My Experience as a Backroads Trip Leader

A new challenge appears: leading bike trips for a travel company!

This summer I was fortunate enough to cross an item off my bucket list: be a cycling trip guide.

It was the biggest routine shake-up and leap of faith in my life since graduating college 4 years ago in May 2020 during COVID. I went from a remote worker in a 9-5 to a dynamic, fun, and fast-paced lifestyle traveling across the US, learning tons of new skills, and facilitating beautiful cycling vacations with incredible people. It was an amazing experience.

How did I find myself here?

Making an effort to utilize my degree in Materials Science & Engineering, since graduation I have been living and working in the medical device manufacturing industry in the small but vast outdoor paradise of Flagstaff, Arizona. It’s been a period of comfort: beautiful friendships, free-time, and flexibility to pursue a slew of outdoor adventures throughout the southwest, as well as the place where I cultivated my love of cycling.

However, for the last two years, I’ve been reconciling my genuine gratitude for my current situation and good fortune with a sense of unease that despite having achieved everything I set out to do when I started college – a good job, good friends, free time, and economic stability – I’ve really been questioning the traditional path of the “American dream” that I’ve been following thus far in my life.

In my 20s I’ve learned that security, stability and freedom are all strong values of mine, and it’s been an interesting learning experience to navigate and envision a life design that allows for them all. A month of vacation, systemically, seems hardly enough to live the type of life I dream of spending on this planet – being open to new opportunities across the globe, exploring off the beaten path and connecting with people from all walks of life.

And to be honest, despite having all of these grand ideas of experiences and adventures I’d like to have in life, at the same time, I also feel like I have no idea what I actually want to do with my life when it comes to work and purpose. I know I’m not alone in this – I’m one of many in a generation raised to believe that happiness and success are found within the confines of a good education, a good job, and a middle-class American lifestyle.

And I’m also one of many in that generation who are finding in adulthood that it’s not that simple or that true: the world has changed. We live in a time of unlimited possibilities and unlimited access to ideas and information. But our society still values a “one size fits all” approach to life and education (sit down, study, and get a job) as opposed to a process of self-discovery, values identification, and exploration into how one’s interests and skillsets may naturally align into a vocation or enriching life of service.

Thankfully, life gave me an opportunity to explore a few months of a completely different lifestyle.

In October of 2023 I got an email from Backroads, a luxury active travel company offering guided biking and adventure vacations across the globe, that applications for field staff (the leaders on the ground running trips) had opened for summer 2024. I figured I had nothing to lose by spending one morning writing my application.

The interview process was lengthy and thorough – but three months and three rounds of interviews later, I flew myself to the US headquarters in Berkeley, CA to attend an in-person hiring event. I walked into what felt like a mix between a cocktail party, team-building exercise day at summer camp, bike skills test, and public speaking show-off with 50 other aspiring leaders- interesting people from all over the world who had amazing stories to share!

As a remote worker for the past two years, it had been a long time since I was in such a social environment. It was so far out of my comfort zone, but so exciting to drop into something so new and different. I was thrilled the next day when I received a trip leader offer from July to October.

Although I was terrified to quit my job for the opportunity, I decided I was going to take it. From the initial application submission up through the final interview- my interest in Backroads was something that I was intuitively sure was right for me – and that natural knowing and trust in self is not how I’ve made many major life decisions thus far as a young adult.

In an experience I can only describe as Kismet – when I broached the subject of the opportunity with my boss, she immediately agreed to give me the time off and hold my job for me.

When something works so easily, you know it is exactly where you are meant to be. The universe was essentially ensuring the experience happened for me – giving me an opportunity to pursue a bucket list experience and explore a job that may provide more fulfillment and passion, and providing a safety net of comfort, routine, and security to fall back into after. Blessings and gratitude where they are due.

So, that’s the backstory of how I got here: a 29 year-old remote worker, questioning what purposeful work might look like and finishing up his first season of active travel trip leading. A lucky guy who spent the fall in the beautiful cycling paradise of Stowe, Vermont, living and working with a passionate and dynamic group of other leaders, exploring communal living, growing, and appreciating an entirely new skillset that lights me up and that I didn’t even realize that I had.

Trip Leader Training

And it all started with New Leader Training. My co-hort of 25 other aspiring leaders and I spent two weeks in Salt Lake City, Utah in an intense experience where we learned a plethora of tools for interpersonal connection, to drive vans and trailers, bike mechanics, hone our public speaking skills, and create the Backroads magic. It was not for the faint of heart.

Pretty much everything about the reality of working for Backroads was unknown for us new leaders. We all packed a couple of suitcases, not really sure what we would need, having no idea where we would be sent to work, or exactly for how long we would be gone, or what the job would really entail.

I really didn’t go into training with expectations, but I underestimated what a challenge it would be. Coming from a flexible remote job, it was quite an adjustment for me to drop into an environment of 12-15 hour workdays, an “always on” environment with consistent social interaction, and being barraged by, and quickly tested on, new skills the entire time.

It sounds a bit extreme, but I really felt like I was pushed to my own physical, emotional, and social limits. During our mocktrip, a 3 day experience where we use all our new leader skills to mimic a mini backroads trip, I contemplated walking out on the training.

I really questioned myself and in moments, didn’t have the self-confidence to believe that I belonged in this community. However, with a little removal and some hindsight, the leadership training offered was extremely valuable and I know I will use the skills learned for a long time to come.

While training overall was pretty intense, I made some great friends, had a blast exploring Salt Lake City, and got to do some amazing canyon riding including bucket list climbs like Big Cottonwood Canyon, Emigration Canyon and Big Mountain, and the Alpine Loop around Mt. Timpanogos. All were amazing and highly recommended.

A couple of days before training ended, we all got our schedules and discovered the multitude of roles and destinations we were assigned. As first year leaders, we saw a few trip leads, some support leads (where you still accompany a trip but are not responsible for any logistics and have evenings off), and unit drives. I was assigned to spend a few days staying in Salt Lake City performing “leader labor” where a select few of us (obviously the favorites) stayed and performed various tasks in the warehouse. We built a lot of trays, racks, and took a lot of snack breaks to watch the Olympics.

I was assigned one support trip in the Black Hills in South Dakota, and for the bulk of my schedule, to spend September and October in the Green Mountain State – leading cycling trips out of Vermont.  As an avid cyclist, I really hit the jackpot!

I also got assigned two cross country unit drives – from Salt Lake to Vermont and from Vermont back to Salt Lake – essentially paid 5-day road trips driving a van, a trailer, and a rack full of 12 bikes across the US. Everyone had different thoughts about unit drives, but I LOVE driving cross country. I’ve driven across the US over 20 times since 2018 – so getting paid to do it is a dream come true for me.

After leader labor, I was given a surprise last-minute unit drive up to Glacier National Park where I had some time off approved to attend the wedding of one of my closest friends, Daniel. He and his wife Audra got married on the shore of Lake Josephine and we finished the day with a hike to Grinnell Glacier, followed by a smaller group taking a 3-day backpacking trip in the Montana backcountry.

After such an intense training environment, spending a few days being a dingy, dirty, and complete weirdo in the woods was exactly what I needed to reset. My time in Glacier was probably the highlight of my entire summer and I got to see some beautiful views and celebrate some beautiful people!

Trip Leader Lifestyle & Work

Ok, ok Beck…. That’s all fun and dandy…. But what was it like actually working for Backroads?! Great question…..!

Honestly? It was so FUN! And so CRAZY! The lifestyle of a trip leader (especially a first year, since everything is new) was absolutely insane.  Don’t get me wrong – being a trip leader has been a lot of hard work. It’s high-end hospitality and customer service- it is a demanding job that requires you to constantly give your best. But for someone up for the challenge of unknowns, excitement, and living out of a suitcase for months on end, the perks and lifestyle are awesome.

We have communal housing available to us in every region where we operate. And when we show up to region, we have plenty of cool new people to meet, access to Ford Transit vans, and a plethora of bikes at our disposal. And perhaps one of the best parts: the community of Backroads leaders is filled with incredible people. Kind, warm, adventurous, and truly interesting souls who have accomplished so many cool things throughout their collective lives!

Everyone’s experience in-season is a bit different because it really depends how your schedule balances time off with assigned work – and you don’t have control over what’s on your schedule, but Backroads really becomes your entire life when you are in-season. The days are long and dynamic – every day really is different and full of new learning and new challenges. You’re meeting and working in a high-end customer service environment with new people every week, and you are living and working with your co-workers! 

Sometimes you get along so well with those people, and your trip runs like a fun dream, and sometimes you have different working styles and it’s not quite as smooth, and those relationships can carry back over into your living arrangement once you’re done.

My brain was really on overdrive. I’ll admit I was mistaken when I assumed I would just show up and get paid to ride my bike. Trip leaders are responsible for so many logistical components. I found myself making confirmation calls for 20+ vendors pre-trip, waking up at 6 am to stage 20 bikes, slinging so many bikes onto van rooftops, scurrying to prepare beautiful picnic spreads, navigating difficult trailer tow maneuvers, acting as a counselor as guests confided vulnerabilities with me, crying over broken dishes in the back of the trailer, truly just handling anything that arose at a moment’s notice.

I really loved the daily integration and room for creativity – there are numerous outlets on trip to let your creativity shine. From drawing and creating your route raps (the overview we give each day of the ride we will be doing), to silly games and activities you can plan into your trip (I made all of my Vermont guests take shots of maple syrup with me), to creating and executing a vision for your Backroads picnics, every trip runs differently based on the creative visions that each leader within the co-leading team brings into the trip.

So for any of the doubt and discomfort I had during training, once I had a chance to adjust to the workload, I really loved it.

I loved getting to hone my ability to give my best. The valuable life and leadership skills that I’ve been given an opportunity to grow in this environment are numerous.

Optimism and contagious positivity, presence and confidence, credibility and public speaking, kindness, truly connecting with others – these are just some of the amazing life skills that are taught, honed, and highly valued in the Backroads community.

And it feels AMAZING to see a version of myself tapping into and growing these skills, and building identity capital as someone who excels and enjoys social situations, as opposed to some of the more negative and oppositional self-beliefs that I sometimes struggle with on my journey through this life.

I’m so grateful for the opportunity to get more comfortable talking about myself, to be more comfortable being confident in my choices, my life path and where I am, for getting to work outside. And when I was lucky, even getting paid to ride my bike!

One other huge component I noticed about being a trip leader is how insular the world is: It’s incredibly hard to maintain relationships with your world outside of Backroads. It’s hard to quite put the words on it, but I’ve found this to be a shared universal experience among the field staff I met.

Time flows differently – when you’re on trip – you don’t have weekdays and calendar days. You really only know what day it is of trip. You’re waking up at 6:30 am and lucky to have 20 minutes to yourself before beginning the multitude of tasks required to create a smooth guest experience.

You’re essentially moving at warp speed and completely “on, outward, and engaged” until you end your day at 10 pm and plop right into bed. This experience repeats itself each day of trip, and you are so engrossed within trip that the world outside of the present barely exists.

When you finally find yourself with down time, depending on your personality, you might not have anything left for others. Typically this is manifested in complete exhaustion (aka just not having the energy to catch up and be fully present with others outside of the sphere who have no context or ability to conceptualize the zany world you’re inhabiting) or, if you’re feeling energized, you’ll probably plug into adventures with those around you.

If you’re someone who needs alone time, once you get it, you don’t want to engage or speak with others, even if the others are people you deeply love and care for and want to maintain closeness with.

A shot from the top of Appalachian Gap and the Causeway in Burlington

While in season I felt so rich in being surrounded by people, and having fun friends to do things with, I also noticed that the nature of this lifestyle offered a lot of parallels to traveling – you’ll meet people and have these in-depth amazing late night conversations – but before you know it you say goodbye not knowing when you might see each other again. The nature of the role just doesn’t allow for the time & proximity needed to build truly deep relationships with people.

As an almost 30-year old who would love a life & adventure partner, it really stood out to me as a component that would impact the sustainability of swimming in this world. Unless you get so lucky as to meet and commit to someone within Backroads (and like I said, everyone is super cool and super beautiful, so this definitely does happen for many), overall, it’s a much more transient, fun, and youthful energy.

And as awesome as the community is, the reality is that people are constantly coming in and out of your life and your space, and you’re always on the move. It’s exciting and fun, but it can also be draining to constantly be meeting new people.

During the busiest times of the season, I was literally meeting new people multiple times a day for weeks on end. I had a lot of the same conversations. For me, I found I was able to eventually adjust into a mode that was social and receptive to others, but also not faking or forcing myself to consistently get deep with people unless it was just EASY.

Throughout the season, I got weirder and more comfortable being fully myself in the house and just accepted that I didn’t need, nor want, everyone I met to know me and become a friend, and that it’s okay to have different level of social desire, especially in a crowd of hypersocial extroverts.

In the last 4 months I lost the control of my day-to-day and having the ability to set aside real time for myself. But I gained a feeling of community, purpose, and pride every day. Even when it was hard, even when I was emotional, and even when I wanted to leave, those pillars stood strong.

I never felt the existential anxiety that had really permeated into my psyche in the last couple years of working a computer job about living up to my potential and taking charge of my life. I never woke up with a sense of dread. Even when physically exhausted, I was content and so engrossed by the present experience that I didn’t worry about anything outside of it.  For that, I am so grateful!

Trip Leading Community

I just want to take one more opportunity to highlight what most other trip leaders would probably echo is the best part of this job: the people – my lord, the people. It’s exactly what you’d imagine when you picture a company solely consisting of personality hires. From divemasters, non-profit founders, and world travelers- the experiences and drive of the 20 and 30 somethings I was surrounded by has been nothing less than inspiring and motivating. Trip leaders and field staff are intelligent, resourceful, dependable, empathetic, extremely hard working, connection-focused problem-solvers full of passion and full of life.

It’s been unbelievably refreshing to be surrounded by people with attitudes and energies that I aspire to be like after spending years working in a job full of  “successful American adults” who have followed the traditional educational and work path – where people are put together on paper, but most are not fulfilled, and most are running on autopilot instead of actively designing our lives.

And when I look at those further along in career development in my company, I realize that I really don’t want to be in any of their positions. But seeing the characters of some seasoned leaders – yeah, sign me up for that type of future!

So it has been incredible to be inspired and to grow into an even more robust and true version of myself. To have mirrors for the type of person I want to be, and to have all of that excitement and love mirrored back to me.

I remember a grueling moment in training, when I was on the line of walking away, where I confided in my mentor that I look around at the kindness, presence, and warmth I feel when I speak to any of the training mentors, and it’s the kind of person that I want to be.

The feeling I felt when her response was “Beck, we see all of those qualities in you, and that’s why you’re here” was heartwarming and eye-opening- it’s something I’ve worked hard throughout this journey to internalize. That my being in the community does reflect same qualities in me. And all of the joyous, kind, new friends that I’ve made see the same.

Now What?

So now here I am, one the many seasonal trip leaders wondering “well, now what?” as our season comes to an end; and processing the experiential learnings and the polar changes in day-to-day life after leaving the Backroads bubble.

I didn’t get a chance to unpack this experience with time off from any work – due to logistical requirements, I immediately returned to my remote 9-5 once the season ended. And as lovely as it would be to continue adventuring and traveling, I’m choosing to look at my situation with the cup full, that I have a solid routine and income to return to, and co-workers and a boss who value and appreciate me. Because being able to bounce between both these worlds this year has truly been a blessing for me.

And as grateful as I am for the work to return to, I’m also allowing the new knowledge that working in a dynamic, outdoor, exciting, people-facing role felt like a great fit for me to simmer, without requiring myself to take immediate and drastic action to uproot my entire life.

Sometimes I feel like I should do that – I feel the pull to completely change everything. But this experience also showed me that I want some consistency and rootedness in my life that is not tied to my work. And as much as I loved being in Backroads life, I could tell that if I did this full-time, I would probably burn out after a couple of years.

We are all continually learning who we are, what we need, and what adds value and serves us. We live in a time where many of us are disconnected from ourselves and knowing what we want – and that’s okay. I can allow myself to be a work in progress, and to still be proud of myself and the life I’ve built, even if I’m starting to wonder if I’ve outgrown it, but I’m still not quite sure what’s next.

For the first time in my adult life, I have no lease, no romantic relationship, and a job that’ll let me work from anywhere. It’s almost an overwhelming amount of freedom. I’m not quite sure where I’m going to live this winter, in the future, or what the path of my life will look like now.

Although, after 5 months of living out of my two backpacks, I am definitely craving some stability and routine. At the time of this writing, I am finding myself looking at new leases in Flagstaff and exploring community-based projects outside of work that might add some more purpose to my days.

And in my true balls to the wall fashion, despite having been nomadic for half of 2024, I’m also watching Flagstaff Zillow being like “should I buy a house?”

If anything, this entire experience has made me a lot more grateful for the job that I do have. I have flexibility, autonomy, consistency, benefits, and I’m valued enough that they encouraged me to pursue this time off.

Being so secure within my basic needs to ponder pursuing a career that I’m more passionate about is an epitome of privilege and I have to acknowledge that. It’s a great exercise for me to explore how much impact my mindset about my external situation has on my actual sense of wellbeing.

And that sometimes I don’t give myself enough credit for what I’ve accomplished in my life. Getting an engineering degree and a high-level decision-making role within a medical device company isn’t just “wasting my life” like one of my more critical self-narratives often tries to tell me. It took a lot of hard work and commitment to get here.

The 20-year-old version of myself that started walking this path wanted to set me up for a life of opportunity and abundance in the future. And look at what I’ve been able to experience and achieve already, even just this year. Sure, I haven’t spent an entire year backpacking across the world or biking across a continent. But I’ve built a life full of friendships, travel, laughter, growth, and enjoying the outdoors together. I’ve focused on investing my money and living below my means. And somehow this year I was able to balance that life with 5 months of traveling.

A 20-year-old version of me would be proud to see my current situation. Not disappointed in him for choosing to keep living it even after having some beautifully eye-opening realizations about life.

A collection of Flagstaff friendships in this beautiful life I have built

So, I’m not upheaving my life and quitting my job (like I shouted to the rooftops that I would – to anyone that would listen) and I’m not sure if I want to do another full season with Backroads at this point in my life (I might! – who knows?!). But I’m very interested in returning in a limited capacity (maybe for a month or two), and with my current job, I have enough PTO that I’d be able to swing this “best of both worlds” situation.

For now, I’m doing my best to take these lessons and self-growth right back into my “routine life” to practice cultivating more presence, joy, and contentment. And working to allow myself to be exactly where I am and feeling exactly how I feel without resistance.

It’s okay to occupy a space of holding conflicting feelings about what I want. I’m practicing trusting the universe and trusting myself that everything will work out well even if I can’t see the end-game clearly. There’s no such thing as a right or wrong decision!

The biggest thing I’ve learned from this experience is that I can achieve anything that I dream of, I just have to decide what’s really worth it for me and then make it happen. And I was inspired to stop aiming for perfection, and to just start this blog, so that’s another plus.

Cheers to such a beautiful and challenging experience, and cheers to whatever will come next. I hope that my words can resonate to trust your own path and your own timing, and to take a leap of faith if you’re on the fence, because when something feels right for you, sometimes the only way to find out for sure is to try it!