Best Reasons to Become an Overland Summers Trip Leader

Spending a summer as a Trip Leader with Overland may just be the most fun job on the planet. Getting paid for rafting down the American River or summiting the Grand Teton will no doubt inspire some jealousy on your return. But leading for Overland offers something more than mere adventure. You’ll learn new skills and teach and guide a group of young teens. You’ll grow and be challenged and celebrate successes together. In the end, you’ll emerge with more confidence, valuable work experience, and a new community.

We asked Will Savage, a member of Overland’s Leader Hiring team, to share some insights into our process. Read the inside scoop just below!

This year, the Leader Hiring team will hire 200 individuals for our Trip Leader jobs. As we have done for the past 38 years, our team spends all year ensuring that we have the best possible summer staff. Every year we hear people asking how to find the perfect summer job. Having spent several summers in the field leading for Overland and many hours interviewing candidates in my role as Assistant Director of Leader Hiring, I have seen just how much this job has to offer. While every leader’s experience is different, there are some common benefits that make trip leading for Overland the perfect summer job. Keep reading for my top five reasons to be an adventure trip leader for Overland.

The Overland community is unique. Over 5,000 leaders and more than 40,000 students have experienced, or will experience, the same highs of a summer. It’s a community that comes together to celebrate success, the outdoors, and each other. For leaders, the summer begins in the middle of June for our pre-summer training: two full weeks where we bring together our leaders, our operations team, and our full-time team to prepare to welcome students to Overland. New leaders will learn through seminars, workshops, and talks from returning leaders.

 My experience with Leader Training my first year was exceptional. It provided me with space to define my leadership style and ask any question I could think of. For all the succeeding summers, it was a time to give back to the community. I helped introduce leaders to Overland traditions like “cheers” and Dessert circle. The Overland community extends far beyond training connecting via community events and newsletters. While you are a Trip Leader for a summer, you are part of the community for life. 

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As a Trip Leader, you are given a huge amount of responsibility. Once you leave training, you and your co-leader(s) will have to work together to problem solve creatively. While you are always connected to the office via cell phone and Garmin, you are in charge of the expedition. It’s an amazing opportunity to full embrace a leadership role. We have so much faith in our leaders and are blown away every summer as we watch them navigate six-weeks of being in the field. Just like how our leaders watch their students grow, we get to watch our leaders grow over the course of one or more summers. We’ve heard countless stories of leaders’ confidence growing after the summer. Returning to school feels easy because they’ve learned they can trust themselves to navigate challenging situations. When you are on call 24/7 in the summer—when you are responsible for the well-being of twelve young people—you grow as a leader and as a person. You’ll discover and develop critical skills that serve you well throughout life. 

Finding a new job is not a task for the faint of heart: the application process is challenging and reaching the interview stage requires grit and determination. Securing your dream job? That can be downright stressful. I read and process hundreds of applications a year looking for the best fits for Overland. What have I found? It all comes down to a few things: your resume, your knowledge of the company, and your relevant skills. That’s what it comes down to for every job, and that starts with your resume. A page long, you need to highlight your strengths as an applicant. As a former Overland leader, that’s easy. A summer spent being a Trip Leader with us will hone your communication skills. Whether it is setting guidelines, planning the day, or working through a disagreement, you are constantly in communication with your co-leader or leaders. The same goes for your students, outfitters, and the office. You learn how to teach effectively as you navigate the unique learning styles of 12 students. Not only will you become an accomplished teacher, you will learn the importance of teamwork, adaptability, leadership, and organizational skills. These skills are incredibly useful and I have used them every-day of my life since Overland. Whether it was leading trips for my college outing club, captaining a college team, interviewing for full-time jobs. The skills and experiences you learn leading at Overland are useful tools for the remainder of your life.

Overland trips are about the students and the places you go. As a leader your role is to take care of the students. The trip isn’t about you, you are there to guide your students, and create a strong group. It is a daunting task, but an incredibly rewarding one. Being able to take a step back and truly listen is a luxury in our modern world. Cell-phones, the internet, and social media result in the answers always being right there. You’re less likely to wonder about the world. It is harder to find space for yourself. Our technology- free trips create a space to be yourself, and to truly listen to each and everyone of your groupmates.

I love middle schoolers! They are so goofy, energetic, and eager to learn.

Being an active listener and showing your interest to students can make a huge difference in your students’ confidence. Taking care to show them care demonstrates that they matter. I recognize that I am not an expert on the matter, but the science is in on this. Having led in the field, I experienced it first hand. Everyone reading this article can remember a time when a mentor, teacher, coach, listened to your idea and complimented it. We remember how powerful that was. As a trip leader, you are stepping into that role and are able to provide that experience, and it is truly so rewarding. 

You are able to see the impacts of your efforts in real time. You witness, firsthand, the growth of your students. You can watch as your group comes together as a family. You get to hear the emotion in your students’ voice as they recount the meaning of their trip to parents. It’s an incredible feeling, seeing the impact you have on another person’s life. 

Overland trips are fun! You are traveling to incredible locations all around the world. You are working with incredible co-leaders and incredible students. I became great friends with all of my cos and am hoping that one day I will see my students become great Overland leaders! Trips have exciting moments of rafting, kayaking, hiking, and camping, but they are filled out by the memories made during games played by camps, stories told over dinner, and songs shared during van rides. 

Becoming a Trip Leader can lead to one of the most rewarding summer experiences. You will have grown immeasurably. You will leave feeling confident in yourself and abilities, having learned useful leadership skills. A summer spent being an adventure trip leader, is a summer well spent. Want to learn more? Read about Tiana’s summer in the Sierras. If you’re ready to join us for a summer of growth and adventure, Apply Now! And then, give yourself the best shot with our founder’s best tips to impress our hiring team! We’ll see you soon!


    Will Savage

    Working in Leader Hiring, I am excited to introduce new leaders from all different walks of life to the Overland community.

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