What happens when you put HIOBS office staffers in the field for 10 days? Apparently, a lot!
Three members of our administrative team—Sarah Cotton, Gen Bristol, and Nina Shepperson—recently took part in our Florida Staff Invitational and came back with a newfound appreciation for the work we do five days a week. There’s something to be said about having the opportunity & privilege to experience firsthand what our students do, but also the impact a course can have.
There were three pulling boats on this particular expedition, and Sarah, Gen, and Nina were each on a different one. Although they all had wildly different experiences, they each had the opportunity to step away from the daily grind, appreciate some time away from their computers and emails (if you’re in the field, you can’t worry about it!), and discover what it truly means to “Go Outward Bound.”
We recently took some time to connect with Sarah, Gen, and Nina, and learn more about their experiences in the Florida backcountry, what surprised them the most, and what some of their biggest lessons were.
1. As three administrative employees, you’re frequently talking to others about the impact of a HIOBS course. What was it like to finally experience one?
Sarah: It was a blast! I have seen the evidence of the magic that happens on HIOBS courses when interacting with students returning from the field, but it was special to experience it first-hand with other Outward Bound staff.

Gen: I’ve learned quite a bit about HIOBS courses through photographing them and reading student evaluations, but none of that compared to actually being out on course.
I was nervous about what I had gotten myself into and had reservations about living in such close proximity with strangers, but within minutes of getting on the water my fears subsided and I quickly began embracing the moments.
The initial awkwardness of meeting strangers quickly turned into inside jokes and bouts of laughter that filled the quiet backcountry air.
We gambled sleeping without our tarp and pushed ourselves physically and mentally. For me, it was an introduction to a life lived more simply, a push away from the daily anxieties that seem to have been plaguing me for the last year, and a return to what it truly means to be connected with self and community. When you’re out on the water, it’s just you, your crew, and the natural elements and I was fortunate to have shared this experience with the most supportive and insightful humans. This course reminded me to live in the moment and despite the challenges, I wouldn’t change a thing.
(Editor’s Note: Aside from her HIOBS work, Gen is also a professional photographer. And lucky for us, she brought her camera on board. The image above is from her as well as a few others in this blog!)
Nina: Having just worked on supporting our Fall Appeal and sharing the word “impact” through our stories and communication, I was eager to go see for myself what we all had been talking, writing, and thinking about for weeks. Safe to say it did not disappoint—I’ve thought about our expedition at least once a day since it ended!
2. What surprised you the most?
Sarah: How well I slept! Not getting enough sleep was probably my biggest fear going in. Of course, it is not the most luxurious setup, but after a hard day out in the elements, it was cozy to curl up in a sleeping bag under the trap crammed in next to my crewmates.
Gen: I was most surprised by how quickly we all adapted to life on the water. I felt myself quickly calming down and realizing that less is more. When you’re in the backcountry it’s only you, your crew, and the boat. I don’t want to say it’s simple, because you have to be present all the time, but it was an incredible reprieve from the rush that my life has been the last year. I felt a sense of returning to self while out on the water and I deeply cherish the experience of self-development and the support of the people I was lucky enough to share the space with.

Nina: My answer is very similar to Gen’s. As someone who enjoys quite a bit of alone time, I was worried that my social battery would quickly run out.
However, while I was reflecting post-course, I realized there wasn’t a single moment when I wished I was away from any of it.
Being on expedition, especially on a pulling boat in such close quarters, you are constantly learning, problem solving, and being productive.
Whether it’s setting up sleeping arrangements, sheeting/cleating, bow watch, navigating, etc., there’s always something to do. While the moments when we did get to reflect—”feet over the gunnel” and anchor watch—were great, I never wished for more time by myself.
3. What did you find most challenging about your course?
Sarah: Being in such close quarters. Group living was definitely an adjustment for me. Anchor watch and other moments of private reflection were key to keeping myself feel balanced.

Gen: As an introvert, I expected the close proximity of living on a 30-foot boat with strangers to be the biggest challenge, but it was the people that made this trip so special. My biggest challenge ended up being my own confidence in feeling up to speed with what we were learning. I tend to second-guess myself but was grateful for the opportunities to push out of my comfort zone and absorb a plethora of new information.
From navigation to knots, to understanding boat terminology, to troubleshooting what to do when all our food got soaked, we were faced with unexpectedly new information at every turn. I’m grateful for the support of my crew and the communal problem-solving that showed me I can in fact trust my gut and push through hard things. (Photo credit: Gen Bristol)
Nina: I found trying to not wake everyone up by stepping over them while heading to the bow for anchor watch (sorry Izzy for stepping on your headlamp) the most challenging.
4. How will having field experience impact your work as someone who works on the administrative side of things?
Sarah: As a Course Advisor, I spend a lot of my time preparing students for the experience of being on course. After doing this course, I am able to more fully describe what to expect, and I can speak from personal experience about the challenges and growth that are part of a HIOBS course.

Gen: I work in development and fundraising and getting to experience a HIOBS course made me realize how deeply impactful this experience is. Our field staff are highly skilled and provide opportunities for growth and challenge.
The confidence I gained through this course was incredibly impactful, and I wish I had known about opportunities like Outward Bound when I was younger. But, like so many others, financial barriers kept me from seeking out opportunities like this one. HIOBS has great scholarship resources, and I’m more determined now than ever to fundraise and educate others about the resources that make programming more accessible to those who are underrepresented.
In addition, this experience also helps me connect with donors who have attended courses in the past. I can now engage in deeper conversations about the impact of HIOBS expeditions.
Nina: I’ve spent a lot of time in the Marketing department reading student testimonials and conducting interviews for our blog and social media channels. After hearing about wet tarps, cold plunges, how great peanut noodles are, and most of all, group dynamics and camaraderie, I can attest along with our students as to how impactful a HIOBS course is. It makes me excited to share more student stories and hear about all of the challenging, crazy, fun, and silly things that happen on course!
5. What do you miss the most about expedition?

Sarah: Crewmates making meals!
Gen: I miss the people I met and the traditions we created. Getting to eat and cook together was particularly special for me and I looked forward to our Chow Circle every night.
I also miss sleeping under the stars and getting to wake up and fall asleep with the sun. It was truly rejuvenating.
Nina: I miss many things, like the camaraderie of my crew, but what immediately comes to mind is the satisfaction that comes with doing a successful tack, knowing you called the right shots while captaining, and simply put, learning something new. It isn’t every day that you learn a new skillset—being in the field gave me a boost of energy to try new & challenging things.
6. What was the biggest lesson you learned?
Sarah: Tackle challenges head on. If a challenge came up on course, whether it was running aground or needing to chart a new course, it was to the benefit of the group to address the challenge right away. That way everyone could use their energy to take action and we could overcome the challenge as a team.

Gen: Getting to share this experience with folks from vastly different backgrounds reminded me to be present and not take life so seriously all the time. This course reminded me to embrace the moment (even when you’re completely soaked) because life is short and there is beauty and adventure even in the challenging times.
Nina: Word for word what Gen said! Learning from my peers was incredible (especially since they were all OB instructors). Having come from schools across the country with varying levels of knowledge and experience, we all had something different to bring to the table (i.e. knot expertise, excellent cooking skills, a good sense of humor, etc.). With all of our skills and backgrounds combined, we made quite the team!
7. Would you do it again?
Sarah: Now that I have experienced life on a pulling boat, I think it would be fun to try a canoe course.
Gen: Absolutely, I would love to try this sort of expedition in Maine next time. I’m curious about the challenges of sailing in different landscapes and would love to see my home coast from a different perspective. This course has also re-sparked my interest in travel and pushing myself out of my comfort zone and I’m eager to pursue more experiences like Outward Bound in the future. I’d also love to continue learning to sail.
Nina: Definitely not. Just kidding, of course, 1000%! Who knows, maybe I’ll even become an instructor….