I Came For The Work- I’m Staying For The Community

The staff at the Chesapeake Bay Outward Bound School are a force to be reckoned with. They drive our work with dedication and passion for our students. After the end of the Spring Apprenticeship and season, staff gathered for a (now annual) backyard crab feast to celebrate each other and the successes of the season. Following the end of the season and celebration, instructor Kurtis Pierret wrote a letter of appreciation to his CBOBS community explaining why he came to our school and why he is not leaving.  

Weighing It All Out

I was hesitant to attempt a career in the outdoor industry. The pay isn’t great, so I wasn’t sure it would let me live the lifestyle that I want. The hours are terrible meaning it’s difficult at best to have relationships when you are gone for half the time without cell phone service. And the work is exhausting physically, mentally, and emotionally.

I knew these things before coming to Outward Bound. I had spent enough time leading trips in college and working as a commercial raft guide to know how difficult all of these things would make my life. I had missed family reunions and special events. I had spent a lonely birthday out on the river. I had avoided certain purchases because I couldn’t afford them. I had avoided dating and trying to make friends because they wouldn’t understand why I was unavailable one week and then extremely available the next. 

BUT, I also knew that nothing felt better than bonding with a group of strangers in the woods as we push our physical, mental, and emotional boundaries. I knew I was pretty good at it and needed to give it a real chance to be my career.

Getting the Job

My journey to OB was unique. Everyone’s is. While I was applying to be a Fall 2019 Instructor Training, I was still in Russia finishing my year of teaching English. I remember staying up late for my chat with Chris, and feeling really good about it afterwards. It didn’t feel like I had just had an interview; it felt like I was talking to a like-minded soul, someone with similar experiences and outlooks that could understand a lot of the things I had gone through because he had done them himself. 

Then… I didn’t get the job. I was both surprised and not. I thought our conversation had gone well, but I also felt like an imposter, like the experience I had had wasn’t what OB was looking for. It had seemed like a long shot to get the job from the beginning.

But another email from Chris asked me to schedule a second time to talk. So, I stayed up late once more wondering what he could say to me after rejecting my application. The phone call came through and I answered. Much to my surprise, Chris told me that OB DID want me. They just didn’t want me for the fall. He asked if I wanted to come in the Spring. 

At the time, I couldn't say for sure that was what I wanted. I told him I would think about it because I live my life one season at a time and I still needed work for the fall and winter before I could really be sure what I was doing that spring.

That second call was in July. He gave me till November to make a decision. I accepted in September after getting another taste of what Outdoor Education work is like when leading an outdoor orientation trip for my alma mater, Lewis and Clark College. That trip felt right. I felt like I was home once more and that I was doing what I was supposed to. It convinced me that I needed to give OB a try.


I’m going to skip past the 2020 part of this story. We all know that chapter well enough in our own ways that it isn’t worth me repeating it. Suffice it to say, I tried some other things and ultimately found myself waiting to be here, waiting to change lives through challenge and discovery.

Finally Starting

The beginning of my time here was slow. Training is hard. It involves a lot of sitting and talking. There’s a lot of pretending to be in certain situations without actually being there. We think about what we might do in certain scenarios until our brains melt or our fingers go numb from the cold. (Maryland in April is surprisingly brisk.)

I learned more than I thought possible in those first two months. It made me excited to see what I could do for our students. I got revved up to attempt to meet the OB standard of excellence in my own programming. I tried new things I didn’t know were possible and dusted off knowledge that was nearly lost to the passage of time.

But more than anything, I helped develop a community.

Turning a House into a Home

The Orianda Mansion is the magnificent building we are lucky enough to call our staff house. After a year and a half of COVID restrictions, it was opened up to us instructors once more. Most of the faces were new to it this year, and it was new to most of us after having been remodeled before the 2020 season.

Inside this wonderfully historic building, we laughed, cried, talked, and played (mostly dungeons and dragons). We fostered a community that was strong and good based on the efforts of all the instructors before us and the changes we wanted to see.

In the moment, I didn’t realize how important those things were to me. I could scarcely name them. They were just life, not the defining moments of my time here. Not the things that make me want to stay.

It wasn’t until our annual Crab Fest that I realized how strong and important this community was to me.

Photo: Rice Ermilio

Why I'm Staying

The crux of what inspired me to write this came towards the end of our crab feast meal. As dinner was winding down, Rice called me and the other Spring 2021 apprentices up to the front. I was initially dismayed because I had just finished eating four crabs without bothering to wipe my face or hands once. Old bay and Crab littered my face and apron. They mixed with sweat to coat my hands and beard in an unhealthy grime. But I soldiered on through the comments because I knew they were made out of love. 

Embarrassment filled my core as I stood just slightly apart from my litter (that’s what we call a group of apprentices) so as not to get any of them dirty with my filth. Rice showered us with compliments before opening the floodgates to the rest of the community to rain down their praise on us. I won’t speak for the others, but I was uncomfortable with their comments. Not because we didn’t deserve them, but because we might actually be all of those things they said and more. We just didn’t arrive at who we are without their teachings and guidance. 

Photos: Rice Ermilio

We exchanged pins and hugs before stepping aside for the next group to be honored. Sam and Jodie took their spots as the only two representatives of the Fall 2019 litter I had tried so hard to be a part of. They pinned each other and there was a slight reprieve where my litter pulled each other into a group hug.

I don’t know who asked it. I think it was Leo, but the question was put to our little group of seven as to whether or not we were staying for the fall. Everyone answered affirmatively, but Shelby caught my eye. Her intense penetrating gaze burrowed through me like it does so often as she double checked my answer. She thought she had heard me say I wasn’t.

After correcting her, I found myself reflecting that I had to stay. I couldn’t leave yet. I’m not ready. Not because I’m not finished growing as an instructor and outdoor educator, though that is true. I have too many lessons, initiatives, and ideas that I want to try with students to leave before the fall is over. 

No, the issue is that I’m not ready to say goodbye to this community that has been so warm, welcoming, kind, nurturing, and loving in ways I didn't even realize I needed. Some of the credit for those things goes to us. Me, my litter, and the other new staff this year. We have taken over the Orianda and made it our own to fundamentally change it in ways that are hopefully for the best. But most of the credit goes to all those that came before us. The instructors of yesteryear that believed this job, this lifestyle, this career, and this community could be more than all of those things put together. The credit goes to people like Shaq who claims to have hosted the very first Crab Fest more years ago than I can count. It goes to people like Bex for making sure we used the staff fund for this year’s Crab Fest. It goes to people like Joey, Mary, and Rice for being exemplary instructors and creating the high standard that we are all trying to achieve. It goes to Ginger and Natalie for fighting everyday to make sure us instructors are compensated fairly. A lot of it goes to Doyle for establishing the norms of the Orianda as House Manager and putting up with the incessant requests and strains that come with the title. It goes to so many more people that I can’t name because we haven’t met yet. You came before me to plant the seeds of love and support in this community that we all get to reap now. Thank you for Striving. Thank you for Serving. Thank you for never Yielding.

About the Author

Kurtis grew up on the edge of cornfields in small town Minnesota. His love for the outdoors came from his initial outdoor orientation trip before his first year at Lewis and Clark College. The experience instilled in him a love for the outdoors and leading others to the amazing places and self discovery he found there. After leading trips all throughout his college career, Kurtis spent the next couple of years travelling the globe in an attempt to  avoid working in the outdoors. But old habits die hard, so Kurtis came to CBOBS as an apprentice at the beginning of Spring 2021. He is now a lead instructor working to improve our programming from every angle.