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Three Lessons Learned Guiding My First Backpacking Trip

Alright, everyone has voted. No one voted to turn back. It looks like we are going to camp on the top of this knob instead of seeking shelter in the valley, where it might be warmer, less windy and drier. Let’s get to it!

My co-guide, Alan, and I took nine headstrong individuals on a backpacking trip in West Virginia. On the last day, we went off trail. We trekked on a combination of old deer trails, abandoned hiking trails and bushwhacked vegetation in dense beech-maple forests to a hidden campsite not marked on the map. That day, we went up, and up, and up to reach our destination. We climbed 1,200ft to one of the highest points on a ridge line in the Allegheny Mountains of West Virginia.

Upon summiting one of the highest knobs in the valley, the dense woodland changed to a full blown spruce forest. The toilsome underbrush was suddenly gone and a thick carpet of pine needles lay at our feet. We could hear the howling winds blowing at the tree tops fifty feet above our heads, but we were protected. The snow and 35 degree weather didn’t penetrate the forest either. We weren’t warm, however we were bold and excited. That night, we would camp through the worst conditions you could ask for in early May.

This was the second group of backpackers I had guided that week on a three day fundamentals backpacking trip through Andrew Skurka Adventures. Andrew is an accomplished long distance hiker, having been named the Adventurer of the Year by both National Geographic and Outside Magazine.

I felt blessed that Andrew selected me to share and celebrate my backpacking experiences with a bunch of folks who were eager to learn. Nature pushed us outside of our comfort zones multiples times, including when we camped on that ridge. However, our group survived with a smile on their faces, knowing that we had gained experiences and a skill set that would prepare us for more adventures to come.

I learned some valuable lessons over that week. Backpacking isn’t an exclusive activity designed for the dirtbags or people with too much time on their hands. No matter who you are, you can go out on an overnight trip and have fun. Not only that, but with some basic knowledge and practice, you can quickly become capable of multi-day trips to more rugged destinations. Backpacking is a great way to experience the outdoors, stay in shape and connect with yourself or a community of people in an intimate setting away from Netflix or an crowded bar. Hopefully, this post inspires you to get out to the great outdoors and tackle on new challenges with curiosity.

Let’s get down to my three big takeaways from this trip.

1) You pack your fears

On a guided trip with Andrew Skurka Adventures, you arrive ready to go. He embodies the old Boy Scout motto, ‘Be Prepared.’ Andrew developed an 8-week curriculum that he holds clients accountable for – fitness, condition assessments, gear checklists, the whole works. The gear checklist was one of my favorite exercises. Gear is hottest debated topic out there.

We discussed gear at length. Another guide, Alan (who runs the backpacking blog, had an intriguing opinion on this subject. When I asked him what excessive items he most often sees in a beginner’s gear list, he responded:

People don’t over pack because they are inexperienced or unknowledgeable. They overpack to compensate for their fears.

Suddenly, I understood the root cause of packing mistakes I had seen with our group. One man on our trip said he often returned home from camping trips with two or three pounds of food. He was concerned he might be stranded or not have enough to eat. Another wanted a heavy two person tent, despite camping alone. She was afraid of not having a personal space to stay dry and organized. A third hiker had a puffy down jacket, a rain jacket, a fleece, quarter zip, a long sleeve t-shirt, a wool t-shirt and an undershirt for a two night trip. But what if he were to become really cold or wet?

I drew recent inspiration from this subject from the book The Life Changing Art of Tidying Up by Marie Kondo. If you are not familiar with this book, Kondo writes a compelling (and best selling) case for how a perspective shift in being purposeful and tidy with the space in your house can fix many of life’s problems. This lesson applies directly to your gear and supplies. To improve as a backpacker, you must learn to critically examine each item you plan to bring with you and weigh its pros and cons.

If you allow fear to overcome reason, you will literally carry the burden on your back and never be able to dial in your backpacking system.

2) Backpacking is a skill

Some people think backpacking is just a talent you are born with. For example, some masochists sleep on a razor thin foam pad and get a good nights sleep. Other fitness junkies hike for 30 miles with a full pack and are not sore the next day. However, the beauty in backpacking is that you can develop your skill set to be able to work towards your own goals and definition of fun. Backpacking is not an inherent talent, it is a skill set that is gained through knowledge, experience and practice.

Most backpackers don’t enjoy their first overnight experience. In fact, every experienced adventurer I know has a list of dumb or misguided adventures. For our group, many of those stories will originate from this trip. Why the hell am I camping in a sorry excuse for a when I could be cuddled up in a queen sized bed scrolling through Instagram? Wouldn’t life be better if I had a steak on my George Forman grill right now, instead of huddling over a janky single flame rehydrate some powdery eggs? How the hell does one dehydrate eggs in the first place?

The good news is that after some of the initial discomforts, you can discover a new, vibrant world that 99% of your peers will never experience.

Let’s look at my trips. We guided two groups of clients for three days. On the second day of each trip, I gave the group a ‘fast packing out of camp’ demonstration. I have the self-supported Fastest Known Time record on the Appalachian Trail in 45 days. Who more so than me would be qualified to lead this?

In the course of 10 or 15 minutes, I would take down my entire set up with a neatly packed bag that was ready to hit the trail. Some folks were in awe, and, to be honest, a few probably weren’t that impressed. However, compared to the time it took to get our group out of camp, the rapid take-down of my campsite was as fast as lightening. I knew my gear inside and out and where each individual item fit inside my pack.

A few people commented that it seemed like I recklessly threw my tent and gear into my pack. What if you need something that you put at the bottom of my pack later in the day? Would you have to unpack everything? Don’t you worry about some of your clothes or gear getting wet? Is that really all the gear you have? My co-guide, Andrew, quickly explained a few key takeaways. Because I had spent significant time trying to hike fast and light, I am extremely efficient. I packed my bag in such a way that dry and wet items were separated and any gear I would need for the day was already conveniently tucked away in an accessible outside pocket.

Since my objective is often to be able to cover good distance and not feel rushed or hike late in the day, I became skilled in hiking fast and light. That being said, my skill set didn’t grow overnight. The more time I spent in the outdoors, the more skilled I became at navigating it with a smile. Each group learned many valuable lessons over three days that they will use on future adventures.

Getting ready for a 35 degree night in May. Photo by

3) Be Prepared

The Boy Scout motto is to be prepared, and the truth is, anyone can be prepared for a backcountry trip. The planning part is easy. All you need is the right stuff. What I struggle with is being mentally prepared. You never know what nature is going to throw at you for any given occasion. A new adventure awaits at every trail head, but you might not be ready for the horde of bugs, a washed out trail, cold or wet conditions, lack of available water sources, a cumbersome backpack, blisters and more.

Our group struggled most with the weather. It rained all six days on us – and the rain was cold, with temperatures ranging from the mid-thirties or low fifties. Brr.

I did not enjoy slipping on cold wet socks onto my feet, and putting those feet into soaked and squishy shoes each morning. Nor was I prepared for the extra cold temperatures and slept cold. Because of the conditions, at times I was selfishly taking care of myself before the group. When we got to the campsite on the last day at the top of the knob, I also didn’t have many good ideas for group activities. My hands and feet were cold. Despite considering myself a master at thriving in adverse scenarios and keep positive vibes going, I fell flat.

So, when Danny, an gregarious guy from Colorado, suggested we make a fire despite the water-soaked woods surrounding us, both the group and myself had second doubts. Everyone was cold and wet. Even if we did get a fire going, it would probably take a lot of effort to maintain and maybe not even give off much warmth. Despite the rough conditions, our group had mentally prepared for the task ahead. We had planned for weeks leading up to the trip to think like a team and the possibility of adverse conditions. We already trekked the backwoods of West Virginia for two days. As a team, we agreed to hunker down to camp on the knob for the night. As a team, we were going to build a fire.

Anyone can take on the outdoors. Not everyone is mentally prepared to be able to tackle the challenges with a smile on their face. Our team did just that. Josh and James went deep into the forest to find the driest wood. Albert meticulously split twigs to create kindling. Alan provided the lighter fluid. Vishal remembered an old trick from India stoke a fire by blowing wind through a straw which worked tremendously and I spent two hours blowing life into it with Alejandro, aka Hamburger. For four glorious hours, we warmed our bodies with a raging fire that lifted the spirits of the entire group. Because you never know what nature will throw at you, you must learn to be flexible and adapt with the resources in front of you, a great life skill on the trail and in life.

In perspective, the challenging conditions were a blessing and a curse. Let’s be honest. No one wants to camp in the rain. Or snow. Or really anything but balmy 70 degree weather. And there can’t be any bugs.

The real truth is that can’t always be the case. Life isn’t always 70 and balmy. However, when you are surrounded by friends, whether new or old, in a supportive environment, you will find ways to lift each other up. The biggest takeaway I have from these two trips in West Virginia is that people are awesome, the outdoors are awesome, and when you take a good weekend to combine the two and get outside your comfort zone, a whole lot of adventure awaits.

Read another fun account of our adventures by Nicole. She has even hiked the Appalachian Trail!

This is the beautiful sunset after a day of snow and rain near the top of the knob. Photo by

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