Season 1: The Core Principles

Episode 007: “I’m Not Afraid to Try Things and Fail.” – Tim’s Story

By November 15, 2024 No Comments

In this episode, Tim Desmond explains the path that led him to the Assistant Director position at the Miller Institute for Entrepreneurial Studies at Hawken School. He explains how being a risk-taker and divergent thinker led to his epiphany of “learning by doing.” Tim discusses the role of writing in the class and how he strives to improve students’ communication skills in a changed world.

Doris: Hey, Tim.

Tim: Hi, Doris.

Doris: Hey. So you came in with me to start to be my co-instructor in this class, and you had been teaching for several years. I’d like you to talk about what it was like for you to start teaching this.

Tim: What was it like? That’s quite a loaded question. I think, like you, I’ve pretty much been an outsider in my profession. I’ve always done things differently, and sometimes it’s been embraced, but most of the time, it’s sort of been frowned upon.

I’ve always had the best interest of kids at heart, and I think that’s why I’ve been tolerated by so many administrators over the years, because that is my ultimate goal. I think in my personal life and as an educator, I’m a risk taker, and I’m not afraid to try things and fail.

I’m also a bit of a restless spirit. So I move through these phases. I’ve taught middle school. I’ve been a director of technology. I’ve been an instructional technologist. Now I’m part of this entrepreneurial program.

So I really thrive in environments where things change. When the opportunity came along for me to join this program, for many reasons I jumped at it. One of those was because it seemed so new and so different and so frightening that I couldn’t turn it down.

Doris: Boy, does that ever ring true. I mean, knowing you as well as I do, everything you said is true in spades. So what is it, when you think about what we do, how we do it, what the educators we’ve worked with are doing, how they do it, what do you think are the most important elements of this?

Tim: The most important element is learning by doing. That’s really at the core of who I am. It’s what I’ve discovered over 20 years as a classroom teacher, and more importantly, it’s also what I’ve discovered in my own life. So I’ve had this parallel existence as an artist, a musician, and a writer.

Doris: A very successful one, by the way, with your pseudonym and you’re a very successful author, yeah?

Tim: Thanks, yeah, but that’s only because that’s what I’ve . . . I did that stuff. I didn’t take classes on being a musician, or I didn’t go to writing workshops and call myself a writer. Those things are good and they help prepare you, but they don’t make you what you are.

An artist creates art, a musician makes music, a writer writes, and that’s how you learn how to do it. You can take classes all day long, you can read all kind of books on something, but until you roll up your sleeves, and you get in and you do it, you’re not it. So I think that’s really at the core of this. It’s what we do with our students.

We don’t spend weeks preparing them for a business challenge or introducing them to a company or even an industry. They don’t even know where they’re going on the morning we take them there. I think that’s what’s so exciting, and I think that’s what’s really appealing to the kids. It’s so different and it’s so engaging that we’re just saying, “We trust you, and we’re going to help you, but here you go. Let’s do this. Let’s not prep for it.”

Doris: That’s awesome. I agree with you, I think at it’s core, that’s what it’s about. Yeah, that’s terrific. As you think about it, boy, we’ve been teaching this together, for lots of kids and for multiple, multiple years here. What are some of the most powerful learning experiences you’ve been teaching for years and years? What are some of the powerful learning experiences you’ve seen kids go through in this that are different maybe than what you saw?

Tim: Yeah, I’m starting to lose track now. I think we’ve done this what, four or five times together now?

Doris: Five times together, yeah.

Tim: Because it’s a semester-based course, we get two opportunities per school year, and so we’re really good now at detecting patterns and feeling the rhythm of the course. And I think it’s something we’ve talked about all the time.

We’ve talked to Alison about this as well, the moment where the kids hit that point in the class where they realize the learning’s all on them. They’re not doing it for the grade, they’re not doing it to please their parents or to please us. I mean, there might be still some of that, but it’s that moment where they go, “Oh, this is about my learning and I can make a real difference here.”

That’s my favorite part. It happens in different places for each kid, but we feel it now. We know when it comes up.

Doris: Yeah, yeah. You spent a lot of years teaching writing as part of the courses that you taught. It sounds kind of specific, but it would be really interesting for me to hear what you think about how students are learning writing in this versus a traditional history class or English class.

Tim: Yeah, there’s really kind of two parts to that answer. Just for some context, I’ve been a humanities/history teacher in middle school and high school for 20 some years.

So the first part of that is most writing is done, and it’s teacher structured and it’s content-based. What I mean by that is you study a particular event or a piece of literature or something, and then you ask the students to respond to it in some way. So there’s sort of a veil of choice there.

I think as teachers, we like to convince ourselves that we’re giving students choice, and in a way we are, but it’s a very narrowly defined choice. It’s like, “You can respond, but only to this.” So I think there’s that piece of writing in a traditional history of humanities classroom, as a student you’re asked to respond to something specific.

Because of that, a lot of kids don’t necessarily engage, because they don’t have ownership, or they don’t have a stake in it. They’re doing it because you’re asking them to do it, and of course they have an opinion, but they’re not fully vested in it. So I think that’s different.

The writing that we ask students to do in this program is really generated out of their own passions, and it’s generated on what matters to them. It’s very timely and it’s very relevant.

Doris: To what they’re doing.

Tim: To what they’re doing and what they’re studying, and a lot of times what they believe. I mean, we have them doing personal blog posts, and we have them doing reflections, and a lot of that is very meta, and it’s not content-based. There is a time and place for content-based writing. I’m not saying there isn’t.

Doris: And even in this class there’s a lot of  . . .

Tim: There is, that’s right. They do book reviews, and that’s content-based. But in these other types of writing, it’s very personal. And I think for most kids, that’s a pretty stark contrast to what they’re usually asked to do. The other piece to that writing question is there are different types of writing, and in most traditional humanities classes, you’re looking at the five-paragraph essay or the persuasive essay or the book report style, topic-based, take in this information, synthesize it, and push it back to me. Honestly, very early on, that’s a necessary thing for kids to learn.

Doris: Absolutely, it’s hugely important.

Tim: But it becomes less and less exciting the older kids get, and so we still do some of that, and I think there’s definitely a place for it. But we also have this whole other spectrum of writing.

So we’re trying to teach kids how do you write an email to a CEO of a company? How do you send a text message? How do you use social media in a way that’s just beyond what you would use personally, how it will be used in the business world? Those are all radically different types of writing.

Doris: But they’re all writing.

Tim: But they’re all writing, and they’re all important.

Doris: And there’s actually stuff to be learned, yeah. There’s such a thing as a bad email and, you know.

Tim: Even your audience. It’s a different audience. When you’re teaching humanities, the audience is the teacher, and that’s probably the only person that will ever see that writing besides maybe your parents, or your tutor if you get in trouble.

Doris: Right, exactly.

Tim: But these other types of writing that we’re asking kids to do, there’s big audiences.  So the way you address an email to your teacher is different than the way you address an email to your mom or to your friends, and sort of finding those nuances in writing in this world, that these kids are in, is really important.

Doris: You did, and also even in the presentations, I was thinking as you were talking, thinking about the amount of teaching we do about writing in a presentation, which is, of course, just on slides, but it’s really important.

You have constructed, this specific example, but I think it says a lot about how you go about all this. You constructed a template for a book blog. If you could talk about, first of all, how we even assign the books, and then how you set up the book blog, and why. I think that’s actually a really important piece of the program.

Tim: Well, we co-created the reading piece of this.

Doris: Yeah, we did.

Tim: So I want to make sure we make that clear. We feel that reading and writing is paramount, and we ask the kids to read and write more. We feel pretty confident that measures up against any writing course. This is honors English credit.

Doris: They tell us that, they say they read more than . . . and it’s not just books, obviously. The research they’re reading.

Tim: But we assign a lot. I mean, they read multiple, I don’t know, six, seven, eight books a semester that’s required, let alone what they read on their own.

Doris: Yeah, it’s actually upwards of eight, yeah.

Tim: But the key to that is it’s a choice, and it’s a choice based on where the student is or where their team happens to be at that moment. So instead of us saying, “We feel this book’s important . . . “

Doris: “For all 16 of you.”

Tim: ” . . . for all 16 of you, every time. Read it now.” We do that in the very beginning.

Doris: That’s true.

Tim: There are a few books that we feel like are really important for everyone to read.

Doris: We assign them, by the way, we know there are patterns and systems to this so we know in their early learning of problem solving and foundational methodologies, we know they’re going to need this at around this time, and they’re going to need that.

Tim: Yes, so having that student choice, I think, is a big differentiator. We do have an approved list, but it’s not a sort of a concrete really strictly defined list.

Doris: That’s right. They can choose any book they want, as long as they tell us why they want it.

Tim: That’s right. They can come to us and say, “How about this one?” And we’ll go, “Oh, yeah, that looks like that would help.” So there’s that component in that because they get to choose it, they’re just initially more invested in the process.

The book review serves a number of different functions. The first and most obvious one is sort of an understated accountability. The book review blog is viewable to everyone in our class, and so it makes it really transparent. It’s also transparent in that it forces students to be accountable to each other.

So part of the book review blog is seeing what your classmates have posted, which books they have read, what they have found interesting, what your previous classmates from other years have read and why they found that interesting.

So that piece of the book review blog is really important, because it gives them sort of a starting point. If they go, “I don’t even know what book to pick, where to start,” that helps.

The book review process itself is structured in a way that gives kids a structure. There are certain components of the book review that they have to include. One of the most important ones is “Why is this relevant to you? Why is this interesting to you right now?”

Doris: And “How does it connect with what you’re doing?”

Tim: “How does it connect with what you’re doing?” So it’s more than just a regurgitation of the review they can pull up on Amazon. They have to then apply those concepts and ideas to what they’re doing at the moment. I think that’s a really important piece of it as well.

For us, we have now created this ever-growing archive of resources, and, yes, there’s a lot of overlap, and kids will read a lot of the same books. But we have a really rich archive now that we can pull from and direct kids towards.

Doris: What I think is one of the things that’s been really exciting that’s consistent with everything else is the numbers of students we’ve had who . . . we’ve had student’s who’ve said, “I hate reading, and I hate writing,” who have come out the other side of this saying, “I actually can’t believe that I really read the books in this class,” as opposed to, I guess, they’re not really reading their assigned books in some of their other . . .

“I really read them because I needed them, and when I read Contagious and I found, oh my gosh, I’m actually using this stuff. Or Blue Ocean Strategy, I’m actually using this stuff, or the book that I read about TOM’s and I’m actually using that stuff.” A rework or whatever it is, they learn how powerful books can be and articles that are dense and at first intimidating that they read and find useful.

I think what you said about having to draw connections is really important, because what they start doing, at some point in the class is they’re doing that naturally, not just about books they read, but news stories they’re hearing from outside. They’re starting to make those connections, “How is that relevant to what I’m doing?”

Tim: Yeah, we fool ourselves as teachers a little bit, especially teachers of writing, and I can say that because I am one. Just because you teach something doesn’t mean they’re learning it.

Doris: Yeah, yeah. My favorite, yeah, yeah, yeah. It’s not about what you teach, yeah.

Tim: Yeah, that’s right. So I can say, “Well, I taught Shakespeare.” That doesn’t mean the kids read Shakespeare.

Doris: Or learned it.

Tim: Or learned it. They may have gotten enough of context to bluff their way through an essay exam. So I think your distinction on kids saying, “I read more now,” that’s true, because we know they’re reading it, as opposed to . . .

Doris: Yeah, getting through it.

Tim:  . . . getting through it or trying to convince us that they’ve read it if they really haven’t.

Doris: It’s something they actually find, like, “Oh, I need this. I need what I can get out of this thing,” as opposed to “I have to get through this thing.” It’s a completely different approach to consuming literature, right?

Tim: It is. This is the world kids are in. It’s an on-demand world. They’re not going to sit down one night and read 12 books they think are going to matter. They’re going to, in the moment, seek out the information they need. Hopefully that’s what we’re teaching them how to do.

Doris: Right, and the other thing I’m thinking about also, is in terms of all these different forms of communication, because they’re working on real problems and interacting with all kinds of different people, and they’re actually, in many cases, trying to get someone to do something. Emailing someone or writing a blog or doing something to get someone’s attention who can be helpful to them.

They care a lot about the effectiveness of their communication, whether it’s their verbal communication or written, and that also means that . . . I was about to name some names, of students who come in, and they’ve always had horrific writing, right?

It’s not that in five months, la voila, they’re a great writer. But they really engage in caring about their writing and thinking about it and analyzing it. Yes, they improve a great deal, but more important, they have taken on the goal, personally, of improving, which lasts beyond the class.

Why does it matter? Now, again, you’re a student, you’re in school, you’ve never been out of school, everybody’s telling you, “Learning math matters, learning to write matters.” You don’t really get why until much later. If you’re a kid for whom it isn’t natural to just care to do your math well or care to do your reading well or your writing well just because you’re told to, working on real problems with real people that you care about really quickly gets them to care.

The last thing I also wanted to ask you about is I was always so amazed by the way you, in a very concise way, the way you’re able to get students to learn about effective presenting, which is also writing.

So if you could talk a little bit about the trajectory these students, from the very first time they do a presentation to the end.

Tim: Yeah, I was going to share a quote, but then I can’t remember it, and it would not really be effective. My general approach, and this is for myself as well, and I think it’s the journey that you’re speaking of for the kids, is this ability to let go of all the stuff they think they have to cram in, and get it to its core. That’s really the essence of true writing. Really good writing is getting your message across in as few words as possible. I think that’s the journey.

Doris: And that shows up in everything you do, yeah.

Tim: Yeah, and I think it’s natural for kids to come in and want to throw everything against the wall to prove to you, the teacher. So backing them off that and saying, “That’s really not as important as getting your message across succinctly. That’s what matters.”

Doris: Right, and when they communicate with someone external, and they hear back that that person didn’t in any way get what they were trying to say, we talk about the fact that they have many failures in the course of the course.

Some of the failures are they have a presentation they care about a lot that they’ve worked very, very hard to put together. And they present and . . .

Tim: The message doesn’t come across.

Doris: The message doesn’t come across, and they have to go back later and instead of saying, “Oh, pat, pat, that was lovely. You did such a nice . . . “It’s like they know “Okay, that person didn’t get it. How can I do that differently?”

Doris Korda

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