Teaching Transformations Podcast Episode 2: Are You Happy Now?

Teaching Transformations

Are You Happy Now?

That’s probably not a question we ask ourselves frequently enough. In this episode, the guys discuss why it’s important for us to fulfill the desire of change in our jobs. In addition, they discuss how their skills have impacted the transitions in their lives.

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  

Am I bringing us in? Or did you? I don’t remember.

Ryan  0:02  

Get us started?

Tim  0:03  


Ryan  0:06  

I don’t know.

Tim  0:10  

I think we just started.

Ryan  0:11  


Tim  0:12  

Why don’t you talk about what happened last week? Like, technically and why that matters now?

Ryan  0:21  

Sure. Yeah. We said we were gonna expose all of our warts and everything, right.

Tim  0:26  

Yeah, exactly.

Ryan  0:30  

So, you know, last week was our first episode, and just listening back to it afterward, I was like, I mean, I found so many problems in my performance, and my, just kind of, you know, the sound. I don’t have good mic technique yet in that, so you know, I could hear my volumes going sort of up and down, and I think it’s just based on my position, and you’ve done so much more of this than me. I mean, you’ve done a ton of podcasts at this point.

Tim  1:04  

It’s conditioning, you know, that that’s what it comes down to.

Ryan  1:07  

Yeah, so I’m gonna work on that–trying to keep my head straight. Hopefully, it won’t be sort of cemented in place, and I can feel free to move, but yeah, it’s a skill, you know, so I’m going to keep working on it. Hopefully, people will be forgiving and maybe give me feedback as I make progress. I also just want to talk about the lead up to last week’s episode because it’s kind of comical, and I know I told you about this, but, you know, Wednesday nights are good nights for me to get side project work done because my son swims. After school, he has a long swim practice, which is, by the way, the second swim practice he has on Wednesday, the second two hour practice is right after school. Then we have a little space in between where we get dinner, and then he has baseball practice from like eight until ten. It’s not near my house, and he doesn’t drive yet, so that’s just the time I get a bunch of stuff done. So usually, I’m looking ahead to, you know, the next day when we record, and I’m thinking about that stuff. But last Wednesday night, right as he was starting swim practice, we got this major phishing email, and people were falling for it. I mean, it was easily a hundred and twenty emails that were coming sort of direct to me that I had to respond to, and I had to, you know, make a formal sort of announcement to the community, “hey, don’t click on this,” so it just kind of ended up taking over the whole evening. Then we get home around 10:30 on those nights, and then looking ahead to the next day, I wanted to test out equipment and make sure my mic was going to work and everything, and nothing was working. I spent probably an hour, an hour and a half, when I got home trying to make different combinations of equipment work, and I never got it working, so then I’m like, “Okay.” The next day, I was like, tomorrow morning, I’ll have to go try to work out a setup, and the next morning, he has early swim practice. I get there at like 7:15, and it took me from 7:15 until we started at 10:30 to get a legit setup that was working all the way around. Then as you know, at the last minute, we even changed. We were going to record this in one program, and we ended up changing to another, but I was just thinking about how comical that was like this is what it’s like to try to do a side project when you have a full time job and other responsibilities. It ends up that sometimes you get these obstacles, and you can’t control that, but I just kind of shook my head like, wow, this was really hard for something that seems so simple.

Tim  4:17  

Yeah, and it doesn’t necessarily get easier, it’s just the challenges change. I don’t know where I heard it, I know it’s a popular colloquialism, but this idea that you’re building the plane as you’re flying it, is a very apt analogy for what we’re doing here. I mean, we’re communicating throughout the week, and then before we hit the record button, we’re trying to figure out what we’re doing. We’re kind of adjusting as we go. We’re recording with no audience, no website, no podcast distribution. We don’t know what the format of the show is, we don’t know where we’re headed–we don’t even know which order the episodes are going to publish in, but we’re still flying. I think a credit to you, you didn’t give up, and not only did you not give up, but you did something that I think 95% of podcasters never do, which is you listened, and you learned from what you heard. I’m approaching, I don’t know, I have 800 or 900 podcast episodes I’ve recorded since 2014, and I still listen to every single- what was that?

Ryan  5:28  

Oh, my gosh. You just froze, and I sat and waited, I was like, okay, it should catch up, and then it just didn’t, so I hit refresh. I don’t know if that was your end or my end.

Tim  5:44  

Well, you know what? We’re leaving this in. I’m not editing that out.

Ryan  5:50  

I think you were just about to say something wise, so I’ll just kind of fill that in in my mind, you know?

Tim  5:56  

Yeah. I think what I was about to say is I’ve listened to every single podcast I’ve recorded, and I listened back because I want to improve performance on the next one. I think you’re doing that, and that’s not easy to do, especially when you first start. The last thing you want to do is listen to yourself on a recording. It’s extremely uncomfortable, but that feeling will go away, and you’ll be so much better for it. Tech issues aside, we are still flying this damn plane.

Ryan  6:30  

Oh, boy. Well, you know, I was thinking about the whole situation of managing job and all of that on top of a side project. I was thinking, yeah, you’re always gonna have obstacles. I mean, you know, there’s no such thing as trouble-free situation, but I guess I was thinking, maybe that’s a reason to sort of accelerate, you know, like if the job is kind of getting in the way of your side project, and you really want to focus on the side project and make it the main project, that that’s a good reason. Probably a lot of people feel that way, and that might be one of the reasons that people accelerate their timeline to get kind of to that post-career situation. I mean, that’s really what you did, right?

Tim  7:25  

Yeah, I mean, comfort is dangerous. To be comfortable is really dangerous. That sounds silly to say on the surface, but in any aspect of your life, I feel like at once, if you’re comfortable in something, you’re either not growing or you’re stagnating. There’s a lot to be said, I mean, we always use it with students, you know, pushing outside your comfort zone, and yet, few of us adults ever do that. We preach that all the time, and we don’t do it. We do the same things over and over and over again, and I think I just kind of had a realization in my mid 40s, that if I didn’t shake myself up, if I didn’t shake myself out of my comfort zone, that’s how the rest of my life would be, and there’s not necessarily anything wrong with that, I just felt like I wanted something else. I wasn’t going to get something else if I kept doing the same thing.

Ryan  8:23  

Yep. Well, the way we left the last episode, we left it with a cliffhanger, so I think we need to pick that up and not leave everybody hanging. The cliffhanger was you know, that moment in, was it August 2017?

Tim  8:44  

It would have been early, it would have been probably January of 2017.

Ryan  8:47  

Right, because of contract season, but that’s the moment that your official independence notice, right, began there?

Tim  8:58  

Yes. I made an appointment with our headmaster, who I’ve had and still have a very good relationship with and was at the school when they hired him and just really bonded with a guy, a lineman in philosophy, and I had served him in the school in various capacities. I mean, I worked in the middle school, I worked with you in the technology and learning, and then I was in the entrepreneurship program, and I came to him in January of 2017, when the entrepreneurship program was, you know, getting national and international recognition, were doing workshops in Steve Blank’s living room. There were hundreds of kids that wanted to get into this program, and I walk into his office, and I’m like, “I’m not gonna sign my contract next year.” I remember he was kind of like leaning back and going, “Oh, okay.” I said, “Yeah, I want to go write science fiction and horror.”, and he was like, “Okay.” He was great, but I was so uncomfortable in the situation because I think we might have mentioned this last time, like, as far as education is concerned, and in my field of my expertise, I wouldn’t have found a better job. There would have been no better job out there than the one I had, and I was at the peak of my salary, like I was sort of way beyond what I would have been in a quote unquote, you know, as a classroom teacher, I was sort of quasi administrator, and he said, “Okay, alright, thanks for letting me know.” You know, he kind of threw a little bit of reality at me, not in a mean way, but he was like, you understand that means this and this and this, and there were some specifics with my family situation and some other things, and I’m like, “Yeah, I know.” He didn’t say this exactly, but he said, you know, if you change your mind, let me know. And man, I had a few weeks where it was really hard because both of my kids were at the school, my wife was in administration, an administrative assistant at the school, so all four of us were involved with the school in one way or another. I didn’t have an emergency fund. I mean, I knew I was gonna get, based on the way my contract was set up, I knew I was gonna get a paycheck in July and August. I would finish in June, and then I would have July and August, and then that was it. I think I was making maybe a few hundred dollars in royalties at the time, so it wasn’t even like I could just sidestep into something, even 50%. I mean, it was not even enough to make a car payment, and I thought, okay, I made this announcement in January. We finished up our responsibilities in early June, so I knew I had really June, July, and August. I had ninety days, and I wasn’t going to scale up to my previous salary in 90 days, but I had to reach some sort of baseline that would allow us to continue living in a house. I had about ninety days to do it.

Ryan  12:31  

Wow. I’m thinking about the gig you had. It was a good gig.

Tim  12:37  

Oh, yeah, it was a sweet gig. I think I’ve mentioned it before. I mean, I was teaching an entrepreneurship program, and even now, there aren’t many of those, but they were even rarer you know, five years ago. I was only teaching in it, but I was the assistant director of the program, so I was involved in a lot of the higher level stuff that I really enjoyed, like the big thinking like the workshops, the programming. I was producing podcasts, I was helping the director with other tasks, like it was a nice gig for a teacher, it definitely was.

Ryan  13:18  

It just wasn’t enough for Mr. Desmond.

Tim  13:23  

No, you know, it’s hard for me to articulate that. I’ve heard other, mostly entrepreneurs who have had big exits, in a totally different circumstance. I’ve heard these people say, I was CEO of a seven figure company, and I just felt like I wanted something else. It doesn’t necessarily have to do with money or material things or status, although it can, but for me, it was just sort of this internal yearning of like, there’s something else I need to be doing, and it wasn’t anything wrong with what I was doing. It just wasn’t what I was supposed to be doing at the moment.

Ryan  14:10  

Yeah, I’ve read a little bit about this kind of stuff. I mean, it seems like there are two or three sorts of flavors of what drives people to make a choice like that. You know, one is they’re just not fulfilled, and they pull out, they plot some kind of change. I’ve read a lot of stats about this. I think the average seems to be somewhere between 50 and as much as 80% of people who are working are not truly happy or fulfilled by their jobs.

Tim  14:46  

I’ve heard something like that, too.

Ryan  14:48  

Yeah, that would suggest that there are a number of people out there who consider making changes, and then the other obvious one is people lose their jobs and presumably pursue some kind of transition out of desperation. I know obviously a lot of that’s happening now and during this pandemic. I think educators are a little more insulated, but that’s not uncommon, you know, there are a lot of people who losing their job not by choice is sort of what forces them to make some kind of major transition. Then, the third one that I thought of is just somebody dying to do something specific, so, I just really, really want to be a writer or whatever it is, and I just need to go do that, and I’m not getting enough for that. It sounds like for you it’s probably more the last one, but maybe a little bit of the first one, too–you just weren’t getting enough of what you were looking for from your job at the time.

Tim  16:03  

Yeah, and I think too, I’d said this, from the very beginning of my career, I knew I wasn’t going to be a forty-year classroom teacher. I just knew that’s not how I’m wired. In my career, I’ve made a lot of changes at the five to seven year mark, and that seems to be where I get into a place where I’m craving something different, and you were part of several of those transitions even at the school, so I think that’s part of it. Another thing I think, too, it’s important for people to realize once you get into your 50s, you might lose the ability to make the choice for yourself. I won’t go so far as to call it ageist, but I would say that once you’re in your 50s, if there’s a downsizing or a reorganization, it’s going to be much, much more economical for your company or your corporation to hire someone out of college to do your job and pay them half as much as they’re paying you. They’re not going to come out and say it’s because you’re at the top end of the pay scale, but that’s the financial truth, and I think whether you call it forced into retirement or early retirement options, those kinds of things are all ways of leveraging newer talent at a lower cost. If it hasn’t happened to you yet, I think in your 50s is where you can expect to start seeing those kinds of things.

Ryan  17:40  

Yeah, and it seems like it would live under the cloak of like, we’re looking for fresh thinking or whatever that might be, and, you know, I get that. I am in a position where I’m at that organization-level conversation, so I’m involved in the strategy of our school, and I do think there’s some reality to that. An organization is good if it has a balance of fresh thinking and mature thinking. I think an organization needs both, but, yeah, that definitely can shift over time, and when it does shift, you might not be on the good side of that, right?

Tim  18:36  

Yeah, odds are, you’re not based on your age. It’s just the reality of it. It’s not a judgment on anyone in particular, but the older you get, the more likely you are to be moved out to pasture. That’s just how the world works. It’s not evil, it’s just the reality of it.

Ryan  18:55  

I can’t believe I’m thinking about stuff like this already.

Tim  18:57  

Well, I mean, it’s putting you ahead of the game. I think there’s so much out there, and we’ll get into this. I know we will. There’s so much in there about Gen Xers who lie to their financial advisors about how much they’re investing in their retirement because they’re kind of embarrassed that they’re not, or the number of Americans who don’t have $400 saved for a basic emergency, like we were not good at thinking ahead. We’re just not. That’s a biological thing we have to overcome, so I think if you’re starting to think about what you want to do after your career and not just how you get there, because that’s where all the focus is right? All the focus is on how do you get to quote unquote retirement and be able to live, but what about how you live like that? That’s really what we’re getting out here. You need to be thinking about that too. If you want to have a fulfilling post-career life, you have to be intentional about it. You have to design it because no one’s gonna do it for you.

Ryan  19:59  

Yeah, you have to before you start figuring out how to get there. You have to know where you’re going. I mean, it just makes sense.

Tim  20:06  

Yeah, for sure.

Ryan  20:09  

Alright, so a couple of questions. Did you ever see that? What was that movie with Rodney Dangerfield? Back to School or something?

Tim  20:20  


Ryan  20:21  

It was the final exam. It was like one question and 114 parts.

Tim  20:28  

Yes, something like that. Good reference man, old school Rodney Dangerfield, I can appreciate that.

Ryan  20:35  

So, this is kind of multi-part, but one question I have is just having made the transition that you did, are you happy now?

Tim  20:47  

I am happier now than I’ve ever been in my entire life. That’s the most honest way I can answer it. At the same time, I have not had fewer safety nets that I’ve had now. I don’t have a salary job, I don’t have a contract, I don’t have long-term corporate clients who hire me for, you know, six or twelve months stretches. I serve an industry that is extremely volatile, and it’s filled with a lot of hobbyists which means discretionary income doesn’t always find its way to a hobby, and I’m talking about authors and writers specifically. Making money from art is extremely difficult. It’s not impossible, but it’s the kind of thing a lot of people can’t do full time. Therefore, whenever there’s anything like a pandemic or financial difficulties, they cut that kind of stuff. My dad passed away a few years ago. That’s an odd thing. It’s hard to describe, but even though I’m a grown man with my own family, and my own kids, I always felt like, well, if I get into a problem, there’s my dad. I can always count on my dad, and now I can’t, and it’s different with my mom. I love my mom, but it’s different, and I wonder if it’s different for women and their mothers versus their dad, too, but I mentioned all of this because I’m more independent now than I’ve ever been, which means I have the greatest amount of risk that I could possibly have in my entire life, and yet, I’ve never been happier.

Ryan  22:36  

Interesting. Have you had to ever lay off your driver or your chef? Like, has it ever been that bad?

Tim  22:44  

Well, the dry cleaner went first. Then it was the stylist, but now I got to keep the chef.

Ryan  22:54  

And I love hearing you say that you’re happy, and I’ve seen that, and I can feel that. Having that level of independence sounds really, really appealing, but it also does sound scary, you know, the risks that you’re talking about I think are risks that probably keep a lot of us from making that kind of step because we look at the balance sheet, and we’re like, I’m not willing to put my chips in here.

Tim  23:31  

Yeah, and hopefully we think fundamentally useful to people like us, to people our age, because I am you, but I’m not you. I was there, and I made a really radical change, and I think what we’re saying is you don’t have to be that radical with it. You can if you’re intentional and you look at your next ten years and you look at what’s on the horizon. If you start thinking now and start planting the seeds now and start designing now, then you won’t have that big risk in five or ten or fifteen years, whenever you sort of make the transition into the next phase of your life. I made it abruptly, and that’s not the advice I give people ever. I always say that was the worst decision I could have possibly made. It turned out well, but it was a terrible decision, so I think if you’re thinking about it now, and you’re planning for it, then you’re going to make an excellent decision. Then, no matter what happens, you’re going to feel good about it because you will have known you’ve done everything you could have done to prepare for success and the life that you want. There’s no guarantee on that, but at least you’ll have peace of mind and your decision making process to get you there.

Ryan  24:50  

And even if all the rest of our stories don’t end up looking like yours, it’s a good point of reference because you’re encountering things that all of us are going to encounter, even if we just retire conventionally. I mean, you talked before about the loneliness, and you had to sort of figure out how to plug into communities in a different way because before that was automatic, you know, those sorts of things that are coming for all of us, even if we just stay on a conventional path, but I think because you accelerated your path, that’s useful for us to look at. We can learn from that and learn from some of the things that you had to work through before we got there.

Tim  25:40  

I hope so. I hope I can help people with that, and it’s not because I have any sort of special powers or abilities, it’s just because I have the experience, and I’m walking ahead of certain people and walking behind others, but I’m walking a path, and no one’s gonna walk directly behind me, but at least you’ll have some indication which direction to go. We’ve both been talking to a lot of people our age about what’s next, and some people are really thinking about it right now. I think for a lot of people, they need some type of routine or regimen because having a free-for-all, while it might be great for a couple weeks or a couple months, that’s not good for a couple decades. People are starting to think about what kind of cottage industry or solopreneur experience can I create or even volunteer work that’s somewhat structured? All the skills that are needed to get to that place are ones I’ve had to develop in order to pay my bills, so I feel like that can be of use to people in a less risky scenario.

Ryan  26:56  

So speaking of skills, how much of your teacher self did you or do you make use of now?

Tim  27:05  

This is such an interesting question, and I have a feeling that this could balloon into an episode on its own. I think when you’re in an environment and you’re in a profession, and you’ve become skilled at it, and you’ve been recognized as being good at what you do, and let’s face it, if you’re in your 40s or 50s, and you’ve been working in the same profession, you are skilled at it, right. I think the danger in that is people start labeling themselves based on what they do versus what they are, and that’s it. That’s an important distinction, so yes, I was a teacher, but I also teach, but those two things are not the same. They’re not mutually exclusive, but they’re not the same, so when I talk to people who are starting to think about what’s coming next, what I always like to do is I I like to unearth, what are the passions or things of interests or the themes of your life that you can draw straight through from the time you were twelve or thirteen years old until right now? What are the types of things that you really enjoy doing, and I’m not talking about the measurable skills, these are more like soft skills, personality traits, tendencies, those types of things. If you look at what I built versus what I was doing, on the surface, they look completely different. On my tax return, I went from profession of educator to profession of publisher/writer. Those are not the same thing at all, but what I’m doing is exactly the same thing. It’s what I’ve always done, from the time I was a dungeon master, and I was creating campaigns in Dungeons and Dragons for my friends, when I was coaching seven and eight year old deck hockey in Pittsburgh, when I was a classroom teacher, and now when I’m a book coach, and I do author work and editing, all teaching is straight through all of that. I think you have to broaden your perspective a bit and think like, okay, well, a skill set that I have is writing a lesson plan, and delivering it in forty minutes. That itself isn’t necessarily going to translate directly to anything, but the ability to communicate a complex idea in a short amount of time to a group of people, universal. It’s not so much about finding where your piece fits into a new puzzle, it’s thinking more about what type of puzzle do you want to be in? Maybe that’s a good way of putting it.

Ryan  29:59  

What if the puzzle you want to be in is financial planning?

Tim  30:06  

Right. Okay, so great example. Let’s assume you’re a seventh grade history teacher, and you want to become a financial planner. My guess is, from the time you were a kid, you were probably looking at the stocks in the newspaper, you were probably opening an Ameritrade account in the 90s, and day trading. You probably listen to podcasts about financial planning and investments and having those conversations with your friends and family. I’ll bet you have people who come to you all the time and say, “Hey, I’m thinking about opening a Roth IRA, where should I go?” Or, “What percentage of my earnings should I put away?” And you’re answering these questions, so while you’re teaching seventh grade history, all of that’s happening, right? When you get to a point where you’re like, okay, what am I going to do? Well, you teach people how to financially plan, and that’s gonna be my answer for everything I lik., I’m really distilling our essence of this down to its most core element which is teaching. Teaching is the only thing that’s going to save the world. It’s the only thing an AI can’t do. It’s the only thing computers and technology can’t fix. It is one human being helping another human being get to where they want to be, that’s teaching. I think you can find that thread anywhere, and especially if you’re a teacher, you have such an advantage because you already have the skill set, you have the experience. All you need to do is transfer that to a different realm.

Ryan  31:40  

That is hilarious. First of all, good job, because I was trying to throw you a curveball.

Tim  31:46  

Oh, I know. I’m not always gonna hit them, but sometimes I will.

Ryan  31:51  

Well done. I totally agree. I pulled the financial planning out just because we always talk about humanities teachers because that’s our background, and I was like, what’s really different than that? But you’re right, and I’ve seen that. I actually know teachers here who teach in subjects that are different from what their passions are, but they’re still working in those areas of passion, just not officially in a way. Yeah, I can totally see that. I also share your idea that we as teachers have a lot of transferable skills. I probably really grossly overestimate that, but I just think like 90% of what we do as teachers or even administrators in education is transferable to other places. There’s a lot more organizational complexity in a school than what a lot of people realize. There’s a lot of attention. You have to pay to culture building, to how you maintain a healthy culture. You have lots of different personality types and lots more latitude for those personality types to co-mingle or, you know, interact in good ways and bad ways. You still have all the same financial stuff like any other organization to worry about, and that’s all just administrative. Then when you start talking about teachers presenting ideas that people can understand, you have to know your audience, right, you have to know your students and what they need and how they’re hearing you. You have to be tuned into those feedback loops. You have to be organized, and some of this ties my research a little bit, but it’s basically proven that teaching is one of the best ways to learn anything. You have to organize things in your own mind in a way by presenting material. That doesn’t happen anywhere else. All of that is just a way of saying, for me, there’s so much of the teaching, any part of the education profession, that translates elsewhere, but I think for me, the big question is, how does the rest of the world see it? Does the rest of the world agree with that? Whether that matters or not may depend on whether you’re independent or not. In your case, all of that applies, and that’s all that really matters because you don’t have to convince somebody that you have all these skills that are relevant in your new field, right?

Tim  34:47  

No, and no one cares what skills, degrees, certifications, or experience I have from my past life. They don’t like when an author comes to me and is struggling with a concept and I need to help them get past this block, they don’t care what letters are after my name, or how many years I did it. They’re looking for someone to help them get to a certain point, and that’s what teaching is. There are world class professionals who are terrible teachers because there are processes internalized, and they can’t explain it. There are quote unquote lay people who haven’t stepped into a classroom since I graduated high school who are phenomenal teachers because they have the ability to communicate and to help people. Teaching itself is a skill set, and I think what we’re saying here is if you’re already a teacher, you have the bare bones, like you have it. If you’re not a teacher, you can learn it. That’s the future and if you get into the internet marketing world and you look at sort of where I am with publishing and stuff now, there’s no shortage of information. You can google anything, and it wasn’t like that ten years ago, right, you can find the answer to anything, and that’s not what we need anymore. What we need are people who can help you know what to do with that information, and we call those people teachers.

Ryan  36:12  

And connect the dots sometimes, you know, sometimes I see part of the role of teachers just being encouraged. I mean, it’s yes, just being somebody to talk to. For me, my best teachers growing up, where I considered all of them to be friends and I, my relationship with them was in some ways, as personal as it was professional. I just felt like I could talk to them, and I admired them, and I think that left a mark on me as much as anything that happened in their lessons or in their class sessions.

Tim  36:56  

Yeah. You think about it to the most meaningful interactions you have with anyone throughout your entire life. You’re either a teacher or a student. It was even a spousal relationship. There are times where I’m the teacher, my wife’s a student, and other times where I’m the student, she’s a teacher. Those are the most meaningful connections, those are the most meaningful experiences you have with people, and we’re now in a place where people are craving that. Pandemic aside, people are craving human interaction, they want to learn from each other. They want to be with people who are doing the same things. They’re burnt out on the algorithm and the pure sort of tech solutions to things. I think people are craving that interaction, and I don’t think that’s going to change in our lifetime. I think that’s the trajectory we’re on. That’s where we’re headed, and I think people who can do that are going to have a much more fulfilling life.

Ryan  37:58  

So okay, kind of apprenticeship. We’ve seen that, I mean, we’re talking about that a lot here in our school, and we see the same theme in other schools as well that people are thinking about apprenticeship as a model for teaching and learning. It’s so funny because it goes way, way back.

Tim  38:21  

Oh, it’s how it’s always been. School as an institution didn’t exist up until a few hundred years ago, not the way we know it. It was all apprenticeship. It was all mentorship. That’s how humans learned for thousands of years.

Ryan  38:36  

Yeah, and community. Apprenticeship sort of does suggest, like, okay, there’s an expert who knows more than me, and they’re gonna share their wisdom. That’s definitely part of it, but there’s also being in a community with people and fostering that community where we can talk about ideas that we have. Again, I keep coming back to it, but we just have people to talk to. We’re not just sort of, you know, rattling ideas around our own brains.

Tim  39:13  

In my author membership group, we pride ourselves on being word nerds, like we talk about things that no one else cares about. There’s some solace in that, and there’s unity in that, and one of the sayings that you will hear in my line of work a lot is when you’re building a community, people come for the content, but they stay for the community. So yeah, people want the online courses and the videos and that’s helpful, but that only takes you so far. They might start there, but what they really want is they want community, they want people who can support them, people they can learn from, people they can help. You can get the instruction from a YouTube video, you can learn how to change your brakes by watching a YouTube video, but that’s not the same as having, you know, a mechanic show you how to do it or to go to a group and say, here’s what happened when I pulled the caliper off. What do I do now? Because that YouTube video isn’t going to have that answer for you.

Ryan  40:11  

Yeah. You’re making me think of the author’s on a train group because I went on one of those with you. I’m trying to think of what year. How many was that, three years ago?

Tim  40:26  

2018, I think? It’ll be three years this year. Yeah.

Ryan  40:31  

Yeah. So three years ago, and it was a small group. What was there, eight people in that group?

Tim  40:38  

I think so. Yeah, eight.

Ryan  40:40  

Yeah, and the Slack space that was set up for that group is still active. There’s still conversations happening in that group. Long three years after the workshops, and the official event happened, but that just, to me, shows the power of community, those people connected in that moment. They’re still connected, they still see value in staying connected, and I do think that’s one thing that teachers are good at is recognizing what that is and how to foster that. They do it all the time in their classrooms, fostering community, the best teachers, obviously.

Tim  41:24  

Yeah, I agree. I think that’s where we’re headed. Especially if you’re in your 40s, or 50s, there’s never been a better time to be thinking about that as part of your future because we were around before the internet, and we’ve seen the internet boom, and I think we’re entering into a post-internet phase where people are realizing that having just an online life isn’t enough.

Ryan  41:53  

Alright. Well, Desmond, where do we go from here?

Tim  41:58  

You know what, man, we’ll just take it one week at a time. We’ll keep sort of plugging away and telling stories, and hopefully, we can help some other people out whose heads might be spinning at this point, trying to figure out what in the heck they’re going to do in the next ten to fifteen years.

Ryan  42:19  

Yep. I think my takeaway today is I’m thinking about you sort of separating out what you do for a living from who you are. I’m just gonna sort of ponder that for the next few days, how that applies to my life. How much of me is in my job, and how much could I actually separate those two?

Transcribed by https://otter.ai


The Dangerous Myth of Reinvention by Marc Freedman – https://hbr.org/2014/01/the-dangerous-myth-of-reinvention 

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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