Outdoor Education

Top Ten Reasons to be a Wilderness Adventures Trip Leader

By Wilderness Adventures March 2, 2023
Group of staff members in front of the Tetons

Every year Wilderness Adventures hires about 90 seasonal overnight staff to execute our trips around the world. As the Staffing Coordinator, I have to know all of the ins and outs of the position – the good, the bad, and the ugly. I have had the privilege of learning a lot about the position first hand with 250+ days in the field leading trips and instructing Gap Semesters with Wilderness Adventures. Now, I have the opportunity to share this position with other folks from around the world who are equally as committed and passionate about getting youth outside! Amongst all of the many things it means to be a Trip Leader, here is a list of my Top Ten Reasons to be a Wilderness Adventures Trip Leader.


1. Community with peers

Every June we kick off the summer with All Staff Training where our Trip Leaders, Trip Counselors, Kayak Specialists, Photographers, and folks on our Leadership Team come together in one place. Though we are all coming with different backgrounds, experiences, and perspectives, everyone has two things in common: a passion for the outdoors and the excitement to share that passion with others. This creates an extremely inspiring atmosphere.

You spend about two weeks with this group of likeminded people and do everything from participating in our classic “Birdie on a Perch” competition to spending 5 days in the backcountry of the Tetons with each other. You’ll share your experience and be able to learn from the experience of others, absorb the views of the endless night sky, set intentions for the summer, and create deep connections around the campfire (yes, this is all part of your paid training!).

Being able to dive into the summer knowing that you have this support system of peers and new friends makes summer that much easier. The connections you form with these new, passionate, positive people are unmatched and all what you make of it!

2. Community with students

The opportunity to be a role model and truly make an impact on your students is an indescribable feeling…but I will give it a try.

Your students are showing up to random airports in cities they’ve never been to with about 10 strangers – two of them being you and your co-leader. Starting at that moment, you become the leader, a guide, a confidant, a nurse, a parent, a teacher, a chauffeur, and a friend for your students. While that is an intimidating set of roles to take on that come with immense responsibility, it is such a privilege.

Our students come from all over the world and have a wide range of experience outside from having skied Mt. Rainier 3 times to having never laced up a pair of hiking boots or been on a trail. You will form connections with your co-leader and students in a way that makes you feel like you have known them for years. You will lead your students through new adventures and experiences. You will help them along when they are homesick, when they are tired, and when they are scared to grab that next hold on the climbing wall. You will show them that they are capable of more than they’ve maybe ever realized, and that is a feeling that sticks with all of us for many, many years to come.

3. Immersion

I think the most unique (and, in my opinion, the best) part about being a Wilderness Adventures Trip Leader is the opportunity to immerse yourself in this experience with the outdoors, with students and other leaders, and with yourself. Many of us are used to having constant stimulation in our lives so sometimes this change of pace can be challenging. That being said, when we set aside the constant stimulation of our lives today, we create room in our days to slow down and enjoy the wonder.

Being in this type of environment forces you to get to know and work with the people around you and to create your own fun. You will talk about every topic A through Z when you’ve got hours on the trail, days on the river, and nothing but time while watching the clouds roll by at camp. These connections you make with your group over 14, 21, or even 70 days are so deep that you leave your trip with people that now feel like they have been in your life for years.

4. Confidence

The #1 thing I hear from returning leaders that makes them want to come back for another summer of leading with Wilderness Adventures is the confidence they found in themselves the previous summer. When you are given the bones of a trip and are given the trust to run with it, it’s a lot of responsibility but an amazing opportunity for understanding the ability you have! You are the person your students need. You are making the decisions. You are creating the magic.

5. Waking up every day in beautiful places

When you work a summer with Wilderness Adventures, you get to spend every day of your contract outside. Now, you will tally up some nights in cozy beds where you’ll shower and watch Netflix, but the high majority of your nights will be spent on the earth, under the stars. While this could sound intimidating if you’ve never done it, this is an experience that will increase your awareness, appreciation, and love for what you have as well as the natural world around you. Every morning you get to wake up to the sun illuminating your tent, the campground’s resident ravens cawing, and the feeling of crisp morning air – it doesn’t get much better than that.

6. Life experience

It’s really easy to paint the Trip Leader position at Wilderness Adventures as all rainbows and butterflies, and many days you will experience that. For every day that is ideal, bright and shiny, there are just as many days where you are going to bed feeling a new type of exhausted. This job is hard. There is more time on the clock than maybe any other job you’ve ever had, but that’s part of the reason we love it and keep doing it (see #3!). And though you are exhausted, you keep showing up.

Like I mentioned earlier, you take on a laundry list of roles as a leader. With the opportunity for growth and learning, you build so much character! A summer with Wilderness Adventures is always something to write home about. It will equip you with endless stories of success, of defeat, and of silliness that will come up in a variety of future conversations whether with your best friend or a potential employer.

7. Ability for growth

Leadership is one of our core values at Wilderness Adventures and that is not just a focus for students. We always want to provide new and exciting opportunities for growth to our seasonal staff. 

Let’s say you start as a Base Camp Counselor when you are 17-years old. Once you turn 19, you can now apply to be a Trip Counselor. You’ve done that for a few years, gotten some more life experience and just celebrated your 21st birthday – now you can come back as a Trip Leader! After a summer of leading, you decide you want to focus on more technical skills. Well, lucky you, we are in search of rafting and climbing guides for MOLA. That was all fun and you have a new found love for Missoula, MT but now you’re wanting to further your impact and immersion with students, maybe focus more on the teaching aspect. You’re now hired as an Instructor for Spring Gap in the Southwest – congrats. Your semester teaching and guiding your students through a life-changing 10 weeks was a huge success…we want you to join our Leadership Team to bring your expertise to families around the world. Next thing you know, you’re knocking on Tom and Catherine Holland’s office door asking to buy the company – watch out!

8. FUN

You’re getting paid to swim in alpine lakes of the Wind River Range, summit Mt. Adams, snorkel with sea turtles in the Galapagos, learn to salsa dance, and kayak next to some of the last glacier melt in the Prince William Sound…need I say more?

9. Learning new technical skills with professional guided instruction

As a trip leader, you’ll lead backpacking trips with your students but when you’re participating in other activities like rock climbing, surfing, whitewater rafting, mountaineering, etc. you’ll work with third-party organizations. We call these folks subcontractors! Your subcontractors will bring all the technical instruction and gear you need for this leg of your adventure (whether it’s a day of rock climbing or a 7-day white water rafting trip!). Our subcontractors do a great job of involving leaders in their operations and sharing new skills. Days with subcontractors are awesome because you have the chance to not step back from leading your student, rather step to the side and have the opportunity to participate alongside them. While doing that, you are building new connections within the outdoor industry and have the chance to learn new technical skills from other professional guides!

10. Transferable skills

“I’m about to graduate from college with my degree in Mechanical Engineering. I’ve been searching for internships in the city and feel like I should focus on getting a job for the fall, but this job does sound so amazing…” If I had a dollar for every time…I would still be here but I would keep a dollar jar at my desk! To lead for Wilderness Adventures, you don’t need to have a career goal committed to the outdoor industry. We have leaders with degrees focused in Outdoor Education, but we also have leaders who take summer off from their full-time Data Scientist jobs to get into the field for a few weeks!

No matter what your larger life or career goal is or if you don’t even know, there are so many transferable skills that you will learn while being a leader. A few skills to highlight for example: peer communication, professional communication, critical thinking and problem solving, time management, budget management, risk mitigation, and vehicle maintenance.


What are you waiting for? Apply now through this link!

Have questions? Email our Staffing Coordinator at rachel@wildernessadventures.com.