Teaching Transformations Podcast Episode 8: The Role of Mentorship

Teaching Transformations

The Role of Mentorship

Join Tim and Ryan as they discuss the importance of being selective about where you’re looking for mentorship and what you’re looking to accomplish with it. They boys review what it’s like to be a mentee as well as their relationships with past mentors.

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  0:11 

I love how we start every week with ten minutes of tech troubleshooting.

Tim  0:18  

Well, we don’t.

Ryan  0:20  

Okay, thank you. Thank you for clarifying.

Tim  0:26  

Yeah, it’s a good start, but I was gonna get you off the hook because I want to tell you about this game I’ve been playing with Joy, and it’s not that kind of game, don’t get all excited. It’s a text message game. So, the other day I sent her this text: I just robbed the grocery store, I’m going to Disneyland. Then I sent her this text a few days later: I’ll say anything you want to hear. I’ll see everything through. Then this morning, I sent her: Despite all my rage, I’m still just a rat in the cage. She’s just texting back: For the love of God, please stop. I’ve gotten into this habit of listening to 90s alternative channels on Spotify and just sending her song lyrics. The best ones are the ones that are in first person. When you first look at them, you’re like, wait what?

Ryan  1:20  

Is she recognizing them?

Tim  1:22  

She didn’t at first. At first she was like, what is this? Then I wouldn’t even reply. I just send a new one, and then she caught on, and now she just stopped doing that.

Ryan  1:31  


Tim  1:33  

Do that to Christina though, see what her response is.

Ryan  1:35  

Well, it’s funny. There are some people I have this shorthand with, and my son is one of them. My friend John was one of them, but like where I send a random song lyric or actually, just a word. One that we’ve done is chicken man which comes from Bruce Springsteen. Nebraska, Atlantic City, I think.

Tim  2:03  

That’s a nice obscure one. You really got to be tuned in to pick that one up. I decided to throw Joy a softball this morning. I’m like, oh, Smashing Pumpkins, she’ll totally get that one. Smithereens, School of Fish, some of those obscure 90s alt rock bands, not so much.

Ryan  2:19  

Yeah. What are the bands that you guys bonded over?

Tim  2:24  

I think it’s really a lot of those early 90s alternative rock bands. It was weird. She was really into the 80s new wave, so she was listening to like Depeche Mode and The Cure, and I hated bands like that at the time. At that time, I was listening to a lot of hair metal and hard rock and towards the end of the 80s, early 90s. This would have been shortly after we met when alternative music really sort of blown up, so we went to see so many bands together. More of the lesser known bands, at least at the time. I remember one of our favorite shows was when we went and saw the GooGoo Dolls on the Superstar Carwash Tour, and we saw it at the Graffiti in Pittsburgh. There was like, I don’t know, maybe fifty people in the club. They were on a stage that wasn’t really a stage, it was just the taped off section of the floor, so they were at eye level when they were playing. They would call people up, and we were college kids. They would call college kids up to sing songs with them. I didn’t, but there were people in the crowd who went up there and were singing GooGoo Doll songs with them.

Ryan  3:35  

Nice. They were a little more rocky back then, weren’t they?

Tim  3:40  

Yeah, they were. They kind of had more of a punk ethos. They were a three piece and kind of stripped down and they’d ride a buffalo, so that had this sort of real Rust Belt working class mentality. Did you and Christina bond over music at any point?

Ryan  4:02  

A little. We met in this master’s program, and Chris Isaac had a big song on the radio at the time that we bonded over.

Tim  4:14  

Wicked Game, right?

Ryan  4:16  

No, it was a little later than that.

Tim  4:18  

Oh, okay.

Ryan  4:19  

Forever Blue I think was the album, and then we got Talking Heads. I shared some old Talking Heads with her that she had never heard, and she really liked it, so that’s part of our music fabric together.

Tim  4:38  

Yeah. It’s some of that nostalgic catnip now, like when I go running, and I pull up Spotify, I look at some of those playlists from that era. What’s fun for me is I really like to listen to albums, so when I’m paying attention, I like to listen to an album from start to finish the way the artist intended, but when I’m like working out or I’m doing other things, I like a little bit of variety. So putting this playlist on shuffle, I’m laughing almost every time a new song comes along. It’s like, oh yeah, I remember that song, you know, but it’s not expected. It’s kind of a pleasant surprise.

Ryan  5:14  

Yeah, and ones you haven’t heard for a while, it can be like hearing them for the first time because you forget.

Tim  5:21  

Exactly. I’m starting to learn the difference between the artist radio versus the song radio versus the playlist. I didn’t really wrap my head around that, my son helped me out with it. There’s a nuance between those. The artist radio is much more general than the song radio. I’d love to know how that algorithm works, like how do they determine which songs go into the song radio? Is it strictly listens? I’m fascinated by that but totally wouldn’t understand it.

Ryan  6:01  

Well, we’ve wandered around this topic here. That has nothing to do with our topic of the day. We said in the beginning we were going to let people look under the hood, and this is one of those things I have to say every week that we talk. I always have in my head, we’ll start off just by connecting a little bit, and then in the back of my head, I’m always like, how do we get to that day’s topic? You’ve been doing this for a while. Is there a way? Does it just come naturally to you?

Tim  6:37  

I don’t think it has to be connected necessarily. We’re going a bit meta here on podcasting, but it’s a pretty common podcasting technique, especially with a co-hosted show where there’s a little bit of ketchup and BS in the beginning. What’s really interesting about that is like, I think if you keep it to a minimum, it’s really interesting. There have been podcasts I’ve listened to where it’s gotten very self-indulgent, and you’re fifteen or twenty minutes in and you’re like, okay, can you kind of get to the topic already? I am hyper aware of that, but one of the interesting observations that someone shared with me is, I’m good friends with Joanna Penn. In the publishing space, she probably has the most prolific podcast around. It’s been going for over ten years now. She said at one point, she considered getting rid of guests because all of her listener feedback said, we just want your personal update. She would do this solo, like she would say, here’s what’s been happening in my life this week, here’s what I’m working on, and people were way more interested in that than they were the interview guests. She didn’t get rid of the interviews. I mean, she still does them, but she’s like, that was a very real thing. To this day, people still say, I never miss any of your intos, but sometimes I skip through your interviews.

Ryan  7:59  


Tim  8:01  

I think it’s part of that bond that people feel with podcasting. We’ve talked about whether you’re in someone’s ear or they’re in your ear, and it’s an intimate platform. It’s different from video and reading, so maybe that has something to do with it.

Ryan  8:16  

Good point.

Tim  8:17  

So yeah, you’re off the hook on connecting the chit chat in the beginning with the main thing we’re gonna talk about.

Ryan  8:24  

Okay. Well, the main thing we’re going to talk about today is mentorship which I think is a topic that, as educators, is sort of near and dear to our hearts. I think we can get into how mentorship is the same as or different than teaching, if it’s embedded in teaching, all of those kinds of things. I would assume that people who’ve had a career in education are going to care about this topic of mentorship and are going to have sort of fond memories of being on either side of the fence with that.

Tim  9:03  

I hope so because it’s getting to be a well of inspiration and opportunity for teachers, especially if they’re not doing it yet.

Ryan  9:13  

Let’s start by defining what it means to us. What does mentorship mean to you?

Tim  9:22  

It’s a bit of a fuzzy definition. At its core, mentorship is a relationship, and that might be different than teaching. I think I’ve always thought of teaching as an activity or an art or something active, whereas mentorship to me is more about a relationship, and it’s usually one-on-one. Most teaching is not necessarily one-on-one. At the core of that relationship of mentoring is, you have one person who is further along in their experience than the other person, and they’re trying to help them get there. It’s a bit of a fuzzy definition, but it’s different from teaching, and then it’s not tied to a topic or a curriculum, it’s more about finding someone in the life stage that you want to be in and having them help you get there on both sides of that.

Ryan  10:33  

Yeah, I think I have a similar sentiment about mentorship. You mentioned relationship, and that’s definitely a big part of it for me. The more I thought about it, I realized, for me, mentorship was sort of the intersection of friendship and teaching, and it is typically a one-to-one relationship. I guess you can mentor small groups maybe, but, you know, when I think of mentorship, it’s really a one-to-one relationship I have with someone. It always involves some kind of education, and it always involves a relationship that I would call friendship for me.

Tim  11:18  

I would agree with that on all counts, yeah, definitely.

Ryan  11:24  

Can you think of examples of being on either side of that fence that stick out to you? What’s the best mentor relationship you can remember?

Tim  11:40  

I should probably preface this, and I’ll come back to it at the end because I think it’s really important. If I hadn’t been involved in mentorship on both sides, I would not be where I am right now. Where I am right now is four years out of teaching, being self employed, thriving in my business, providing for my family, preparing and saving for retirement. None of that would have been possible without mentorship. I’ve done all kinds of mentorship on both sides, and it’s probably the single most important thing in getting me to where I wanted to be. As a mentee, I’ve had a number of very important and influential mentors, and it’s always difficult in these kind of situations to talk about them because I’m always gonna leave somebody out by accident, and I don’t mean to. I figured instead of talking about, I mean, over a dozen. There’s been a dozen people who have really helped me in specific one on one ways, but you asked me about the best, and I’m not necessarily going to talk about the best, but I’m going to talk about the most significant pivot that happened. That came from Chris Brogan who was sort of unofficially mentoring me. He’s very successful in entrepreneurship and in business, and a few years ago, I was really looking at him as sort of the role model. Not necessarily his industry or what he was doing, but his lifestyle and the way he engineered that, and we were having commerce. I was kind of having a crisis of conscience a few years ago, and I was trying to decide, like, do I put my stake in the ground and build my own brand? Which is what I ended up doing, you know, as J. Thorn, or do I hitch my wagon to somebody else in terms of a certification or an integrator for a visionary, like coming on as part of a team as opposed to making my own team? I think I was lacking the confidence to do it myself. I went to Chris and said, listen, I have this opportunity. It’s gonna cost me like $5000 or $6,000 to get this certain certification with a certain influencer, but then I get into their pipeline. I’m gonna get clients this way. In this conversation, he was like, why do you want to put someone else’s name on the back of your shirt? You can do this yourself. Everything you’re telling me you want to do, you can do that. I knew it, but it took him to say that, and that pivot changed my entire life, and I’ve told him that. We’ve joked around about it, and I’m now in his paid mastermind group which is kind of crazy because this was not a paid relationship at the time. It was that one conversation that crystallized something for me, and it wouldn’t have mattered how many books I was reading about entrepreneurship or if I was in an online course or if I was listening to podcast, I would not have had that insight if he hadn’t asked me that question in that way at that time.

Ryan  15:10  

So some of it is timing?

Tim  15:12  

Oh, yeah. Maybe some people can, but I look back and see that timing in hindsight, I didn’t necessarily know it in the moment. I think that’s why I’ve always looked for mentors, and I’ve always mentored people because you just don’t know when the timing is right. If you wait to say, okay, now I’m ready to find a mentor, you might have missed a window of opportunity you didn’t even know about.

Ryan  15:41  

Do you think you can seek it out? Can you orchestrate a mentor-mentee relationship, or does it just sort of have to happen naturally?

Tim  15:53  

I think you can. I think it’s hard. I mean, it’s hard either way because I know we’re going to talk more about this, but especially for when you’re talking about an unpaid situation, just a peer mentorship. The person who’s doing the mentoring isn’t going to get anything out of it, and they know that. That’s part of the deal, that’s the whole pay it forward. Chris knew a few years ago that I was not going to advance his business or his career in any way–he was purely giving back to me. That makes it hard to get mentors in this way because that’s the nature of it. Usually, you know, the more successful people are, the more narrow bandwidth they have for those types of things. So, yeah you can orchestrate it, you can ask people for help. I started asking Chris for advice, and at one point, he said, listen, anytime you want to talk, just give me a call. I took that as the invitation to mentorship, and I didn’t abuse it. I only called when I really got painted into a corner. You can set it up, you can be looking for it, but I think you also have to expect that you might have to ask several people before you find one who’s willing to do it, and that’s part of the part of the game, too.

Ryan  17:22  

Going the other direction, I know you’ve been a mentor to a number of people, but is it unpaid? Is it paid? Does it depend?

Tim  17:37  

A little bit about that, it kind of depends. I look at the author mastermind group that I run, and that’s sort of like a group mentorship. It’s not necessarily one-on-one, although those twelve people do get one-on-one access to me, and that’s paid and works wonderfully. I think it’s a great business model. The people who are in it get great value out of it, and many of them continue to sign up every single cycle, so I feel really good about that. There are certain times where I’ll sense someone needs some help, and I will offer it. Strangely enough, it’s been rejected more than it’s been accepted which really surprised me. I’ve had situations where I’ve offered help to people who I know want to get where I am, and they didn’t take me up on it, and that’s fine. It’s totally fine. I don’t have any hard feelings about it, it just kind of surprised me. There also have been people who have asked me not for mentorship, but have asked me a question. I felt like, man, if I just spent a little time with this person, I could save them years of agony. I almost felt obligated to do that, and usually they’re friends. Jeff Elkins is a great example. Jeff was a friend of mine listening to one of my podcasts, and him and I were talking, and he’s like, I don’t really know where to go next. I was sitting there thinking, man, if I don’t help this guy, he’s gonna spin for years because I could see where it was going. I had been there, sso I offered to help him. It’s weird, just like the Chris Brogan example. It started out where I just offered it to Jeff and I offered him help, and now he’s part of my mastermind group. Later on, he joined, so yeah, it’s similar to teaching. When you’re in a classroom, you have those fifteen or twenty or thirty students, and there’s usually a couple that you identify as, like, wow, if I just give them a little bit more time, it’s going to be making an exponential difference in their life, and you can kind of feel that. That’s the way I’ve been approaching it as a mentor.

Ryan  20:05  

I’m trying to think if I’ve ever even had a paid mentorship experience. I paid a career guy for like a year or so to meet with me x number of times during the year, so I guess that would qualify. He did help me, but I don’t think of that relationship as a mentorship relationship because I think for me, I put a lot of weight on that friendship piece.

Tim  20:36  

Yeah, he sounds more like a coach.

Ryan  20:40  

That’s probably right. So, what’s the difference there? A coach is someone you don’t necessarily have that kind of relationship with?

Tim  20:49  

I don’t know, it’s hard to differentiate that. I don’t know if I can articulate the difference between a coach and a mentor. I can feel it, but I don’t know if I can explain it.

Ryan  21:07  

It’s just semantics probably.

Tim  21:08  

Yeah, it could be. It always feels to me like whenever I’m working as a mentor versus a coach, I almost feel like there’s more of a personal involvement, there’s more something personal at stake. I’m a book coach, so I’ll have clients who I coach through a book, and that feels way different than being a mentor to somebody.

Ryan  21:34  

To a certain extent, right now yours and my relationship with this project is a little bit of a mentorship relationship. You’re mentoring me because you’re further along that path, so all of these things that we’re doing like this podcast, I mean you’ve done 500 some podcast episodes, and I’ve done however many we’ve done together which I think is still single digits.

Tim  22:02  

Well, when you came to me and said for fifty grand a month you wanted my services, I was like, how can I pass that up?

Ryan  22:11  

Yeah. You take credit, right?

Tim  22:14  

What kind of credit?

Ryan  22:16  

The bad kind. As I was thinking about people that I consider to be mentors, for me, it went way back. I would call my sixth grade teacher my first mentor.

Tim  22:33  

Oh, no way.

Ryan  22:36  

I just connected with him. I started hanging out after school and talking to him, and he was a really interesting guy. Teachers, you can’t explain the chemistry–sometimes just certain styles speak to you. He was known as a major hardass. He did stuff that nobody would get away with today like throwing desks and stuff like that, but I just wasn’t afraid of him. I don’t know what made me start sort of hanging around after school and talking to him, but he hung around and talked to me for long periods of time, and he was a basketball coach, and I became his like manager. He was coaching the grade level ahead of me, and he taught me everything about running a team, how to run practices, how to keep the stats and the score book and all that stuff. At the time, I was in sixth grade, and that felt really cool to me to learn that stuff, so I don’t know if that qualifies or not, but when I was just kind of digging back through my memory of who would have been my first mentor, he’s the one that came to mind. I would say my uber mentor was Dave Dalton, and I met him when I was at a local school district. I was still an english teacher then, but I was interviewing for the tech coordinator position for the high school, and he was a consultant for the district. He worked at the university that ultimately I would go work at, but he was a consultant for the district, and when I watched him ask questions and take people’s answers and expand on them, I just thought it was brilliant. I ended up getting the job, and we connected. We went on a professional development, we went to a conference together, so we got to know each other, and the friendship kind of blossomed, and he eventually bridged me into a job at this university. Then, he became my PhD adviso, but it was really multilayered. I mean, he even mentored me in woodworking. One thing we had in common was that we’re both kind of dilettantes, or a more positive spin on that would be Renaissance men, I guess.

Tim  25:19  


Ryan  25:22  

We both have lots of interests, so when I told him that I was interested in starting to do woodworking, I didn’t even know he did it, but he started talking to me about his stuff. He invited me to come to a shop which was at his house and basically taught me everything I needed to know to get going. The one place he saved me a ton of time was just in tools. He was like, I’m the kind of guy who just keeps buying the tool until I find the one that I like. He showed me and was like, I have this drawer full of jigsaws. You can go through this process, or you can just get the one I tell you to get. So, that became my way. I was like, okay, what saw should I get? He’s like, get this one. I didn’t even hesitate. I just did it, and it always worked for me. I think it comes from recognizing that first of all, you have to have a connection with them, you have to have simpatico of some type. Then, recognizing that they’re where you want to be and trusting that they can give you the advice to help you get there.

Tim  26:37  

Yeah, it sounds like a deep level of admiration was part of that mix, too.

Ryan  26:42  


Tim  26:43  

I mean, whether that was your teacher, Dave, it sounds like you really admire those guys.

Ryan  26:50  

So, you know, that relationship was completely unpaid. In fact, he would constantly just give me old tools and stuff. He was a very generous person, and he was constantly giving me stuff. This concept of paid versus unpaid I think is an intriguing one. You’ve had both kinds of relationships, and sometimes they’ve transitioned from one side of that to the other, probably not normally going from paid unpaid. I guess it could work that way, but the ones you were talking about sort of went from unpaid to paid at different times. Does that change the relationship at all when that happens?

Tim  27:39  

It does. I would argue for the better. There’s this altruistic, idealistic view we have where we’re all just helping each other out all the time, and that’s great. I’m not trying to be overly cynical, but there’s also reality, too. We’re all immersed in our own world with our own concerns and our own problems, and it’s hard to carve out time and energy for other people. I mean, that’s just the reality of the world that we’re living in. I think what paid mentorships do is they clearly delineate the expectations of the relationship in a way that is best for both sides because if I’m mentoring somebody and I know that they’re making a financial sacrifice for my help, I’m way more invested in them and in their outcome. It’s just human nature, you know, like I care, and I try to tap into a sense of empathy and think, what’s it take for them to afford this? What sacrifices are they making? I need to honor that, and I need to deliver. From a mentors perspective, if everyone has skin in the game I think it’s definitely better. I’m not saying the unpaid mentorships don’t work, but I think there is an element. There’s a transactional element to paid mentorships that I think benefits both sides, and from the mentee side, if you are looking for a mentor, you can fast track so much in your career by investing in good mentors than hoping to find one or asking for them or not using them at all. I know there is some debate. I know you’re going to talk about a few articles and a few resources where there is this blurred line between the benefits, you know, the cost benefit ratio of mentorships and how the finances work, but in my experience, I’ve found on both sides that having an investment in it makes a tremendous difference.

Ryan  30:01  

Yeah, so I was kind of interested in this question, and I did start poking around online. There’s articles out there, I’m looking at one right now: Why You Should Pay for a Mentor by Clara Diaz Ortiz from 2018, and it gives lots of really strong arguments for why the paid mentorship is important and why it’s better as you’re describing.

Tim  30:32  

I know she listed a couple of good like three main points. Do you want to hit those real quick just so we can know what the gist of that is?

Ryan  30:40  

Okay, so her three main points are it’s hard to get good free mentors, quality mentorship is better than free mentorship, and good mentors have good connections.

Tim  30:55  

Yeah. I think those are very valid arguments

Ryan  31:00  

That makes sense. When I think about my relationship with Dave, he really did help me with my career at Kent a lot, and he helped me in many ways. I think I just really got lucky, I mean the fact that he was willing to keep investing time in me, and it was a friendship for him, so he was getting that out. We were both getting that out of it, too, but that’s rare especially in your line of work. This is where I want to talk a little bit about Dan Ariely’s book. Have you ever read Predictably Irrational?

Tim  31:47  

I don’t think I have, no.

Ryan  31:49  

You gotta put that on your list.

Tim  31:51  


Ryan  31:52  

It’s super interesting. Dan Ariely, his book Predictably Irrational was my introduction to a newish field called behavioral economics. He’s done a lot of research about a lot of different things. A big theme that emerges from his work is relativity, so the way that we’re willing to pay certain prices for things based on that price’s relationship to another price versus when you don’t have that point of a relationship. I’ll try to be quick here, but like one of his early examples in this book is the economist advertisement, and it had like three options: $59 for print only, $125 for online only, and then $125 for online in print. The middle option is really a throw away option, it’s a decoy, but they’ve ran tests where they’ve pulled that option out. First of all, when that option’s there, you have that point of reference, oh, I can get the online version for $125, or I can get both the online and print for $125. When that option is there as a point of reference, a very high percentage of people choose the both option. They pay the $125 and get both, and very few choose the in print only, but when you take that option away, zero people choose the middle option. That would be expected. No one’s gonna choose online only for $125 when they can get online and print, right? When you pull that option off the table, it reverses, and the vast majority of people choose the in print only for $59 or whatever that was, and very few people choose the both with $125, so this is just one example of the types of things that he has researched. Another one is related to market versus social norms, and his research shows that it gets really problematic when market norms and social norms mix. There are some examples, like if you are moving and you’re good friends with your neighbor, you wouldn’t have any problem asking your neighbor to help you move some boxes into your car or whatever, something like that. If your neighbor owns his own moving company, it’s a little different because he does this for a living, and that’s sort of mixing market and social norms.

Tim  35:07  


Ryan  35:07  

There have been all kinds of studies where they’ve had people who are lawyers offer legal services for free or for a small fraction of their normal rates. Actually, they get a lot more people buying and a lot more lawyers offering services when it’s free instead of for a fraction of their normal rate because it keeps it in the social norm versus crossing over. It opens up a bunch of questions for me about social norms and versus market norms, and when you were saying you favor paid mentorships, you gave some good reasons why. Before you started explaining that, I was thinking, in a way, you’re kind of refuting this argument of keeping social versus market norms separate. I think actually, the more I listened to you, the more I think you were kind of helping to make his point because as your relationship progressed, this was going to start to chew up more of your time. This is part of what you do for a living, so if you didn’t formalize that, it would have been problematic probably for both of you, but especially for you, because I think you would be like, this is sort of my job, but I’m not getting paid for that job.

Tim  36:49  

Right, that’s true.

Ryan  36:54  

It’s funny, I think that the chapter was chapter four in that book, but he opens it with this description of a guy who’s at Thanksgiving with his family, and he’s really enjoying this large dinner and enjoying a glass of wine. It’s the dinner sort of ending, and he looks fondly across the table at his mother in law, and then he stands up and pulls out his wallet, and he’s like, mom, this has been such a great dinner, how much do I owe you for this? What would make sense? He’s like, $300, $400? It’s a completely fictional scenario, but it really makes the point, like there is this sort of boundary line between social and market norms. If nothing else, I feel like we should just be aware of that and conscious of it and maybe sometimes make a conscious choice to be one way versus the other.

Tim  37:52  

Yeah, and I’ll just add a little thing on to that. As you were describing that, I was thinking back about some of the people who I’ve more recently mentored, and they’ve had issues or problems outside of my typical scope of services. For example, I don’t mentor people on the first draft of their manuscript. That’s a service I provide, that’s like editing or a diagnostic service. The people who I’ve recently mentored had these sorts of issues or problems outside of that beyond the norm, and I think maybe that might be part of my unconscious equation. This is a problem that I don’t see very often, and I really liked this person. When I put those two together, I want to help out because mentoring is not the same as doing pro bono work. Those are not the same thing. I’m not necessarily doing what I normally do for free. When I mentor, I’m mentoring something that’s usually kind of left or right of center. It’s not one of my package services necessarily.

Ryan  39:16  

Right. Would you say it’s more structured?

Tim  39:23  

I would say it’s more individualized. If someone comes to me and they want help with their draft, there’s a process that I can take them through regardless of who they are and what the genre is. I’m like, okay, here are the steps. We’re gonna do a one-on-one, but here’s where I’m gonna take you. Whereas with mentoring, it’s much more listening. It’s me listening to what these people are facing and reflecting back like, okay, here’s what I’m hearing you’re saying, and then the other part of that is more about me relaying my experience versus giving advice. In those situations, I can say to someone, I was there, and this is what I did. I don’t know if it’s right, but here’s why I did it, and here’s how I felt about it. Maybe that’ll be helpful when you make your decision, so it can be structured, but I think it’s definitely individualized.

Ryan  40:26  

Has there ever been anyone that you’ve played both roles with? You’ve been a mentor and a mentee.

Tim  40:35  

Yeah, and it’s funny. Our mutual friend, Jim Kukral here in Cleveland is a great example. Over the years, Jim and I have become good friends, but we’ve also become mentors for each other. When we first met, he was my mentor. I was looking to break into publishing, he was like an internet marketer, he had been self employed for fifteen years at that point, and he was giving me a lot of great advice. This is going back, you know, eight or ten years ago. I think over the years, those roles have shifted a multitude of times. Right now, Jim is going through a transformation, he’s kind of changing. He had cancer in 2020, he had the pandemic, turning fifty. He’s decided to go in a completely different industry, and since he’s made that decision, I think I’ve been mentoring him in that. That would be an example of over the course of many years, the roles being very fluid depending on the situation.

Ryan  41:48  

Yeah, that sounds like one that’s a little more casual. You’re not like, okay, well, I’ve now mentored you for three more hours, and you mentored me, so throw me a hundred bucks.

Tim  42:05  

Yeah. Those situations between Jim and I would manifest as meetings for coffee. One of us would have something and would be like, hey man, I’m thinking about doing this, can we get together for coffee and talk about it? Both of us feel free to do that with each other. Whenever we get together, it’s usually because one person has an issue or a concern or a problem, and they need help with it, but that can change. Sometimes that happens monthly, sometimes we might go six months without that, other times, it might be a few weeks in a row. It just all depends on what each of us are going through at the time.

Ryan  42:47  

I love being able to slip back and forth across that divide. Again, for me, it just ties back to that relationship. If I have a close relationship with someone, then that happens very naturally. It’s sort of based on friendship, and it’s like, oh, you help me with some things, I help you with something. I actually feel better when it’s more balanced that way because you know, there were times with Dave when I felt like I wasn’t able to give back to him that much, but he just kept giving to me. There were times when I wish I could, and I looked for ways, and I did find ways, but when it’s too one-sided, especially when it really is fully in that social norm, space, it just doesn’t feel good after a while.

Tim  43:52  

Yeah. That’s the nature of it, though. Where we started, I think there’s a certain understanding that if it’s not a paid mentorship, you’re most likely never going to be able to equal the value that your mentor is giving you. That’s just kind of how it goes. It doesn’t feel great, but that’s the truth.

Ryan  44:15  

Yeah. So for the ones that are paid for you that are more formalized, do you have a shingle out? Is it word of mouth?

Tim  44:30  

It’s weird. I’m really so invested in the mastermind model right now which I don’t think is technically mentorship. It’s something different. It’s probably a hybrid between pure mentorship and pure teaching. It’s probably in the middle. I think one of the long term limitations of mentorship or client work, for that matter, I mean, we can get very general about, is that it doesn’t scale. There’s a ceiling to it. There’s only so many one-on-one meetings you can have in a day and in a week and in a month. There’s only so many people that you can help one-on-one in any situation. It’s not efficient, like it’s not an efficient teaching modality, but it’s necessary. For the most of time for students, it’s the most beneficial, but it’s just not practical. I think for me, what ends up happening is people kind of get pulled into my orbit, and they become part of my community. They reach out for help at certain stages or with certain issues. At this point right now, I don’t have any sort of paid mentorship relationships, and I don’t have a service listed on my website that says mentorship. It’s an ask, usually on a previous relationship, so it’s someone in my community or someone who I’ve worked with before who has a bigger problem, and they’re like, you’re the only one that can help me with this. I know what you’ve been through, I need, and that’s where I think he can be more formalized. I even used to have one-on-one services on my website, and I took them off. I don’t do them anymore. Well, I do them, but I don’t list them as a service because for that reason there was a period of time where I was only doing one-on-one coaching, and I mean, I was going back-to-back. I was from one meeting to another to another on Zoom. This is pre-pandemic, you know, there were whole days that went by, and I was like, okay, I just sat on Zoom all day. When you do one-on-one work, it’s hard. I don’t know how therapists do it. I don’t know how they just cycle people through their office all day every day. It’s emotionally taxing, and I just get to a point where I’m like, I just can’t sustain this.

Ryan  47:03  

Yeah. You made some really good points there. There are some limitations to a classic mentorship model. I mean, the inefficiency being the most obvious, I guess, but that’s not really sustainable for anybody. What I take away from that is probably, whether you’re a mentor or mentee, you should be selective about where you’re looking for mentorship and what you’re looking to accomplish with it. Right. It’s not everything, you know, mentorship doesn’t make sense when a good old class will do. If I wanted to learn Photoshop or something like that, I can just go take an online class or look up instructions. I don’t need to go seek out a mentor for that.

Tim  47:58  

Yep. We both mutually admire Tim Ferriss, and he talks about that a lot. This is a guy who gets hundreds of emails a day with people who are asking for help and his guidance and his mentorship, and I’m paraphrasing his approach here, but the idea is, he says, don’t ever send me an email where you’re asking me a question that you could Google. That’s just disrespectful. He almost says he doesn’t want to hear from anyone unless they’ve exhausted every resource. They’ve read all of his books, they have listened to all of his podcasts, they have done all the research. Then they come to him and they say, here’s what I’ve done. Here are my options. What should I do? I think of that framework as sort of the genesis of a mentorship. You should be to the point where you’re like, I don’t know where else to go, I’ve exhausted all possible resources on my own, and now I need that level of help. It’s vague because that’s gonna be different for different people in different situations, but I think to your point, you don’t look for mentorship. When a recipe will do, you’re looking to go off script. You’re doing something that would be considered an outlier, and there just aren’t resources to help you with that. That’s when you look for mentorship. It’s not necessarily the basic skills acquisition. 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


31-year-old self-made millionaire: I spent $70,000 on mentorship in 6 months—here’s why it was worth it – https://www.cnbc.com/2018/04/11/31-year-old-millionaire-i-spent-70000-on-mentorship-in-6-months.html

Why You Should Pay for a Mentor – https://medium.com/@claire/why-you-should-pay-for-a-mentor-49748bc11270 

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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