Teaching Transformations Podcast Episode 16: Rewriting Your Story

Teaching Transformations

Rewriting Your Story

Everyone has a story—what’s yours? Join Tim and Ryan in today’s episode where they discuss common obstacles we face when deciding to take different paths and the approaches we can take to overcome them.

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  0:00  

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

Ryan  0:03  

So what do you read?

Tim  0:06  

What don’t I read?

Ryan  0:06  

That’s really what I should have asked you.

Tim  0:07  

I’m a reading fiend, I really am. I fit it into every nook and cranny of my day.

Ryan  0:10  

Nice. Any particular genres? Is it fiction, nonfiction, everything?

Tim  0:27  

It’s everything. What’s really funny is I was not a bookworm as a kid. I didn’t really read anything outside of required schoolwork until around like fifteen or sixteen, and I discovered Pet Sematary by Stephen King, and then I just read everything of Stephen King’s. Then you get into college, and you’re just so overwhelmed with all the reading you have to do. I had a liberal arts degree, so I was just overwhelmed with the amount of reading I had to do. I’m not one of those people who always has my nose in a book. Ryan Holiday talks about this a lot about how like books are the most underutilized privilege gift that we all take for granted. The statistics on reading in America are just devastating. The average American reads like two books a year, half of Americans don’t read any books at all. It’s crazy, the amount of accumulated knowledge and wisdom that are in books. I just can’t believe everyone isn’t reading off the top.

Ryan  1:58  

We do take a lot of things for granted, and that certainly has to be one of them.

Tim  2:02  

I mean, you look at everyone from like Warren Buffett to Richard Branson, Obama, you look at any successful person, and they will all say reading’s the most fundamentally important thing you can possibly do to better yourself and better your life just because you’re gaining all the experience of someone else’s life without having to spend the years living it. Alright, let me step off my soapbox now and tell you what I read. I read a ton of nonfiction. For some reason, I can read nonfiction faster, so I’ll read like two to three nonfiction books a week, and then I’ll read one to two novels a month.

Ryan  2:46  

Wow. That’s impressive.

Tim  2:48  

What are your reading habits like?

Ryan  2:53  

It’s almost exclusively nonfiction now, but most of it is audio because that’s how I fit it in. It’s commutes, it’s working in the yard, working on my car, so I’ve had an audible subscription since 1999 or 2000. I ran a marathon back then, and I would just listen to books while I was running, and I’ve been hooked ever since. I was an English major, so I used to read a lot of fiction, a lot of short stories. Short story was kind of like my favorite mode. Did you ever get into short stories?

Tim  3:40  

Yeah, yeah, I love short stories. The gothic horror stuff like Poe and Lovecraft, I love those. I can reread those stories so many times, and I’m also a really big fan of mid 20th century sci-fi like Ray Bradbury and Isaac Asimov. I love their short stories, and I came back to my roots in my author group. We all took a challenge for 2021, and my challenge was to write a short story every week for the whole year, so knock on wood, I’ve been doing that, and that’s been a lot of fun.

Ryan  4:17  

How many stories in are you now?

Tim  4:20  

Oh, I think number nineteen goes up Sunday.

Ryan  4:26  

Wow. Good job, man.

Tim  4:29  

Yeah, thanks.

Ryan  4:33  

You ever read The Swimmer?

Tim  4:35  

I have not.

Ryan  4:36  


Tim  4:38  


Ryan  4:38  


Tim  4:40  


Ryan  4:41  

Nine Stories? So, The Swimmer was John Cheever.

Tim  4:47  

Oh, Cheever, okay, I know Cheever.

Ryan  4:48  

The cool thing about that story, it is just like a diamond. It is so perfect, but it was written as a novel. It was a hundred pages, and he decided that it should be a short story, so he whittled and whittled and whittled that down into this perfect short story. That’s what I would recommend to anybody. A%P is by John Updike. It’s about this young store clerk who’s got a summer job at the A&P, and he’s a checkout clerk.

Ryan  5:04  

Okay, so this is a grocery store, I wasn’t quite sure if that was the abbreviation or not.

Ryan  5:30  

Oh, yeah. These girls come in in bathing suits that are his age, and he, as a young man, sort of takes an interest in and follows them around the store. I won’t give it away, but it’s this really, really interesting confrontation that happens, and how he responds to it is so telling about human beings. That’s what I love about reading stories is they’re very revealing about what it means to be human and the stuff that we all deal with and go through. Cathedral is Raymond Carver. Some people credit that with reviving the short story after it had kind of died out for a while. One of the best of all time. Then Salinger, Nine Stories. Those stories, I think, were all published in the New Yorker, and then they compiled them together.

Tim  6:37  

Catcher in the Rye is one of my favorite books of all time, so I have to go read all these now. Thanks a lot.

Ryan  6:45  

Yeah, and I’ll just circle back. You mentioned Stephen King, and I know you’re a big fan of his, and you’ve read a lot of his stuff. I think he’s totally taken for granted. I think because he’s sold so many books, and he’s been such a popular author, it has taken away from credit to the quality of his writing. Pet Sematary is a great example of that. If you go read that, it’s so well written.

Tim  7:19  

He became his own genre, for better or worse, and I think we may have mentioned this before. I talked to people who are a little bit younger, and they don’t understand that back in the day, Stephen King was considered a hack. The literary world didn’t respect him. He was not looked upon favorably from people who thought they knew how to write, so it’s been an incredible transformation for him to see the stature he has now compared to what he had in the early 80s.

Ryan  7:50  

Well, you get how many of your books and stories are made into movies, and I think that’ll help your reputation a little.

Tim  7:59  

Yeah, for sure.

Ryan  8:03  

I want to play on this theme of stories because we all have them. We’re all living stories and writing our life stories, so I want to delve into some questions here. What are the stories we’re living? What are pivotal moments from our life stories? How much of our stories are we writing and then enacting versus being written by others? How much can we revise our stories? To start, tell me your story.

Tim  8:43  

My story. So, my story right now is I walked away from the golden handcuffs to take control of my time in my life. That’s my story right now.

Ryan  8:59  

Alright. Well, can you take us back to the beginning? Go way back.

Tim  9:05  

How far back?

Ryan  9:06  

All the way back.

Tim  9:07  

I will. I’m not being cheeky. There’s sort of a context to this because I’ve been thinking about this episode, what we’re going to talk about, and one of the things that I realized is that I think people who claim victimhood are not going to like this episode. If you like to blame other people in other circumstances for your problems, you should probably stop listening right now, and the reason I say that is it’s a challenge to see how you manifest things in life. I mean, that’s what we’re talking about with stories, right? You sort of create your own story, and then you enact it, and your story can be the boss is a jerk. If only that boss wasn’t there, I would be a superstar. Then you can live that story out. Or, you can say, the boss is a jerk, and therefore I’m going to find a new boss or become my own boss, and you can live that story out. There’s an element of choice here, and there are people who get really entrenched in their lives and in their problems who don’t see it that way. I’m not talking about bad things that happen to people, unexpected things, I don’t mean that. I’m talking about the reality that you create. It is something you create for better or worse, and it’s something I have to be reminded of, and it’s something I fall victim to quite often. Even my story, I am where I am now, but if you asked me that question ten years ago, my story would have been completely different, right? Going back to your question, what’s the beginning of the story? I would turn it around on you and say, well, which story?

Ryan  11:14  

Yeah, so what I’m trying to get at is, first of all, I agree with you, but secondly, even that point of view wasn’t formed by your life story. Some of it chosen, some of it not chosen, you know, so that’s what I wanted to get into. What made you who you are, and how much of that is fixed? How much of it is malleable? How much of that can be rewritten? Since you had to jump to the punch line, the end of the story with all this, I’ll just say the reason that I think this is worth digging into is because I think that second act, you know, stages of lives are opportunities to rewrite our stories, but I think that happens best if we know who we are and how we got there, so that was kind of my reason for wanting to get into this topic. Not that I’m qualified in any way, I’m not a therapist, I’m not looking to be a therapist or anything, but I do think even your point of view, I bet there are strands of it that trace all the way back to when you were really young.

Tim  12:46  

Yeah, I don’t know. It’s an interesting question because it gets to like, how much did you come into the world with? How much did you develop once you arrived? I think about my childhood, I was incredibly compliant. Up until the time I was a teenager, I did everything my parents told me to do. I was extremely polite and respectful, quiet, and I’m not necessarily saying this is a good thing. I was a really, really good kid up until the time I was a teenager, so I can’t say, well, I’ve always been a rebel, I’ve always had this streak in me that I was gonna damn well do what I please. No, that was not the case. I was raised to be the old adage of children should be seen and not heard, and like that was how I was raised. Even when I started to rebel as a teenager because my parents had such a strict idea of what children were supposed to do or say or be, those battles were even more intense, and I kind of dug my heels in even further, only to spite them, not for sort of any moral high ground, so I really don’t know. I don’t know where it started. I mean, I rebelled as a teenager, I almost dropped out of college for many of the same reasons. I’m like, I’m doing this because my parents want me to, I don’t know why I’m here. My dad talked me into staying, and I did, and then what did I do? I turned around and immediately entered a profession full of very compliant people. Let’s be honest, educators are not rabble rousers, we can’t be. We have to be nurturing and empathetic. We’re not the ones who are supposed to be causing the problems. I spent decades as a very compliant, somewhat eccentric, minor pain in the butt for my administrators, but not a troublemaker, you know, and I stayed in a conservative career as a compliant employee. I don’t know if there’s a thread I can trace back. What were you like as a young kid, or how were you raised?

Ryan  15:25  

Hold on, we’ll come back to that. First of all, this moment, I’m calling it a moment, but I’m sure it wasn’t a specific moment, do you remember there being consciousness around your compliance and letting go of that and making a choice to be more rebellious? If so, what factored into that? Was it the people that you’re around? Like, how did that happen?

Tim  15:54  

Okay, so this is gonna sound really shallow, but it was about my hair. You arrived in the 1980s, you know what the hairstyles were. I would say around 1983, that’s kind of when it started. Def Leppard was really popular, I wanted a mullet. At the very least, I wanted long hair, and I can remember my parents absolutely forbid it, and they could never give me a satisfying reason. They would say things like, well, I’m not going to church with you looking like that, and I was like, first of all, what does that have to do with anything? And who cares? What does someone seeing me with you with long hair have to do with that? There was never a satisfying answer to that question, and that’s when it started. I think I used music, and in relation to music, my peer group, as a way to dig my heels in and take a stand and be like, no, I can have long hair, and it doesn’t matter. It has no effect on my character or has no effect on my ability to do my homework. I remember part of my rebellion in high school was growing my hair out and getting my ears pierced, and at the same time, staying on the dean’s list because I wanted to prove to my parents that like, this external appearance doesn’t matter, so I worked really hard at being a rebel and hanging out with the bad kids and doing bad things. At the same time, my grades are fine, so what are you complaining about?

Ryan  17:40  

Yep. I definitely grew my hair out. Maybe not as much as you did, but I grew it out. I had the earring.

Tim  17:50  

You had to have had a mullet. Everyone had a mullet.

Ryan  17:53  

Mullet-ish. Yeah, I didn’t go super short on the sides.

Tim  17:57  

Right, but definitely had it longer in the back.

Ryan  17:59  

Yeah, yeah, where it starts curling up on your collar and stuff, and I had the earring in 10th grade. I was kind of like you in many ways back then, you know, partying on the weekends. I’ll just be honest, I drank a lot in high school, that’s just what people did at my school. I was plugged into that scene but then did really well in school and was a good student, really involved at school. One key difference, and this might explain some things is, my parents weren’t pushing any sort of agenda on me. My dad’s parents had been very strict, and I think he always resented that, so he kind of went the other way with his parenting style. My mom was just pretty relaxed about things, too. The day I came home with an earring, I don’t think they loved it, but they weren’t going to make a big deal about it or anything. Right. Because I had that sense that it was okay, there was nothing for me to buck. That probably plays into a little bit of my whole story. I’ve never felt like I had to rebel against anything because I just didn’t feel like anything was in my way or nothing was sort of keeping me from being what I wanted to be. I will go back and talk through my history a little bit. I grew up in a small town. It’s like an athletic football town. I wasn’t the most athletic kid in the athletic football town, but that’s where I went to school. I grew up in a neighborhood, very unsupervised. The one thing that I understand now, or I should say I came to understand as an adult that I didn’t when I was young, is what it means to grow up somewhere small. I had sixty-five kids in my graduating class.

Tim  20:26  


Ryan  20:29  

There are many private schools that are bigger than that. I mean, the one I work in is twice that big. What we sell to the world is we know your kids, and I know that’s true, but in a small place, you’re known. Everybody’s known. Everybody can be somebody, you can’t blend in. It’s sort of a given that everybody matters in a way, so that’s something, going back to taking things for granted, that’s just always been something that is a baseline for me. Probably, as a kid, I didn’t understand that that was related to being in such a small place. The other thing I would say is from a very young age, my dad was really empowering to me. I remember I was really young, and I was helping him with tools and with projects, you know, I tore down this metal shed in the backyard by myself. He gave me the hammers and said, okay, go take care of that.

Tim  21:40  

Here are the tools, go rip down an old rusted shed.

Ryan  21:43  

Yeah. But it’s funny, a few years ago, my dad was, they live in a duplex now in our twin plex, and they were prepping the other side to rent out. Their renter had moved out, so some of the family had gone over to help out with some things. I had my younger son Preston with me over there, and I watched my dad hand him a paintbrush, and he said, just paint this door here. Preston’s never done that, and I bet my dad didn’t even think twice about it. He’s like, just give him the tool, give him direction, let him go. That was a critical moment for me because I was like, man, I haven’t done that with my kids. I always am worried about getting messed up or whatever, so I just do everything, and that’s not great. I don’t feel good about that. Especially considering where I come from and how embedded it is in my identity, for me, self reliance is like the kernel of my identity. We’ve talked about the car repairs and house repairs and stuff like that. It’s just who I am, and I’m kind of proud of it, but I couldn’t change it if I wanted to, and it goes all the way back to those early years. I mean, I’m afraid of heights now. Before I was even in high school, I remember helping my dad replace the roof on the house. When I was up there, I didn’t have a safety harness on, I wasn’t trained, he just showed me how to do it. I know that’s a core part of who I am. Again, being in the small town and having so much opportunity for things, you know, I got into theater and athletics and student government and all that kind of stuff because you could.

Tim  23:51  

I want to dig into something you said there because I think there are core elements of who we are that then help us write our stories. Self reliance is at the core of who you are, at the core of your identity. So, how does that affect the story you tell about yourself?

Ryan  24:14  

It makes me think that I either am in control or should be in control of my destiny and that I should be able to find my way through problems, and if I can’t, there’s a problem. I would say that’s my worldview. Now, going back to where you started at the beginning, I have found myself at times feeling stuck. There are times when I’ve been in the same professional position for longer than I wanted to be, and yeah, I probably have stories about being overlooked and that kind of thing. When you’re an adult, it’s not about you, so there’s certain things that you might live with because you have, as my friend John used to say, mouths to feed. He said his dad used to pull that one out on him, and he always pictured like a mouth just…

Tim  25:17  

Eating somebody’s mouth.

Ryan  25:21  

But in terms of being decisive and saying screw this, I’m doing something different. Your ability to make those hard pivots might be a little different. You made a pretty hard pivot with those responsibilities, so I’m not saying it’s impossible. When there’s a will, there’s a way. My mom used to say, you are where you are because you want to be there. If not, you would do everything in your power to change it, and I do think that’s largely true. Again, for me, it’s important to step back and think about this stuff and recognize because I think we all get trapped sometimes in our own little mental loops, and we forget we do have willpower, and we can make choices, and they’re not always easy. Sometimes they’re gonna have risks and/or consequences that we don’t love, but that doesn’t mean we can’t make them.

Tim  26:26  

Yeah, and I think that’s why it’s so important to have either friends or small communities of like-minded people in those moments because I think about making the decision to leave my job and become a full time writer and publisher. I didn’t do that completely on my own. I mean, I did, but I felt like it was a risk I was willing to take because I was in a community of other people who were doing the same thing. I changed my story from, this is impossible for me, there’s no way I can do this to saying, other people around me like me are doing this, so why can’t I? That’s the power to change that story, to believe it or not believe it. It doesn’t mean that there’s no risk, and it doesn’t mean that you’re guaranteed that risk is gonna pay off, but it does allow you to change the story. I think we’re constantly enacting the stories we tell, so as soon as you change one, then you’re immediately starting to take actions that are different than what they were before. You know this as a runner, the first time you start running, especially if you’re in your 40s or 50s, it’s painful. You don’t get out there and be like, hey, this is great, I’m a runner now. You almost have to start telling yourself that story because the physical evidence is so to the contrary. Your legs hurt, your lungs burn, you feel like you’re gonna die or throw up or possibly both, so you have to rewrite that story. You have to say, no, I’m a runner, and I’m gonna go do what runners do, and even though it’s painful, it’s not like that forever. That’s where the power of the storytelling comes in. You can choose to say, which I did this for decades, I don’t have the body of a runner, like, my legs are too long, I get shin splints, I don’t like running. I could come up with any number of stories that would support that, and therefore I didn’t enact any of what it would mean to be a runner until I got to the point where I said, okay, I’m a runner. A pretty crappy one, but I’m a runner, and I’m gonna do what runners do. That started me off on a whole different path, so it’s easy to overlook the stories we tell ourselves, but I think at the core, they’re incredibly important.

Ryan  28:59  

Yeah. Well, I saw that with your hard turn into running. Was that a year ago?

Tim  29:08  

A little over a year ago, yeah.

Ryan  29:09  

And you were very conscious about it. It’s funny to hear you use that as an example of a story because that makes total sense to me. You basically said, I’m gonna write a story about me being a runner, and then you started, as you put it, enacting that story. That is powerful, and I think it’s probably a reason why you’ve stuck with it. You do that stuff daily or close to it, but it started with that mental shift, like I’m going to write a different story now, and I’m going to stop telling myself the story about not being a runner. I would bet that your story about writing and about the risk you were taking when you left teaching, I bet you that story is something like, what’s important to me is to do something I love and to have control and independence. In my story, that’s going to be the centerpiece, and it doesn’t matter, and I’m going to accept all potential consequences that come with that. Once you wrote that story and started living it, that’s a different kind of story than I’m gonna dabble in writing and just see where it goes. I think the word is intention. There’s a lot of intention that comes out in articulating something specifically, and I definitely have seen that work for you. It has me thinking about the ways that I maybe could be more intentional sometimes about identifying like, this is what I’m going to do right now.

Tim  31:06  

Yeah. I don’t think I fully realized that until several years after I left the classroom and was no longer teaching because for years, what held me back was, well, what would I do if I fail? What if I create the story and it’s wrong? For some reason, I overlooked the idea that I could just write a new story. I look back now, and I know from where you are, and if you’re currently in a full time job or if you’re currently teaching, walking away probably feels next to impossible. I know, I felt those feelings. What I failed to realize was, I was not going to end up under a bridge down by the river. Maybe that’s some sort of false sense of myself, or maybe it’s my own ego that let me think that, but I’ve never thought like, well, if I walk away from teaching, then we’re going to be homeless. What I realize now is that I could rewrite that story. I could say, okay, if next year my author business tanks, I’ll just go get another teaching job. Now, to me, it doesn’t even faze me. I’m like, I’ll go make money some other way if it doesn’t work, but it’s the inflection point of that decision. It seems overwhelming. It feels like you’re making a decision between your life and everything you care about, and you’re putting it all on the line, and you’re risking your family’s well being. For most of us, that’s not true. I think the worst case scenario is if you try something and it doesn’t work, you can just try something else or you could go back to what you were doing. That’s what was lost on me, and having a few years out now, I can look back and see  I was never really in the jeopardy I thought I was.

Ryan  33:16  

Yeah. Something I’ve realized about myself over time is that I describe myself as a defensive thinker. I like to be ready for the worst, so whenever I’m thinking about making a change or whatever, that’s where my mind instantly goes is, what is the worst case scenario? And I try to see if I can get comfortable with that and identify ways I might deal with it. I don’t know where that comes from, but again, it’s sort of hardwired into me. I know I refer to Tim Ferriss all the time, but there’s a piece in his book about doing that, like actively think through the worst case scenario, and how bad is it? How likely is it to be undoable? If you give up your job, what if things had really not gone well? What’s the likelihood you could get back into another teaching job? Teaching jobs are everywhere.

Tim  34:22  

Right. I mean, it might not be the exact position you had at the exact school that you had, but you’re not going to be living under a bridge or anything.

Ryan  34:32  

At the same time, I have good friends and former colleagues that have like three to five years left before their time is up, and even if you’re not loving it the way you used to, if you’re not hating it, there’s something to be said. I can’t understand why you would just write it out. Maybe you don’t hate it at all, maybe you actually still like what you do, and that’s just your timeline, like, that’s okay. If that’s your reality, what I think about is, even if you’re okay and you’re going to finish your career and be happy doing so, it’s the changes coming either way. You’re going to have to write a new story in that scenario, too, and are you ready for that? Have you thought about who you are? We did a lot of that in our 20s and in our younger years, and then over time, we stopped thinking about who we are, and I’m not saying we become robots, but we just get into a groove, and we don’t self examine a lot. This isn’t criticism, I just think that’s what happens and that transition times in our lives are an opportunity, an important opportunity, to kind of look at who we are and who we want to be still, and hopefully because we’re older, we have more tools to articulate that and to actively build towards something we want.

Tim  36:19  

I think your mention of time is putting the bow on this conversation. I think it really does tie it all together because what we’re trying to do here for ourselves and for the listeners is, we’re trying to make you understand that time is on your side right now. You don’t have to make these drastic decisions, like you don’t have to rewrite your story today, you can start drafting your story. Now, you might be three or five or ten or fifteen years away from retirement, so you have an opportunity to slowly, carefully, intentionally methodically, start writing the story that you’re going to enact because as you said, that change is coming whether you like it or not. At some point, you’re either going to choose to quote unquote retire or you’re going to be forced into retirement, and then you will have no choice. You will be living a new story. So, start now. Start thinking about that now, thinking about what that life is going to look like and that story you want to create, and start drafting it. This is the perfect time to do that. Folks who are our age especially, this is the time. As we’ve talked about before, our kids are getting older, they’re less reliant on us, our external responsibilities are lessening, so now’s the time to kind of turn that back in and refocus on ourselves and start thinking about what that next phase is going to look like and start drafting the story.

Ryan  37:51  

Yeah. What is that? The ten-year overnight success story? I know I wrote about this in the first journal post that I did for this project, and I was talking about how I think we exaggerate inflection points. Even though I know we have them, and you had that inflection point of turning in your notice and leaving the teaching job, but at the same time, how many years did you side hustle, right, and build toward that before you did that? Even if you were going to retire conventionally, it would have made sense to just gradually start building that as you’re able to so that you could really hit the ground running, and you wouldn’t be wasting time when you get to that moment in your life when you’re like, I really can do what I want if I built the framework that enables me to do that.

Tim  38:56  

Yeah. It was almost ten years from the time I started dabbling with novel writing until I became self employed. It wasn’t an overnight thing, it wasn’t a rash decision. I mean, it’s a very binary decision, but it wasn’t a rash one, and I had time on my side, you know. I could start dabbling, I could start experimenting, testing things out, and ten years later, I kind of knew, okay, this is the path I’m going to take again. No guarantees, but at least it was like, this is the stream I’m gonna step into. Let’s see what happens.

Ryan  39:30  

Yeah, time is on our side.

Tim  39:34  

That’d make a great song.

Tim  39:36  

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


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