Teaching Transformations Podcast Episode 20: Things We’ve Learned

Teaching Transformations

Things We’ve Learned

As season one comes to a close, Tim and Ryan are eager to share what’s helped them get to where they are now. From a discussion of books to podcasts (and even to people), you don’t want to miss this episode!

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

Seize the Day!


Tim  0:01  

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

Ryan  0:12  

Is that Lenny Kravitz?

Tim  0:15  

Dude. Lenny Kravitz. That guy is amazing.

Ryan  0:20  

That link you sent me was something. Wow, that guy looks good for fifty-six.

Tim  0:26  

Yeah. It might have been in the fall, but I think he was on the cover of Men’s Health, and he’s got these abs, and the dude looks like he’s twenty-five!

Ryan  0:42  

I look like that with my shirt off.

Tim  0:45  

When you’re surfing in Australia.

Ryan  0:48  

I just don’t take my shirt off that often.

Tim  0:51  

Well you should do it more often apparently.

Ryan  0:57  

Yeah. Well, good for him.

Tim  0:59  

I don’t know if you listen to a lot of his stuff. I’m not like a huge fan, but the stuff he does is just really good, it’s really high quality. He knows who he is, and he’s like one of the last rock stars, I think in a way. He kind of carries himself like a rock star, and I like that.

Ryan  1:21  

I know he plays a lot of his instruments on a lot of his recordings, and I’ve always respected that. The only thing that has turned me off occasionally is these video clips of him like falling into the crowd. I don’t know, I’m sure for them, that’s bonding with the people or with the crowd, but there’s something that feels like, I’m a God, or there’s just something that feels a little over the top about that.

Tim  1:54  

Well, when you have those abs, I mean, you can do those kinds of things.

Ryan  1:57  

Yeah. Somebody’s gonna get hurt. Somebody is gonna hit their head on those rocks.

Tim  2:03  

Don’t hit your head on Lenny Kravitz’s abs. That’s the takeaway from today’s episode.

Ryan  2:08  

So, it’s been a long season. Episode 20.

Tim  2:16  

Yeah, this is fun. The stats aren’t good on podcasts. Most people bail after six or seven, I think, is typically when pod-fade begins, so the fact that we’re at twenty is good. We didn’t really have a big plan for this going in, you know, we just kind of looked at where we were and knowing what we wanted to do, we’re like, you know what, let’s break it into seasons, we’re approaching twenty, that would give us some time. We both have some things coming up in our real life schedules, so we can be able to take a little break, hopefully get a guest appearance on some other podcasts in the meantime, some of the work behind the scenes. We’ll continue to put out the weekly newsletters, so the alternate version of the curated resources and then the personal essays that you’ve been doing, so we’ll continue doing that, but yeah, this is fun. We’re kind of making this up as we go along, and I like that.

Ryan  3:16  

Yeah. I’m still getting used to that.

Tim  3:22  

As a teacher, you want the lesson plan, you want the unit plan, you want to know the beginning and end, and I know how it feels. It’s definitely a little unsettling to not have a master plan necessarily, but my hope is that once we start having guest appearances on the podcast or we have other podcasters coming here, I think things are going to pick up a bit as far as we’re concerned, as far as numbers and things. In the meantime, it’s just more of the same doing what we do and hopefully growing that audience a little bit at a time.

Ryan  4:00  

Yep. Well, since it’s the last episode of this season, I thought we would take stock of wisdom, not necessarily from this year but things that have influenced us over the years and maybe just go back and forth. One of my favorite music shows that I saw a few years back was with John Hiatt and Lyle Lovett, and it was an interesting format because they were both on stage with their acoustic guitars, and I wasn’t sure what they were going to do. I didn’t know if they were going to play songs together, but one would play a song and then the other one would play a song, and they just went back and forth. Occasionally, one would join the other with harmonies or something like that, and it was a pretty cool format, I hadn’t seen before. That’s kind of what I’m imagining here, sort of volley back and forth. I was gonna have you go first, and maybe it would be best since we don’t know how far we’re going to get on our lists, too, you might want to start with your best nuggets of wisdom.

Tim  5:19  

I’ll certainly do that. In full transparency and going a bit meta on this, in our Slack communication, you said, let’s talk about three to five things that we learned. This is not a judgment on you by any means, I don’t want you to take it that way, but I think the way we approached this kind of reflects where we are on the journey, like you sort of chose things that you’ve read or listened to, and I think that’s because you’re at the very beginning stages of this whereas I’m about four or five years in, and I thought about it from the perspective of like, where have my bruises come from? It’s an interesting juxtaposition. I think it will be interesting to hear how it plays out because of the different ways we approach this. Is that a fair observation?

Ryan  6:20  

Yeah. Now I’m going to my message, so here’s what I said. I said, we each come up with three to five nuggets of wisdom that we picked up from things we have read, seen, heard, or experienced. So, you went right to experience to which, but I do think that it speaks to where you are, like you have a lot to say on that front. I mean, I can speak from experience, and I often do, it’s just maybe not so much related to the central topic of this podcast or to entrepreneurship, but I haven’t started a business yet.

Tim  7:00  

Yeah, that was exactly my point. I opened up yours, and I looked at mine, I was like, these are very different.

Ryan  7:12  


Tim  7:13  

Alright, so you want me to start. Do you want me to pick my best one?

Ryan  7:18  

That’s what I would do. Unless we want this episode to be three hours.

Tim  7:24  

No, we don’t, and we don’t want to bury the lead either. I like that, let’s start with what we think is our strongest. I’m gonna pick this one because I think it’s one that isn’t talked about a lot, so that’s how I’m saying I think this is the best one because that might be something that people haven’t heard yet or haven’t heard a lot whereas some of my other ones are more common, and it’s nobody gives a shit about what you’re doing. I mean that in the most playful way. You may have experienced this, but we’re all really self absorbed. Every single one of us, myself included, we have this myopic lens, you know, we are moving through our story as the hero, everyone else is a supporting cast member in the narrative that we’re telling. In that, I think we forget that nobody really cares what you’re doing. You may have experienced this: you email good friends, and you’re like, hey man, I’m really excited I’ve got this new podcast and this new list, and this is what I’m doing with Ryan. And they’e like, cool, or they don’t reply, or they don’t listen. I’ve had what I consider to be these groundbreaking, earth shattering moments in the publishing industry, and I email my list, and it’s crickets, you know, and it just reinforces this idea that most people don’t care about what you’re doing most of the time.

Ryan  9:10  

I 100% agree and have seen and felt that for sure. It’s funny to hear that be your number one. That’s a good number one, I’m with you on that. I mean, even just with this project, I’ve mentioned it to people who I was sure would be like the primary audience for this, “I think you’re gonna dig it,” and they made it clear, like right up front, yeah, not that interested. It ties to one for me, I’m not going to make this a different one, but I think just because you do something and put it out there doesn’t mean it does anything. It doesn’t mean it has any impact on the universe, and the first time I came to that realization, I’m remembering when I was in my twenties, I was tire carving, and I think I’ve talked about that or written about it, but that’s when I first started playing around a little bit with entrepreneurship, and I decided I wanted to try to sell recipes in like the classifieds of a cooking magazine. I was like, I found this recipe of my grandma’s food cake, and I put it in there. I was like, okay, I just gotta sit back and wait for the checks to start rolling in. This guy I worked with, he and I were talking about this stuff a lot, he jokingly sent me a fake check for an order of like a thousand of these recipes or something, and it was literally the only response I got from it. The lesson I took away from that was, just because you put something out there doesn’t mean anybody’s going to give a rat’s or pay attention in any way whatsoever.

Tim  10:56  

Yeah, and if you’re around publishing for about ten minutes, you realize that, too. Many of the people I hang with and my friends in the publishing industry, they’re waiting for that one thing to catch, and it might take publishing a hundred things to get one thing that gets a little bit of interest, and that’s just the universe. That’s just the way it is. Some people get that one thing on their first try, and the other 99% don’t, and that’s just how it goes.

Ryan  11:30  

Definitely. Well, be ready for that, I guess, if you start putting stuff out there. So, my first nugget of wisdom traces, most of mine are going to trace to things I’ve read or heard, not that I feel like I need that. I do enough thinking on my own, but a lot of times, you know, I’ll really ruminate on something. I’ve referred to him before, but Tim Ferriss’ Four Hour Workweek, I think that came out in 2007, and out of many things that I’ve read over the years in terms of having an impact on my real life thinking, that just messed with my wiring in a good way. It got me to think differently about time and how we think about time, how we act about time, what it means, how to control it. It got me to think about patterns that we follow unquestioningly. He was talking about when he was a young man, and one of his first jobs was a sales job. He watched, basically, the marching orders where, “get in here at nine and get on the phone and be on the phone all day long,” just making sales calls, sort of brute force, throw all this time at it, and he immediately saw this problem of when he was making sales calls, it was business to business stuff, that there would be these gatekeepers that wouldn’t let him get through to talk to the people who he needed to talk to. He realized that the gatekeepers got there at nine, and if he made his calls at eight instead of at nine, he would skip all the gatekeepers, and he would get right to the people he needed, so he would spend an hour getting way better results than spending that eight-hour day. He had a lot of examples like that, but that book just made me think about many ways that a lot of us do that day to day, you know, we just brute force throw time at things and don’t necessarily think more smartly about the yield that we get from that time.

Tim  14:02  

Yeah. That’s an incredible book, and I’m pretty sure you were the one who turned me on to that book because I think you read it before I did and told me about it. It took me ten years to internalize a lot of what was in that book, and like you, when I first read it, it definitely messed with my wiring, but I was not in a place where I was ready to do anything with it. It took me ten years before I started to step into that when I became self employed, but I can trace a lot of my own feelings and perceptions now about self employment and entrepreneurship back to that same book, so I agree that’s a cornerstone one, I would say. I think that’s almost a must read for anyone who’s our age and looking to eventually move out of a career, retire, however that happens to go.

Ryan  14:59  

One of the terms that I learned from that book is social reinforcement of certain illusions. There are a lot of ways that we socially reinforce certain behaviors in one another, and one of them is acting busy. We’ve talked about this, like the idea that we always have to be exasperated and running ragged, and we wear that as a badge of honor. When you dig into it, not only is it ineffective, but a lot of times it’s just bullshit. It’s acting.

Tim  15:35  

Yeah, so true. Alright. I’m going in reverse order, I guess, from what I think is more common advice to less common. The other thing I think I’ve learned through experience is that the worst case scenario is never as bad as you think it could be. It sounds so simple on the surface, but it’s hard to think about that in the moment, and I go back to my decision making process that really was only over a course of a few weeks. It was not an extended decision making process but the window of time I had to decide that I was not going to sign my contract for the following school year. All of the scenarios that I had to run through, and I remember at the time, it seemed like a life or death decision, and now I look back, and it wasn’t, but it felt that way because I was about to give up all the security, everything I’ve known, everything I’ve “built” for my entire career, and I was about to walk away from it. My worst case scenario went to like, cooking a can of beans under the bridge in a shopping cart, but like, that really wasn’t the worst case scenario. The worst case scenario was, we struggle paying some bills for a few months, and then I get hired as a substitute teacher. The worst case, especially when we’re talking about life choices definitely around finance or career, we often assume that there’s a catastrophic, worst case scenario, and while that exists, I think the likelihood of that happening is pretty slim.

Ryan  17:36  

That’s very true. I think that keeps a lot of us, I’m sure myself included, from making more bold choices because we’re afraid of that, and I don’t want to minimize that. There’s a lot of real risk for people, and when you have family, you have other people that are sort of hooked on to your wagon. It’s bigger than just you, and that puts even more pressure on us to make sure we don’t screw it up. Those fears are real. I’m going to refer to another book here, and you’ll notice a lot of these are, well, these first two at least, are sort of from the same time period. I was doing a lot of heavy listening back then and a lot about, I don’t know if entrepreneurship is the right word for it or not, but a lot of books that had to do with economy in entrepreneurship. I still listen to some of that sometimes, but lately, I’m more into human stories and stuff like that, but yeah, Daniel Ariely’s Predictably Irrational which came out in 2008 was fascinating. It exposed me to a field I didn’t know about which is a relatively new field called behavioral economics and just a subset of economics, but it’s really psychology wrapped around economics. A lot of it really digs into human behaviors around markets and around economics, and the studies that were discussed in that book were just fascinating to me. One of the takeaways is, and I may have referred to this before, but that it’s not good to mix market norms and social norms. If you’ve got a neighbor, most of us wouldn’t think twice about asking a neighbor that we’re friends with to help us move something or move out, but if your neighbor owns his own moving company, that has different implications, right? Because that’s what they do for a living, and that’s a little more sticky and complex because you’re asking them to do what they do for a living, and that’s one of many examples of where market norms and social norms don’t mix well. The argument is they really should be kept separate, and I have come back to that in so many ways in life. I have to remind myself of that. I’m like, I need to be aware of that, and that’s why I probably shouldn’t go to this person for this favor or that person. Again, I’m a thinker, so I process stuff like this all the time, but sometimes some of these things mix together. I realized as I was thinking about this episode that there’s some ideas from both of these first two books I’ve talked about that have started to blend together a little bit for me, and I think it comes back to keeping economies separate from one another. The Tim Ferriss book was all about the way that we economize, and our work world is all based on time. Everybody gets paid for x number of hours per day, right? I know not so much for teachers, but many people punch a time clock, they get paid for their eight hours. It’s not necessarily about productivity. There’s an assumption that exchange for time equals productivity, but there are many cases where it doesn’t really translate. When I start combining these two ideas from these two books together, I start realizing it’s hard if the basis for your economy is productivity.

Ryan  22:13  

And that’s the way it is from the ground up. That’s one thing, but if it’s time, that’s another, and it’s hard to mix those two things, so it’s hard to go from one to another without fundamentally shifting. I feel the same thing is happening here at our school because we’re playing with a lot of these Mastery School concepts like getting rid of grades and stuff like that, but it’s really hard to make that shift midstream because everything was built on the premise of grades, so how do you dismantle that? For me, it all just comes to, how do we fundamentally define things? If things are fundamentally defined around time, it’s really, really hard to impose productivity orientation overtop of that. Does that make sense?

Tim  23:03  

It does. I have to wonder, I was somewhat optimistic that the pandemic might finally up-end education in a positive way, but I don’t think it has. From the inside, do you feel like there’s an opportunity slipping away here to redefine that’s not based around time?

Ryan  23:24  

I do, and space, even. I look at all the video conferencing that’s happened and the skill that’s developed around that,and I see that as a positive something that we could build on and we’ve probably wanted to build on for a long time. The problem is, everybody’s so burned out from the year that they just want it to be over. There’s an association now of like, okay, Zoom is associated with COVID, and I just want that to be behind me. Unfortunately, I think mentally, that’s probably going to get in the way of us being opportunistic.

Tim  24:02  

Yeah, that’s a shame. Good one. That’s not a book I’ve read, so I’m definitely gonna check that out. Alright, my next one, this is one I didn’t really want to face, and I don’t think most people like to hear this, but if you don’t set your intention, someone else will set them for you or some other thing will set them for you. There’s a false assumption that we operate under which is, if I don’t make a decision, I don’t have to make a decision, but really, not making a decision is a decision. I’ve had this conversation with my wife multiple times. She’s not a decision maker, she does not like change, she does not like to make decisions. She would just kind of ride things out, and I’m like, well, but you’re not really riding things out, you’re just turning control over to somebody else even though you feel as though you have this theater of control where you’re like, I’m just not going to decide, and I’m like, no, you have. The way that looks in a very stark way is that if you’re not intentional with what it is you want to do with your time, what it is you want to do with your resources, if you leave that to chance, other forces will come in and by default, set those for you. Here’s an example. Let’s say you’re not thoughtful about your living situation. You have a mortgage, and your wife or your husband decides, we have a mortgage, and that’s it. We’re just gonna pay on it till the house is paid off. In a time like now where housing market prices are soaring because there’s very little housing stock, especially in our town, in our part of the country, this could be an opportunity. If you don’t make a decision to explore that opportunity, then that mortgage is setting that intention for you, so by choosing not to look at the possibilities, you are, in fact, letting your bank make that, and that might be fine. That might be okay, but I think you have to have that realization.

Ryan  26:27  

That’s very Rush.

Tim  26:29  

It’s very what?

Ryan  26:31  

Rush. Wasn’t that in a Rush lyric? It was like, “if I choose not to decide, I still have made a choice.”

Tim  26:37  

Oh yeah! I didn’t even pick up on that. That’s from the song Free Will.

Ryan  26:44  

Yep. I totally agree with that, and this is a place in my own life I’ve really tried to get better at, and it will forever be a work in progress, trying to not let life happen but to really shape it the way I want to. It’s easier said than done. I think this is one of those things where you have to develop habit and mindset around it and then keep building on that and keep trying to get better at it, but yeah, I totally agree. Some things that feel like they’re not a choice, you know, maybe they are more of a choice than we want to give them credit for.

Tim  27:29  

Yeah. We just slide into routine so easily, and a lot of times, we lose sight of the fact that we can change that routine. I’m not saying it’s easy or that everyone can do it for every situation, but becoming slave to the routine and not being intentional about creating it is problematic.

Ryan  27:54  

Alright, so I’m gonna go to another book here. Another book that I have read in recent years that I actually listened to, most of my books are listens, not reads, is Rob Lowe’s story, I Only Tell My Friends, which came out in 2011. My kids really enjoyed listening to that, so we’ve been through it a number of times in the car. He’s a surprisingly good writer, surprisingly thoughtful, human. I shouldn’t even say that, but I think we have this image of superstars or celebrities and especially overly good-looking celebrities, like Lenny Kravitz. I mean, he’s a real person, and he has a lot to say. Anyways, I really enjoyed his book. The last chapter is about his time on West Wing, and that was a show that I liked a lot, so I was pretty intrigued by that. He was on that show for four years, and I wouldn’t say a falling out, but he and his bosses on The West Wing didn’t see eye to eye in terms of his role, what his involvement in the project meant. That’s why eventually he left after four years, and the show went on for another three after that. His issues were both financial but they were also creative, and I think he felt like, okay, the financial part of it isn’t where I want it to be, but can I at least have a bigger creative stake here? Can we develop more storylines around my character? And that didn’t happen. The way he related that and the way he used that situation and decided to make a change because it wasn’t working for him was based on this self belief that he had. He knew he had in him the skills and capacities to hit stuff out of the park, and he wasn’t being used the way he wanted to be, so he had to make this hard choice to leave the show. Again, back to the whole fame thing, famous people go through stuff like this, too, but there are lessons in that story that I think are relevant to all of us, which is there are times that some of us are going to get overlooked by our bosses, or we’re not going to be using our skills in the way that we want to. When we recognize that or when we feel that way, it’s important to act on it in some way or another. Self advocate or find something else or whatever because if you’re not doing that, it’s an easy way to develop a victim kind of mindset about life, and it sort of ties to what you were saying in your last point. We want to push people to be active and to not let things happen.

Tim  31:27  

Yeah, and that really is an important thing to remember, too, is that even someone like Rob Lowe, who from the outside has got it all together, there’s still human issues that we all deal with. Maybe it’s not Rob Lowe, but maybe it’s the teacher in the other classroom or the football coach, and you’re just like, wow, that guy or that woman, they’re so on top of things, and maybe they’re not. Maybe they’re having their own struggles and their own issues, and I think how we then interact with each other, that’s where that empathy comes in. I have to try and remind myself of that because I’m in a position where I deal with some sort of customer service issues, as you do as well, and I have to remind myself that like people are coming to me either in crisis or they have a problem. Again, they’re the hero in their own story. They’ve been wronged or offended, and it’s not personal. That’s something that gets lost in cancel culture and Twitter mobs and internet rage is like, everyone’s dealing with something, and you really have to be empathetic and keep that in mind. I’ve got one more. You want to do one more each?

Ryan  32:50  


Tim  32:51  

Well, this one is not a big shocker. Maybe it will be if you’re a bit younger listening to us, but I’ve definitely learned time moves faster the older you get. I don’t know what the proportion is, but I know that things that happened twenty years ago, to me, feel like just the other day, and I can also remember being in my early twenties and thinking that forty and fifty were just so far off. I don’t know if it’s a cautionary tale. I don’t know if I’m preaching to the choir, but the way that translates into my day to day life is just making more of every minute. That sounds so cheesy and cliche, but to me, it’s just about enjoying every aspect of my day because I don’t know how many I’ve got, and then they go fast. Even if it’s interactions with my kids or joking with my wife or even going for a walk in the evening, I try not to take that stuff for granted.

Ryan  33:59  

Yeah, I’m with you. I think we just naturally take on that wisdom as we get older, but losing loved ones is one of those hard reminders for us about how quickly life can slip away. We’ve all lost people that were important to us too soon, and unfortunately, it’s one of the ways we learn not to take things for granted and to really make the most of time. I’m really with you. I would just add on to that that I also am choosing to ignore all of the signals that certain things are like off limits when you reach a certain age and stuff like that. I think we had a previous conversation about this, but I mean, that’s why I like that Lenny Kravitz story that you shared with me because here’s this guy getting deeper into his fifties, and he’s not playing the mid-fifty-year old, you know, he’s playing the twenty to thirty year old, and I think he feels like it. Making those choices, too, like, are we going to play somebody who’s getting older or are we going to play somebody who’s perpetually young? That’s a choice we can make.

Tim  35:39  

Yeah, it is. There are physical limitations, I mean, I’m sure there are even things that Lenny Kravitz can’t do at fifty-six that he could do at twenty-six, but still, I think your point is that it’s more about a mindset. It’s more about an attitude than anything else. You got one more for us?

Ryan  36:00  

Alright, so this is another book. This is a little more recent. This is The Infinite Game by Simon Sinek, which came out in 2019, and it really breaks down the ways that a lot of people get trapped into playing finite games instead of infinite games. He uses a lot of business and life examples. Just to be succinct about it, finite games are games that have a definite beginning and end. There’s like a goal to win, to have the highest score, the lowest score if it’s golf, or something like that, but the game is highly defined and contained, and it has a really simple goal. Many of the games we play in life and in business are not that simple. How do you win the game of education? How do you win the game of marriage? Those are games that we’re all playing. How do you win the game of life? No one’s gonna win. Your time runs out, like, you can’t say whether you’ve won or lost.

Tim  37:16  

Well, you need a spinner to hit twenty every time you move, right?

Ryan  37:19  

Right. If you look at most success stories, they kind of decode this way even in the business world. He used an example of like, early on in the whole mobile device game, Apple already had the iPod, and Microsoft introduced the Zune, and the Zune was a superior product from a design standpoint at that time. Microsoft’s goal, their openly stated goal was to beat Apple at this game. Their goal was to gain market share, to win that finite game, and Apple wasn’t playing a finite game, they were playing an infinite game. Their goal was to respond to their customers and to keep improving, and the results are what they are. They’re obvious and, and Apple won the war so to speak, but some of this plays out in real life scenarios, too. He used the example of the Vietnam War. The Vietnamese were playing an infinite game, and the United States was playing a finite game, and that put us on two different trajectories. The Vietnamese had been fighting the Chinese for thousands of years. This was about their survival. It wasn’t about campaigns or about winning this particular battle, it was much bigger and deeper than that and went well beyond the group of people that were there at a particular moment. I don’t know, this book, again, messed with my wiring a little bit and got me thinking about how some of this plays out in our real lives. What are our goals? What kind of game are we playing? Is it finite or infinite, and how would we approach it differently depending on our mindset on that?

Tim  39:35  

I love this book, and it reminded me that not every game we play can be quantified with points, right, which is the message, too, especially when it gets to interpersonal relationships. Over the years, I’ve been friends with people and we’ve been friends with other couples, and they’re the couples who keep score. We’re not one of them. I don’t think you guys are either, but there are couples who are like, well, you went out to poker night on Saturday therefore I’m going shopping with the girls on Sunday. There’s this tit for tat, like we’re trading, we’re keeping score, and that’s not the kind of game I want to play in my personal relationships. Actively, that’s the practical application for me and the real world is, there are certain things where I’m not looking for Even-Steven, perfect distribution, there’s just things I’m going to do, there are going to be things other people do for me. They’re not necessarily going to balance out, and that’s okay.

Ryan  40:39  

Yeah, I’m with you on that, and definitely, Christina and I have always been that way, and I think that’s why we get along so well–we don’t play those kinds of games. I feel like that works for us. That’s healthy. Before we completely shut down the topic, and especially since I went the route of referring to things that I’ve read and seen, I wonder if you could just take a moment and maybe share a couple of either podcasts that have influenced you or that you would recommend to people or books or speakers to pay attention to. Not necessarily digging into the meaning of it, but what recs would you have of things that have influenced your thinking in the past ten to twenty years?

Tim  41:41  

There are two that pop into my mind: one who I’ve been following for over ten years and another one who I’ve recently gotten to know better, and I think these two people are really shaping me more than anybody else. The first one is Seth Godin. Whether it’s his Akimbo podcast, his daily blog, any of his books, his books are phenomenal, he is a thinker’s thinker. The guy comes up with concepts and makes connections that are just stunning, but they’re stunning in their simplicity and effectiveness. I’ve been following him for well over ten years. I would highly recommend any of his books, podcasts, or blog. One that’s more recent, which is kind of ironic because I knew him at Copyblogger way back in early to mid 2000s, is Brian Clark. Brian Clark doesn’t have any books out yet, but he’s got a couple of communities that I’m a part of. He’s got a newsletter called Further, he’s got the Unemployable Initiative community, and Brian’s thing is 7-Figure Small, and Brian is really good with coming up with these labels that immediately identify what it’s about. 7-Figure Small is about having a seven figure business without having all the overhead and all the resources that are required to build it. I’m drinking his Kool Aid right now, and I’m following a lot of his blueprints, and that’s been over the past year or so. Then Seth is the one who I’ve sort of felt like has been riding shotgun with me the whole way, dipping in and out of his books and podcasts and things.

Ryan  43:29  

Yeah, cool. Do either of those guys have podcasts?

Tim  43:34  

Both of them do. Brian Clark’s might just be for the community. I’d have to double check that Seth’s podcast is called Akimbo, and I think it’s been running for several years now, and they’re just him. He doesn’t do interviews. They’re usually less than thirty minutes long, and the real goal is the listener questions he asks at the end of every episode, so if you’re looking for short, tight, thought-provoking weekly podcasts, Akimbo is highly recommended.

Ryan  44:08  

Do you have to listen to it on 3x?

Tim  44:11  

Only if you’re me, and you’ve got ten more episodes queued up behind it.

Ryan  44:18  

That’s cool. The couple I would mention would be, I’ve really enjoyed How I Built This with Guy Roz. It’s an NPR podcast. The one episode that sticks out was the one with Chipotle founder Steve Ells where he talked about starting Chipotle, and it was just interesting because it wasn’t complex, it didn’t need to be. I think we have this assumption that anything we start up has to sort of be really hard and lose money for years before it gets off the ground, and he just did the simple calculations in his head and had the simple premise, and it worked from the moment he started. There’s a bunch of good episodes there. I liked that podcast. Listen to that one. Planet Money is one that I’ve listened to. There’s so many episodes of it, man, it goes back to like 2008, and it’s still running strong. It’s hard when you have that many piled up. If you’re new to it, it’s hard to figure out where to start. You can’t imagine listening to all of them, but if you’ve never heard it, and you’re interested, I would just say scan the titles and poke into one that’s interesting, but those are a couple. The other person I would mention, I saw Guy Kawasaki speak a few years back, and he is the premise of his show. His presentation was less is more, but he said his hard rule on slideshows is no more than ten slides ever. I wouldn’t say I’ve necessarily been able to follow that, but I always think about it when I’m making a presentation.

Tim  46:15  

Yeah. I’m a fan of Guy Kawasaki stuff. He’s another really smart and insightful person.

Ryan  46:24  

Alright, well, any thoughts as we wrap up season one?

Tim  46:30  

No. I hope you’re still enjoying it as much as I am. I look forward to our conversations. Even if we weren’t recording these podcasts, they would be fun for me to do. I’m excited about taking a little bit of a break from the podcast and thinking about where we want to go with it and hopefully growing an audience, so I’m looking forward to that. What about you?

Ryan  46:53  

I just want to have Lenny Kravitz abs by the time we start season two, so I have some weeks to work with. That’s my goal.

Tim  47:01  

That shouldn’t be a problem.

Ryan  47:02  

Yeah, I think I got this.

Tim  47:05  

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


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/ 

6 Steps to Finding Your Second Act in Retirement – https://www.kiplinger.com/slideshow/retirement/t012-s004-6-steps-to-finding-your-second-act-in-retirement/index.html 

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