Teaching Transformations Podcast Episode 11: Talking Collaborations

Teaching Transformations

Talking Collaborations

What does collaboration mean to you? In this week’s episode, the two friends take a deeper dive into the benefits and downsides of group work in the classroom setting as well as in their current jobs.

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!


Tim  0:01  

Welcome to Teaching Transformations: Designing Your Post-Career Life with Tim Desmond and Ryan Wooley.

Ryan  0:12  

So did you pull out your snow shovel this morning?

Tim  0:18  

I’ve really been enjoying some of the April Fool’s, they’re not really pranks, I guess promotions maybe? We’re recording this on April 1, 2021, and in my industry anyways there were a couple of great ones that came out that wouldn’t be funny to you or anyone else but just companies I work with put up a little April Fool’s thing. It’s been kind of fun.

Ryan  0:41  


Tim  0:43  

I did run today.

Ryan  0:44  

Good. And you didn’t fall?

Tim  0:47  

No. I took a picture though because we have a neighbor who likes to, against our wishes, I mean we’re not strongly against them, but they come over and hang plastic easter eggs in our trees every year for Easter. They did that last Sunday, so now I went out this morning and took a picture of like after I ran, all the Easter eggs are covered in snow.

Ryan  1:13  


Tim  1:15  


Ryan  1:16  

It’s weird. Especially in northeast Ohio, it really flip flops this time of year like you know, last week we were in shorts.

Tim  1:28  

Yeah. A couple days ago, it was like sixty-five or something. It’s crazy. There are weather swings in different parts of the country, but I’ve lived in several parts of the country, and March and April are kind of nuts because you add that lake effect snow element. I’ve told people, I remember one year, I don’t remember exactly what year it was, but we came back from our Colonial Williamsburg trip with the sixth grade, and it was the last day of April, and we got like four inches of snow. We had a snow day.

Ryan  2:03  

Yeah, I remember a few times having snow in May.

Tim  2:08  

Yep, but I’m guessing snow is not our topic today.

Ryan  2:12  

No. So let me ask you a question. When you were teaching, did you have your students do a lot of group work? Did you use that as a part of your teaching method?

Tim  2:27  

Define a lot. I’m sensing where this is going.

Ryan  2:34  

Multiple times a week.

Tim  2:38  

Probably not that often. Maybe a couple times a month.

Ryan  2:44  

Okay. Well, first of all, I’m deliberately using an old school term, group work.

Tim  2:51  

I noticed you didn’t call it collaboration, you called it group work.

Ryan  2:53  

Right. Can you tell me a little bit about experiences you had? Let’s start with as a teacher, using that style of teaching where you put students in groups working on projects, like for you, was it successful?

Tim  3:18  

You know, I’ve honestly always had a love-hate relationship with group work or collaborations or whatever you want to call it in the classroom because on one hand, I’ve seen real amazing things come out of teams of students. On the other hand, I’ve spent an inordinate amount of time managing train wrecks. It’s not the fault of the kids, it’s the fault of me for putting them in that situation, like I don’t blame the kids, I blame me. I’ve seen both. I’m sure you have, too. I’ve been on both ends of that spectrum, and when I was a history teacher, I didn’t do as much as I did when I was teaching entrepreneurship. I mean, the entre class was entirely team based like 85% to 90% of it, and it’s complicated, and the pendulum swings. There were times in my career where I really emphasized working in teams, and then there were other times in my career where I didn’t go to it as much, and I see that in my professional career as well. Yeah, in the classroom, I’ve gotten mixed results.

Ryan  4:32  

So, you said love-hate. My relationship has been mostly hate, and even observing other teachers who are big proponents of using collaborative style teaching, I’ve just seen in my observation, teamwork definitely has its place. I want to circle back to your comment about entrepreneurship because I could see that being a place where it would be really valuable, almost essential, but when it’s inserted into places where it doesn’t really have a purpose, it’s just sort of being put there because I think teachers feel like they have to put it there. I think that’s where it really falls apart, and in my role now, since I don’t teach a lot directly, I’m around teachers, and I support teachers, I still teach something, but I have the opportunity to see other people teaching and sometimes see students when they’re out in groups throughout the school. Man, I gotta tell you, so many times I see them off task. I’ve heard students and my own children complain about, like, oh my gosh, so and so did absolutely nothing, I had to do all their work for them. Before COVID rearranged everything, we were carpooling with another swim family. They have a freshman girl, and she and Preston, you know, we’d be driving to school together, and they would sometimes talk about school related things. It was almost daily they had this complaint, you know, it’s like, I got stuck with so and so, they don’t do anything, I’m so tired of this, blah, blah, blah. I’ve seen that side of it so much that I become pretty skeptical about it even though I know it’s important, and I know it serves a function in the right circumstances. I guess I want to go back to the entre program because like I said, I saw a little bit of what you guys were doing there, and that to me seems like the type of place where collaborative team based teaching and learning really fits in. I don’t know, is that your feeling about it? Did it really work there? What did it look like?

Tim  7:06  

Yeah, for the most part, it did. I did a startup weekend together a few years ago which was sort of a similar experience. You’re put into a team of three or four people, and you have a singular task, and I think in those kinds of situations, it does work really well. In entre, especially in teams of four, which is what we found was ideal, in teams of four, you have enough distribution, and you also have some protection against someone totally checking out because sometimes in partners it’s hard to hold that accountability, and when you get into teams of three, you get like one team of two teaming up against the other team of one. In a team of four, there seems to be more balance for some reason, so yeah, I think in certain very open-ended challenges like in entrepreneurship where you’re not really sure what to expect or what’s expected of you, then a team can be really beneficial. Again, you know, there were countless hours and calories invested into completely dysfunctional teams. It’s not a panacea, you don’t just throw kids together and magic happens. It takes a lot of work, it takes a lot of structure, and it honestly takes a lot of training, especially in the classroom. Any skill, you don’t just throw kids into something and expect them to be able to do it, you have to gradually work towards a level of competency. Teamwork is a skill set. It’s not algebra, but it’s a skill set, and I hate the term soft skills. I don’t think there’s anything soft about it. It’s incredibly critical and important, but you can’t just expect kids or people for that matter who came up in a very traditional educational environment to just be able to collaborate right off the bat. It doesn’t happen that way.

Ryan  9:12  

Yeah. Well, the luxury students don’t have is if the chemistry is not good, they still have to do it. They can’t choose to go find another teammate that they have better chemistry with because that structure has been kind of imposed on them by the teacher and sometimes even roles. Did you guys prescribe roles for your students in those teams?

Tim  9:44  

There were suggested roles, but there were no hard lines.

Ryan  9:47  

Yeah. You didn’t say like, okay, Sally, you’re going to be the recorder, and Billy, you’re going to be the one who holds everybody accountable? You didn’t do that kind of stuff?

Tim  9:58  

No. I think the danger there is then kids lock into roles, and ideally what you want in a team situation is you want to change roles, so if you very narrowly define them, then certain kids are going to pick certain roles every time, and they’re not going to want to do anything else.

Ryan  10:18  

Can you try to recall a situation where it really worked and you saw a team really accomplish something like in entre or elsewhere? I’m thinking more still within your teaching role.

Tim  10:37  

Yeah. My classroom memories are fading somewhat rapidly. I mean, entre’s pretty obvious for people who know the program, but if I think back to more of my middle school experience, there was a culminating project that I did in sixth grade. We studied colonial American history. That was the curriculum, and at the end of the year, I don’t even know if they still make these–remember this old Tom Snyder software simulations? If you guys remember those or even have them, the best way I can describe them is they’re almost like the choose your own adventure. There’s like five or six rounds of decisions, and then what the software does is, it’s very simplistic software by the way, I mean it came out like twenty years ago, but what it does is it shifts your options based on the prior decision that you make. The one that I used in this example was Revolutionary War. Now it’s not called the American Revolutionary War, but it’s sort of set like you get the same things. You have the colonialism, you have the oppressive royalty versus the colonies, and then the colonies are feeling exploited, and the crown doesn’t feel appreciated. They take all of those elements, and what you’re supposed to do is you just have to navigate the simulation which is very much like real life. It’s not like doing a Harvard case study where you know the answer and you just, oh, well what did they do, and then you study it. These kinds of simulations are more like alright, well what are you going to do, and then what are you going to do based on what that simulation kicks back to you, so in that circumstance, it was great to have teams of four because what would happen is the kids would get to a point where they would have three options. That’s where the magic happened because how do you decide on three very difficult choices? If you’re doing it by yourself, you could just go with your gut. You might not learn much, but when you have to do it in a small group and you have to articulate why you think the team should do something, I saw amazing things there. I saw kids contribute in ways that they had the entire year, and I think it was because they knew that it was a completely dynamic outcome and that it wasn’t just an exercise for the sake of teamwork.

Ryan  13:15  

Yeah. It wasn’t sort of predefined, it had some game elements to it, it sounds like.

Tim  13:20  

Yeah, very much so.

Ryan  13:22  

What else? I’m just trying to tease out other things that were making it work in that situation. The numbers, you said worked for what you were trying to get done.

Tim  13:33  

Time. Time was a big variable. I would use a timer. I put a timer up on the smartboard on the projector so everybody can see it, and you only had a certain amount of time. Again, it was a very real world thing because in real life, you don’t have the luxury of unlimited time or resources to make decisions. Sometimes you have to make decisions before you’re ready, and I think having that element of time and having the kids aware of it really forced, I won’t even say consensus, but some level of agreement. There were times when there were tears, there were raised voices sometimes, but what was different was it was always about the issue and not about the kid, and I think that’s what made that exercise so successful.

Ryan  14:26  

Yeah. I remember my eighth grade social studies teacher doing a simulation with us where he put us into groups, or maybe we chose. We might have like pulled straws out of a hat, or I guess you don’t pull straws out of a hat.

Tim  14:45  

That would be quite an interesting exercise there.

Ryan  14:49  

We might have pulled slips of paper out of a hat or something to establish groups. It felt very random, but once we were in groups, we were randomly assigned countries, so we became part of a country. Then he built some sort of scenario where he was like, here’s what’s going on in your country, these are the things you need, these are the resources you have, this is your relationship to these other countries, this is what you need from them, what they need from you. Tthere’s a little more setup, but then he kind of set this thing spinning, and then it went for a few weeks, and I was so engaged, and I know everybody in that class was. We felt like it was a scenario. I mean, going back to what you said, the outcome was unknown. We knew that whatever decisions we made in terms of partnerships with other countries or turning our back on other countries, I mean, we had to like back out of partnerships. It just opened up all this cool stuff to think about, especially for eighth grade students. When you have a group, you need consensus before you make decisions, so no one was really in charge. Before we decided what we were going to do in all these different scenarios, we had to at least have a majority opinion. Anyways, I guess I’m thinking about what we as teachers have learned from our teaching experience about collaborations and what we can take from those situations into our post-teaching or post-education lives. I wondered if you can think about what, if anything, from those experiences did you take with you? I want to get into talking about some of the collaborations you’ve had in your second act and what those have looked like. Maybe none of it has sort of carried over or applied.

Tim  17:15  

Well, it’s really interesting. I think we’ve touched upon this in a few different ways, but I’ve always been a musician, or I’ve always really been into music. I think I started jamming with other people when I was fourteen or fifteen. The past few years, I really haven’t been playing with anyone, but for most of my life, I’ve been either playing in a band or just having jam sessions with people, so in the creative pursuits, and most of them, especially in music, collaboration is just a given, like, that’s just how music is made. Of course, there are exceptions. You have your Trent Reznors and Prince or Dave Grohl, like you have these people who can play every instrument and record all their own tracks, but that’s pretty rare. Most of the time, you’re talking about artists who are collaborating, so for me, it was natural. When I started getting into publishing, it’s completely unnatural for writers. The traditional perspective and what most writers think about is sitting out in the woods in a cabin on a typewriter just typing away. That’s what it means to be a writer. Collaboration in the publishing industry and in the author world is a real challenge, and one of the things that I brought over from my classroom experience was this idea that you have to teach those skills, or more accurately, when you’re in charge of your own life, you have to learn those skills. Luckily, you know, being behind the desk for many years, I kind of knew what that felt like, but most people don’t. People our age, Gen Xers, we probably went to school in rows. There probably wasn’t much teamwork or group work when we were in school, so where else were you gonna learn it? You don’t necessarily learn it anywhere else, so I really had to remind myself that people and writers, the people I serviced in retreats or workshops or client work, that you have to work up to it. You were part of Authors on the Train, and one of the things that Zach and I talked about with that collaborative work was that you start with a short story. If you want to test collaboration, you want to think you’d be a good partner with someone else. You don’t sit down and agree on, you know, a fifteen-book series, you start with a single short story. Can we write a short story together, and what skills do you need to do that? What roles do people need to take, and how does that all work? That’s kind of where I’ve helped people through that. I think that’s the biggest lesson I’ve learned about collaboration, and I’ll say, too, I’m known as a collaborator in the indie publishing world, but the pendulum swings back and forth for me, too. I mean, I’m in a period of my life right now where I’m doing much less written collaboration and much more project collaboration, and that was probably the opposite five years ago.

Ryan  20:20  

Since you brought up Zach, can you talk a little more about that for the listeners? I know a little more about that collaboration because you guys talked about it a lot at that retreat, and it was fascinating. It was a really well-oiled machine, just the way you work together. I think that was part of what we were digging into at the retreat was how to establish collaboration, and you guys talked a bit about what majors work. Can you just go a little deeper into that? Like, where did it start? How did you meet one another? How did it evolve? You know, what became of that? I know what you guys published together, but if you could just fill in some of those details, too.

Tim  21:13  

Yeah, I’ll do my best on that. I was running the Horror Writer’s Podcast, and Zach was a listener. He would always comment and ask questions, and he was a really engaged listener. At one point, the guy I was co-hosting with, we decided we weren’t going to do it together anymore. I think Zach had mentioned, like, ah, I might like to do that, would you be interested in starting back up? That was sort of the beginning. Zach and I were co-hosts of the Horror Writer’s Podcast together for I want to say at least a year before we started talking about maybe working together, and it just so happened that as we were in 2015 or 2016, I guess, Zach and I were in a very similar life stage. We were both sort of in our day jobs and looking at a horizon where we might be able to become self employed, so we were at a moment in time where we kind of matched up with what we wanted. When we went to New Orleans with Joanna Penn and Lindsay Buroker, and I think that was in 2017, that was when we finally decided Zach was going to leave his job, I was not going to renew my teaching contract, and we decided that our best bet was to kind of lock arms and do this together to take both of our existing audiences, we had both been publishing our own books up until that point, and really just concentrate only on our co-written stuff. Over the next couple years, we published, I want to say, I don’t know, I’ve lost count, twelve, fifteen, eighteen books together. We had this really intense period of collaboration, and what we would do is Zach was sort of the drafter. He would get the rough words down, and then he’d just hand them off to me. Then I would do all the revisions, and that was sort of our general process. We were able to leverage both of our platforms, and we sold a lot of books, and it helped us along as far as our mutual careers were going. More recently, over the past couple years, we’ve sort of moved out of a similar life phase. He does the Writers, Ink. podcast with JD, and now, we’re still really good friends, we still have titles together, but we haven’t co-written anything together in over a year, maybe two, and we really don’t have any plans on the horizon. Part of that is because Zach’s daughter has got to the age where he wanted to be more like a stay at home dad. His wife makes most of the family income, and he wanted to be home with her. He wanted to be a stay at home dad which meant he had a limited amount of time, and he wanted to work on his own series. At the same time, I was getting much more into client work and author services and editing, and I didn’t have the bandwidth to do the co-written stuff, so it was kind of like this inverted funnel. We came together for a period of time, we collaborated a lot, and now we’re not collaborating as much, and we might again in the future, but a lot of that was dependent on life stages. It was definitely a means to an end. We’re really good at it. We’re not doing any of it now, but it’s certainly a door that will always be open for both of us.

Ryan  24:42  

At its peak, what made it work? I mean, when you guys were like churning out books, and you were just humming, how did that work?

Tim  24:53  

We had a little bit of luck. We had a good market position. Really our most successful series was a post-apoc series that we set in New Orleans, and our twist was, there were these vampire-like creatures that were invading New Orleans in the world and causing this thing. This was sort of at the peak of The Walking Dead popularity, and timing-wise, we had a million downloads, a million pages read in that first book in the first 100 days which was quite an accomplishment. Then over the past couple years since we released that series, coming up on four years, we’re up to like 3.8 million page reads, so we had that one really good series that kind of stuck, and I think the reason we had some of that success is because we had a system in place. Zach would sit down, and he would write the chapter, and we use Google Docs, so he would write the chapter in Google Docs, and he would ping me and say, okay, that’s done. Then a few days later, I came up right behind him, and I’d be revising. Essentially, we were writing a book in probably half the time it would have taken us to do it individually because we were drafting and revising at the same time, and then as soon as we were done with one book, we’d start right into the next, so we had books releasing every thirty to forty-five days. We just kind of had a system, and it worked because both of us were 100% in on that system.

Ryan  26:25  

That’s a lot of things coming together at once. You talked about life stage, you had similar goals, you had a common interest in a particular genre, so all of those things are lined up. You also complemented one another in terms of what you each were good at and wanted to do. The fact that he liked to do the initial drafting but didn’t like to do the sort of refining, but you were the opposite. I mean, right? I just think about all those things coming together at once.

Tim  27:07  

It’s not easy.

Ryan  27:08  

Yeah, and it seems unlikely. I’m thinking about all the tech that’s out there that supports matchmaking, like romantic matchmaking. I wonder if there’s anything out there that helps people identify potential collaborators? Have you ever heard about any tools like that?

Tim  27:32  

We’ve gotten that question so many times over the years, and it is unusual, and it’s hard. I always tell people, you see my success with Zach. What you don’t see are the fifteen or twenty collaborations that fizzled out, flamed out, didn’t work. There’s a big graveyard of failed collaborations in my past, and even us now, what we’re doing now is a collaboration. This is my opinion based on my experience, but I think life stage is the biggest, biggest indicator of a good match, and that’s why I’m not sure if an algorithm or an app would be good at that. It could be. I’m not talking about Zach, like I collaborated on a five-book series with Clint James, and he’s about my age, and he’s got kids, like there’s alignment there. JD Barker is my age, and we collaborated, so I think you look at what you and I are doing, you know, we’re the same age, we’re looking at retirement. What are we going to do with that time? How do we want to live that? I don’t think I could collaborate on the Transformation stuff with someone who was twenty-five. It wouldn’t make sense. So, part of me says I’m sure there are Facebook groups and things where you can jump in and find people with similar interests, and that might be a good place to start. I think a lot of times it’s just about trying stuff and realizing not everything’s gonna work. We have a long friendship, we kind of knew this was gonna work, but there’s no guarantee on any of that, and sometimes you have to go through some failed collaborations before you figure out what it is you want. That’s not a judgment on the other person, it’s just sometimes you’re not a good match or sometimes the timing isn’t right. What I tell people is it’s sort of like dating. If you sit in your house and you’re like, okay, I’m not gonna date until I find the exact right person at the right age, and they gotta have the exact right interest, same interest as me, you’re going to be sitting there waiting for a long time chances are, but if you just start dating and start meeting people and start socializing, you’re eventually going to start to connect with people in different ways. It’s not a great answer because people want the button, they want the hack, but I don’t think there is one. I think it’s a relationship building exercise. Sometimes it works great if you’re friends first, and other times, it doesn’t. It’s a very highly individualized process, but if you’re always on the sidelines, you’re never going to be in a position to start making steps forward.

Ryan  30:25  

Yeah. You just have to try it and be willing to let it evolve I would say.

Tim  30:31  

Yeah. Zach and I had aspirations that were aligned, but neither of us dug our heels in and said this is how it’s going to be. The whole Authors on a Train thing wasn’t planned. We didn’t sit down and be like, let’s create this wonderful retreat for writers. That was because Zach reached out to me, and then I asked him to join the podcast, and then we started writing together. We both love New Orleans. We wanted to go there, and then we decided to take a train. We asked the ladies to come with us. At the end of that trip in a conversation over a couple beers in the French Quarter, Authors on a Train was formed, but that was not a plan, that was all an evolutionary process that came out of our relationship, so you just kind of have to have faith in that. If you have a gut feeling it’s the right person, keep going, and if something doesn’t feel right, maybe you stop, but you can’t necessarily map it all out ahead of time.

Ryan  31:35  

Is the Authors on a Train stuff still documented out on the interwebs?

Tim  31:42  

Yeah, we still have authorsona train.com. I bought that domain, and we have a landing page there. I think it’s the last one, but that’ll give you a sense. That’s the sales page for the last trip that we ran, that’s still up.

Ryan  31:55  

I think we talked about this on a previous episode, but you’re still going to do some versions of that in the future potentially, right?

Tim  32:03  

Yeah. That’s probably a q2 or q3 2021 conversation Zach and I have to have. People love them, we love doing those, and we’re hoping to continue those. The other thing is, every one of those, and you’re involved in this, too, we publish this short story anthology, and that’s kind of nice because people can see what’s the end game, and I think that having that common goal is a great way to drive collaboration instead of just having some open-ended like, well, let’s just write together and see what happens, we’re like, no, let’s go write short stories and publish an anthology. Having that direction is helpful.

Ryan  32:44  

I think you’re onto something with the whole life stage thing. I do think that’s a critical element because I’m thinking about people. I have friends that cut across all different ages. I have some that are older than me, some that are my age, some that are younger, but especially like that ten to fifteen year difference, you know, there are people that have young children in the house. I remember those days, and I loved them. I was totally, completely engaged as a father and a husband, and I wouldn’t change anything I did, but I also think there’s part of me that’s kind of glad that I’m past that point. It’s not like, oh, I’m done being a dad. I still have a great relationship with my kids, I still spend a lot of time on it, but it’s just different in the sort of constraints that exist at that life stage. It would make it hard I think to collaborate with someone who was just in a very different place.

Tim  33:59  

I think that’s part of why Zach and I are not working as closely together now, like his daughter’s five. That’s a whole different parental experience than when your daughter’s fifteen and your son’s eighteen, so yeah, I totally agree with that. I have said that on trips and things. We think that’s overlooked a lot. People discount similar life stages, but I think that really matters.

Ryan  34:26  

Well, even you and I, we’re at a similar life stage, and we are building on a friendship, but there are times when it’s hard for us to work things out just because the fact that you are post-career, and I’m not yet. Every week, I’m always embarrassed because of how long it takes for me, you know, I’m always like last minute trying to get my setup going and everything, so that chews a lot of clock, and I don’t know. To be honest, I think this is our eleventh one that we’ve recorded, I’m actually surprised that we’ve been able to keep it going because I just assumed this is gonna be hard to maintain, but I think we’re committed.

Tim  35:20  

We all have twenty-four hours a day, no one gets any more. We prioritize what’s important. I think this is important to both you and I. We make it happen even though it’s not easy.

Ryan  35:29  

Yeah, and I guess we talk a little bit about how we divide our labor up at least when it comes to the podcast. Do you want to explain that?

Tim  35:46  

I think generally speaking, you sort of take the lead on the front end, and I take it on the back end. Your primary responsibility is coming up with topic ideas and thinking about questions and how we want to frame conversations, and you did a lot of that work in a big batch up front which was nice because now we kind of have a reservoir of of things to draw from, so you kind of present that and frame that conversation. My role is to then take that and with my wonderful virtual assistant, my lovely daughter, to package it into something consumable, so that’s where we take it. I do the audio editing, and then Brenna does the transcription and the show notes and the graphics. We’ve got you on the front end and then me on the back end, and then we come together for these conversations, and I think that’s a really nice balance. It feels good. It feels like we’re both really invested in it.

Ryan  36:47  

I agree, and these aren’t hard boundaries or roll definitions. I mean, you’ve decided on a few of our topics so far, and I know that will continue, and sometimes you lead the conversation and ask more questions.

Tim  37:02  

And with the newsletter, we’re splitting the writing responsibilities. That’s another aspect of this that we haven’t really talked too much about yet on the podcast because we don’t have an audience yet, but very soon we will. That’s a big part of this, too, is having that weekly communication that gets sent out, and we’re splitting those responsibilities.

Ryan  37:27  

I think we’re gonna run a little shorter today because both of us have appointments, but any sort of last thoughts you want to throw in about just collaborations in general? Any recommendations we can make for people or observations we can make about things that we’ve seen that either worked or haven’t worked out there?

Tim  37:55  

I would say what I’m doing, what I’m actively doing, what you and I are doing is about  all I could say from my own experience which is seeking out people who have similar values, experience, and aspirations that line up with mine. Most of the time, it’s life stage, but it doesn’t always have to be, but I think just observing what’s happening around you and taking small steps, and it might be something simple, like meeting someone for a coffee or joining a Facebook group of like-minded individuals. Again, you got to get off the sidelines. People aren’t going to magically find you, so I think if you’re interested in building something with someone else, which you should be, then taking small active steps towards that is the best way to do it in my opinion.

Ryan  38:47  

Yeah. I also think it’s important to know who you are and know what you like to do, what you’re good at, and try to align with people who you can compliment in some way.

Tim  39:01  


Ryan  39:03  

I feel this a lot at work. I’m probably thought of as someone who doesn’t collaborate or doesn’t like to collaborate, but it’s not really that. Here’s what I don’t like: I don’t like to come into a room with a blank whiteboard and try to frame out some concept with a group of people from scratch. I know I struggle with that because for me, I need to process something mentally without it going into fifty directions along the way. Did you ever see this? There’s a video that was going around out there for a while. It’s out on YouTube. How to Write a Mission Statement that Doesn’t Suck.

Tim  39:56  

No, but it sounds like the kind of video I would enjoy.

Ryan  39:59  

I really recommend it. It’s out there on YouTube, and these are the guys who wrote Cash. I’m trying to remember the book they wrote at the moment, I’m gonna forget it. Made to Stick, I think.

Tim  40:18  

Oh, yeah.

Ryan  40:22  

This video is hilarious, but for me, it captures everything that is broken about this idea of like, oh, every time we need to create something, we got to get a group of people into a room and whiteboard. If you just watch this video, it all sort of makes the case for me. Again, it’s not that I don’t want to collaborate, I just don’t think that’s the way to do it. For me, stylistically, I like to come into a room with something that’s been formed already, sort of like a draft of something and ask people, and I think it’s great when multiple people do that and can compare and contrast drafts, but anyways, I recommend checking out that video. It’s hilarious, and it captures the challenges of working with other people on idea stuff.

Tim  41:17  

Nice. Alright, I’ll check it out. Thanks for listening. Go to teachingtransformations.com and get instant access to Transformations, the free weekly email with the best personally curated resources to help those in their late 40s or 50s to design a post-career life.

Transcribed by https://otter.ai


HOW TO WRITE A MISSION STATEMENT THAT DOESN’T SUCK – https://entrepreneurial-life.today/how-to-write-a-mission-statement-that-doesnt-suck/ 

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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