’m being totally serious about it. After about a year or so of being self employed, I lost track of a lot of those cultural touchstones. I have to keep some semblance of those because my family still runs on traditional ones. My wife has a nine to five job and my kids go to school, so I have to be in somewhat of an alignment with that, but personally, and the pandemic has made it even worse, but for me, every day is just another day in good and bad ways. I work every weekend, but I also play every day. Yeah, it’s odd. I think that’s what I’ve missed the most about the pandemic which is gonna tie into our conversation today, was having sort of things to look forward to. That involves some travel or some collaboration or just things that are not part of my routine. That’s what I look forward to now instead of these fabricated breaks that occur in other aspects of life.

Ryan  6:07  

Yep. I remember during my student teaching, there was a teacher that I connected with. He wasn’t my main teacher, but he’s just somebody that worked at that school. He was in his last year of teaching, and I ran into him a year later, after he retired. I was like, hey, so how’s retirement going? He’s like, oh, it’s great–I don’t know what day of the week it is unless it’s garbage day.

Tim  6:36  

That’s a good point. I do know when garbage day is.

Ryan  6:41  

So, this piece about looking forward to travel is a good segue into today’s topic which I’m really excited about because it ties to a shared experience that we’ve had. What I want to talk about today is the Authors on a Train experience that you’ve organized. I will just say, one thing I’ve seen you do that I’ve been really impressed by and maybe a little surprised by, is just your ability to see tangential possibilities. I saw you sort of walking down this author path, and then you found all these really cool creative ways to kind of bend that. What I saw is sort of an unconventional kind of journey. There’s a bunch of other ones, and maybe we’ll have time to talk about those, but I wanted to start by the authors on a train just because we had that shared experience. I think it’s a good example of one of the ways that you really found ways of stretching your author self into other avenues.

Tim Desmond  7:57  

Yeah, I’m excited to talk about it because it was fun to have you with me on that experience. That’s one of the places outside of our professional relationship where we had an opportunity to work together, and it was a lot of fun. I will say, it’s sort of a big takeaway from this because we’re going to sort of talk about something very specific as opposed to a high level concept, although there’s going to be some of that in this conversation. I think the big takeaway for this is that we are in a place now where all you have is unconventional stuff, like we’re just swamped. We’re swamped with everything. I was going through my podcast player, and I was unsubscribing from podcasts, not because they were bad or I didn’t like them anymore, but just hearing some of the same stuff over and over and over. Same people saying the same things, and it’s just very conventional. When you talk about finding those tangential things, I think it’s one of the threads that have been woven through our conversations together which is this idea of, you know, Scott Adam’s Skill Stacks, where you you take something that you’re really good at, and you combine that with a passion or a hobby or an interest, and you create something unique. Even though I couldn’t articulate that and I wasn’t intentionally following that path, it’s sort of been the trail I’ve locked my entire life–being somewhat unconventional and doing things a little different way. I’m always looking for those intersections of what people expect and what I can bring and sort of molding those together into something unique and different. That’s the key for me now and in the next ten to fifteen years for anyone I talked to. I’m always saying find that intersection for you, create something that’s unconventional that hasn’t been done before, by mixing or merging things because there’s just so much conventional stuff out there. I just don’t think you’re gonna get anywhere if you’re following the tried and true path that other people have been creating for years.

Ryan  10:10  

Yeah, I love this idea, I know we’ve talked about it before, but of stacking, because I do think that’s the key to really finding something unique because we all have unique stacks of things. We’re both educators, and there are a lot of educators in the world. If that’s the only thing we’re standing on, it’s not going to be that unique. I mean, even if we’re really good teachers, but if we combine that with the other things that we’re good at or interested in, that’s where we really start to differentiate ourselves.

Tim Desmond  10:45  

Yeah, even experiences. Experiences that you’ve had or have happened to, you can become part of that stack. I think when we talked about where Authors on a Train came from, the original idea came from a pain point of mine, something I experienced. It wasn’t even an interest I had, so it’s gonna be fun to explore that a little bit.

Ryan  11:06  

Yeah. Alright, so we should explain what this is for people who are not familiar with the concept, which I can’t imagine everybody out there isn’t familiar with Authors on a Train.

Tim  11:17  

 Line it up.

Ryan  11:21  

It’s maybe a little bit of an itchy thing. Just walk us through what it is before we start to get into the sort of when, where, and how.

Tim Desmond  11:33  

My good friend, Joanna, came up with the label. We’ll talk about her later, but she’s like, yeah, this is Authors on a Train. The concept is, myself and my business partner, Zack, offer these writing retreats for people. Essentially, they are a writing retreat, but they’re also sort of a destination vacation, a bucket list kind of thing. We’ve done two variations. One, I’ll talk about now because you were part of it, is Authors on a Train New Orleans. What we did was, we took ten, eleven, twelve authors. A handful, not a lot. We meet in Chicago at the Amtrak Union Station, and we board an overnight train that runs from Chicago to New Orleans. We kind of hang out in the lounge there. There are sleeper cars, so we pair people up. You end up having the evening to socialize, there’s a couple meals the next day, you pull into New Orleans. The next day, in the afternoon, we go to a hotel in the French Quarter or multiple hotels, and people pair off. The idea is, we’re going to spend five days roughly in New Orleans, and we’re going to be doing a couple things. We’re going to be doing workshops, so we’re gonna be doing writing and craft-related stuff. We’re going to be doing marketing workshops. The attendees pair off, and their goal is to create and write a collaborative short story, and then what Zack and I do is we take all these short stories, we publish them into an anthology, and then we sell it with proceeds going to charity. The idea is, you show up in Chicago, you ride the train in New Orleans, you explore the city, you work, you’re completely immersed in this experience, and then you leave. Then, you know, a few months later, you have a keepsake, which is this anthology of short stories which we also sell for charity.

Ryan  13:38  

It’s funny you use the word vacation in your list of descriptors because it actually felt that way to me when I participated in it. I think that’s part of the magic of it. I mean, I don’t know how many other people are out there like this, but I don’t like sort of lazy vacations. I don’t like to go sit around and sunbathe or whatever.

Tim  14:04  

A day, maybe.

Ryan  14:05  

Yeah, right. I mean, it’s nice to get warm. We’ve talked about our climate challenges around here, and it’s nice to go somewhere warm and soak that up a bit, but I just want to be mentally stimulated when I have breaks. I look forward to that, and I definitely felt that. It was just funny to hear you describe it as part-vacation because it kind of is that, but that’s going to appeal to certain people who are looking for an active style of vacation I guess.

Tim Desmond  14:38  

Yeah, and you get to craft that. Without getting into the weeds of the agenda, the idea was Zack and I providing some sort of guidance through this writing and publishing process but also creating these pockets of time for people to take a swamp tour or go see you the famous New Orleans cemeteries or go and eat at these restaurants or stroll through the French Quarter and be inspired by the art and the cuisine and everything in the music that New Orleans has to offer. There is a bit of a vacation element to it, and we think that’s part of the appeal. It’s good that you said that about vacation because from a high level marketing standpoint, we are trying to exclude everyone except the handful of people who go, wow, going somewhere else and writing the whole time sounds awesome, I want to do that, because that’s not a big segment of the population.

Ryan  15:33  

Yeah, it’s very niche, but you know, a lot of us who’ve been in education have been to the standard conferences, and it’s always fun to get on a plane or a train and go to a different city and hear people speak. In my experience, typical conferences are passive. They are targeted at a broad audience, so to find those few nuggets of things that are really applicable to you, sometimes is a chore. You can sit through a lot of sessions before you get to that one that just speaks to you, and I always say when I go to conferences, I’m happy if I find that one or two, because that’s just the way it is, where this is much different than that because it’s so targeted. You’re really looking at a small group of people who have a very particular interest and playing off of that. That’s got to be tied to the magic of it and what made it successful.

Tim  16:43  

Yeah, I think that’s one of the big differences in a lot of more professional conferences or even workshops, in that you are fully immersed in the experience. We went out to dinner together, not a segment of us, everybody. That’s the difference. If you go to a conference and you find five or six people that you connect with, and then you go out and have drinks with them, that’s great, but we’re talking about everyone that’s involved sitting around the same table together. I forget the name of the hotel, famous jazz hotel, we went to that one night, but we were all in the lounge on couches in a big circle, all of us hanging out and drinking and having a good time, and for me, that’s the difference because Zack and I have run larger conferences, and we still host those. When I say larger, I’m talking a few hundred people, not to mention the conferences where there are thousands of people, but these are really small, intimate gatherings, and I think that’s what makes them different because you can’t replicate them necessarily. You can’t scale them. They’re personality dependent. Again, going back to our big takeaway from when we started talking today is like, that’s the differentiator. That’s what makes them different, and I think people who are looking for something new, you know, this is for them.

Ryan  18:07  

Yeah, I can tell. Just having been through the experience, we had some fun and more relaxed time in the evenings. We had dinner together. There was a night we walked., I forget the name of the street, Prince Street? That’s where the bands are frequently playing out on the street, right? It was great, and I felt that personal connection with people. I felt that all day long, I mean, during the work parts of the day as well. I think that really is testament to when you’re really around people who are passionate about the same things. It really makes work not feel like work so much.

Tim  19:01  


Ryan  19:03  

Let’s back up a little bit. Tell me how you came up with the idea. You mentioned Joanna.

Tim  19:12  

Yeah. It came out of a pain I had. We were running entrepreneurship workshops for the entrepreneurial studies department that I was part of, and we were doing those in California, and I have some inner ear issues that make flying really a challenge for me. If I absolutely have to fly, I will do it, but it causes severe pain, and I think it has to do with air pressure in the cabin and the change in altitude. It really messes with my ears, so I said to my then boss, this is a big deal. These were workshops in California, and it was a big deal, and I said I’m not flying. She’s like, well, but you have to come in. I’m like, okay, but I’m not flying. If it were life or death, I would do it for my family, but I’m not doing it for my school, and I kind of jokingly said, I guess I can take a train, and she’s like, okay, look into it. I rode New Jersey Transit from Northern New Jersey to Manhattan for a while, I rode subways, but I had never been on a passenger train, an Amtrak. I went and I found out taking the train across the country was a bit more expensive than flying but not by much. I mean, we were talking a few hundred dollars, not thousands. I was like, okay, well, I’ll tell you what. I can take a train from Cleveland to Chicago, and then I can get on the Zephyr and go from Chicago all the way to San Francisco, so I did that, and I absolutely loved it. It was a forty-eight or fifty-two hour trip, so you’re on the train for two days. It’s not for everybody, but you get all your meals included. There’s a stand up shower, you have your own sleeping bunk. On the way out and on the way back, I just wrote. I have my laptop, there’s no Wi Fi, the cell reception is terrible. I must have written thirty, forty thousand words. It was awesome. I was staring at the window, going through the Rockies, and I was like, wow, this is really amazing. When I got back from the trip, and this must have been in, I don’t know, 2015 or 2016, I was kind of joking about it on social media. On Twitter, I posted something about getting all these words on the train, and one of my friends, Lindsay Broker, who’s a really big-time indie sci-fi author, said, that sounds cool, we should do that. I immediately wrote back and said okay, let’s take a train somewhere, and we’ll come write something together. Then she messaged me offline or off the platform and was like, are you serious? I’m like, why not? Let’s find two other people, we’ll go as a foursome, and we’ll work on something. We’ll figure it out a novel, and we’ll see what happens. I reached out to Joanna Penn, who I’m good friends with, and she’s like, yeah, that sounds amazing, let’s try it. I asked Zach, and he said sure, so that was it in March of 2017. About four years ago, the four of us did the route that became Authors on a Train, we met in Chicago, we went down to New Orleans, we spent a week there together, we ended up writing a novella together within one of my horror series, and that’s how I got started. Basically what happened was, Zach and I, on the last night, were sitting in one of the bars in the corner, just kind of having a beer and some wings and talking about the experience. I was like, man, this is awesome. All four of us just had the most amazing time. It was like heaven. No responsibilities–just write, create, talk, hang out, listen to music. I was like, we should do this for other people. We should do this for other authors. We could host it and take them on this similar thing. We went back to Lindsay and Joanna were like, what do you guys think of this idea? And they’re like, yeah, we have no interest in doing it, but you guys should totally do it, so that’s how it started.

Ryan  23:26  

That’s cool. We glossed over that pretty quickly, but I’m not sure everyone would have been able to just so quickly crossover into like, we could turn this into something, we could do this for other people. I do think that’s one thing that you’ve always been really good at is just sort of recognizing like, hey, this could be something, so congrats for having whatever it is that enables you to do that. There is something magic about being on a train. My first experience traveling that way was back in the mid 90s. This was after I graduated college, and one of my college buddies moved to Boston. He invited me to come hang out with them for a couple days, so I took a train there, and it was another overnight thing. When you’re going from Cleveland to many of these other cities, you have to leave at like two in the morning or whatever it is, so it’s a little rough on the sleep side of things, but man, it is just so cool to wake up on a moving train, get a cup of coffee, sit and stare out the window. I love it.

Tim  24:44  

I do, too. You don’t have to worry about directions or traffic. Someone else is driving.

Ryan  24:50  

Oh, yeah. Well, how’s the concept evolved since then? I mean, we kind of started with the beginning. Are you still doing them? Have they changed?

Tim  25:06  

Like many things, a pandemic has thrown a monkey wrench that ruined 2020 and pretty much 2021. Hopefully not all of it. Zach and I went with Lindsay and Joanna the first time, and then we ran the two subsequent years. We ran Authors on a Train New Orleans, and you were on the second of those two. Then in 2019, we decided to change it up. We did Authors on a Train California, so we met in Los Angeles, and we took the Pacific Starlight or Coastal Starlight all the way up to San Francisco. We rented this big mansion in Oakland, California, and we lived there with authors for three or four days. We had UberEats, and we were cooking our own meals. It was the same concept, except it was California, so we were going to do that in 2020. That was right before the pandemic, so we did that in 2020, and then a few months later, the pandemic started, so we scrapped it for 2021. We might look to do it again in 2022, probably California again, but we’re not sure. Zach and I really liked these immersive, experiential, unique experiences, so we started developing these, what we called World Building Workshops. They’re less intense than Authors on a Train because we do them on a weekend so people don’t have to take off work or anything like that, but they are genre and city specific. Again, this is that intersection, right? We’ve held three, and we have two more coming up this year. We did Night of the Writing Dead. We did that in Pittsburgh for the 50th anniversary of the Night of the Living Dead film which George Romero filmed in Pittsburgh, so that’s the connection there for zombie writers. We did Rock Apocalypse in Cleveland. We did that in the Rock and Roll Hall of Fame. We rented a room out there, and we wrote post-apoc stories with a rock and roll flavor. Then we went out to Seattle, we did Sci-Fi Seattle, so we rented a place at Mopop near the Space Needle. Then, we were going to do Vampires of New Orleans over Halloween weekend in New Orleans in 2020 that we pushed to this year–fingers crossed that will happen. In July of this year, we’re going to Salem, Massachusetts, and we’re going to do Witches of Salem. We’re gonna do like an urban fantasy witch fiction kind of weekend thing in Salem, Massachusetts, so that’s sort of become our thing. That’s what we’re known for in the author community, and we don’t repeat any of the World Building, so it’s not false scarcity. We tell people we’re taking fifteen people max, and that’s it. There are so many places in the world, and there’s so many opportunities to explore other cities. It’s not to say we won’t repeat one of the World Building weekends, but as of now, we’re not, and we’re trying to make them really unique and really special.

Ryan  28:20  

That sounds like it’s really feeding you as well. It sounds like you’re going to these really cool places that are fulfilling. Any kind of travel itch that you might have, you’re getting to sort of map out these destinations. That sounds like a lot of fun.

Tim  28:42  

Yeah, it is. Me in particular because I handle most of the logistics, I’ll come up with a list of ten cities and themes, and I say, okay, Zack, what do you think? Which of these really appealed to you? We get to look at those, and we were really looking at this year as maybe going overseas. We had some interest in Europe and doing some things there. Zack, and I make a little bit of money on this, you know, it’s worth our while, but it’s not a full-time gig. It’s another revenue stream that feeds into the revenue river so to speak. It’s extremely fun for us. I mean, we’re responsible. There’s some burden of responsibility that comes along with that, but you’re right, like we were picking the cities we want to go to, we’re picking the kind of stories we want to tell, we’re choosing the people who want to do this with us, and it’s a blast. Most of the time when Zach and I are on these, it doesn’t feel like work in the least.

Ryan  29:53  

What is it about experience? It seems like it sort of sets the table for a different way of thinking, I guess. I don’t know if you know where I’m going with that, but like, there’s something about getting away and going somewhere different. Are you making use of that?

Tim  30:21  

Absolutely. I think that’s part of the draw. In this day and age, you’re never more than a device away from your loved one, so it’s not like going out into the Alaskan wilderness for three days and hunting your own food. It’s not that type of immersive experience, but there is an expectation there, and it’s easier for attendees to present that expectation to their loved ones. They’re saying to their husband or their wife or their significant other, I’m not going to be available. Of course, if there’s an emergency, by all means, I’ll attend to it. Knock on wood, we haven’t had anyone have to leave mid-event or anything. This immersive experience is both literal and symbolic, right, it’s moving you out of your comfort zone, it’s taking you out of your day-to-day routine, out of your responsibilities, and allowing you to allow your spirit to open up and just accept what’s coming. I think there’s a great degree of trust there, and Zach and I take that very seriously. We know people are trusting us with the experience, so there’s a lot of prep work and a lot of thought that goes into those, but you’re right, there’s just this power in an immersive experience, and it goes back to education as teachers. We know the power of experiential learning. When I taught sixth grade, one of my highlights of the year was going to Colonial Williamsburg with the whole sixth grade because instead of talking about history in the classroom, they could walk Duke of Gloucester Street and experience 17th century America for themselves. There’s real power in that immersive, experiential learning piece, and it’s always been something that personally lit me up. Even as a classroom teacher, I was way more interested in the field trips than I was standing in my own classroom. It also ties into this idea of the difference between sort of a clan, a tribe, and a community. Those terms are all used interchangeably in different ways, and they’re not the same thing. I think when you get these really immersive events like this, you’re forcing a clan mentality like we had on Authors on a Train. You talked about people having bonds for the rest of their life from just spending a few days with people because of the nature of the experience, so I’m much more interested in being part of a small clan than I am a tribe or larger community.

Ryan  32:55  

Yeah, well, that was three years ago now. Three or four. I think I mentioned this before, but that group of people that were together, very small group of people, who were together for those few days, they still keep in touch. There’s still an active Slack Space, and they still have accountability partners. The fact that they’re still connected and still working together just shows the kind of bond that was created during that experience because how often does that happen after a conference? You’ll meet people at conferences and stuff, but you’re not keeping in touch with them or still working on projects together.

Tim  33:37  

Yeah, totally agree.

Ryan  33:40  

You talked about taking people out of their normal space, and I think that’s important, but also, there’s something about going somewhere, too. Like you said, when you go on these field trips, and you can actually see, okay, this is the battlefield where it actually happened, there’s something different about that than just watching a movie about it in class. I definitely felt that during the New Orleans trip just being there, just looking around at the architecture, reading a little bit about the history. It really primed the pump for me when we went to write our stories. I was collaborating with Chris during that experience, and it was really helpful to look around and think about what the history of this place was, and that definitely fed into our story. I know all the other stories there too, but it was very particular to that place. I don’t know, I can’t say enough about what you can take away from these kinds of experiences where you create a destination, you go there with purpose, and you guys did a really good job of orchestrating all of the activities. A lot of work happened there, you had a lot of workshops. There’s a lot of structure to the work. People learned a lot about the collaborative process that you and Zack use, but also, there was this immense camaraderie that developed that continues to this day. What a cool idea. It’s so funny. It seems like it just came out of nowhere. You guys just randomly had this experience and were like, hey, we could turn this into something.

Tim  35:38  

Yeah, I mean, tongue in cheek, it kind of did, but it also didn’t. It’s a teaching shop. I know this is gonna sound like a broken record, but I really believe this idea of taking your teacher skill set and just transplanting that into a different place. If you think about it, for most people who are not teachers, their last experience with school was getting their diploma and spray painting the gym wall or something on their way out, right? They don’t have a ton of fond memories of school as an institution, it was just sort of something that they had to do. The average person doesn’t have those chops to be able to put that kind of structure in that event. You can certainly go with the group of people to a city, but if you don’t have teaching experience, you’re not going to know how to structure that in a way that you get that experience out of it. It’s not necessarily magical. To me, it was me taking the skill set that I’d developed as a classroom teacher and just transplanting that. You probably recognized it. There are a lot of things that I do in workshops and that I do in one-on-one client work that’s right out of my classroom, whether it’s motivation, techniques, or criticism or feedback. That’s all stuff that just works whether they’re five year olds or fifty year olds, it doesn’t matter. What I always have to fight in those situations, which is what teachers deal with, is the distractions. I’d love to know for you, how did you handle the distractions? You have a lot of responsibility in your job, and even the school was in a different place a few years ago. I feel like it was probably even more intense than it is now, so how did you disconnect in a way that allowed you to embrace the experience and not be worrying about what was happening back on campus?

Ryan  37:48  

To clarify for our listeners, I’m a director of technology for a school, and yeah, it can be very intense. Everything touches technology, so there’s just a constant stream of little issues or people asking questions or whatever, so it never really stops, but also, I’ve been in this line of work for a long time now. One of the reasons I’ve had longevity is because I compartmentalize. That’s part of my personality, so I can put things away, I can close them off when I need to. That’s why I don’t get emotional. I don’t overreact to situations. I could be in a tough situation at work, deal with it, go home, and forget about it. I think it’s that part of my personality that’s probably helpful, but when I go away on trips like this, I kind of forget I have a home life. I forget I have a family, and I hate to say it that way. My family is the center of my world. I mean, they’re everything to me, but you know, I know in order to really be present in that experience, I have to close off all the other noise. That’s the only way to really take something away from it. I don’t know how much of that is just naturally baked into my DNA or how much of it I actively try to do, but maybe it’s a little bit of both. Some of it is probably just the way I’m wired, but some of it is I know that’s what is going to set me up to take the most away from an experience is to just not be distracted. It can be hard sometimes, but I think you have to be intentional about that.

Tim  39:37  

Yeah, you’re really good at keeping a level head, not overreacting, being thoughtful, precise. I can see that playing into that strength for sure.

Ryan  39:48  

Yeah. I did see a lot of your teacher self coming out in that experience. I’m assuming I probably was the only other kind of career educator type that was part of that.

Tim  40:03  

It’s funny you mentioned that. I don’t know if you know that Chris is a retired teacher.

Ryan  40:06  

Oh, that’s right. Now that you mentioned it, I do remember that.

Tim  40:10  

Yeah, and in the UK, so it’s a slightly different system and culture, but yeah, I think that’s the only one.

Ryan  40:19  

The way that you sort of went back and forth between different kinds of experiences, there was a blend. There’s a little bit of direct instruction. There were collaborative pieces, sort of what you would consider group work, there was open ended time, you know, and that’s what great teachers have learned to do is to make use of all of that. You did a really good job of structuring the whole experience. For you, this was second nature, these are techniques that you would have used in your class, but they work really well in this format, too. Do you know of any other kind of similar event based experiences outside of the ones that you guys do? You talked about all the ones that you’re involved with, but are you familiar with any other similar kinds of things out there?

Tim  41:15  

There are, you know, I obviously don’t know, everything that’s happening in my industry, in my space. Writer workshops have been around for a long time, and people do them in their own ways. A lot of them, in my experience, are pretty much direct instruction, which is fine if that’s what you’re looking for. You go to a writing guru, and you listen to them lecture for a couple days, and then you leave, and there’s a lot of value in that, but I don’t think there are a lot that are as immersive and interactive and experiential as the ones Zach and I have hosted. Again, I think that comes back to my teaching background and knowing that the attention span on a lecture is quite short, especially for adults, even though we don’t necessarily consider that. I’m sure there are other experiences out there. I’m not trying to pat myself on the back here, but Zach and I embrace the idea that we are working individually with every one of these authors. This isn’t something we can scale up to a seven figure business like that’s not the goal. For a lot of people who are creating content or creating services for other industries, that’s their goal. Eventually, they want an exit strategy, or they want to hire people to do a lot of the groundwork for them at some point, like their eye is on the horizon and the future, and because of that, the very nature of what they’re doing isn’t as connected. You can go to a writing workshop or a conference, even ones that are the same size of ours, but you’re not going to have the same experience because it’s hard work. It’s hard work to roll up your sleeves and get in there with people, and I think, again, this is where teachers have an advantage. Now your average person, when they think of a workshop or conference or summit, they’re imagining standing on a stage and talking to people for forty-five minutes and maybe answering a few questions. That’s not what we do, and good teachers, they don’t keep that distance. They get right in there with you. I think having the desire and the knowledge and the experience to do that and get in there next to people, and you know, Zack and I wrote a story and we did our story development talk in the room with everyone and got feedback. We’re part of the experience, like we’re going to dinner with people, we’re going out to drinks with people. It’s not like, okay, I’m walking off the stage, I’ll see you at 9am tomorrow when I’m behind the podium again. We’re in it, and I think good teachers do that naturally. If you are a teacher and you can do that no matter what industry or what interest you have, if you bring that, you’re just gonna stand out immediately.

Ryan  44:12  

Yeah. What’s the feedback been like from participants?

Tim  44:17  

Well, it’s been awkward for me to say they loved it, but like, they do. We’ve gotten written feedback, we’ve done video testimonials, we’ve had audio testimonials, and people say it was a once in a lifetime experience. We’ve had people say it’s been a life changing experience, not because the anthology sold millions of copies, like the anthologies don’t sell. It’s not about the royalty check for those, it’s about the experience and holding something up and saying, I did this, I made this, here’s tangible evidence of this experience and its value to me. As teachers, we’re really good at starting something and then crossing the finish line with it because that’s the nature of our job. We have to move kids on to the next level, we have to get them to the next unit, but once you’re no longer a student, you don’t have those expectations on you. If you don’t know how to do it, when someone comes along and says here, let me walk you through this, it’s kind of a special moment. I don’t ever take any of that for granted. I mean, it’s marketing gold. Every time we announce one of these World Building workshops or Authors on a Train, they basically sell out in a matter of days. We don’t have to run ads, we don’t have to hold webinars to recruit people. People know about them, they know what the experience is, and that’s because of the feedback from the people who are on these trips. If Zack and I were saying, wow, this is a once in a lifetime trip, it’s gonna change your life, whatever, everybody says that, but we have people who are on it saying that, that’s really authentic stuff.

Ryan  46:03  

Yeah. Well, early in the conversation, you talked about sort of disconnecting from some of the podcasts just because there are so many people out there saying the same things, and we do live in that kind of world. Now, everybody has something to offer you, right? We have to be good at becoming, I know, this word gets used a lot these days, but we have to become curators of all of that. This strikes me as something that’s really, really different, that there aren’t a lot of people who have figured out that there’s really something to this experiential learning piece and bringing together people in small communities, so congrats on sort of cracking that nut. I’ve never seen anything out there that looks anything remotely like these experiences, so I applaud you for your creativity and your ability to see a possibility and create something out of it.

Tim  47:10  

Well, thanks, man. You are a big part of it. As an attendee and a fellow educator and someone who has given me feedback on it, your opinion and your feedback was really important, too. I’m really excited about eventually what we can help our listeners do with this kind of stuff. I mean, my head just spins with all the possibilities. I think about people who are naturalist and following bird migrations or people who are really into architecture and going to a particular city and studying the art. There’s just so many possibilities, and the one thing in common, the thing that holds it all together, is this ability to manage a product and to manage people and to manage an experience, and that’s teaching. If you’re a teacher and you’re listening to this, sky’s the limit.

Transcribed by https://otter.ai


Authors on a Train – http://authorsonatrain.com/ 

Transformations – The free weekly email with the best personally curated resources to help teachers in their late forties or fifties to design a post-academic life. – https://teachingtransformations.com/ 

Teaching Transformations Podcast – https://teachingtransformations.com/podcast/ 

Intro and outro music by Penthouses. “Come to Ohio” from The Weatherman album available on most music platforms.

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