A photograph of a CH-47 Chinook helicopter against a bright blue sky.

The Bigger Challenge with Kim Wilton

In this episode, host Adam Davis discusses risk and comfort with Lieutenant Colonel Kim Wilton, a helicopter pilot in the Royal Canadian Air Force and his friend of over three decades. In addition to flying in missions around the world, Kim has also been a long-haul trucker, a college radio host, and is currently a farmer, a baker, and a biker who spends a good amount of time teaching other people to fly helicopters. In Adam’s words, “Kim is less influenced by comfort than anyone I’ve ever known,” and in this hour, they explore what can be gained by stepping into discomfort and embracing the bigger challenge—whether in a job, in life, or in something as seemingly straightforward as a conversation. 

Show Notes

About Our Guest

Kim Wilton is a Lieutenant Colonel in the Royal Canadian Airforce, a helicopter pilot and flight instructor, and a former long-haul truck driver.

More on Risk, Discomfort, and Military Service from Oregon Humanities


Adam Davis: This show, The Detour, is about people and ideas. About how ideas come to life in people, and how they live. Sometimes when we're planning episodes, we start with an idea or a question we hope to explore, and then we find people who will help with that. Sometimes we go the other way. We start with a person and then work back to the ideas their life and words bring to the surface.

This episode is one of the latter kind, the kind that starts with a person.

Kim Wilton: Like, I have a pretty sweet life, right? Because I motorcycle to work in the morning, I fly helicopters during the day, motorcycle home, then I get into a combine and chew through some wheat, right? Like, that is my dream day and that's what I live quite often.

Adam Davis: A long time ago, more than three decades, I met someone who I had heard about first. A woman who, I was told by the guy who was my manager at the first real job I ever had in a music and video store in Chicago, a woman who had been riding her motorcycle around North America and had stopped in Chicago and was working at the shop for a spell. Her name was Kim.

I no longer worked at the shop when Kim was there, but I would pop by every now and then to catch up with John, my former manager, and he told me I had to meet Kim. So I did. And John was right. Kim and I became friends in Chicago for a few months before she packed her few belongings into a very small backpack and lit out again on her motorcycle, which she called Jezebel.

From the moment she rode out of town through the present, Kim and I have been exchanging letters. Through these letters, I learned that sometime after leaving Chicago, Kim started driving trucks. And after she drove trucks, she became a helicopter pilot in the Royal Canadian Air Force, and flew a ton of missions in Afghanistan.

Kim is still in the Canadian Air Force, mainly teaching other people, some from Canada, some from other countries, to fly helicopters. And she's also become a farmer, and a baker, and even though Kim might not say this about herself, I can say, as someone who's been reading Kim's letters for decades, that Kim is also a writer, and very good with words.

This past March, Kim came to Portland, and at a certain point while we were talking over a meal, it became pretty clear to me that I should ask her if she'd be game to have a recorded conversation about some of her big life choices. Flying helicopters for the Air Force. Driving trucks. Riding a motorcycle. And also, what it might mean to make these choices and do these things as a woman.

Kim didn't love the idea of being recorded. It made her uncomfortable. But Kim is less influenced by comfort than anyone I've ever known. And she generously ended up joining us for a conversation in the XRAY FM studios in North Portland. We talked about a lot of things, and as we talked, it turned out that one of the big ideas we were talking about was risk.

So here's Lieutenant Colonel Kim Wilton, who has been operating large, complicated, dangerous machines with serious purpose for many years. I hope you all enjoy hearing Kim on The Detour. And Kim, thank you for being willing, once again, to step into discomfort, embrace a modicum of risk, and take this detour with us.

Kim Wilton: Adam, did you have a radio program in university?

Adam Davis: Briefly, in college, with a couple friends.

Kim Wilton: What was it called? I don't even remember, because I was like—it was with Rob Hanson and Jordan Reed. I can't remember. Yeah, it was super brief. WKCO was the radio station.

Kim Wilton: Okay, that's good.

Adam Davis: Did you?

Kim Wilton: I did. It was called Storytime. I had it for about a year, and I would go in and I'd read a story I'd written that week and then put music around it.

Adam Davis: You'd read your own stories?

Kim Wilton: My own story, yeah.

Adam Davis: Wow.

Kim Wilton: I used to have recordings of them somewhere, but it's a long time ago.

Adam Davis: So you would write stories once a week for the show?

Kim Wilton: Back when we were young, like, you'd be prolific, right? So I'd write like a story a day, like it was ridiculous, and uh, so I'd pick one from the week and I'd read it.

Adam Davis: You'd pick one of the many stories you had written that week?

Kim Wilton: And then I'd put like ridiculous music around it, like the B side from like those, those story books, you know, those little albums with the page when Tinkerbell rings. They always had the B side, which for music, like, for like crazy music.

Adam Davis: And you think you still have recordings of those?

Kim Wilton: I might in a box somewhere.

Adam Davis: And you think you have written versions of those stories?

Kim Wilton: Oh, for sure. For sure, I have that. But, uh, you know, in my museum, in my archives.

Adam Davis: The Kim Wilton archives.

Kim Wilton: Yeah, that's right.

Adam Davis: Keiren, are you recording yet? You are? Great. So, let's keep, so, um... I just said the Kim Wilton archives and you said, yes, uh, I probably have the stories somewhere. And I wonder if it makes sense to like formally start this informal conversation with the fact that, like, I've known you as Kim Wilton for a long time, but these days you also have and have for a while also had a, you have a kind of rank and a title. What is that?

Kim Wilton: Right now I'm Lieutenant Colonel Kim Wilton.

Adam Davis: For which?

Kim Wilton: For the Royal Canadian Air Force, the RCAF.

Adam Davis: So you're Lieutenant Colonel Kim Wilton for the RCF.

Kim Wilton: RCAF.

Adam Davis: RCAF. I left out the A, which seems important.

Kim Wilton: It does. No force without the air.

Adam Davis: How did you end up becoming Lieutenant Colonel for the RCAF?

Kim Wilton: Well, I say attrition, right? You know, like, that's how I end up as a Lieutenant Colonel, but honestly, you, uh, you show up and you work hard, right? So, but I'm in the, I've been in the RCAF for 22 years. So, um, Yeah, that's just the rank I'm at right now.

Adam Davis: What you've been doing?

Kim Wilton: Uh, I fly helicopters for the RCAF. I have a tactical background for the first 10 years of my career, and then the last 10 to 12 years I've been in the training regime, so dealing with making new pilots.

Adam Davis: Flying and training other people to fly.

Kim Wilton: Yes.

Adam Davis: We were talking a minute ago about stories you wrote and read when you were in college. Did those ever involve you flying big objects?

Kim Wilton: No, I never had plans of being a pilot. That wasn't, uh, that wasn't in the story. When I was young, I thought only wealthy people became pilots because it was really expensive to get a license. So, uh, it was never something I considered.

Adam Davis: So how, like what ended up bridging the distance between that thought that other people did that and then you ended up doing it?

Kim Wilton: Um, I was a truck driver, as you know, for a number of years, and when I first started driving truck, I was delivering a load to, um, a warehouse near Vancouver International Airport, and I saw a helicopter landing, and at that time, I was just starting out, so I was with, uh, Ken, this older gentleman was teaching me how to drive, and he was explaining he had a buddy who drove chopper, and it cost about 50 grand, and I was like, “Okay, note to self, I will save $50,000 and I will become a helicopter pilot because that looks amazing.”

The idea of being able to land and take off anywhere, like didn't need a runway, all of that. So that's what I did. I saved $50,000 and then someone said to me at some point on the road that, well, you can join the RCAF—at that time we weren't Royal, we were just the Canadian Air Force, the CAF—and, uh, they'll pay you to train. And so I enrolled and it worked out.

Adam Davis: So it was seeing that thing land?

Kim Wilton: Yes.

Adam Davis: What was cool about that?

Kim Wilton: Uh, helicopters are magic, right? Like, um, when—have you ever been in a helicopter?

Adam Davis: I was in a helicopter that you had landed outside Chicago and then a long time ago when I worked for the parks service, I was in a helicopter twice in Hawaii.

Kim Wilton: So when you were in Hawaii, cause the one you saw with me, you just, it was just parked there, the one in Hawaii, when you were in it, it felt different than a plane, correct?

Adam Davis: Absolutely.

Kim Wilton: It, it's this... It's like an alien craft that can go anywhere. Like my favorite’s when it's in the hover environment and you're like that looks interesting, I'm just going to move sideways to get to it or I'm going to turn around the nose to get to it. That maneuverability is amazing. And the fact that you can land on a mountaintop or land on a rooftop of a hospital. Like the ability to land anywhere. I mean, I just think it's phenomenal.

Adam Davis: Was it hard to learn how to fly one of those things?

Kim Wilton: Um, yes and no. So I think anyone can learn how to fly a helicopter. It's a physical movement, uh, like it's learning how to drive. The military, why it's challenging, um, we have, we have an attrition rate, uh, to get to the wings standard is because we want it done in a very fixed amount of time. Um, so when the military is looking for certain parameters that you're strong at so they can train you quickly. So it is challenging. It's harder than a fixed wing, for sure.

Adam Davis: Because there are more variables to deal with?

Kim Wilton: You have different controls. So a fixed wing is almost like 2D. You've got the yoke and you've got your rudder pedals. Uh, but there's a third element with helicopter. So you have your cyclic, which is controlling your attitude, which is your left hand. You have got a collective. I'm sorry. It's your right hand. Your collective and your left hand is deciding your height. And then you have your pedals still that are sorting out your drift. So it's there's more variables. It's different.

Adam Davis: Sounds different. Sounds hard. Sounds like drumming, but more consequential.

Kim Wilton: There is a relationship to that. So I once met, uh, this person in the military said the people most successful for getting through pilot training were people who had a sports background who were drummers, like for helicopter pilots. And I did play drums in high school, so maybe that was setting my course for me. And I didn't know.

Adam Davis: You didn't know.

Kim Wilton: I didn't know.

Adam Davis: And you've been training people to do it for 10 years.

Kim Wilton: I have.

Adam Davis: Can I just ask, like, is there a personality that seems more suited to it?

Kim Wilton: I think it's like anything. It's simply, if you're passionate about it, you're going to figure it out, right? And at least in the military, people who've gotten that to that point are very motivated.

Like, as I joke, I don't teach grade 10 English, right? Like people want my job that I'm teaching. And for the RCAF, we only give wings to about 100 people a year. So maybe 40 45 helicopter pilots a year. So it's a very small club. So the so what for that is I've a very motivated student. So they're—they take what you give them.

Adam Davis: I gotta ask, how many of the 45 a year are men? How many are women?

Kim Wilton: So the official number right now is we're about 5% female for the pilot trade in the Canadian Arroyo, uh, Canadian forces. It's different numbers for different militaries around the world, but Canada is one of the highest, uh, for the number of women at the 5%.

Adam Davis: 5%, one of the highest.

Kim Wilton: Yes.

Adam Davis: When you were going through?

Kim Wilton: When I was going through, it was 2%. Um, and as I said before, I was a truck driver. And, uh, when I was a truck driver, that was 1%. So... When I left trucking and became military, I was doubling my numbers, right? I was going from 1% to 2%, which sounded amazing.

But, um, so yeah, so the numbers aren't great. Overall, the air, the military has 17% female for Canada, which is one of the highest in the world, actually. Unless you get into the weeds of countries that have conscription, like you look at countries like Israel, I think it's Sweden or Switzerland. There's a few countries that have a few dynamic programs like that. But in general, Canada has one of the highest, and we still have a long way to go. Like there's targets and desires. The goal was to be 25.1% female by 2026. We're not going to make it. We're probably increasing just under 1% a year-ish right now. And the US numbers are fairly similar. They're a little bit lower, but so close, fairly similar.

Adam Davis: I love what you said about doubling the numbers as you went from driving trucks to flying helicopters. There are probably too many differences in the experience of like driving trucks on one hand or flying helicopters on the other. Maybe I'll ask about similarities.

Kim Wilton: There's quite a few similarities. So, for example, uh, I flew the Chinook helicopter operationally, which is the big one, tandem rotor. It's about a hundred feet long from tip to tip on the rotor, or the base of the helicopter, so the airframe is about 50 feet. And a tractor trailer is 53 feet long. So it's about the same dimensions. So there were some similarities because ultimately, it's operating equipment. Whether it's a helicopter, a truck, a tractor, it's all equipment, and just figuring out those dimensions you care about. So, what I mean by that is, for a truck, I care about how I swing around corners, or when I'm backing up, how it maneuvers left and right.

Uh, when I was getting my private pilot's license, so then I'm thinking more about the wings and my width and what that looks like when I'm taxiing out so I don't hit something. I'm not even thinking about—that's several car lengths, car widths to the right that I wouldn't have to think about if I was in a car or motorcycle. So it's just different dimensions, but it's the same idea.

Adam Davis: And maybe I should note what you just said, if it was in a car or a motorcycle. And when we met, the motorcycle was your vehicle.

Kim Wilton: Yes, uh, I love motorcycling. Um, at that time I was traveling all over on my motorcycle all through North America. Yeah.

Adam Davis: And there you were a hundred percent of the people doing that. As part of the program you were on. You were on your own program.

Kim Wilton: I was on my own program. I finished university, and I was lucky enough to have no student debt and had the road open and a bit of savings. So I spent two years traveling around North America on my motorcycle.

Adam Davis: So motorcycle, truck, helicopter. You've talked so far about both the truck and especially the helicopter primarily in technical terms. But I'm curious if I can ask about the cultural experience of, especially, let's start with helicopter.

Kim Wilton: Um, cultural experience, helicopter. How do you mean?

Adam Davis: I mean, what were the people like that you were training with and that you fly with?

Kim Wilton: Okay, so, I wouldn't say it's any different whether I'm a pilot or I'm infantry or I'm an intelligence officer. What I love about the military and I didn't anticipate when I enrolled is camaraderie. So I did not have a background in team sports. I played a lot of, I did a lot of sports, like individual sports though. So, um, it's camaraderie like a team sport, but more. Because since then I have played team sports. So when you go through basic training—so for me, it was a 13-week course in Saint-Jean, Quebec, with, you know, there was about a hundred of us in four platoons from all over Canada that I had never met before.

And by the end of the 13 weeks, like some of them are still some of my closest friends, right? Because, uh, you're embracing the suck together and you're training together, and it's just, you're all for the same goal, of whether that's building a rope bridge or doing some small party tasks to get through that basic training.

So there's this camaraderie that exists in the forces that is beautiful, quite honestly, right? Like it's my favorite part when I was deployed, being with my team. It's even now, when I go to work, the people I go to work with, like we're a small Air Force, some of these people I've known for 20 years in it and like I'll see them for five years and then I won't see them for a decade. But I know for any of them, I can touch base with them today. If I have something, like I have a problem, and I know they'll help, right? Like they're reliable.

Adam Davis: So camaraderie. Was camaraderie affected by your gender as far as you could tell?

Kim Wilton: I was very fortunate because I think there's a few things that work to my favor. I came from a trucking background, so it's a pretty tough world, the trucking. So, I came in as a mature student, if you will. I enrolled when I was 29 years old, and so many people I was going through were younger than me. So I guess I had street cred. I was a bit older, um, and I was a bit tougher because I'd just come off the road of driving for six years.

So, um, I was given—I had that going for me, as well, it's the, if you can do the job, then what's there to give you a hard time about, right? So I'm passing the courses, I'm doing the flights, I was successful. Um, and I mean, I'm fairly easy to get along with, I think, as well, so that helped, having a good sense of humor.

I mean, I don't know, all through my flight training and most of my career, I'm generally the only female. In the past few years, like when I've been on squadron or deployed, um, my favorite FO, first officer, Sylvie, like we're still BFFs. So there's a few females in there, but generally, um, it's not uncommon for me to be the only female in the room. But I've certainly never seen it to be a factor.

Adam Davis: Do you like it?

Kim Wilton: Uh, no, I'd like more females in the room. So, um, you're always doing what you can to spread the word or increase the numbers of women—even just trying to enroll or going through the selection process, just to get the numbers up. So I would like more. Yeah.

Adam Davis: Yeah. So you said deployed, kind of as a little bit of—it passed fast, but I want to go back to that.

Kim Wilton: Sure.

Adam: Deployed where and for how long?

Kim Wilton: So I did two deployments to Afghanistan between 2008 and 2011, flying the Chinook, um, in Operation Athena is what Canada called it at that time, with NATO forces. So I was working with Americans, Aussies, Brits, the whole entourage. So I was there for a total of 15 months between my two deployments.

Adam Davis: And flew?

Kim Wilton: Flew the Chinook. So I flew—um, I did a hundred combat missions between the two tours, a bunch of—I was a maintenance test pilot as well, so a lot of maintenance flying. I have just over 800 hours on the Chinook.

Adam Davis: So a little bit ago, I said you were talking about, you had talked mostly about the technical experience of flying, and then I asked a cultural question, but it seemed like the question I was asking then was about the culture during training in Canada. Did you know when you enlisted that you were going to end up being deployed?

Kim Wilton: Uh, I certainly knew deployments were a thing, absolutely. Canada at that time—so I enrolled in January 2001. So at that time Canada's role was generally peacekeeping, so Bosnia had happened, a few other things like that. And then obviously September 11 had a huge impact, not only on the States, but on the world, right? And, um, so when I enrolled, I had no idea that was coming up and how—what a gamechanger it would be for my life, because that's how I ended up in Afghanistan.

Adam Davis: This is too broad a question, but like, what was it like to end up in Afghanistan?

Kim Wilton: So it would—I can't—it would be the peak of my flying career, without a question. Um, it was really challenging for lots of reasons. But often things that are challenging are also the most satisfying. I had no doubt in the mission that we were doing. So as a Chinook pilot, I was flying troops and their stuff from point A to point B. Sometimes just in a logistics way and sometimes in the middle of the night, uh, on an operation.

So it would vary, sort of thing, the parameters, but I moved stuff and people. And, um, as I, when I went to give a mission brief before every mission, because I was usually the AC, the aircraft captain and the air mission commander, and so, I mean, we were there to combat evil as far as I was concerned, and even the little part that we were doing, whether it was keeping soldiers off the road or supporting the Afghan National Army or the Afghan National Police or other NATO allies, um, we were there making things more secure for the citizens of Afghanistan.

Adam Davis: I assume the language that—what you got about the mission was not something like what you just said. It was not combat evil.

Kim Wilton: No, it'd be more like—there would be the high level that I wouldn't see because I was just a line pilot. So the mission I would get is: We need to get troops inserted into this LZ, landing zone, for this timeframe. Or you need to drop this M777 artillery piece here at this timeframe.

But a typical day would have multiple missions within it, like, uh, because I would be flying all day. So it would be kind of putting those all together, and to me, that would make it very clear to my crew what we're doing, like, why we're doing it—because there were moments that it wasn't fun and moments it was dangerous—that’s why we're doing it. And it was pretty clear; everyone was on the same page. That's why it was so challenging, because you go to work today, wherever you are, not everyone at the office is on the same page of what the goal is of that institution or that day, but in Afghanistan, it was very clear every day what the goal was, right? It was to get allied forces from point A to point B safely and to support the Afghan country, right, as it stood up its own, its own capabilities. So there was no—the clearness of the goal and the desire to get that goal made it really satisfying in many ways.

Adam Davis: It felt to me like you named two goals. The first one seemed much clearer than the second. The first one being to get allied forces safely from point A to point B. The second one, to support the country, the citizens of Afghanistan. That seems like potentially quite a complicated goal.

Kim Wilton: Yes. So that would be the higher-level goal. For me, in my day to day, what I'm doing is helping them get to that goal. But I'm one piece in that phenomenally complicated operation of Operation Athena. I'm just moving like 30 guys here and a little thing there, a little thing there, in this huge complexity of that theater. So that's why I think of what I'm doing is—it's more close to me because it's what I'm doing that day. But big picture, what I'm doing is supporting the bigger goal.

Adam Davis: Yeah. And you refer to very full days. Where did you sleep?

Kim Wilton: So the first tour—so Canada was late to the war, so we didn't—we're a bit late to the party, I used to joke. So we didn't always get the best apron space for our helicopters or the best lodging. So the first deployment—and we still had it great compared to most.

So the first tour, I was in modular tents, so long tents, just on the flight sign. So I was in the, the female tent. So there was eight of us in the tent, so eight to a tent. And then we'd have a shower/bathroom trailer that we'd access, and we were on one side of the—so we were in Kandahar, and we were on one side of the airfield, and then our helicopter's on the other side of the airfield.

Um, second tour, same distance, but I was in like hard stand the second time. But again, both were amazing because I had air conditioning. So yeah, it was loud. Yeah, there was rocket techs once in a while on the camp or something like that. But nothing compared to the guys out at the FOBs or the people we were supporting. It was pretty comfortable.

Adam Davis: So I'm thinking about the fact that you just, I think said that there were eight women in the temporary housing you were in. And it made me think about gender stuff. So there's within Canadian Air Force, allied forces, and then there's the country you were in, Afghanistan, which has its own gender stuff going on. How did that hit you?

Kim Wilton: I was like in a totally separate country within a country. So, um—and then I was even within a country within a country within a country because I'm in the Canadian lines. So I am wearing a Canadian uniform, I'm with my Canadian peeps, and yeah, we're supporting all the other countries, but I'm in my Canadian line, so I trust my fellow Canadians; we're all there for the same effort.

There's a lot, like—the Kandahar airfield, it’s a big camp. Like there's thousands of people there. There's civilians, military, Afghans, non-Afghans. So there's even parts of the camp you'd have to be careful of—like, I'm armed at all times, that's why it's ironic. But then to step outside the wire or fly outside the wire, like that's like that's a different world, right? Like that's like—as far as a woman, like that's, it's insane, right? Like it's just it's to go from North America is one of the top countries in the world as far as quality of life for females. To Afghanistan is one of the, is one of the bottom ten easily, right, for quality of life for females. So, it's definitely a land of extremes. And you, you would see it flying over it, for sure.

Adam Davis: And did you feel that sense of, like, it seems to me one way to describe it would be a sense of danger.

Kim Wilton: Uh, for sure. Uh, I mean—I think about it in different ways. Like we would always think about what if we went down, for example, like we had crashed or shot down and we'd have all these protocols to follow. Fortunately, never happened for us. Like we—there were some issues for some crews—not getting shot down, but accidents. But it was always, they were secured LZ right away and extracted by friendly troops. But you think as a female, it's not only getting taken, but there's going to be that likelihood of rape or assault that comes with that.

So you think about those things—but really periphery, because it's not changing my mind about the mission or what I'm doing or how I'm doing it. Is that what you mean?

Adam Davis: I think that's what I mean. What do you mean it's not changing your mind? You made it sound like you understood it intellectually, but it didn't land in a deeper way. I guess I wonder about that. Did it—how did you keep that sort of compartmentalized or at bay?

Kim Wilton: I believed in the mission, and I believed that we were doing our part to support Afghanistan, and I was certainly doing my part to support allied troops, and you're already just putting yourself in danger being there, so it's just, it's just another piece of danger.

Adam Davis: It's just another piece of danger. Right. That's a dismissive way to talk about what sounds pretty serious to someone who's never done anything at all resembling what you're describing.

Kim Wilton: I guess so, but for me, what I was doing was pretty safe compared to the guys doing the road moves. Because the reason Canada took—Canada didn't have Chinooks. Uh, well we used to have sea models, but we retired them. So when Canada decided to go to Afghanistan, we didn't have a helicopter element in Afghanistan initially, and we were losing a lot of troops to IEDs on road moves. So, um, a report was written, the Manly report, in Canada, and it was this discussion, do we stay in Afghanistan because we're taking so many injuries and losses. And the recommendations of the report—there was a few recommendations—and one of them was we need medium lift helicopters to stay and so that Canada bought six used demodels from the states, took possession of them in Afghanistan. So all this was to get troops off the ground, and you could feel the energy of the trip.

So the goal was once we were there, for example, when guys finished their tour, and they would be out at FOBs (fort operating bases), which is where they'd be positioned out all over the provinces, is that they would—their last trip out would not be in a road move. That was the deal. So there were like—the most exhilarating flight, I think, was one night. It was out of Mazangar, I believe. It's, it's dark, um, and I'm picking up 25 troops, 30 troops. It's their, their tour's done. They've survived six months, which is amazing. And they have been in combat. And as soon as my wheels lift up—and a Chinook’s really loud—you can hear them cheering in the background. Like you can literally hear them cheering as you're lifting off to take them back to kaf because they figure— Kandahar airfield—because they figured they've made it, right? Like they know that. So that was what was the most gratifying being there. It was great working with my crew, but it was the soldiers we were supporting.

Adam Davis: What was the hardest part of being there?

Kim Wilton: Um, I think it was near the end of my first tour because there was a lot of air losses happening. So it was like every day another helicopter or another aircraft was going down. So the danger element was, you were very aware of it. Um, yeah, and some of them were close. Like it was an MI8 that was literally crash landed while it was on final to the apron where we were parked. Like some of my crew members were the ones pulling bodies out of that crash. Like there was just something happening every other day that summer. It would have been 2009, 2008. It was just—there was—it was dangerous.

Adam Davis: Was that something you had to learn how to apprehend?

Kim Wilton: Um, I mean, what you, your, your coping mechanism was being smart about your mission, right? So you plan your mission, you figure out your best in routes, out routes, you take advantage of the intelligence available.

You, I mean—I had total faith. I never flew without escorts. So what that meant is two Griffin helicopters that are always watching out for my best interest and my crew—like, keep that Chinook alive because we're a pretty big target. Um, so you do all these things to increase your odds. You change your tactics getting in out of places. You change your time of day, you change your pattern. Um, so you do these things to increase your odds.

Adam Davis: You're listening to The Detour by Oregon Humanities.

It's tough to think about odds in that context. It makes total sense and it's also tough at the same time. So just telling you that while listening to you and also wondering about, I was thinking about how you talked about, uh, the camaraderie and also that there were some connections between driving a truck and flying a helicopter. And I guess I wonder, were there parts of driving a truck other than the dimensions and the vehicular aspect—either with respect to the danger or dealing with being in the one or two percent—that you feel like prepared you for this?

Kim Wilton: Yeah, but different. Like, there was a danger element to trucking. So I was trucking, I guess, 1996 to 2001. So quite a few years ago now. And I drove solo for much of that. And, uh, female truck drivers really were very, very rare. I probably saw enough on one hand in the entire time I was driving. They were very rare. So it would not be uncommon for me to have people trying to break into my truck.

I was like—a typical moment, and this would just be a snapshot in a day, is I would pull into a rest area in the States, off one of the interstates. It would be empty. I would pull in. I would get out of my truck to walk and use the facilities. By the time I walked out, it would be full of trucks, because it had gone out in the CB radio that a female had pulled into that rest area. So... You just get to—so you had to develop this pattern of making sure you parked smart, like, and just would watch your back.

Um, so I would make a point of parking in company parking lots, right? I'd make a point of, like, not just locking my door, but I'd have a seatbelt that would go around the handle of my door and click in, so you'd have that extra second fail save, or you'd also, like, it sounds extreme, but you'd have a hammer close—because I'm Canadian, I'm not armed, and you can tell that when you're looking at another truck with Canadian plates, they're not going to have a weapon, as most American, many American drivers will have a weapon.

So you just take precautions to increase your odds. So it's the same—I guess it's the same idea.

Adam Davis: Yeah. We're smiling at each other now, which other people probably can't see. Uh, I don't know what the sound of quiet smiles is, and especially smiling, for me it feels like a tense smile because of the way, in both cases, what increasing your odds sounds, again, really tough.

Kim Wilton: Yeah, but everyone does it in their life, right? Whether it's, um... Paying attention when you're getting money out of a bank machine if there's anything behind you, right? Uh, making sure that you change your password once in a while so that you're secure. We're all taking measures all the time for our safety. So it's the same idea. And it just changes what your element is, how safe your world is, how many, how many levels of security you have to put in place.

Adam Davis: So you spoke pretty clearly about why the mission in Afghanistan, the missions in Afghanistan, felt motivating and had real clarity, and I can see why the risk and the danger there, like, ah, they're worth it.

You've just described another level of risk and danger in driving a truck. What made driving a truck worth having to do that as you prepared to go to sleep?

Kim Wilton: Well, I love trucks. Like, I love driving. So the job interested me. I needed a job. Um, I mean, there's risk everywhere, right? Like, it's just, you just get on with business.

Adam Davis: Though there's more risk in some places than others.

Kim Wilton: There are, absolutely. So, uh, a load to Calgary to Toronto, my risk level is low. My risk level would honestly increase when I would cross south.

Adam Davis: Into the United States?

Kim Wilton: Into the States. But that's where much of the work was. Like I did a lot of stateside, as we call it. So um, that's just the demand of the job and you would pay, you're paid for that demand piece. Just like, no one wants to go to New York City, so you get paid more for that on top. So there's different things. And it's just part of just seeing the world, right, and doing the job.

Adam Davis: It's disheartening and totally predictable to hear you say that it got worse when you crossed the border into the States.

Um, before you were driving trucks, you were riding a motorcycle, again solo, around the continent as I understand it.

Kim Wilton: Mostly Canada and the States. Mexico just a little bit. It was a little too sketch. So, mostly States and Canada.

Adam Davis: When you say it was a little too sketch, I think, huh.

Kim Wilton: Well, I didn't speak Spanish at the time. And, um, yeah. I was young, too. I was 21. And, uh, it was just, it was just getting a little uncomfortable.

Adam Davis: Just, and I should say, like, we've known each other for, what, 32 years or something?

Kim Wilton: Something like that.

Adam Davis: And I think of you as someone who is less attached to comfort than maybe anybody I know. And you're kind of shrugging at me as I say that. Like, what do you think about the word comfort or where it shows up for you?

Kim Wilton: Um, I don't think about it.

Adam Davis: Do you go after things that aren't comfortable?

Kim Wilton: Um, I look at—when I have options, I look at what's going to be the bigger challenge. Because that's the one I should follow. I try not to make decisions based on money. When I'm making career choices, I look at what the challenge is and what I could learn from it. Like, if it will make me better at something, I guess.

Adam Davis: What feels like the challenge or the challenges you're most engaged with these days?

Kim Wilton: These days, my challenge. Um, with the military, my challenge is working at the Lieutenant Colonel rank because I'm supervising people. So it's supporting people, like my team keeps getting bigger and bigger, and figuring out what the mission is there. And then, uh, as you know, I have a life outside the military. So I farm as well. Um, so that is probably a pretty big challenge as well.

Adam Davis: Um, the challenge of supporting a team of people at a school. Uh, does that feel sufficiently enlivening to you?

Kim Wilton: Um, yes, because I like being able to help people, right? Like support them so that they're able to do a good job.

So we've all had good bosses and bad bosses. So I like giving people the opportunity and the support they need so that they can attain what they want to attain, whatever that desire is, whether it's becoming a better instructor or working on a particular problem or project. So I like giving them the support to do that.

And then I like working on my own projects within, whether it's making a new training plan or making a new, um, some sort of project like that.

Adam Davis: And then when you're not doing that, you're, you're working on a farm, which feels, it feels so different from flying a helicopter in a war zone or driving a truck on highways across the country or a couple of countries or riding a motorcycle by yourself, including in places where you don't speak the language. Does it feel continuous with those or does it feel like a real departure?

Kim Wilton: There's some things that are continuous because it's operating equipment, so my comfort space is, because I'm still driving truck for the farm, I'm operating combines, tractors, like, I'm very hands on for operating equipment. So I'm spending a lot of time in the tractor seat or the combine seat, so that's very familiar to me. And operating equipment, figuring out what's right, what's wrong, what needs servicing. So that's similar. Combines, again, a bunch of rotors inside rather than outside, so that's similar.

There's differences because now I'm thinking about seasons, crop rotations, weather patterns, though the weather pattern piece and aviation kind of overlap. But, uh, so there's a lot of dissimilarities, but ultimately it's just another, it's a challenge, right? It's just another challenge in a different way.

Adam Davis: When we started talking with these funny headphones on and these microphones in front of us, we were talking about, uh, stories that you wrote when you were younger. Why were you writing stories when you were? I have no

Kim Wilton: I have no idea.

Adam Davis: Yeah?

Kim Wilton: Yeah.

Adam Davis: What kind of stuff were you writing about?

Kim Wilton: Um, I don't even—I never go back, so I don't know. I just read. Like you, I loved reading, still love reading, so I read a lot. And when I was in high school, my plan was to finish high school, get on my motorcycle, drive to Mexico, live on a beach for a dollar a day in a hammock and write a novel. My parents were not supportive of that, and they strongly encouraged me to go to university first. So I did, and then I went to Mexico and found the beach. But I never got around to writing the novel. So I think the stories were just this dream of maybe, it's like that stepping stone to writing a novel, but I think there's enough great writers out there that I don't need to fill that niche. I can just operate equipment and grow crops and that'll work out too.

But I'm looking forward to your novel. I really wish you would get around to it, Adam.

Adam Davis: Well, uh, keep encouraging me. That might be the biggest challenge you've mentioned so far. Um, it's interesting, uh, thinking about… I want to say the body of work, although some of it is unpaid. It's sort of an orientation towards how you are in the world that I think for you, even as you sit here, you describe it as if you have a kind of unremarkable way of—even the gesture you're making now, which is dismissive.

Kim Wilton: It is. Like it's not remarkable. Like to me, it isn't. Yeah.

Adam Davis: But you must encounter people like me who say, Huh, you're doing something unusual. You're doing something that makes me want to know more. Is that something you get a lot?

Kim Wilton: I get more people making assumptions of who I am. So um, I mean the term right now, mansplaining, like I get people like sometimes explaining stuff to me and I'm like, I'm good, I've got 5,000 hours. But thanks for explaining to me what a pitot tube does. Like I have those moments a lot, um, [that] is more my experience these days.

Or I'll, like—I don't like working the air show circuit. Like, I really detest it. So the air show circuit is, you land your helicopter and it's a static display, maybe an aerial display, and it's a way of, um, you know, having interaction with the public of what the military does. Um, because I just can't handle the insane questions. It'll be like, it'll be—I've been at air show displays. I'm working with one other person, and they don't fly the aircraft. I do. We're both in uniform, and the guy will ask—someone will ask the guy the question, he will say, “I don't know, you'll have to ask her.” And you can see the pain of him asking me the question and my ability to answer it.

Or I get questions like, “So have you been flying this long?” And when I say “Over 20 years,” you can see like the discomfort, right? So I just—that's what fatigues me. So, um, that's what I experience more now, is people's assumptions about people.

Adam Davis: You referred to a difference before between Canada and the U.S. in terms of your sense of danger when you were driving trucks. That feeling of annoyance at who the guy comes up and talks to, uh, is that the same or does it feel different depending on which country you're in?

Kim Wilton: Um, I don't spend enough time in the States anymore, so I don't know.

Adam Davis: So what you were describing was what happens in, in your own country?

Kim Wilton: In my own country, yeah.

Adam Davis: Huh.

Kim Wilton: And I understand why, because I don't, like—there's not a lot. Like 5% of the Air Force is female pilots, right? So, I guess I understand it, but it's made me very cognizant to not make assumptions about people. Um, so I—but I've had that my whole life, where I've noticed that people have made assumptions about me. So, I'm very cognizant of it.

So, for example, in farming. Farming has got its own sexism issues, believe me. So, um, it's very common for the salesman, whether he's selling whatever product, he will always go to the male in the farming couple. So, uh, for example, when I'm approaching a couple who are farming, I'm cognizant that I try and start with the female, right? To, like—little things like that, the assumptions that people make, I find tiring.

Adam Davis: Mmhmm. Are you seeing any change at all over your life in the assumptions people make or the roles people are showing up in?

Kim Wilton: I would say in the military. So within my bubble of the military, I don't get surprised of what I am. Like, it's such a small military, most people would have heard of me or know me or have no problem believing me, especially because when I'm in a formal uniform, we wear our resume, right? Like I have my medals from what tours I've been on, what commendations I have. So I, right—there's no question of who I am. So I don't experience that within the military.

Um, and in civilian streets, if I'm wearing a uniform, they just see military, so they don't understand the code, but they—I'm wearing it, so I must be good. As far as the civilian side, I'm not sure. Because again, I got off the air show circuit a few years ago, because I couldn't handle it, so I don't know.

Adam Davis: It just seems like you have chosen to be in contexts where the gender differences are so stark that it would be, it'd be an interesting perspective from which to gauge whether there's anything changing over a couple decades or whether it feels like here we are again. And you talked about being tired.

Kim Wilton: I mean, I hope it's changing. Like I know for the, the Air Force, we're really looking at, you know, people like me going out and talking to people, so—because you don't know it's an option until you see someone else has done it, and you're like, Oh, it hadn't occurred to me that I could, uh, be a downhill skier. That's a thing for someone my color or my gender or my whatever, right? So, um, so I think most people are aware it's an option now. I don't necessarily think that means that people think they want to do that option, but that they know they could be that maybe.

Adam Davis: How much is that in your mind when you've done these things? How much have you been thinking about these choices, not only for yourself, but also thinking, maybe I'm making it more likely that other women will?

Kim Wilton: Uh, I'm very cognizant, I would say over the past at least five years, that I have a responsibility, um, to—that I'm mentoring at all times, whether I realize it or not. And that I have a responsibility, to help others, um, and to be present so people know it's an option.

So, you were asking me the other night, you know, what, what my career goals are within the, the RCAF. And I was like, I don't know, but I know that every time I get another position, sometimes or often, I'm the first female in that position, and that's important. It's not for me to [say] “Look at me, I'm the first,” but that it can be done so that more and more can do it. So I think I feel a responsibility for that.

Adam Davis: You're visiting Portland.

Kim Wilton: At this moment, sadly, yes. Since I'm sitting in this booth.

Adam Davis: Sadly, because you've been confined to this also challenging experience. Which I'm kind of enjoying.

Kim Wilton: Well, it's steep rent. Maybe I should have got a hotel. I don't know.

Adam Davis: Um, like what's it feel like to be walking around where you don't have your resume on your person?

Kim Wilton: It's great. I love not being in uniform. I like not people not knowing who I am.

Adam Davis: Why?

Kim Wilton: Um, because I'm a fairly private person. So I don't have a social media presence, for example, and this isn't my scene. So I like it when people don't know who I am.

Adam Davis: I'm sorry to be—I mean, I'm sort of sorry to be inflicting this particular challenge on you.

Kim Wilton: You’re not at all sorry.

Adam Davis: Um, I guess I'm thinking—I keep going back, while we're talking to, like, college Kim’s radio show. Reading your own stories, which doesn't sound that private.

Kim Wilton: No, it doesn't. But, I mean, 19-year-olds aren't that smart. I mean, you just, you're just having fun and doing stuff and, yeah. It was a long time ago.

Adam Davis: Okay. You know, ideally 30 years from now, we look back and go, there I was at 52 thinking I knew. Now I've gotten smarter. Do you feel like you have sort of questions about what you're up to now that feel like challenging questions, live questions?

Kim Wilton: Um, I'm not sure. I'm just kind of busy working at whatever the short-term goals are with work, with farming. So long term, I mean, strategy’s always work hard; don't be a jerk. Seems to generally work out. So I was just going to keep with that strategy.

Adam Davis: Just work hard; don't be a jerk. Find something challenging.

Kim Wilton: Yeah. And just keep pressing.

Adam Davis: Okay, um, Keiren, as you've been listening, can I ask you, like, anything that you want to ask about?

Keiren Bond: It's Kieran here, the producer of The Detour. I was engineering this interview, and as I listened behind the glass, I was struck by many risks Kim spoke about. Risks associated with truck driving and military service that Kim found herself in because of violent and predatory behavior of men. How these things had happened to her because she was a woman. This observation couldn't be entirely separated from my own lived experience, but even as I tried to take my own views out of it, it still felt like something that Kim didn't elaborate on, and that listeners might want to know more about.

So, I asked her how, if at all, these situations had changed her relationship with men.

Adam Davis: Keiren, through the glass window, just asked, given so many of the experiences you've had, I think Keiren’s wondering, have your experiences conditioned your thinking about men in a certain way?

Kim Wilton: Well, 99.9% of my experience have been positive, right?

Um, so yes, I have these, uh—or I had at different points, uh, whether that was when I was trucking or in Afghanistan, these different security measures so that I would be safe. But majority of time, I have had a great time working with both men and women, and I was always very cognizant, for example, when I told that anecdote about when I was trucking and being very careful where I parked, that I was also one of my strategies, a self-defense, was the air horn, because I knew there was enough good guys out there that would come help me.

So I've never had this inclination to be anti-male, because I've got so many great male friends, both in trucking and motorcycling and aviation that have helped me get where I am, right? I couldn't have learned these disciplines without them because all of my, almost—pretty much all of my teachers have been men. Most, many of my mentors have been men. So it's been easy not to hate them.

Adam Davis: That's somewhat heartening. I think, I don't want to—just in the interest both of this experience for us as friends and my experience as a man of, so the whole gender, I don't want to keep this going any longer than it should.

Um, let me ask you just a question or two about this, like how, what level of discomfort have you had talking about this stuff?

Kim Wilton: To me, it's not uncomfortable talking about it. It's the recording and making it public because I am very private. So I like the privacy aspect. And I'm also like, we're in a weird world right now where things get taken really out of context.

And things that, like, you see it all the time, if right now with someone who just says something or wrote something, and even if they were wrong, they're slayed for it. And it's a very unforgiving world right now. So that's where I also get paranoid. So I mean, I don't have a social media presence for a bunch of reasons, but I don't like how the world reacts to when people make mistakes and not letting them say, “I'm sorry,” or just understanding people make mistakes and chill out. So that's really what that discomfort I feel about recording is that piece because what soundbite gets taken and misunderstood.

Adam Davis: I mean, the good news is we don't have a lot of reach.

Kim Wilton: Great. I'll be sure to give you some negative reviews. I wonder, people are always asking on for iTunes or whatever it is. I'll be sure to have some negative reviews to bring that down.

Adam Davis: Just to drop it even further? That sounds wonderful. Um, well, maybe, I'm trying to read your expression, Keiren. Another question from Keiren. You seem to go towards the bigger challenge. Why do you choose the bigger challenge?

Kim Wilton: Big picture, I don't know the answer for that. But I know that you get—I, what I've learned from living that is that I get a better payback from it. Like I become, I get more satisfaction from the bigger challenge, and I become a better whatever it is, right? Um, so it, uh, it makes me stronger. I think as an instructor in one course I took once mentioned that it's at that uncomfortable point where you learn, right? When you're pressing yourself so you're not comfortable is when you learn. So I think those bigger challenges put you in that space more often.

Adam Davis: Can you describe what it feels like to fly a Chinook?

Kim Wilton: Oh my God. It's so amazing. Okay, so it has this vibration. It's a lateral vibration. So kind of like a semi, but a bit more of an up vibration. So there's a lateral vibration just while it's rolling on the ground. And then you have the ground taxi piece. So it has wheels. So just maneuvering it and how you steer it is so different. But okay, now we're going in the air. It's the weight. So right now, I fly mostly a jet ranger. It's quite small. Uh, it's kind of like flying a. a little dune buggy in the air. It's quite cute and sporty. But the Chinook is like so weighty and powerful but yet so maneuverable. So I can like, stop in a dime, I'm never short of power. Like, it's just brilliant to fly. It's so amazing.

Adam Davis: Is it possible to explain to some lunkhead like me who's never done it? Or do you just assume not?

Kim Wilton: For you in the back, for someone in the back, it may not feel more amazing. But I know for the—so I did pretty much all of my flying in Afghanistan for the Chinook or at different National Guard units in the States getting ready to go. It's the ability that I need to land there. I need to get in there strategically and doing this crazy 180 and stopping on a dime to get there. And I know I have, would have the power at the bottom when I'm coming into that hover. Uh, just having such confidence in that machine. So, um, yeah, no, it's a beautiful aircraft.

Adam Davis: Yeah. And what's it like to drive a motorcycle?

Kim Wilton: Motorcycle's pretty good too. So my, like I have a pretty sweet life, right? Cause I motorcycle to work in the morning, I fly helicopters during the day, motorcycle home, then I get into a combine and chew through some wheat, right? Like, that is my dream day, and that's what I live quite often.

So motorcycling is very similar to flying. It's that freedom. Sometimes it's better because I don't have a crew; it's just me. And it's just that constant. What's different than a car is that you feel a bit more in the environment, whether it's the smell of what you're—the canola fields you're going by, or more interaction with the wind. Um, but, yeah, it's pretty nice.

Adam Davis: I think I want to leave it there.

Kim Wilton: Okay, great. Me too.

Adam Davis: Thanks for being game to talk.

Kim Wilton: Not a problem. Thanks for being interested, I guess.

Adam Davis: I guess. Yeah. Alright.

Kim Wilton: Okay. Yeah.

Adam Davis: The Detour is produced by Keiren Bond. Dave Friedlander is our editor. Ben Waterhouse, Karina Briski, and Alexandra Powell Bugden are our assistant producers. I'm Adam Davis. Thanks for listening. See you next time.


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