Introducing Teaching Transformations
Welcome to the first full episode of Teaching Transformations! Retired teacher, Tim Desmond has teamed up with current teacher and administrator, Ryan Wooley to discuss why it’s important for us to be thinking about how we’ll spend our time in retirement. The two old friends and former colleagues discuss their past and hopes for the future.
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!
In this episode, you’ll discover:
- Who we are
- Why we’re here
- What we hope to accomplish
- How we can help you start to think about what happens when your career is over
Transcript:
Tim
How’s it going? It’s okay, man. Uh, you know, it’s it’s early 2021. And it’s it’s a sunny day in Cleveland.
Ryan
Yeah. Well, that sun makes a huge difference. It does. I had a couple of options for where to set up to record this today. And I picked the one with a lot of Windows.
Tim
Yeah, I think that’s, I think that’s a good call for sure.
Ryan
I just want to say, I’m so excited to reconnect with you over this project. You’ve always been one of my favorite people I really loved when we used to work together. And I’m glad we’ve been able to stay in touch. But I think this is gonna be a lot of fun. And I’ve already had fun, just, you know, talking to you over the past couple of weeks.
Tim
So, likewise, man, I know we’re gonna, we’re gonna get into this a little bit, but like, I, I had this idea for a project like you, you were the top of my list, like, I was, like, if you weren’t, if you were gonna say no, then I would develop a list, but I didn’t have one other than you.
Ryan
That’s funny. I’m flattered.
Tim
take it for what it’s worth, you probably won’t get many more compliments.
Ryan
Um, so I think it’s probably useful for us to start with just who we are. And I think, you know, we’ll get into, like, what we think we’re doing here. But who are you, man?
Tim
Who am I? You know, that’s a that’s a harder question than it seems on the surface for me, because I’ve been living sort of like a double life for the past 12 to 15 years. So I’m Tim Desmond. But I’m also J. Thorn. You know, I’m, I’m an educator, but I’m also an author and a publisher. And, you know, we’re gonna explore that a whole lot more, but I’m a guy. I’m a Gen Xer. I’m a family man. I’m a parent. I’m a husband. I’m a music lover. I’m a reader. And I’m starting to sound like Atlantis Morissette. Who are you?
Ryan
Funny, a lot of those same things only I don’t have the dual identity thing that you have going on, we’re definitely going to dig into that. That’s, that’s been an interesting, really fun story to watch unfold. Yeah, I’m a technology director for a school. I’ve been working in schools for a long time. I used to be an English teacher. Before that I was an English major. I think long ago, I thought I was gonna be a writer and sort of like a writer, maybe writer slash lawyer like John Grisham style, but I ended up going into education and, and so I’ve been working in the field now for gosh, 20, some 23 years, I think. My wife is curriculum director at a public school. We met in our our teaching program.Three kids, like you lots of, you know, love for music, lots of hobbies. That’s kind of my story. Gen Xer.
Tim
Yeah, I know, we were colleagues for a long time. And and I you know, that’s gonna come out in the conversation, too. I don’t know if we’ve mentioned that yet.
Ryan
Yeah, why don’t we just go there? How I’m trying to I was looking at stuff last night to just try to put it on a timeline. I know I started here, I still work at the school that you used to work at. And I started here in 2008. So we, I’m sure we met. Soon after that. I started a one to one program here and you. You were a sixth grade teacher at that time. And a techie teacher, you are always I saw this in some of our early messages. You were like, asking me questions about why is class pages down and stuff like that.
Tim
That would be me.
Ryan
Though, we think that’s how we got to know each other. As you know, I was the tech director, and you were a tech, very tech savvy, middle school teacher. We kind of connected there. And then you became an ally in that, in that program. We started the one to one program, you were a really key sort of early influencer. And so I think after we became friends, it was a couple years later, I think this was like 2011 or something like that. We were moving that program into the Upper School. And that’s when I needed somebody like you at the Upper School and I think I was you were like the only person I thought I was you were the first person I call him and luckily, you were interesting.
Tim
Yeah, I started the school in 2004. And, and I vaguely remember the interview process. I think I remember saying at the time to hire anyone but Wooley but you know, I didn’t wasn’t carrying much clout then. So they they went against my wishes. But yeah, I think we I think we bonded pretty early on in the in the late 2000s. Because we know we were and are in similar life stages, we kind of grew up in a in the same part of the country, we kind of have the same values. You know, I was a teacher for 23 years before I, well, I don’t know, if I retired, that’ll be another conversation. But before I left education, so Yeah, I agree. Like, you know, whenever you get into a workplace, I think you have sort of colleagues and then you have people who are more than colleagues and eventually become friends. And I think that’s what happened with us. So it was great to work sort of with you and under you and, and and supporting, you know, what was happening in the Upper School and we had several professional relationships over the years.
Ryan
Yeah, I even dug up some, like, I found this early exchange.
Tim
Oh, no.
Ryan
Soon after we started to work together. This is a I’ll just read it sort of back and forth. This is you. When are you leaving Ohio? Noonish. I’m at Lyndhurst right now. Okay, I’ll wait until one o’clock to ransack your GM office. Okay, pee in the corner. You: already did or so to get back, you know, to talk to you when you get back. That was kind of the nature of our you know, when I think about that time, it just takes me back to, you know, watching this journey unfold for you. And I think that’s going to become a big part of what we do here is I think your story is one that that we we need to capture and tell because it’s a really interesting one, and it can connect to you know, a probably a lot of our, our listeners stories, assuming we have listeners at some point.
Tim
Yeah, I think too, like, it’s, it’s also good to recognize that we were being very thoughtful about this podcast and about telling our stories. But, um, we’re not scripting things and, and, and, and, and part of this process is our process of starting this project together. That’s, that’s a roundabout way of saying that, that this is not going to be a highly produced NPR style show. Like we’re, you know, we’re working through this organically and naturally, things are gonna kind of change and evolve over time. And we’re as much exploring this process as we are our past.
Ryan
And we’re not gonna we’re not going to pretty it up. We we want people to see that. And we want to bring them into this process, even as we make, you know, pivots along the way.
Tim
Yeah. Because, you know, like, in any good story, you know, there there were and are down moments, and there are things that we know, we’re going to talk about that aren’t going to be pretty So yeah, I think that’s, it should go without saying, although not all, not all podcasts, take that approach. So it’s good that we’re kind of putting our stake and ground around that, that level of authenticity, meaning that like, it’s warts and all here.
Ryan
Well, that makes me feel better already. Um, so that’s a good segue. Actually, why don’t we back up? And just sort of address, you know, what do we think we’re doing here? What What is this?
Tim
So this is a well, I’ll take I’ll take the mantle for this because I, I came to you with this idea, although you were having an are having very similar thoughts. But you know, as we record this, it’s it’s January of 2021. And we just finished one of the most incredible years, we might ever experience in our lifetimes in our generation. And even before the pandemic started. I knew like I’m turning 50 this year, and I’ve never really given much thought to my age before. I don’t know how you are with that, but like, it’s, I really started thinking more about it. And I was like, wow, 50 like that. That’s a that’s a different kind of milestone. And I started to think about like, Okay, well, like technically, I could start drawing on my retirement accounts at 59 and a half, like that’s not even 10 years and I think back like 2011 doesn’t seem that long ago. So I started getting into this this highly reflective somewhat nostalgic for lack of a better term mindset of like, well, what am I going to do with the rest of my life? And not not the question that you asked when you’re 23. But when you’re 50, and and and you see that horizon, and you know, you don’t have 40 or 50 or 60 years ahead of you, and I was really starting to question like, what is it I want to do? What kind of impact do I want to have? And, you know, I’ve, since 2017, I’ve, I’ve been self employed, I retired as a teacher and started my own business. And and I became this J. Thorne character. And now I, you know, I wanted to think about, okay, well, where do I go next? Like, what kind of impact do I want to have next? And I started thinking around this idea of, well, what’s what’s it mean to be retired when you’re a GenXer, or when you’re a baby boomer like retirement, it looks different now than it did 10 years ago, or 20 years ago, or 30 years ago. And there’s a lot out there around how you get to retirement, there’s a lot of financial advice that you can consume is the fire movement. And and there’s, you know, there’s, there’s a ton of information. But there’s not a lot out there talking about, what do you do when you get there? Like when you wake up and you’re retired, and you don’t have to go anywhere, you don’t have to do anything. You know, sitting on a beach for a couple weeks might be cool, or, you know, watching TV for a month might be cool, but what do you do with the other 30 or 40 years you’ve got? So I think that’s kind of what this is, is like trying to figure out like, what is that gonna look like for us? And how can we help other people who are going to be in that same situation?
Ryan
We’ve talked about this, I don’t you know, that the word retirement just, I don’t know why, but it just bothers me. Like, it conjures images of me, like, taking my Walker out to the mailbox. In a bathrobe. Exactly. So, and we’ve talked about that, you know, post career life, I think there are different ways of thinking about about this. think we’re using the term retirement because it’s, it’s what people understand. But I think that we’re really looking at many different flavors of what that means. Like, you know, we’ve already started to scratch the surface on your flavor. How old were you when you retired from teaching?
Tim
Yeah, I guess I’m in unretirement, as Brian Clark would say, which I just discovered, he’s kind of coining that term. Brian Clark from Copyblogger, and a fellow GenXer and sort of one of the one of the first guys who was early on in blogging. Yeah, I agree. I don’t like the term retirement. I don’t. And retirement is a mouthful. But like, we don’t have anything better yet. So you and I are going to be kind of figuring that out as we go. I mean, we talked about post career and other other terms for it. But, uh, yeah, I mean, I technically in 2017, I did not renew my contract at the school, which meant I was technically retired from teaching at and that would have been at age 46. And so here we are coming up on four years later, and I have a stable substantial author business that supports my family and my mortgage, and I have one kid heading to college and, and the other one, three years from now, and, and making a living doing it. And and I think, you know, for me, the idea of retirement isn’t doing anything, it’s more about the freedom to do what I want, when I want and how I want to do it. And so, so yeah, I don’t know what the term is. I, I’m kind of there. It’s kind of weird. And like, I’m, I’ve dealt with and deal with some of the same issues that traditional retirees face. And like, you know, you lose a social network, you lose friends, contact with friends, you you lose the collegiality that you have in a workplace. I lost all that, even though I was only 46.
Ryan
And I remember you talking about a lot of that. It’s, it’s funny, like, I didn’t, I never thought I still don’t think of you as retired. I just, I thought you just transitioned your career, but, you know, and I don’t want to get too caught up on on sort of, you know, this term or the definition, but it was just more, I’ve just wanted to try to unpack, you know, my own conceptions about this stuff. And, and I think you represent, you know, a non conventional sort of timeline and in approach. So, you know, I mean, and I think we’ve seen everything from that to you know, people who retire very conventionally, you know, dude put in a foot. We were friends with a lot of people that we’ve seen who were just a little further along than us who, you know, put in a full career in teaching and then you know, put away their chalk, and now they’re retired. It’s funny you say you talk about the loneliness and stuff I don’t think I’m great at keeping in touch with. I mean, I had some pretty close colleagues that that retired and I’m just not the best at keeping in touch with them. But I would love to go back and ask some of them, you know, like, What are you up to? What does it feel like all those? Well, let’s, I want to dig into your story a little bit more. It’s, like I said, it’s been, it’s been fun to watch. It’s been surprising to watch, I never expected you to leave your teaching position four years ago.
Tim
Me neither.
Ryan
And I mean, how you got there? It’s, I guess, I, you know, I, I watched it happen, but I don’t know that I fully understood sort of where it came from, and how much of it was pre planned versus just sort of figuring it out as you went. So, you know, why don’t we dive into that a little bit? I’m, like, what drove you to establish your independence? And did you know early on that that was a goal you had?
Tim
I wish I could say I did. I had some master plan. I think I was being very reactionary. You know, I just I’m sort of doing a lot of research and reading around our generation or, and, and people who are retiring now. And there are a lot of studies that suggest that the happiness curve hits a valley in your 40s. And it starts to come back up in your 50s. And that people as they age, they are technically more happy. And there are there are various reasons why that’s the case and theories as to why that’s the case. But I think I hit the trough. I think I hit that low valley in, in my early to mid 40s. where, you know, I looked up at one point, and I kind of had that thought, like, Is this all there is, and it sounds like such a privileged position to be in to be able to say that, like I recognize there are a lot of people who, who struggled to just survive every day. And here I was in a position where I had a great stable job at a great school, making decent money, you know, owning a house in a good neighborhood. And there’s a sense of guilt I had of like, Who am I? To like scoff at that, like, Who am I to ask, Is this all there is? And so I, internally, I wrestled with this, this feeling of like, being grateful for what I had, and at the same time, recognizing that I wasn’t, I wasn’t manifesting my best self, like, I just felt like I had more to give. And so I think, what happened was I right around in the late 2000s. And, you know, we’re both tech guys. So this is not surprising. I was sort of watching what was happening with Amazon, specifically Amazon and Kindle. And I was really intrigued by this ebook concept. And I was, early on, I was sort of a fan of this, I thought, Wow, it would be great if I could have a device that looked like a book, but I could fit hundreds or 1000s of books in it, and just just read that, like, to me, that sounded like a dream as a reader. And, and so early on, in that, as I was consuming it as a reader. I started getting these thoughts like, Well, why couldn’t you try this? You know, like, because I was reading parallel articles of people who said, like, Oh, yeah, they’re opening up this thing called Kindle, Kindle Direct Publishing. And you don’t need an agent. And you don’t need a publisher, like you can upload a Word document, and you can sell it directly on the Amazon Marketplace. And in 2008 2009, that was world shaking. I mean, we take it for granted now. But like the ability to be an artist and reach your, your global audience directly, was a paradigm shift that I had never felt in my life. And so I know, I’m being a little esoteric about the answer, as opposed to practical, but I kind of just had this feeling like, Well, why not me? Like, why not? Why not try this, like, what’s the worst that could happen? And at the time, I was, I was playing in a rock band, and I’ve been in bands my whole life as a musician and in the band. We decided that our real names weren’t cool enough. So we came up with the stage names, and my stage name was J. Thorn. And I took the J was my middle initial, and Thorn was one of my favorite songs of one of my favorite bands. So So I thought, okay, J. Thorne sounds like that sounds like a frontman for a heavy metal band like Tim Desmond does not right. And it’s all the band, all the guys in the band came up with with the stage names. And, and so it sort of naturally bled over and I was like, Okay, well, if I use a pseudonym, and I fail miserably, no one’s gonna know. So why not try it? And I think that was that was the that was the real genesis, I didn’t have a master plan. I wasn’t like, I didn’t have a 10 year plan. I didn’t have a 10 minute plan. I was just like, I’m gonna try this. You know, as a teacher, I have the benefit of having some time on weekends, some time in the summer, depending on how I, you know, manage my other responsibilities. I had the bandwidth to try it. And and so I was like, why not me?
Ryan
Wow. That’s hilarious. You basically you just poked at this. You’re like, Oh, this is interesting. I’m gonna try this.
Tim
Yeah. Yeah, pretty much. I mean, it was it was a pretty big poke, because I can remember in I think it was, I think it was 2000. It was either 2008 or 2009 is when I started drafting my first novel. I read Stephen King’s on writing. And I was like, Alright, rub my hands together. I’m all set. What else do I need? I had it all figured out. So I sat down, and I wrote like, 135,000 word epic fantasy that was god awful. It was so terrible, but I thought it was like, I thought I was doing it, you know. And it took me like, it took me 10 months. So it wasn’t like, it wasn’t like, Okay, I’m gonna set up my KDP account. And that’s me poking at it, like I did it. But I didn’t have any clue as to what I was doing. And even several years later, I still didn’t have like, in 2012, which, you know, we’ll get into that. And, and even in 2014, when you came to see me speak, I kind of told my horror story of starting out. But yeah, I didn’t have a clue. And, and, and I had, I think, like you I’m a bit of a I’m a dilettante, and I like to dabble in things. And I like to experiment. And, you know, I experimented with, with music. And I experimented with entrepreneurship. And I experimented with a number of other things. But it was this writing thing, for some reason that I, it was something it was something nagging at me in my in my brain that I couldn’t let go. And I think that’s, it was that sort of chasing that, like, I remember reading Lord of the Rings, which was the movies that come out in in the mid mid early to mid 2000s. And I remember, like an idiot reading Tolkien going, Yeah, I could do better than this. And I think every every author has to have that, like, you have to have that sort of mix of, of ignorance and ego to go like, yeah, I could, I could do this. I could I could write something better than this. Because otherwise, you’d never get off the starting block. So yeah, I poked at it, but I poked at it for a good while.
Yeah. Wow, I that’s interesting. I don’t think I knew that backstory. I think I just especially given sort of how quickly you became prolific. I think I just assumed, like, this had been sort of just a nagging urge that you’ve had for a long time to go into writing and, you know, and then the floodgates open, and it all just happened. But I mean, I know it didn’t all just happen. It took a long time to grow that, but I think about I mean, you know, how many years ago is that now? 12.
Yeah.
Ryan
Years is ish, right? I mean, how many? you’ve published a ton of books. And you kind of got going pretty quickly with that. How? Tell us a little bit about, like, how many, you know, where you are in your publishing career right now?
Tim
Yeah, I’ve heard my wife and other women describe childbirth, in that if, if the memories were strong enough that no one would ever have a second child. Because like, there’s sort of this selective amnesia that happens with women where they know they give birth and that physical, the physical sensation and pain is a memory they forget. Otherwise, they wouldn’t do it again. And I, I think for for me, and for writing, it’s the same way. Like I think every time I finish a book or novel and I publish it, I forget what it took to get there. So yeah, it’s, it’s hard to quantify because the publishing landscape has shifted dramatically, since 2009. If you’re a reader, you might not have the same sense of it as you’re an author, but the ability to self publish on Amazon radically changed the game. And one of the in one of the ways it changed it is it changed the definition of what we call a book. It started starting or well onto the onto the path of distorting the medium. And so when people talk about a book now a book could be a 20,000 word, document, or it could be 150,000 word novel. And so people just call book, right. So it’s hard to define, you know, what what a book is. But something objective that I like to use is word count. Because that’s something that’s measurable, no matter how those words are, are dispensed. I’m, I’m ballparking it, I’ve published about over 2 million words of fiction. You know, if you look at my Amazon page, there’s a couple dozen titles. But again, some of those are short, some of those are long, I have about a half a million words that I published, and then unpublished because they were so terrible. And, and there was a point i’m not i’m not at this pace. Now, I don’t think this is a it’s not a sustainable pace, at least it wasn’t for me, but I was at a pace in the, you know, early 2010s, where I was publishing three and four novels a year. So that that would be, you know, a quarter million words of fiction a year. And so yeah, once once I kind of once that writing bug got into me, it was sort of became a compulsion. And, and so that’s, that’s where a lot of that productivity came from. And I think that’s a, that’s a natural trajectory for a lot of novelists and that you kind of start out writing a ton. And then the more you get into it, the the less words you produce, but I think they’re better quality words.
Ryan
And, but, I mean, you still had your full time job when you started all this? How did? How did you do that?
Tim
I don’t know. You know, in, in 2009, my kids were six, and three. So finding, like, you know, finding the, like, they’re teenagers now. So they don’t even care if I’m in the building or not. But like it that you know, and six and three, you know, like, they’re, they’re there, there’s demands there, there are requirements that you the kids have. And for years, I would get up an hour before I had to. And that hour was when I did my writing. And it fluctuated, sometimes I would get up at 430, sometimes I would get up at five. But the idea was I gave myself an hour of uninterrupted time to get my words in before my day job started my teaching started before kids were, you know, asking for milk in their cereal and asking me to tie their shoe. And it’s, it’s not easy. It’s not glamorous, it’s not sexy, but like, that’s what it took. So there were years, literally years of me getting up an hour, an hour before everyone else just to get those words in.
Ryan
I remember you using the word side hustle. And you know, that’s definitely what it what it looked like, from my vantage point. I mean, because I you know, we were talking about your, your writing and sort of how much you’re doing. I’m like, gosh, has he even is even doing work while he’s here? Because how is he getting all this done? But I mean, some of that just ties to your work ethic. And you know, you’re a person who I’ve always admired your ability to just make things habit and really stick with things. And I know that’s, that’s a big part of why you were able to be so productive. So early on.
Tim
The other part of that was, man, I was having a blast. I was I was so much fun. Like, I think that like that’s not an that’s not in our in the in the general Zeitgeist enough, like this idea of, are you having fun. And I think in my early to mid 40s, I lost that, like I, whether it was the burden of responsibility or being, you know, the primary wage earner for my family, or the responsibilities of being in a teaching position or other factors, like, there were things I was doing, I was good at, but I just wasn’t having fun. And for me, like, it sounds crazy to get up at 5am. Because, and sit and do something that most people consider a punishment. Like most people consider writing a punishment like, you know, whether it’s in school or at home, it’s like, oh my gosh, don’t make me write words yet for me. Like I would I couldn’t wait to get up and get to the next scene. And and I think that I would like to say I’m, you know, I’m so disciplined and I’ve developed these habits, but just like the like being in a band, like I would sacrifice a few hours of sleep once a week for band practice. It wasn’t easy, but man, it was fun, right? Like there were there were moments where, you know, it was we’re here in Cleveland. This time of year, it’s dark at five. It’s 10 below zero, I get a load all my amps up into the car. Like that all sucked. I just wanted to stay on the couch. But man once I got the band practice was so much fun. And that’s what kept me going for week after week. I think there’s an element of really enjoying what you’re doing that that gets overlooked a lot.
Ryan
Yeah. And that’s something we’re gonna have to dig into a lot. I mean, this isn’t, you know, this isn’t going to be just about sort of process. And it’s not, this isn’t a how to write this is a, this is going to be about sort of discovery and rediscovery, because that’s what a lot of people do, I think when they, you know, make make these kinds of transitions in life, they figure out who they are, or who they, you know, they can be sort of who they’ve been waiting to be almost.
Tim
Yeah, it’s, you know, we’re hopefully going to be aspirational here. And I think one of the one of the real top level object objectives I have with doing this podcast and working on this project with you is that you don’t need to, and you shouldn’t wait until you get your, your gold watch, or your placard when you retire to be thinking about this stuff, like whether you’re, whether you’re 30, 40, or 60, you can be thinking about these things you can be thinking about the hobbies, or the past times, or the experiences you’ve had, that were so much fun, or that you really enjoyed, and thinking about what those might look like post career and like. So that’s what we’re talking about now, like, I accelerated that. I moved that way up. Because I was too stupid to know any better. You know, and I did that at 46. You don’t have to do that. 46. But you can start thinking about it, you can start planting those seeds. And hopefully, that’s something we can help a lot of people with.
Ryan
Yeah, I mean, you know, in many ways, that’s what I’m trying to do. I mean, I, I’m still in my full time job. And as far as I can tell him, I’m still gonna be in it for a while longer. But I’m starting to think about it like, you know, I’m approaching 50, I am a year younger than you, I just need to make sure we’re clear on that.
Tim
Yeah, definitely gonna make that clear.
Ryan
But, you know, yeah, of course, I’ve been thinking about this stuff. I mean, my oldest is in college, he’s in the middle of his freshman year, my youngest is a freshman in high school, and he’s taller than me, I’m like, you know, I’m looking, I mean, four years down the road, my youngest is going to be in college, and I won’t be driving all over the place. I mean, that’s going to change probably in the next year or so if nothing else, I’m just gonna have found time. And, you know, I, I want to make the most of that I want I want to, I want to be purposeful about designing that, that time and figuring out, you know, like, just hearing you talk about the writing, like, you know, it lights you up, I want to make sure that I’m sort of structuring my life in a way that I can do more of what lights me up.
Tim
Yeah, I think that’s, that’s key. And, and it’s okay to that, that changes over time. And I think that’s something else I want to be really conscious about. And when we because I’m, you know, I’m 11 or 12 years into this already, even though, you know, I, I didn’t leave my job until 2017. I started this many, many years earlier. And, and I think what lights me up now is not the same thing that lit me up in 2009. And that’s okay. You know, like, I, I think the important thing is to be thinking about, what what are you going to do when those external forces are no longer in play? So whether you whether that is your boss, your job, your clients, your physical location, like, what when those when those are released? What are you going to do? And that’s what I can’t wait to explore. And, and I know that like, you’re not, you’re not there, you’re not where I am yet, but I’m not where I am yet. Like I, you know, I’m looking ahead at at, you know, the next 10 years, the next 15 years, and I’m thinking about, what do I want to be doing 10 years from now, it’s probably not going to be exactly what I’m doing now. Right?
Ryan
Yeah, I think there’s, there’s just so many different pathways, there’s, there’s going to be so many different stories that we bring into this, everybody’s going to have their own reality. You know, I look at your path as a really interesting one. It’s not one that I think I could have done, even if I sort of had the conscious will to try it. It’s just it wouldn’t have fit into my life pattern. Right. Right. And, but I’ve admired it, and I think it’s interesting, and it’s a good point of reference. And I, you know, I guess I hope that’s something that we’re able to do here is to give people a variety of points of reference like that, like, here’s, here’s what one path could look like. It could be pretty aggressive, and it could, you know, if you’re sort of here, maybe this leads you to a post career life sooner than you thought you might get there. There are ways to do that, right? But there are there are also ways to sort of happily continue on the path that you’re on, but sort of be ready to make the most out of your, you know, your post conventional career life.
Tim
Yeah, I mean, I will get into the specifics of this. But in 2017, when I decided not to return to the classroom, I had two monthly paychecks that will come my way because I opted for my my my salary disbursement to come over 12 months, so I had two paychecks, I knew were coming. And nothing after that. And I had, I was at that time, I was making about $300 a month from book royalties. So I joke all the time, and I’m like, I would never, ever give that advice to anybody, but like, but on the other side of that I had this desperation of like, Okay, well, this is do or die. Like, there’s no safety net here, I’m either gonna make this happen, or I’m not. And, and, and there was sort of, no, there was no buffer there. So I think what I want people to hopefully take from my story, and something we can help you and everyone else do is to find that, to find that trajectory that best suits you, your level of risk, your level of interest, your timetable, like you don’t have to quit your nine to five job to start thinking about what you want to do post career, you can start planting those seeds, you can start doing things decades prior, that will put you in a really good position once you get to the moment where you’re going to have to make some hard decisions. Right.
Ryan
Yeah, I mean, you know, I can’t imagine making that move that you made. That was that was a bold move. That would be scary.
Tim
Some say it’s bold, some say stupid, but I think both work.
Ryan
I mean, it’s worked out. And there’s something to be said for going all in. And, you know, so I mean, that’s, that’s the thing that’s really, for me inspirational about your story is, you know, you, you sort of like cut away your safety net, you’re like, I’m gonna force myself to make this happen. And you did that, and, and I just I, I still, I’m sort of astounded that you pulled that off, but.
Tim
Well, thanks, man. And, you know, the payoff for that is that I retired from teaching at 46, that that’s the payoff, right. So if if you’re, if you’re thinking about, you know, your what’s coming after your career, you don’t have to make that sort of drastic decision. If you already know you’re good for you’re good until you’re 55, or you’re good until you’re 65, then, like, that’s not one of the variables you have to consider. So, even though the risk was great, but but so is the payoff. And that’s, that’s true with any decision we make in life, right, the greater the risk, usually, the greater the payoff. And, and I also don’t want to, I also don’t want to get caught in resulting. So I love Annie Duke, she wrote a great book around, she’s a professional poker player, and she wrote this great book around decision making process. And what she says is that poker players get into trouble when they start resulting. And what that means is, you look at the results of a decision, and you base your decision on the results. And that you when you hear that you go, Well, yeah, Isn’t that how it should be? And it’s like, no, it’s completely wrong. Like, because my story is a perfect example. I made a terrible decision. But the results paid off. But that was not the good, that was not the decision to make, right? Like the the best decision would have been to have a year of savings, or to have investments that I could live on or to have rental properties that could fill a gap like, then making that decision would have been a good decision. So I made a terrible decision. And I and I got lucky and it paid off. But that doesn’t make it a good decision.
Ryan
I’m just processing that. I think I do that a lot. I mean, I really do kind of measure decisions based on the results. But you know, who, like the results sometimes are completely accidental?
Tim
Yeah, I mean, a lot. There are some things that are in your control. But there are many things that aren’t like, you know, there’s a certain like, here’s an example. And in my story, I happen to meet the right person at the right time, who gave me advice on a book cover. And that single conversation led to me getting 34,000 downloads on a book promo, which then led to me kicking off my my publishing career as an indie. But I, I didn’t plan I didn’t make a decision to meet that person. I didn’t. I didn’t intentionally arrange that conversation. So yeah, it’s resulting is dangerous. It’s what we naturally do. It’s the wrong way to look at it’s the wrong way to analyze your decisions because there’s just so many things that are not not in your control.
Ryan
Right, but I mean, the other side of that is intentionality, right? Like you, you actually, you know, you put your you actively put yourself in a position to sort of have conversations like that. And that’s kind of the other side of it, too. It’s not this isn’t. This wasn’t accidental, you didn’t fall into anything you did your opportunity, right?
Tim
Yeah. I mean, it’s the old Ben, I think it’s the Ben Franklin quote, right. Like, you know, you are as Henry Ford, you know, you create your own luck, you put yourself in a situation where, where things are in your favor. So it wasn’t when I when I say it was a bad decision. I don’t mean it was a rash decision. I just meant, like, if I were to do the traditional pros and cons list, I think the cons on that decision would have heavily outweighed the pros. And if I if I went strictly from a logical standpoint, I never should have made that decision. But it doesn’t mean I wasn’t thoughtful about it, or I wasn’t thinking through some things. It was just I was willing to take a risk and and the decision itself was a bad decision. But the risk paid off.
Ryan
Just talking about luck. It’s reminded me of my favorite quote about luck. Gary Player, have you ever heard his quote about
Tim
No, I think I have. But what is it?
Ryan
Pro golfer? He said, golf is a game of luck, the more I practice, the luckier I get.
Tim
Yes, yeah. And I think that I think that’s a riff on, like I said, Ben Franklin, or Ford or someone. Yeah, that I mean, that that’s, that’s totally true. Right? So yeah, is there it’s, it’s tricky, right? Because you come to those decisions in life. And you have to recognize that there’s an element of luck, circumstance, fate, higher power, like, whatever label you want to use. There is some element that that is completely unknown. And you can’t possibly know like, you can study a decision for years, and make it and have a consequence that you couldn’t have possibly intended. Right.
That’s why we’re here, right? This is our wheelhouse. We are too meta nerds. Man, you and I like to talk about the big ideas and life quandries, it’s all like, you know, the format of this selfishly is gonna be a blast.
Ryan
Well, there is. So many things I want to jump into. And I think the, I think what I’m wrestling with is, you know, we can only do so much in one episode, and we have lots of time, hopefully, to sort of, you know, dig deep into all these different areas that I know, we’re gonna want to jump into. What do you want to I mean, how do you want to wind up this episode here? I feel I feel like you know, we wanted to sort of dig in, figure out what this was. Talk a little bit about our histories.
Tim
Yeah, yeah, I think this is setting the table. You know, the, the conversation is, maybe the next logical place to go is to really drill down on on that moment in, you know, 2017, when I, when I went to the headmaster and said, hey, guess what I’m not doing next year. I’m not teaching for you. Like, because we’ve sort of touched on that. And I think it might be more interesting to really go into depth, because it’s that was only four years ago, and in a very vivid memory, and maybe, maybe kind of dig into that. How those events played out where I was in my career, because the other thing we haven’t talked about, and I think you can you can, you can back me up on this, the position I left is a highly was a highly coveted position. As far as in the in the world of education goes like, I had probably the best teaching gig you could ever. And like, I think about some of the situations that people teach in and the one I walked away from, and again, it doesn’t make any sense on paper. So so maybe that’s a bit of a cliffhanger. Like, what what was this guy doing? That was so good that, that he walked away from it?
Ryan
Oh, yeah, we are gonna dig into every part of that. There is a lot there. I mean, like I said earlier, I was proud of you in a way just because I you know, you had been a friend and I’ve been watching the story unfold, but but also like, I was like, Wow, that’s a that’s a bold move. I was a little nervous for you, too. So yeah, I can’t wait to dig into, you know, sort of how you got to that moment what it felt like in will that’s going to be a big Pandora’s box. We’ll save all that for next time.
Tim
Yeah, and one thing we haven’t mentioned yet that I think might be a put a nice bow on this conversation is other than my wife. Nobody has seen this. But you like I’ve had friends that have come in I’ve met a few years ago, I have friends who I was friends with before I started this. But other than my wife, you’re the only other friend I have, who has seen it, from the very beginning to where it is now. And so I think you’re gonna be pretty good at pulling out some of those, like, what the hell were you thinking questions? Cuz no one else even knows about them?
Ryan
Well, there’s that. And I, you know, there are times I feel like I know the story, but then I learn I learned new things. I mean, even just earlier, you know, hearing you talk about sort of how, like, I just always assumed you have this driving sort of urge to be a writer and in it, you know, it seems like that happen much later than I than I knew. And that’s just an interesting detail. I mean, you know, so I look forward to discovering things that I just didn’t know about your story, even though I watched it, the whole thing from beginning to end.
Tim
I was I was much more interested in becoming a rock star than an author.
That’s another podcast.
Ryan
I think that’ll do it for today. I, again, I love digging into this stuff with you. It’s so great to reconnect. I look forward to getting into all the nitty gritty details of this story with you. But next time we’re gonna we’re gonna go back to that jumping off point we’re gonna we’re gonna get the whole inside story on that.
Links:
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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