Outskating Your Demons

By Ilana Strauss, produced by Out There Podcast

Released on October 7, 2021

Welcome to Out There Podcast. Our stories are written for the ear, so for those able, we recommend listening while reading along. Transcripts may contain minor errors; please check the audio before quoting.

WILLOW BELDEN: Hi, I’m Willow Belden, and you’re listening to Out There, the podcast that explores big questions through intimate stories outdoors.

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(Out There theme music begins to play)

Sometimes, when bad things happen, they can kind of surround you and, over time, they can start to define you. So if you break free and leave all that negativity behind…what are you left with? If something bad becomes a huge part of your life, and you get rid of it, who are you?

Today’s episode takes us to the Eastern Seaboard, where a young woman named Molly-Anne Dameron finds herself face to face with the darkness she’s trying to outrun. Or outskate, really. 

Ilana Strauss has the story.

And - trigger warning: this episode discusses addiction, mental illness, and suicidal thoughts. It also includes adult language. 

(Out There theme music ends)

ILANA STRAUSS: Well, this all started because I was like, “Hey Molly. Wow. It's been a while. And we're both in LA. What have you been up to?” And you're just like, well…

(Ilana and Molly-Anne laugh)

MOLLY-ANNE DAMERON: I've been on a 400 mile skateboarding trip. 

ILANA: Yeah, you were like, “Sorry, I haven't gotten back to you! I've been really busy over the last two weeks.”

(Molly-Anne laughs)

So this is a friend of mine, Molly-Anne. And she had just attempted to skateboard from Maine to New Jersey.

MOLLY-ANNE: I was kind of terrified for my life in a sense. So I decided that the only way to save myself was to go on the skate trip.

ILANA: Can you connect the dots a little bit? Because I don't totally see the connection.

MOLLY-ANNE: Can I ask you a question real quick? 

ILANA: Yeah. 

MOLLY-ANNE: Okay. How much do I say?

ILANA: Uh, everything.

MOLLY-ANNE: Okay. So even like the dark bits, it doesn't matter? 

(quiet music begins to play)

ILANA: Okay, so to understand Molly-Anne’s story, there’s something you got to know. Molly-Anne suffers from dissociative identity disorder, formerly known as multiple personality disorder. She’s 26 now, and she’s been struggling with mental health since she was a little kid. 

MOLLY: Suddenly you could be you. And the next moment you could be like a literal psychotic person, or you could be acting like a child.

ILANA: Her episodes get pretty intense.

MOLLY-ANNE: I don't know if my brain is telling me truth or not. And when I look around at things, it's like looking at a literal nightmare — the entire world is crumbling and there's a plot against everybody. And everything, like, has this coating of, like, dirt and grime and sadness. And, like, you have x-ray vision into everything happening around you, or you think you do. You can see all of the emotions and all of the sadness and all the pain.

So sometimes I'll hear things and I'll hear, like, it's kinda my own thoughts, but they're not my own.

ILANA: What would they say?

MOLLY-ANNE: Often they'll tell me to kill myself. That could go on for like an hour. It could just be over and over and over. You should kill yourself. You should kill yourself.

(music fades out)

ILANA: Sometimes, Molly-Anne will have an episode while driving. 

MOLLY-ANNE: I'm just sobbing. And I'll just step on the gas, and then I'll break right before I hit the other car. And I'll do it over and over, but I can't see properly cause I can't stop crying.

ILANA: She’ll threaten other cars and even come close to crashing. 

MOLLY-ANNE: In a lot of ways it's super embarrassing because, like, that's not normal looking. Like, why would you do, like, finger guns at a car? It's like, “I want to fuck you up. And I want you to know that.”

And at the same time, it's like, “I need help. Like, fucking help me, because I can't stop doing this.” But like a driver in front of me who I'm flipping off is not going to help me.

ILANA: She needed help, but when it came to fighting her demons, she felt alone. Her mental illness separated her from other people.  

Molly-Anne had tried therapy and medication, but nothing solved her problems. Then as a teenager she started using drugs. They made her episodes less extreme, and made her less afraid of the world.

MOLLY-ANNE: It was the first time that I felt like I knew who I was, and it gave me that sense of self that I never had. And I didn't have to feel like I was constantly dying or fighting for my life.

ILANA: But of course drugs were not a magical solution.

MOLLY-ANNE: I had spent so many nights thinking, ‘Am I going to wake up tomorrow? Is my heart racing too much?’ Because I would do so much cocaine that, like, I could literally feel my chest was sore. Your chest being sore because your heart is racing so fast all day, every day, is not a good sign.

ILANA: In 2018, her grandfather had a heart attack and passed away. His death hit close to home.

MOLLY-ANNE: So I would go to bed sometimes and think, ‘Do I text my mom that I love her? Do I, like, what do I do? What if I don't wake up? Like, what if I have a heart attack?’

So watching somebody die, especially die through cardiac arrest was like, “Oh shit.”

ILANA: So the day of his funeral, she decided something. 

MOLLY-ANNE: I said, “That's it. I'm done.” And I didn't do anything again.

ILANA: Didn’t do anything again, as in she went off drugs. Completely. Cold turkey. She thought going clean would make her a functional member of society and let her achieve what she wanted.

MOLLY-ANNE: The irony to it is that it never gave me any of those things. People don't talk about when you get clean, but like, it's not always fucking rainbows.

(soft music begins)

ILANA: Her mental illness episodes got worse. She started hearing voices she’d never heard before.

MOLLY-ANNE: I’d been going to AA since I was 16, and nobody once told me this is what you deal with when you get clean and you have serious mental illness.

I feel so robotic and in constant survival mode all the time, because I’m always having to analyze my surroundings, and myself, and it's fucking exhausting.

ILANA: Molly-Anne felt like she lost this carefree, adventurous spirit she’d been on drugs.

MOLLY-ANNE: I would just hop on a plane and leave. I was happy to just move to a foreign country alone. And I had completely lost that when I got sober.

I had no idea who I was off of drugs, because I had started using when I was 16.

(music fades out)

ILANA: Then, in 2020, the pandemic made everything worse.

MOLLY-ANNE: I was terrified. I didn't want to get COVID. I'm not only a drug addict. I've, you know, smoked my life away for the last 10 years. And, and I have chronic problems because I did too much cocaine and, and I'm not risking getting COVID. I don't need more problems in my life.

ILANA: But staying safe was, well, dangerous.

MOLLY-ANNE: I had had a lot of people I knew die from overdoses during COVID.

Quarantine can make you go crazy. Right? I think that's been scientifically proven. You're like seeping into the walls. And you think, ‘What is my life worth? How do I still find the good pieces in me that existed once upon a time?’

(music begins to play)

ILANA: Finally, she hit her limit.

MOLLY-ANNE: I didn't know if I was gonna make it in sobriety if I didn't get out. 

And you ride across the country because this fucking mental illness is fucking eating at your brain, and you have to decide whether or not you're going to stay alive or you're gonna be dead.

ILANA: Ride across the country. Molly-Anne had grown up skateboarding, and she’d always played with the idea of traversing the country on a skateboard.

MOLLY-ANNE: It always sounded really cool, but kind of ridiculous.

ILANA: Alright, let’s be clear: skateboarding across the country is not something people typically do. Like, even long-distance skaters typically only skate for like a day or so. In fact, in all of her research, Molly-Anne had only found a few other people who had tried to do something like this.

But suddenly, a trip like this felt very necessary. Very right. 

MOLLY-ANNE: It was a way of proving to myself that I could make it. That I was still alive. That whatever happens in my brain doesn't mean that that's my whole being.

ILANA: She saw it as a way to recapture that adventurous spirit she lost when she got sober.

MOLLY-ANNE: I went into it thinking this trip's going to be a reminder that I can still be that person who knew how to find some freedom and knew how to live.

ILANA: Molly-Anne decided not to skateboard across the entire country. Instead she’d go from Maine to New Jersey, a journey that would take about two weeks. 

Why that route? She grew up in Connecticut, and lately she’d felt kind of drawn to visit her hometown, though she wasn’t sure why. This trip would give her a chance to find out.

(upbeat music begins)

Reality check: Molly-Anne is not some sort of professional skateboarder.

MOLLY-ANNE: I also hadn't skated in like a year and a half. I hadn’t been on a skateboard. 

ILANA: I didn't know that.

(Ilana laughs)

ILANA: And actually, skateboards are too small for this kind of journey. She’d be riding on highways full of trash and rocks, and those can send a skateboard flying. She’d need a longboard — it’s kind of like a bigger skateboard with big wheels that can ride over debris.

ILANA: You hadn't longboarded before? 

MOLLY-ANNE: No. 

(sound of laughter

MOLLY-ANNE: No. 

ILANA: Longboards move differently than skateboards though, so it would be kind of an adjustment. And making that adjustment for the first time on a trip like that would be…well, a lot. But she was determined.

MOLLY-ANNE: It was one of those times where you, like, you just don't look back. Like you just decide, and you don't look back, and you do it. And you don't think about it...but if you miss that moment, you're not going to do it.

(music ends and sound of traffic rushing past in background begins)

MOLLY-ANNE: I’ve been going up an incline for like two miles.

(sound of someone breathing hard)

Twenty-five pounds on my back…I think I’m gonna fucking die. 

ILANA: So this clip you’re hearing — it’s from Molly-Anne’s audio diary, from the start of her trip. 

She had started her journey full of all this hope that she’d finally prove to herself she could be an individual apart from her mental illness and addiction. But the first day was not going smoothly.

It wasn’t for lack of preparation. She had packed a backpack full of clothes, medical supplies, and tons of masks and hand sanitizer. She’d gotten tested for COVID — negative, luckily. Then she traveled to Maine and started riding. 

(sound of longboard wheels rolling down a road)

MOLLY-ANNE: Suddenly it's just like this big hill up, and the hill just never ends. It's a real issue. The hill just keeps going. And then I reached the top...and there's another hill.

And now I'm on, like, this deserted highway. It's like 6:30 in the morning. There's nobody on the road. And I remember that my aunt had said, “Well, it's hunting season, so make sure you have your vest.”

It's all forest around me. I'm like, ‘There could be a bear.’ I stick my vest, like, on. I strap it to my front. Like, I'm terrified, please don't shoot me.

(music begins to play)

ILANA: Molly-Anne sees a home on the side of the road. And there’s this dog sitting outside.

MOLLY-ANNE: It’s like this huge Great Dane.

ILANA: The dog sees her.

MOLLY-ANNE: Dogs HATE skateboards, like hate them.

ILANA: It starts barking.

MOLLY-ANNE: And so I’m just like, ‘Alright, stay cool. Like, look ahead. Don't act like anything's wrong.’ And the dog runs down the hill at me. It's like, it's coming to attack me. 

I just ran for my life across the road, and it followed me. It ran after me, and I screamed, and it finally just stopped. 

(music ends abruptly)

And after that, I think I just shook.

ILANA: This is from her audio diary.

(sound of wind begins)

MOLLY-ANNE: I nearly got attacked by a dog that chased me out into the street. A giant, huge, “I don’t know what the fuck it was” dog. And of course I yelled at it. Because why pull out your pepper spray when you can yell at a dog? Fuck!

(sound of cars driving past)

ILANA: Over the next few days, Molly-Anne gets used to avoiding dogs and riding over highways.

(sound of cars driving past in background)

MOLLY-ANNE:  It’s exhausting, dodging cars and rocks and all the crap on the road. Like, who told you littering was cool?

(traffic noises grow quieter)

MOLLY-ANNE: I can't even fathom how I walked up hills with semis inches away from me. How I rode on highways and got into people's cars and the beds of their trucks. It...it feels like a distant dream in some way.

(traffic noises stop)

ILANA: Then one day, something happens. 

(quiet, intense music begins)

Molly-Anne’s riding through Maine and she hits this construction zone. The whole shoulder is closed for miles, meaning she can’t keep riding. She’s figuring out what to do when this car honks at her. At first, she doesn’t give it much thought. Cars honked at her all the time.

MOLLY-ANNE: That would keep me going. Like, I would get really pumped. Like, people would wave to me and, like, cheer me on.

ILANA: But this time, the car pulls up next to her and stops.

The window rolls down. There’s a couple inside. They ask what Molly-Anne’s up to. She explains her plans. They start talking about their son.

MOLLY-ANNE: They said, “He passed away a month ago, but he would have thought this is so cool. A girl riding down the coast, like, that's amazing. And we just wanted to stop and see if you need anything. Do you need a ride past the construction zone? Like, where are you headed?”

ILANA: It was suspicious.

MOLLY-ANNE: You know I thought, ‘Okay, your son died. Like, that's a really good story. You know, that's like the story that kidnappers would tell you, right? They'd be like, yeah, my son just died. Like, get in my car please — come on, feel pity for me.’ Like, that was what ran through my head. Yeah. I had my phone ready. Like, I had 911 ready on my phone. I was prepared.

Are these people about to kidnap me? Like, should we get in cars with people, because we don't do that in America. We don't...we don't hitchhike.

ILANA: But she needs to get past the construction zone, so she gets in the car.

(music changes to a contemplative tone)

MOLLY-ANNE: And they said, “So why are you riding?” And I told them, “Well, I'm sober. And I'm, I'm kind of doing this for myself. And, and to represent everybody who… who has lived in silence and, and maybe wasn't able to make it.” And they said, “That's amazing. We've been sober 27 years.”

ILANA: They’d been thinking a lot about their son that day.

MOLLY-ANNE: They showed me a picture of him and his, his name was Alex.

ILANA: He’d overdosed. 

MOLLY-ANNE: They said, you know, he died a month ago and like, this is the hardest day we've had since he died. And we just needed to get out of the house. And then we stumbled upon you. And they were like, “You’ve given us so much hope. We needed this today.” Like, I needed them and they needed me.

(warm music begins)

They were exactly why I went out and did this, because of somebody like Alex who suffered in silence and who died from addiction. He was my story. He was me in so many ways, and I didn't know the kid. He was my greatest fear. Like his story was what I was trying to avoid by doing this. And also trying to tell by doing this.

ILANA: The couple drops her off, but they stay in touch.

MOLLY-ANNE: And they sent me text messages saying, “We're so proud of you!” And like, “Keep going; you're an inspiration.” Like, “Alex is riding with you.” It weighed heavily on me because I felt like in so many ways, like this kid who I didn't know was riding with me.

ILANA: They also made her realize something about herself: her identity didn’t end at her skin. She was part of this larger community.

MOLLY-ANNE: There were people who I could count on, even if I didn't know who they were. Good people out there that cared.

(music ends)

ILANA: So things were going well. Until Molly-Anne got to Massachusetts…

WILLOW: Hey, it’s Willow. We’ll hear the rest of the story in a moment. But first…

There are a lot of different ways to see the world. Long-distance skateboarding is one, but you don’t have to go on an epic journey like Molly-Anne in order to get something out of travel.

If you’ve been feeling some wanderlust lately, you might be interested in a podcast called Out Travel the System. 

Out Travel the System is one of our sponsors. It’s brought to you by Expedia, and its mission is to inspire and inform about travel. That can mean anything from building your bucket list, to taking concrete steps to take that next trip when the time is right.

The podcast finds people who are passionate about travel, including a commercial airline pilot, a woman who travels pretty much year-round, and a man who wants to have visited every country in the world by the end of this year. Out Travel the System is available wherever you get your podcasts.

And now, back to the story.

ILANA: So up until this point, things are actually going pretty well. Molly-Anne knows her purpose. She’s encountered kind strangers. She’s making good progress. But then she gets to Massachusetts.

(sound of strong wind blowing and cars driving past)

MOLLY-ANNE: The wind is fighting me. We’re having a giant battle. We’ve been at war...and I think I’ve lost. I’ve definitely lost.

(wind fades out)

ILANA: She passes by Cape Cod, where she and her family used to visit.

MOLLY-ANNE: It was really lonely being there by myself. And I just sat in my hotel room and cried. And I think that's the moment when I realized, like, ‘I don't know how to keep doing this.’

ILANA: When she gets back on the road, things feel off. She starts to feel this sense of impending doom.

(sound of wind, cars driving past, and longboard wheels on the road)

MOLLY-ANNE: It’s getting really stormy. And I don’t like stormy. Me and storms don’t mix well. We require medication when that happens. Oh god, what the fuck is that? 

(rain starts coming down hard)

Oh my god. I think it’s raining.

(quiet music begins)

ILANA: It wasn’t just the bad weather that was bothering her. It was the stuff going on inside her head. Molly-Anne had gone on this trip to escape the worst bits of her mind. But now that she’d been on the road for a while, she was realizing she’d brought her mind with her. And now, alone on the road, she felt an episode coming on.

MOLLY-ANNE: And then it started, and there was really no turning back from there.

I tried to destroy my board. I literally tried to chuck my board, and like pound my board to destroy it. I was like, “I'm done skating. This is it.”

ILANA: So you were just like chucking your board at the ground?

MOLLY-ANNE: At bridges.

ILANA: You were chucking your board at bridges?

MOLLY-ANNE: Yes. Yeah. 

I think I just looked like a crazy person walking down the side of the highway

ILANA: And what was kind of going through your head?

MOLLY-ANNE: I just felt like a fool. Like, ‘I want to destroy this. Like, why did I even come out here? This is crazy.’

And I was... I was this close to walking into a bar. Like, I don't think I've been that close to drinking my whole sobriety. I was fully committed to going and getting drunk, and stopping the madness from happening.

(music ends)

ILANA: But then something occurs to her.

MOLLY-ANNE: I need to get to a beach.

ILANA: A beach. The beach had been kind of a symbol for her on this trip.  

MOLLY-ANNE: Every time I would ride by the beach, I would kind of feel more alive. And I always felt like I was connected to that story. Like the Alex story, my own story, when I was on the beach.

ILANA: So instead of going into a bar, Molly-Anne calls an Uber. A girl picks her up.

MOLLY-ANNE: And she said, “If you need anything tomorrow, if you need me to come pick you up and take you to Connecticut, like I will do it. I will get up, just call me and I'll be there. And I'll take you.”

ILANA: They drive to the beach.

MOLLY-ANNE: And I got out of the car, and I just sat on the beach, and I didn't move for like three hours.

(gentle music begins)

ILANA: During those three hours on the beach, her mind was in overdrive. She was starting to realize something important: she couldn’t run away from her mental illness. 

MOLLY-ANNE: What caused me to take this trip doesn't stop existing because I took the trip. And it will always come out, and it will always be there, and even though it's existing here, I'm not going to let it stop me from doing what I came here to do.

ILANA: Molly-Anne’s mental illness was a part of her. But that didn’t mean it had to control her. It couldn’t stop her from doing incredible things — like skateboarding from Maine to New Jersey.

In fact, she’d soon come to realize that it might actually help her reach her goal. 

(music fades out)

Not long after that day on the beach, she arrives in Connecticut. She wasn’t too far from Westport, the town she grew up in — a town she had some pretty difficult feelings about. 

MOLLY-ANNE: A house that was my childhood home, a house that raised me, wasn't a house that fostered something good in me. 

And it was a house that I needed to say goodbye to, because it destroyed me. It destroyed everything that was good in me and had created the monsters that I had worked to understand.

ILANA: And as all these complicated childhood memories start coming back, she rides into this roundabout.

(sound of wheels rolling past)

MOLLY-ANNE: And I get cut off by a whole swarm of cars. And I freak out.

(tense music begins)

And the episode starts again, suddenly. And I'm ready to walk out into the middle of the road and let a car hit me.

I said, “This is not happening right now.” And I booked it.

I was in this mode of, like, ultimate strength. Like, fucking, it was beyond my normal strength.

ILANA: A destination forms in her mind. Westport: the town where she grew up. 

MOLLY-ANNE: That's where the demons started and came out, and fighting them in the same moment that I was riding through them was like the culmination of that whole trip for me.

Every single hill I hit, I pushed uphill. I rode in the middle of the street. I didn't care what cars were around me. I just did not stop.

ILANA: Molly-Anne was riding 18 miles an hour with 25 pounds on her back and a hole in her shoe.

MOLLY-ANNE: I was just riding through lights, whatever. I'm not even breathing. I don't even know how I'm breathing. I don't stop. I don't drink water, nothing. 

ILANA: She rides 50 miles  — that’s like two marathons. That’s long even if you’re on a bike, and she did it on a skateboard. But she finally gets there. 

MOLLY-ANNE: And I just started crying and I just, I was just balling.

(music fades out)

It was like not only was I having an episode in the middle of the street, I was riding through my town that broke me. And I was refusing to, to feel broken in that moment, to let it break me. 

(more cheerful music begins)

ILANA: A few days later, she makes it to New Jersey. She had skated 400 miles in two weeks. 

MOLLY-ANNE: In the two years I've been clean, I hadn't done something that really meant something to me. It was, it was two years of just trying to survive, and finding the best way to survive. And I needed to find some meaning in that. And this gave me some of that. It gave me some, some of the pride that I needed to keep going.

ILANA: So it sort of changed how you thought about yourself?

MOLLY-ANNE: Yeah, I think so.

ILANA: Since getting off drugs, Molly-Anne had struggled to figure out who she was, and how she could survive with her mental illness. During the trip she realized she couldn’t leave her mental illness behind, but she was a person who could accomplish amazing things despite it. And actually, her determination to overcome her demons is kind of what made the trip possible in the first place, and it even gave her incredible strength near the end. 

And Molly-Anne learned she didn’t have to do it alone. Just like her demons were part of her, other people were part of her too.

MOLLY-ANNE: The people that I met along the way were what kept me going. I was surprised by humanity. Like, that there were people who showed up out of nowhere and were there for me when I was alone. And that was amazing, because I went out there feeling like those people didn’t exist, and this world was lacking those kinds of people. But in reality, we just don’t always see those people.

(music continues for a few moments)

WILLOW: That story was reported and written by Ilana Strauss. She’s a journalist living in Chicago, and you can follow her on twitter @ilanaestrauss. That’s I-L-A-N-A-E-Strauss.

(music fades out)

Coming up next time on Out There…

When Grace Gordon decided to start dating women, her friends and family were really supportive. But embracing a queer identity didn’t turn out to be as straight-forward as she had imagined. 

GRACE GORDON: All of a sudden, I wasn’t just talking about the IDEA of dating a woman, I actually had the opportunity to do it. And that was somehow terrifying.

WILLOW: Tune in on October 14 for a story about learning to chart your own course in life — and on a mountain bike.

A big thank you to everyone who has been sharing Out There with their friends, including Michael Mowery and Laurie Richardson.

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(theme music ends on a last whistling note)