How to do everything wrong on your second solo backpacking trip

Ben Mann
9 min readMay 21, 2018


In April I took an impromptu trip to San Diego. Work had been stressful for a few weeks. I wanted to mentally reset and take time for self-care. I thought it’d be fun to sleep in the woods instead of a hotel or hostel, and would take less planning to boot. I thought I learned my lessons last time, but everything is contextual!

Near San Diego I found Cleveland National Forest and Otay Wilderness, which both qualify for no-permit camping (or so I thought). I called the ranger station for Cleveland since parking seemed easier and I wanted to know where the best spots were. They were closing in 5 minutes, but the ranger told me Dripping Springs had a 20 mile loop with great camping spots. I’d need to email her a PDF permit application and they’d approve it in the morning retroactively. At the time I was sitting in my rental car in the parking lot of a CVS eating an entire box of cookies, which seemed like the perfect time to tether my phone, fill out the PDF and email it back. If I had called 5 minutes later I would never have found that PDF or picked that trail!

Let’s back up and talk about why I was eating all those cookies. I had made last minute plans to go on the trip with one friend and meet with three others. All those plans had fallen through for various reasons and I found myself alone. For the previous few weeks I’d also been avoiding all carbohydrates on weekdays. All that combined with being blocked by bureaucracy at work, I felt an urge to let myself go and do whatever I felt like doing. I wanted some kind of release. Cookies were the start of that release, and I hoped this hike and the trip would be too.

Now that I was confident I could go anywhere I liked in the park and had the best spot in mind, I started the 2 hour drive over. Soon the cookies hit me. I could hardly keep my eyes open. I pulled over at a random gas station and slept for 2 hours in my car. I brushed my teeth and planned not to eat until the next day, partly out of repentance and partly from not wanting to have to think about what, when, and where I’d eat next.

By the time I got to the park the sun had set. I was still sleepy after my nap, so I planned to hike for less than an hour before pitching my tent and passing out until sunrise. If I felt more energetic later, maybe I’d even find time to do some writing! I packed only what I needed that night and set out.

I parked for free outside the campsite area. As I walked by all the reserved spots, I gloated to myself that these people had to plan ahead, whereas the whole forest was my playground tonight! My pack felt light on my back, my headlamp was fully charged, and I felt relaxed and ready for a hike.

At the trailhead I found this nice map. I saw a fork early in the trail. Right led to the peak, left to a basin with some water features. Fearing a repeat of my last adventure with water, I decided to take the peak trail.

As I hiked up switchbacks, the temperature dropped to 40F with winds gusting to 15 mph. With my puffy jacket on, I was sweating too much even with the zipper open. But with it off, I was cold. I didn’t have gloves. When I took pictures I noticed I could hardly move my fingers enough to unlock my phone. I decided to leave it off anyway to avoid getting sweaty.

Some other hikers leaving their emotional signature for me
Why did they leave blueberries on this cairn??

After a half hour, I started to feel anxious about finding a proper place to make camp. The trail only seemed to be getting steeper and narrower, with brambles and sheer cliffs up on the left and down on the right. This spot was too rocky, this spot too windy, that spot too small. As I continued, my thoughts and attention turned increasingly to finding a spot and planning what I should do next. I kept making deals with myself: “Okay, at 8:45 I’ll turn back.” “It’s 8:45… but I’ve come so far! There’s got to be a spot. I’ll turn back at 9.” My mind was filled only with finding a place to camp. I was not having fun or relaxing. Two hours later at 9:50pm, I was still hiking up the mountain. I had only planned to hike for an hour! My head spun with self criticism, fear, and doubt. “Why did you take the right fork? Why didn’t you ask the ranger where you should camp? Why didn’t you just take that spot you saw 20 minutes ago? Why didn’t you bring any food or gloves? What if you don’t find a spot? What if you pick a spot that’s on a slope and fall off the mountain in your sleep? I’m bad at camping, why did I come here? I’ll never find a spot.”

I hit the last of my agreements with myself at 9:50pm to turn around. I stopped hiking up the mountain. I checked my blood sugar using the continuous glucose monitor I’d been wearing for two weeks. It had crashed the hardest in the entire two week period, which probably meant I was hypoglycemic. That would explain some of the anxiety, irritability, and dysphoria.

Target range is 100–150. Diabetics have serious trouble outside the gray band, but non-diabetics will feel something too.

I took stock. I recognized that I was doing this to myself. The suffering was in my mind. I had wanted a relaxing vacation. Instead, I was on the verge of a panic attack. I calculated that if I hiked all the way back down, I could either pitch my tent or sleep in my car by around midnight. I realized that I had redirected the frustration of other parts of my life onto this search for a campsite. My lack of autonomy at work, all the friends that had bailed on me, my recent breakup, and my struggles with stress eating all contributed.

If I wanted to relax and let go, I’d have to start by giving up on my expectations for this hike. Recognizing my panic, I looked through my box of anti-panic habits. Journaling would help get things in perspective and stop my negative self-talk, but I couldn’t journal and hike at the same time. I decided to talk to myself out loud as I hiked down, and if I happened to see a spot I missed on the way up, I’d stop, but assumed I would sleep in my car if necessary. I had idealized where I wanted to camp, and now I’d have to take what reality would give me.

I put my jacket back on, and as I spoke my self-support, the mental clouds began to lift. “Your friends couldn’t make it. Things came up. They wanted to meet with you and are probably disappointed that they couldn’t. It doesn’t reflect on you that they bailed. It feels bad because you were excited to spend time with them. You’re grateful to have friends you’re excited to hang out with. At work your launch is delayed. That’s frustrating. But until you get permission to launch, you can keep moving things forward. You don’t have to wait. In a year you’ll look back and see you didn’t end up delayed for long. You have the freedom to take a hike like this. You’re fit enough to go a few hours over your plan and not be sore or winded.”

After half an hour, I was enjoying the hiking for what it was, not what I wished it to be. I no longer fixated on my mission to find a spot. An hour after turning around, I found it! It was just a widening of the trail that I must have rejected earlier because it didn’t match my expectation, but now it looked like paradise. I pitched immediately without stakes, popped in some earplugs, and passed out in all my clothes and jacket.

The next morning I woke with the sun to an incredible view.

Just as I finished packing up a group of older hikers approached. They stopped to say hello and express their surprise at seeing me coming down the mountain at 7:30am. One asked “Did you cowboy camp up here? Is that a ukulele on your back?” I proudly explained that I had camped right where I was standing, and that it was my tent she saw poking out of my bag. We all laughed and parted ways.

When I got to my car, I noticed how exhausted I still was. I slept another few hours in the drivers seat and headed out to find breakfast.

What went well

  • $30 Walmart tent was great! I even brought it through airport security in my carry-on with no issues.
  • Puffy coat saved me from freezing to death.
  • Self-support worked!
  • No bugs at all.
  • Good pacing. Never felt the urge to stop hiking due to fatigue.
  • Packed light. Didn’t bring any food and only 300 ml of water. Didn’t miss it.
  • With all my clothes and jacket on, I was comfortable in my 19F-rated sleeping bag, but it took a while to warm up. Low blood sugar was a confounding variable.
  • National forests are the best! Not having a limited number of permits reduces the friction of planning a trip like this to the point where I’d consider doing it a lot more often.

What to improve

  • Bring gloves.
  • Save enough time to talk to the ranger and get suggestions for specific camp areas rather than a 20 mile trail.
  • Go earlier; find a campsite before nightfall.
  • Self-support earlier.
  • Wear boots instead of Nike Flyknits. It’s better not to notice every rock you’re stepping on.

My biggest takeaway from this experience isn’t the logistical points above. It’s the mind-game I played with myself. I had convinced myself that I knew exactly what I wanted the hike to be before I began. As reality gradually forced me to acknowledge that I wouldn’t get what I wanted, my only reasonable choice was to let go and make do. My theme for 2018 will be letting go of the details in mental images of what I want. The details don’t matter. The moment to moment experience matters. Life is like a hiking trail. It’s easy to think that if a trail is labeled “Peak Trail” then we must follow the trail all the way up to the peak, and if we don’t, we’ve failed. I don’t want to be on any particular mission, like getting to the peak or finding a spot to camp. I want to appreciate the beauty surrounding me, and my freedom to attend to it in whatever way I see fit, whether my hike ends up being hours longer than I expected, whether I reach the peak or not, whether I have to turn back at some arbitrary point and end up finding what I was looking for after all.



Ben Mann

Software engineer, tinkerer, aspiring mad scientist