In 2022, Cal Dobbs became the first known transgender person to triple crown, which means he hiked all of the Appalachian Trail, Pacific Crest Trail and Continental Divide Trail. Cal's next wild idea involves running across the U.S to raise awareness for trans rights.
In 2022, Cal Dobbs became the first known transgender person to triple crown, which means he hiked all of the Appalachian Trail, Pacific Crest Trail and Continental Divide Trail. Cal's next wild idea involves running across the U.S to raise awareness for trans rights.
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Shelby Stanger:
One of my favorite things about going after wild ideas is they often have a ripple effect. When we achieve something big, like finishing a race or surfing our first wave, it's like getting a deposit of courage into our bank account. Afterward we realize that we can do so much more than we ever thought. Cal Dobbs is a young endurance athlete who's made a lot of courage deposits. Cal started living a wild life when he asked himself this question.
Cal Dobbs:
You look at what you have or what's available to you, and you say, "But wasn't it supposed to be bigger and more wonderful than this?" And if you answer yes, then you better go get it.
Shelby Stanger:
In 2022, Cal became the first known transgender person to triple crown, which means he hiked all of the Appalachian Trail, Pacific Crest Trail and Continental Divide Trail. These are three of the longest and best-known trails in the US. Combined they're almost 8,000 miles long.
Now Cal is going after his next wild idea. Instead of hiking, he'll be running across the country for trans rights. Cal goes by both he, him, and they, them pronouns. Since Cal's preference is he, him, that's what we'll be using in this episode.
I'm Shelby Stanger, and this is Wild Ideas Worth Living an REI Co-Op Studios production.
Cal Dobbs grew up in Venice Beach, California and ran competitively in high school. He went on to become a collegiate cross-country runner. Cal learned a lot about himself during college. He found out that the further he ran, the more he liked it, and he started entering ultra races. College is also where he fell in love with through hiking.
Cal welcome to Wild Ideas Worth Living. So let's just start with this. You're this LA kid from Venice Beach and you triple crowned. So for people who don't know, triple crowning means you hiked the entire Pacific Crest Trail, the entire Appalachian Trail, and the entire Continental Trail. Just doing one of those trails is a major, major feat. So I'm guessing college, did you have an outdoor club?
Cal Dobbs:
Yes. My journey to the outdoors, I like to think of it as me finding my way back to myself. I didn't grow up backpacking. I grew up running around the concrete blocks in LA and then I did go to college in Pennsylvania in a suburb of Philadelphia. I was on the cross country and track teams, and what I discovered with myself in running is that the longer the distance got, the better I did. So I was like, okay, I'm an endurance athlete. I'm running the 5K. My coach wants to put me in the 10K. That's cool. And then I learned about ultra marathons and I was like, that's it, I'm going to do that.
Shelby Stanger:
How old were you when you did your first ultramarathon?
Cal Dobbs:
20.
Shelby Stanger:
That's impressive.
Cal Dobbs:
Yeah, and I loved it, but I always wanted to push that limit. That is something just like you said, that when you have that quality, when you have that grit where you just want to find what that line is as an athlete, you caught the bug, that's for life. It's never going to go away.
So I was getting ready to graduate and my last spring break, a couple of months before graduation, my dear friend took me on my first backpacking trip ever in the White Mountains in New Hampshire and I absolutely fell in love. I'd never seen anything like the White Mountains. And we got to the top and he goes right there, that's the AT. And I was like, AT, what are you talking about? What's that? And he's like, the Appalachian Trail. I'm like, what's that? And he explained it to me and I was like, that, that is what I'm doing when I graduate.
So two days after graduation, I was at Springer Mountain heading northbound on the Appalachian Trail. Full disclosure, I do not recommend a through hike with zero backpacking experience. It feels akin to the kid who's like, "Oh, I got a B and I didn't even study." It's like, well, you know, don't get points for not studying. So I don't take pride in not being prepared for things, but I also value that experience. And I think basically my AT through hike, pardon my French, was such a shit show that when I got to Katahdin, and then it's a miracle I made it all the way to the end, I still felt like there was a lot left for me out there on those trails. I felt like I made the friends of a lifetime that I am still friends with. I have all these crazy, ridiculous stories you get on a through hike.
I mean the AT is bonkers.
Shelby Stanger:
What's your trail name?
Cal Dobbs:
My trail name is Starburst and that is not after the candy. That is how I cry a lot on trail and I usually smile when I'm doing it. They were like starbursts, which speaks to how emotional and moving and spiritual of an experience a through hike inherently is if you let it.
So I finished that hike and, of course, I was filled with pride and just so changed by that journey, I just got this sense that I wasn't done, that there was more that nature had to teach me, more growth to be had, but I was flat broke and I didn't have any money. So I was like, well, let's go get a job for a while. The classic through hiker cycle of you work, you hike, you work, you hike. And so I moved back to LA and I got a teaching job, which I loved.
And then a couple of years later, the pandemic hit and I was really faced with a decision that I think a lot of people can resonate with, which is that the pandemic changed everything. And if there was one thing that it taught us, it's that life is very fragile and our time here is finite. So if you have the guts, you have a decision to make. And I asked myself if I died tomorrow, would I feel I had lived a full life?
And the answer was no. So I said, all right, well what is it that you need to do to answer yes to that question? And I said, I need to triple crown and I need to run across America.
Shelby Stanger:
Between completing the Appalachian Trail and starting the Continental Divide Trail, Cal spent three years teaching in LA. He set out from the Continental Divide trailhead in 2021 and arrived at the terminus in Mexico five months later. Then in the summer of 2022, Cal went after the final jewel of his triple crown, the Pacific Crest Trail. Even though he was really looking forward to this trip, nature threw him some curve balls.
Every through hiker I've talked to has a very unique story about either when shit goes wrong or how the trail changed them.
Cal Dobbs:
Yes.
Shelby Stanger:
I'm curious if you have a story that you repeatedly tell your buddies at the bar or wherever, coffee shop?
Cal Dobbs:
Oh, I have a story for you. In retrospect, very unwise. We almost died out there, but my big, I do not recommend it, but at the same time, I'm glad it happened. So on my PCT through hike, I'd already done the Continental Divide, which is sort of the daddy long legs of the trails. People are like, "Oh, it's the hardest one." I'd already done the CDT. So I'm flying pretty high. I'm like PCT, no problem. But because the PCT is so popular these days and because, unfortunately, climate change exacerbating the wildfires we get here in California, I knew that I had to finish the trail. So I said, I'm going to start as early as possible. I got my permit for early March, which is a very early start date. Most people start a month or more after that.
But I wanted to get ahead of the fires. So we start in early March, me and my partner and my dog, and we make it to Kennedy Meadows South, which is the foothills base of the Sierra Mountains. We get there very early. So if anyone's familiar with the Sierras, they know they got a lot of snow up there and you're supposed to start later to wait for it to melt.
But we plowed right through there and me and my hiking partner were actually the first through hikers, through the Sierras last year. And we had the good fortune of it not being too high of a snow year, but it was still very snowy and it was just very dramatic being out there. I mean, those are some of the most popular mountains in the country and nobody experiences them the way that we did. We went through Yosemite. We were the only people in the entire national park. I mean, how many people can say that?
Shelby Stanger:
How is that?
Cal Dobbs:
Because the park was closed. I mean it's open for the PCT hikers, but there's no visitors. All the roads are closed. There's no rangers out there because there's nobody there. And the snow, it's just too much snow. Nobody wants to be out there and for good reason let me tell you, because we headed into Mammoth, which is right before Yosemite, first hikers there when we started heading out of Mammoth, and we ran into the folks behind us and they were like, "Hey, there's a big storm coming, 30% chance of snow tomorrow." And we're like, "Oh, 30, that's nothing."
So we head into Yosemite.
Shelby Stanger:
Oh no.
Cal Dobbs:
What we didn't know was it was 30% chance tomorrow, a 100% chance the five days after that. So everybody else got the memo. They stayed in town to wait it out. Somehow we missed the memos, we figured we'd be fine.
So we head in into Yosemite National Park and it starts snowing, and we're like, well, it'll stop. And needless to say, it did not stop. It snowed for the next five days. We did not have enough food to have our mileage slowed down that much. The trail was fully covered, so we had no idea where we were going. It was very dangerous. There was one particular slope on a mountain where, and of course, we had ice axes and micros spikes, and it was this very steep drop off directly into a raging river. And that is probably the closest I've ever been to death because one misstep and you will die. I hope I never say that again. I'm not a daredevil, I'm actually a very risk-averse person. I actually really love my life, but that was also the most beautiful place I have ever been. I mean, it was quiet. It was so quiet. I've never felt peace in the outdoors like that.
Shelby Stanger:
What was something you really learned about yourself through hiking that you didn't learn anywhere else?
Cal Dobbs:
Oh, that's a great question.
Shelby Stanger:
Let me ask you this too. This might be a different question, but was there one trail that changed you the most out of all three?
Cal Dobbs:
Okay, I have my answer and I'm going to combine those two questions. Specifically, it really started, or it didn't start, but it really clicked into place for me on the Continental Divide Trail, the CDT, because it is the most rugged, it's the most remote of the trails, the longest distance between towns, no cell service whatsoever, I think as beautiful as I just said, Yosemite is, and the PCT is the CDT was the most consistently breathtaking trail of any of them.
You go through Glacier National Park, the Wind River range in Wyoming, the Rocky Mountains, go through Colorado, and then the desert. You finish in the desert in New Mexico. So because it's so remote and because there's these long stretches where you don't really see another soul, it's also the least popular of those three through hikes. So there's not as many hikers out there.
That is the trail where I really learned to love being alone. And I fell in love with my own company and I began to fall in love with myself.
I'm a very extroverted person, a very social person. But what I realized, especially growing up being the star athlete, you're getting a lot of attention and we start to feed off it. And I'm sure there's lots of athletes out there listening to this who really resonate with that, and it kind of becomes like a fix or a drug. And then I pretty much live my whole life up to that point for the approval of other people, for the accolades of all these achievements. And then I started through hiking and there's really nobody there. There's no one clapping when you cross the finish line. There's nobody there saying, good job Cal. There's nobody even there being like, how's your day?
Nobody. No one's there. It's you and nature. And that was terrifying for me when I first started hiking. It brought me to my knees, if I'm being honest, and I almost quit. And then I realized there's a reason why everybody likes me. Not to sound conceited, but I'm like, well, everybody else seems to like me. Why don't I like me? Everyone loves Cal except for Cal.
This is a lifelong process for me and for everyone is self-love and self-care, a daily practice. But the CDT is really where, like I said, those voices started to settle. I really came into my transness. So I was really stepping into myself, really stepping into my identity and really starting to decide who I wanted to be, what I wanted to do.
Shelby Stanger:
To honor the lessons he learned on the trail Cal is finally pursuing something he's wanted to do for a long time, run across America. In March 2023, just one day after this interview, Cal started his run, he sent us an update about how it's going from the road. You'll hear that and more after the break.
In 2022, Cal Dobbs became the first known trans person to complete the Triple Crown. After completing one life-changing wild idea, he dove right into another running across the country.
Cal has wanted to do this since he was just 10 years old. Now, 16 years later, he is finally making his dream a reality. But the social landscape of our country has changed a lot since he was a kid.
Today, the US feels more politically divided than ever before, especially when it comes to trans rights. For Cal, who is trans-masculine these issues are very personal.
I want to talk about this run across the country because your why for doing the Triple Crown was one reason, and now you have this why to run across America. How long is this going to take you?
Cal Dobbs:
So it's going to be between 2,400 miles and about 2,800 miles depending on my route.
Shelby Stanger:
The route.
Cal Dobbs:
Which should take me about four to five months, depending on how slow or fast I decide to do it.
Shelby Stanger:
So tell us just a little bit about where you're starting and where you are planning to ending subject to change.
Cal Dobbs:
Yes. So I am choosing an unconventional route. To my knowledge, no one of the hundred or less people who have ever run across America, none, I don't think any of them have taken this route, which I think is pretty cool.
So I'm starting right here in my hometown in Los Angeles, and I'm running south through California, Arizona, New Mexico, Texas, Louisiana, Alabama, Mississippi, and ending in Florida. And of course that was on purpose. Those are the battleground states for a lot of this anti-trans dialogue and rhetoric. These are the places where transgender people need love more than anywhere else in the country right now. That was intentional. I also just love the Southwest. I was born and raised here. My family lives in the south. I love the south, I love Texas. I've got a lot of friends from Texas. I spent a good amount of time in Texas.
Unfortunately, at the legislative level, they don't love trans people too much. But I think on the interpersonal level, Texas is full of a bunch of loving individuals and I'll be running with my support crew, which is my friend and my two dogs.
My friend is also a through hiker and trans. And then I've got a film crew that'll be flying out a couple of times along the way. So yeah, I intend to stop along the way at some major towns in like Phoenix, Albuquerque, Austin, Houston, New Orleans, ending in Tallahassee. And in each of those places, I'm really hoping to do what we've been talking about, which is building connections, building community.
I am not here to change anyone's mind. I'm not here to preach. I'm not here to do any of that. I'm really here to learn and offer what I have to give to the people who want it. There's a phrase that I love, which is go where the love is. And that's really what this run is about. It's about spreading joy.
Shelby Stanger:
You're going to host community meetups at some of these stops, many of these stops. What does that look like?
Cal Dobbs:
It's about finding the groups that are already doing this important work of advocating for trans people. And I want to come and uplift that work by building connections and also doing fundraisers. I also think it's really important for trans people, especially youth. I'm a teacher and I know the gravity that it has for a trans kid to see a transgender adult who is thriving, who is happy, who has all of the things that they want to embody, because that's the narrative is, oh, if you transition, no one will love you. You'll be ugly, you'll be gross. This is wrong, this is bad. You know, can't have access to gender-affirming healthcare. You say you're a girl, but you still have to compete with the boys, which is so dysphoric and humiliating and it's rough. I mean, it's rough being a teenager just in general.
Can you imagine being a trans teenager? So I want to be a beacon, and the data says that it just takes one person sometimes in the life of transgender youth to totally change it around.
The suicide rate for trans youth goes down. I think something like 80% when a trans kid has one adult in their life that respects their pronouns. So we know that a lot of the mental health issues that queer and trans kids face, a lot of the high suicide rates, that has to do with the culture that they're living in. It's not because they're trans, it's because of the reaction that they're getting and the response they're getting to being trans.
So if I can host a community event where I can talk to the kids, ask them about their dreams, and then I am a trans person living my dreams, that's partly why I took a sabbatical from teaching, because I realized I was showing up to class every day encouraging my students to pursue their dreams, and then I'd be a hypocrite if I wasn't living that when I told my kids that I was going to take a break from teaching and I wouldn't be there next year, and I told them why, and I'm very transparent with my students.
I can't tell you how many parents came to me and said, "My kid is going to remember you as a teacher forever. And it's not because what they learned in the classroom, it's because what you are going to do outside of the classroom, how you are modeling living your dreams."
Shelby Stanger:
Aside from being a great role model for his students, Cal is a truly skilled teacher. He's warm and open and doesn't shy away from hard topics. Lately, there's been a lot of conversation about trans people and sports, particularly trans women. I had some questions about these issues and Cal handled my curiosity with clarity and openness.
Cal Dobbs:
Let's not beat around the bush. All of this anti-trans legislation is targeted primarily at trans women, especially in sports, specifically. So why is it all targeting trans women? And I, it speaks to this larger conversation that we need to have as a society that we're all implicated in, which is patriarchy and sexism, right?
The reason that we fear or that society fears trans women more than trans men is because people don't understand transgender identities. So when an ignorant person looks at a trans woman, they see a man and men are threatening, you look at a trans man, you're like, "Oh, that's just a confused woman." And women aren't threatening, right? And it's not anyone's fault. It's all subconscious is because a lot of the rhetoric treats trans women like men. The bathroom bills are all about sexual assault and oh, I don't want a man in the woman's bathroom.
Statistics show us that 0%, truly 0% of reported sexual assault cases this year were perpetrated by trans women. And the majority of those are perpetrated by cis men. It's all fear-based, fear of the unknown, which is why we see this legislation being posed by people who have clearly never even met a trans person. And I'm a very firm believer that if you just have a human connection, and we see that, I have a personal example.
Literally yesterday I had to call my bank for some difficulties I've been having with my account. I think we all kind of armor up before we call the bank. All right, it's war. It's battle time. I'm going to get what I want and it's going to be hard and you will resolve this. I'm not going to talk to 10 different people. And I called, I was ready to be pretty adversarial, and this person answered the phone, and they're so warm and they're so kind, and they're so helpful, and they're like, unfortunately, there's only so much I can do. I've got to transfer you to my supervisor. So if you don't mind, I'll place you on a brief hold.
And then I said, yeah, sure. So they placed me on a hold and then they're like, I'm so sorry, it's just going to be a little while longer. We're on hold again. And then, because she was also waiting for this supervisor to answer the phone, she comes back on the line and she's like, I couldn't get in touch with him yet. I'm still on hold, but I think I'd like to be on hold with you if that's okay. And I was like, yeah, sure. And she goes, because I'm, I'm just so curious, you were mentioning what you do for work. You were mentioning you're an professional endurance athlete, and I'm just so curious, what does that mean? What do you do? And I'm like, I told her about my through hikes, and I told her I was about to run across America, and she was blown away.
And she was like, "I have so many questions for you." And she was telling me about her daughter and just, we had a blast. We didn't even realize we were on hold. We were just chatting. And finally the boss answered the phone and we wrapped up. And at the end of the call, she said, "I'm probably not supposed to do this, but is there a place I could follow along your journeys?" And I said, of course. And I gave her my website and my Instagram handle, and she said, "I just want to let you know are such a beautiful person. You're such a light in this world. You've made my day. I'm so excited for all your adventures." And I was like, "Ah, thank you," and we hung up the phone and I immediately got a little sad because I thought, how would this person's opinion of me change if they knew that I was trans?
Because I didn't talk about that on the phone. I didn't come out to this person, and disclosure is a big thing for trans people, and also I need her help resolving this issue with my bank. So I was like, oh no. Is she going to look up my website and my Instagram and is she going to be like, "Oh my God." She told me she lives in Texas too and I don't like to judge. She's like, I live in rural Texas, and I'm like, Uh-uh that's the epicenter for all this rhetoric and dialogue right now. And I'm worried maybe she wouldn't have felt that way if she had known.
And I went about my day and I got on my phone a couple minutes later and checked Instagram and I had a message request and it said, "Hey, this is me from the lady from the bank. I just wanted to say, I'm so glad I found your page. I think what you're doing is so cool. I live in Texas, and if I saw that your run is heading through Texas, and don't tell my boss, I'm reaching out to you, but if you're ever running through here, I'd love to come say hi or maybe bring you something." And I looked up where she lives and I am running through her town.
Shelby Stanger:
Oh, that story gave me goosebumps. As of June 2023, Cal is partway through his run across the country. Here's a note from him about how it's been going.
Cal Dobbs:
"Hey, what's up? It's Cal. I'm recording this from a gas station in San Antonio, Texas, which is about 1500 miles into my 2,500-mile transcontinental run. I've been having so much fun meeting trans people and allies across America and hosting community events and fundraisers to bring love and resources to the trans people most impacted by this unprecedented onslaught of anti-trans legislation."
Shelby Stanger:
Cal Dobbs, thank you so much for coming on wild Ideas Worth Living. We're rooting for you over the next few months as you finish your run across the country.
At the end of Cal's Run, he's hosting a 5K in Tallahassee, Florida called The Trot for Trans Lives. You can participate virtually or in person.
To learn more about this race in Cal's journey across the country, check out Cal's Instagram at Cal_hikes. That's C-A-L underscore H-I-K-E-S.
Wild Ideas Worth Living is part of the REI Podcast Network. It's hosted by me, Shelby Stanger, produced by Annie Fassler, Sylvia Thomas, and Sam Peers Nitzberg of Puddle Creative. And our senior producer is Jenny Barber. Our executive producers are Paolo Mottola and Joe Crosby.
As always, we love it when you follow the show, rate it and write a review wherever you listen. And remember, some of the best adventures happen when you follow your wildest ideas.