The Attempt Episode 8: Ups and Downs


Brass skips ahead and finds himself in the epic Sierra Mountains.

The Attempt is produced by Julia Drachman with help from Doug Beyers. We are a production of Bad Cat Media, created in partnership with The Trek. All music in this episode is from Blue Dot Sessions.  

Also, there is a moment in this episode when Benjamin says “August” when he means to say “October.” I chose to leave it in because – as I’ve come to understand – the days, weeks, and months blend together on the trail. I hope you’ll excuse any resulting confusion and enjoy the time warp that is long-distance backpacking.

The Attempt is sponsored by Gossamer Gear, manufacturers of functional ultralight backpacking gear, designed by hikers.


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Julia: Hey guys. So, I think it’s important to start this episode by wishing Benjamin a happy birthday. On September 15 of 2019, somewhere around the town of Dunsmuir, Benjamin turned 25. Which is one of those birthdays that feels big, but like not a lot actually changes. There’s just one little thing – when you’re 25, you can rent a car without paying that extra surcharge. Which seems unhelpful when you’re on the trail, but, as luck would have it, on the very day of his 25th birthday, Benjamin rented a car. On the morning of his birthday, Benjamin woke up crazy early in Dunsmuir to take a 3 AM train to Sacramento. And from there, he rented a car and drove to South Lake Tahoe. So basically, he ended up the day 411 miles south of where he started. Now, I’m not a thru-hiker myself, but this seemed a little weird to me. So I called him up to ask him why he skipped ahead.


Benjamin (on the phone): So the way the trail works is that if you’re going soutbound you’re much more restricted on time because typically you can’t start until July. And that means that you have to scamper through Washington, Oregon and Northern California in order to get through the Sierras before October 1. And that’s a much tighter timetable then northbounders have.


Julia: It turns out, this whole skipping-ahead thing is pretty classic for southbounders. See, they have a really narrow window of time for their start time. So a lot of them do a lot of hopping around from one section to another in order to finish the whole trail in one season. But Benjamin had been hoping to just go straight through. And it wasn’t really until he got to Oregon that he realized that just wasn’t going to happen. He was gonna have to skip ahead if he wanted to make sure he saw the Sierras.


Benjamin: And so it was probably around Northern Oregon that I was like, yeah, no, there’s no way I’m gonna make it. And I had the choice of whether basically to skip NorCal or The Sierras. And so many people had told me that the Sierras were their favorite part. So I did 150 miles of Northern California, which is kind of the first quarter of it and then at the town of Dunsmuir they have a train station so I thought that would be a good point to get off the trail. And I took a train – a midnight train – to Sacramento, rented a car in Sacramento and drove to south Lake Tahoe, which is kind of the way that the P. C. T. designates the northern edge of the Sierras.

Julia (on the phone): Got it.


Julia: The whole question of whether to skip or not came down to a personal choice – it was a question of Benjamin’s priorities. Was it more important to him to strive to complete the thruhike and potentially miss one of the most stunning parts of the trail? Or was he willing to sacrifice that perfectionist thing in order to increase his chances of seeing the Sierras?


Benjamin: And my friend Antoine said, the reason – I said, come on dude, skip with me, we’ll do the Sierras together, we’ll definitely get through in good weather, it’ll be fun. And he goes, “It just wouldn’t feel right for me personally to reach the southern terminus and not have finished everything.” And I couldn’t really argue with that because that’s his personal feeling. And my personal feeling is, I’ll get to the southern terminus and I will know that I have not completed the thruhike. But I’ll still feel good. But he knows he wouldn’t so he probably made the right call for himself.


Julia: And that is exactly what they mean when they say, “hike your own hike.” This is a phrase Benjamin picked up on the trail and now I say it all the time. Basically, don’t waste your energy comparing your experience with other people’s experience. Do what’s right for you. And so what was right for Benjamin was to skip ahead. He decided to leave those 411 miles of Northern California behind – he could do them next summer. Instead he spent his birthday in transit, heading down to South Lake Tahoe. And all the while, he was gearing up for the epic challenge that is the Sierra Mountain range.


Julia: You’re listening to

Benjamin: A podcast my sister makes

Julia: It’s called the attempt

Benjamin: I see what you’re trying to do!

Julia: (Laughing) Alright…


Benjamin: Ok I am wrapping up September 16, cooked dinner, went to bathroom, set up my tent. Now I’m just taking my socks and shoes off, and I’m gonna get in my hopefully warm sleeping bag shortly. Today was a day of ups and downs. I felt really discouraged at one point. I think it was a combination of being disoriented about skipping. I really did feel out of whack, like I didn’t know which direction I was walking. I couldn’t picture it. And then it got really cold and started snowing, in some areas like a couple inches, and I lost the trail and I had to go back and I—my hands were so cold, I couldn’t use my phone to do navigation. And there was this one guy who was just the classic: “oh you skipped? You skipped a good part.” And that kinda brought me down because I was feeling uneasy about it anyway. And then it just started to get really beautiful. And that honestly turned things around for me. And we kinda entered the sierras – the foothills of the sierras – which is where I am now. And I was making fresh tracks in the snow. I didn’t go particularly fast today, but I started to kind of feel a little better walking again. The whole thing kinda turned around. I really don’t want to drink water because I’m gonna need to pee, but I’m so thirsty. (Drinks water) Ah, as I said that I started cramping. I really do need to drink water. Shit. Alright, I think I’m set. I think I have everything. (Sign) Change into my warm sleep clothes, and then go the fudge to sleep. That’s all for now.


Julia: Maybe it’s just me, but this really reminds me of Benjamin’s first week on the trail. He’s pumping himself up, trying to feel good, reminding himself how beautiful it is – but you can just hear that worry in his voice. Like he’s wondering what he’s gotten himself into? Which I guess isn’t that surprising – in some ways, skipping ahead means that he is starting over again. He’s in a brand new mountain range and climate, and he’s literally walking through a snowstorm – which he definitely hasn’t done yet. So not only is he still feeling uneasy about skipping ahead. He’s also having to adjust to all the new logistical decisions – like, what to wear in the snow, how to navigate the cold, how much water to drink, how many miles he can expect to cover each day. And as he goes on, the climbs start to get more and more extreme.


Benjamin: Ok this is gonna be pretty brief. I just crossed into 10,500 feet. Heading toward Sonora Pass. I think this is the highest I’ve ever hiked. We just did a pretty frickin’ hard 2500 ft climb over a couple miles, thought I was done, got to what I thought was the pass, realizing I had another ½ mile and 300 ft, which was devastating. Today has been the hardest day for me physically. Most days, around 6 pm, I’m running out of daylight or positive attitude. Today I’m just running out of energy. I am gassed. My legs are very tired. But the good news is we’re camping about 3 miles from the highway so tomorrow morning we can get a hitch in pretty easily. OK that’s all for now.


Julia: This is one of the things that makes the Sierras so satisfying – they are absolutely brutal. You don’t get those gorgeous views without putting in the work to get there. And I think in a way, it’s that hard work that really ends up curing Benjamin of his skipping-ahead blues. Sometimes, nothing feels better than good, hard work. Oh, and good company helps too.


Benjamin: Oh ok so today was a great day. Around 10 AM I ran into old friends and one new guy. So, Beacon I met. (Beacon or Brian) and then Calum (Salt Lick) and Spit Fire (Laurent). They had skipped a different stretch and so we kinda reunited here, which was great. Today turned out to be the toughest day of hiking that, in my opinion, really kicked my ass. Especially coming over the high pass when it just kinda shat snow on us. Um, but we had kind of this specific goal in mind of getting close to the road so we could hitch in easy tomorrow. And I felt like we – like I was definitely gonna hit that. I wasn’t gonna stop short today. Calum battled through an ingrown toenail, which did not look fun. In general, it was a toughie. But we all learned how to shred it!

Others: (Laughing) Shred it bro!

Benjamin: And I am warm and cozy in my sleeping bag right now. And just had some Mexican chicken rice. Feel pretty good. And hopefully I won’t have to pee out into my vestibule too many times tonight. That’s my hope. Alright, that’s all.




Benjamin: Hey Julia. This is a different sort of recording than normal. So, I’m walking – and there’s no one around me – and I could tell there was no one in front of me for a while so I played a podcast out loud on my phone. And I wanted to listen to something that I knew I liked but hadn’t listened to in a while. So I picked your episode about the sun. I think it was called, “The light is doing a show today.”


Julia: I just wanted to pause for a second to explain — he’s talking about different podcast here – one that I made before this one, called Going Forward. And the episode he’s talking about is all about our relationship with daylight and designing our lives around the sun. Anyway, back to Benjamin.


Benjamin: And I was – first of all, I liked it the first time I listened to it. But after hiking for 2.5 months – and being so regulated and impacted by the sun – I was kinda blown away anew. It literally brought tears to my eyes. This month, I’ve probably said to 5 or 6 different people, I can see why ancient people worshiped the sun. Because it’s so important for me. And I also have said that my top five moments on the trail are all sunrises or sunsets. Which kinda goes into the balance between like – you need the night to appreciate the sun. And it’s also just notable that everyone’s talking about the days getting shorter and we feel it. When you’re outside all the time, you feel that in a different way. And the other thing I was thinking about is hiking in the night, which I do almost every day now, I’m not very fast, so to keep my pace, I typically hike 30 minutes to an hour into the dark. And there’s this balance in that, that it’s uncomfortable, you put your headlamp on, but… there’s something almost like… it’s like a cold shower on a hot summer day. Cold shower isn’t the best thing, but on a hot summer day, it can feel really good. And the contrast with the peace of night is pretty cool.


Julia: I hadn’t really thought of this before. The sun is so precious when you’re hiking – partially because the hours of sunlight are finite. And you’re so aware of it because you’re outside all the time. But then, every morning, it comes back again. The rhythm of it all – the ups and downs of the mountain passes. The cold and the warm. The snow and the sunshine. The day and the night. Each makes the other more valuable – and the balance is what makes the process of hiking all day feel variable and interesting. No one would thru-hike the PCT if it weren’t for that balance – the variety of experiences you have along the way. It would be like running a marathon on a treadmill. And for Benjamin, it seems like that rhythm and contrast is kind of carrying him through the tough parts. And there are definitely tough parts.


Benjamin: It is September 19. I am getting ready to go to bed. It was just a couple funny things that haven’t really gone my way. (Laughing) First of all, I was really excited to listen to the episode of The Attempt. When I was in town today, I made sure to download it. And during a rough patch today, when I was trying to push miles, I was like, “when I get into my tent tonight, I can listen to it.” But I downloaded the wrong fucking episode. (Laughing). It’s hilarious… (Fade down) …I think the infection under my toenail is back. It went away but now… (Fade down) … I also ran out of fuel and all my dinners require fuel, so I guess I’m going to be cold soaking now, which a lot of people do, but not with this Pasta Alfredo shit. So it’s gonna be 3 nights of pretty bad dinners…(Fade down) It’s quite cold. It snowed on me 3 out of 3 days in the Sierras… (Fade down) Woke up today cold as hell but feeling pretty good. But then after about 30 minutes of getting ready, I started to have this horrible stomach ache. Really don’t feel good, so I’m taking it easy. Basically walking hurts. Keeping the possibility of having to backtrack to go back to a town… had to loosen my hip belt because it was too tight… I feel a little better after taking a couple Pepto Bismol… (Fade down)… I’m not going too fast, but I am moving forward. Because I don’t want to just sit around… (Fade down) …But I just don’t know how I would go up a pass like this. It hurts too bad. Yeah, I hope my next update is better. Goodness gracious I’m cold. I should get into my sleeping bag.

Benjamin: So one of my favorite NBA writers Zach Lowe has this column – I think it’s called “Things I think I think.” So it’s just kind of a funny way to… if he’s not sure about something… It’s a funny way to put out hot takes without staking himself to them too much. So here are some things I think I think. I think I’m going to run out of toilet paper before I get to Tuolumne Meadows in 60 miles. I think I’m gonna get through the Sierras before the snow gets bad. I think the trail goes this way. Yeah, OK. That’ll count as one. I think my stomachache from this morning was altitude sickness. It feels a lot better. I think I’m gonna start cold soaking all my meals in the desert and become one of those guys. I think I’m gonna finish the trail between November 8 and November 12. Um… yeah. That’s good for now.




Benjamin: Saturday morning. I am off to my latest start in months and I am happy with that decision. I felt really shitty last night. I woke up with headaches every couple hours. I think the altitude is really getting to me. I didn’t sleep well. (Crinkle sound) I’m filtering water. That’s what that noise is. The plastic bottle crinkles. And I think the worst thing I could’ve done is gotten up at 5:15 and be on the trail at 6:45, which is normal. So instead I got up at 6:30. And then lay there for a while then had a relaxing breakfast. I had some of the delicious chocolate that my mom sent me. I packed my bag really nicely. (Laughing) Which was kinda like a small pleasure but makes me feel very organized. (Sigh) I’m taking it easy on myself today. I’m still gonna push it while I’m on the trail. See if I can make good time today. But my headache has gone away and I’m feeling a lot better.


Julia: Now, this no longer reminds me of the beginning of the hike. I think he’s getting more comfortable living in the uncertainty that comes with being out on the trail. Rather than getting twisted up into knots about every little thing, he’s choosing to laugh about his uncertainty. To not cling too tightly to the things he thinks and instead to roll with the punches. I think he’s also getting more comfortable with discomfort. It’s snowing and cold and he has altitude sickness? Ok. It’ll pass. And it does. And in the meantime, he focuses on chocolate and the pleasure of taking a slow morning. And slowly, surely, the discomfort passes.


Benjamin: I got a mouthful of peanut butter tortilla but I’m at Smedberg Lake which is about two thirds of the way up Benson Pass. I have another thousand feet to go up to the pass. But it doesn’t look too bad and I’m really enjoying my rest here. This is maybe my favorite lake in California. Yeah, definitely my favorite lake in California. Yeah, I mean, this is just awesome. Sun is out. No one else is here. Someone is behind me, she’s on her way, she’ll probably chill here with me for a bit and she’s really cool.


Benjamin: No it’s literally just recording.

Flawless: So I introduce myself, say my name?

Benjamin: And then just either how your day’s going, how your week’s going. What’s on your mind? What you’re looking forward to?

Flawless: Ok, it’s already recording, whoops! Ok my trail name is Flawless and it’s an ironic name. And today it felt particularly ironic because we’ve just been going over crazy terrain and I feel like I got my shit rocked. (Laughing) My feet hurt. My knees hurt. But came over the top of this hill and Brass was sitting here at this lake and it’s probably the most unreal place I’ve ever seen. I don’t know what it feels like but it’s good. And I’m really looking forward to a cup of coffee at Tuolomne Meadows in two days. I’m trying to think of what else would be interesting to say… (Fade down)

Benjamin: Alright, I’m gonna do an update on the last few days. A couple days ago I got into Tuolomne Meadows. I don’t think I’ve made a recording since then. And that was kind of nice because there were other Southbounders there. And we all kind of made a plan to camp at the base of the next pass and then tackle it the next morning. And we did. So the next day I was hiking with all different people. And partway through the day I realized, wait a minute, I could camp tonight or I could power through and make it to the parking lot by this feature called Devil’s Post Pile. And if I did that, then I could get a ride into Mammoth so I turned on the jets – which was fun – and I got there and the parking lot was just empty. And I was like ok, fair enough. I’ll camp here. But after waiting, 20 minutes, just sitting there, waiting for it to get dark, I saw headlights and this older former park ranger kinda crazy dude was pulling out and I got in front of his car and was like “please take me.” And he was kind of hesitant but he did. And so I took the next day off in Mammoth. I kinda toyed around with the idea of pushing on at night, but I was like, no, I hauled ass to get here, I’ll stay, I deserve the full day. Had 2 relatively decent nights of sleep, I don’t sleep past 5 anymore but whatever. I woke up this morning and I talked to my good friend James Page. And as I was hanging up, I was like, “Ok dude, I’m gonna go hit the baker and then grab a hitch out to the trail.” And he goes, “What is your life?!” And it was a little reality check of what a charmed existence I have: it’s like 6:15 in the morning, my only things on my agenda are to go to the bakery and hitch in. And I did. I got a really easy hitch. And then today I really started out slow, I was really struggling as my body adjusted to the altitude. I wound up 3 miles short of my initial goal. I set out to go over a pass and I ended just below it. But this is the best campsite I’ve had the entire trip. I’m like – it’s just so damn pretty. These big rocks above me and a lake and a river and it’s awesome. And I’m eating dinner now. Alright!


Julia: A couple nights later, Benjamin found himself at a very different sounding campsite.


(Wind sound)


Benjamin: I really hope my tent stays up. Fuck. So it’s uh about 8:30 at night, I don’t know if you can hear the wind but we’re about 11,000 ft, at the end of September and I guess it gets pretty windy and stormy here in the Sierras. So tonight is supposed to be wind chill down to 8 degrees. So we are bundled up, my friends Spark and Phantom are really nice guys. They’re sharing a tent, I’m in my solo tent. They’re sharing to keep warm. I’m in my solo tent, wearing basically all the clothes I have, and we’re nestled in some trees to give us cover. But tent is still kinda popping around a bit. Had a nice warm dinner and got in my sleeping bag and sleeping bag liner. Without my sleeping bag liner I’d be fucked. It’d be bad news. But these past few days have been good. We’ve been going up over passes. And they all are about 12 to 14 thousand feet. So it’s a long slog, maybe a 20 mile hike to get up to one, or 10 mile hike up, 4,000 or 5,000 ft elevation gain. You get to the top and you’re in snow and crazy wind, then you hike back down to the warmth of the valley and do it all over again. I like that – I like the sequential nature of the journey, feels like you’re breaking it into chunks. Ok, I’m getting cold.


Julia: These are objectively really tough conditions – 8 degrees with wind chill, camping on a snowy mountain side with wind whipping at your tent. And it just makes me think that, the only thing that makes it possible to do something like this, is knowing that eventually, it’s going to end. And Benjamin’s starting to think about that more and more. As his time in the Sierra’s come to a close, the finish line is starting to come into view. And I think it makes windy nights like this one not just survivable – but even kind of fun.


Benjamin: Hey it’s August 3 and we are I’m in a group of 4 right now, some really cool guys, Spark and Phantom and AI. It’s been a while since I made a recording, but we’ve actually finished all the high passes of the Sierras. Closing in on just a month left so feeling like I’m making progress and having a lot of fun.


Julia: Near the end of Benjamin’s trip through the Sierras, he and his group at the time decided to take a little detour to go up Mount Whitney. It’s technically not part of the PCT, but it’s a popular add-on. So the morning of the ascent, they woke up in the middle of the night – in the pitch dark – so they could try to make it to the top by sunrise. And just a little while before the sun made it up, Benjamin got to the top of the mountain and stepped into a little wind shelter to wait for his friends.


Benjamin: Oh man, ok, this is one of the best moments of the trail so far. I just got to the top of Mount Whitney, the tallest point in the lower 48. And there’s like 7 of us and I’m the first one up and holy shit it was so fucking cold. The wind almost blew me down 5 or 6 times. It was just in our face. Kinda feeling altitude sickness, headache, stomachache, but at the top there’s this little shelter and I’m putting all my layers on and I’m gonna watch the sunrise. Show starts pretty soon. I’m excited for otheres to get here, everyone should make it pretty soon. Feels special.


Julia: Just a few minutes later, the rest of the crew – Spark, Phantom, Mary Poppins, and 6:30 – got to the top too. And just in time for the show…


Benjamin: There it is!

Others: Woo! Hahahha.

Other: Slow down, sun! Ow owwwwww! (Howling)

Benjamin: 6:44.

Other: Your app was right.

Other: No, one minute too early! Fuck the sun!

Benjamin: (Laughing) Fuck the sun?

Other: Owwwww! (Howling)

Benjamin: Suck it, America. We get first sun!


Julia: You’ve been listening to The Attempt, produced by me, Julia Drachman with editing help from Doug Beyers. We are a production of Bad Cat Media, created in partnership with The Trek – a media company dedicated to thru-hiking and long distance backpacking enthusiasts. Find all the episodes of The Attempt at You can find more information about Bad Cat Media on our website, Or you can follow us at @badcat_media on instagram and twitter. The music you heard in this episode is from Blue Dot Sessions. Also, if you’re enjoying the show, maybe you want to write us a review on apple podcasts or your favorite podcast app! Reviews help the show get discovered by people and also they also totally make my day. So you can do that, or, you can go old school and just tell your friends about it. Either way, we really appreciate it! Thanks so much for listening—next episode will be out in a week.


Benjamin: I got in front of his car and was like “please take me.” He was pretty hesitant because he had to move stuff around in his car, but he ended up being a really interesting dude. He had stories about – like this one time he was like, “this bear was really interested in me, around the campsite, and then the bear got the garbage bag that I was storing my fresh meat in.” And I was like what? And he goes, “I like meat so I like to carry fresh meat with me when I backpack.” So like, that’s why the bear was there. SO then he started storing meat in his sleeping bag. Which I thought was interesting. He was like “there wasn’t too much blood.”




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