What It’s Like To Be A Backroads Trip Leader

As a chronic the-grass-is-always-greener kind of person, I’m always looking for the next opportunity so I was incredibly excited when I was hired as a Trip Leader for Backroads in early 2018. I was looking for a way off the ships and this seemed like a golden ticket. But unfortunately, it was not the fun and glory that I had envisioned.

Read on to learn about my experience as a Backroads Trip Leader and whether or not it would be a good fit for you.

But first… let’s dive into what it involves to become a Backroads Trip Leader.

Becoming a Backroads Trip Leader

The first hurdle – and it’s a hurdle! – is getting offered a Backroads Trip Leader position. The interviews are intense and you’ll be up against some of the most interesting and incredible people you’ve probably met.

If you make it through the interviews and are offered a job, here’s what comes next.

Backroads Leader Training

My journey toward becoming a Trip Leader for one of the most well-respected travel companies in the world began with an intensive two-week training course in Salt Lake City. And when I say intense, it was intense.

• We learned how to work on bikes including fixing a flat in under five minutes, replacing all cables and housing, and adjusting brakes and shifting.
• We had classes and workshops on leadership skills and how to deal with all varieties of traveler personalities. 
• We learned the ins and outs of Backroads’ software and internet portals.
• We were schooled on how to drive the Backroads vans and trailers including backing the trailers up into tight parking spaces.
• We put our arm muscles to good use by racking and unracking our bikes from the top of the vans a million times. 
• We practiced putting together gourmet Backroads picnics and we had a cocktail reception to see how leaders display themselves in upscale situations.

The two weeks of training culminated with a three-day mock trip out in the outskirts of Salt Lake City. Our training group was divided into two teams and we had to perform every aspect of a real trip including grocery shopping, packing the trailers, making sure the bikes were in working order, cooking meals, staying on top of logistics, interacting with guests (who were our trainers and mentees), problem-solving, etc, etc… 

It was A LOT of work, but so much fun. Our training group bonded incredibly well and as true leaders – we all worked efficiently together. 

After two weeks and a little graduation ceremony, we were given our leader schedules for the first half of the summer. Some leaders went abroad to Europe, others flew up to Alaska, and a large contingency went to Glacier and Teton National Parks.  

Where was I sent?

I was assigned to the wine and food destination of Northern California. As a foodie, I was quite pleased. These are posh trips and I would be eating and staying in some of the top restaurants and hotels in California. I would also be leading some trips in Yosemite and the Redwoods.

Sounds pretty amazing, right? 

So What Went Wrong? 

Truthfully, I did not love being a Trip Leader with Backroads.

Don’t get me wrong, it’s a great company with great people and amazing opportunities, but it just wasn’t for me.

After about two months of work, I came to the conclusion that I don’t enjoy being a leader, at least not in this capacity. I am not a super charismatic person that can get a group excited about the days activities and as an introvert, I need a lot of alone time – something that is extremely hard to come by as a Backroads trip leader. 

Furthermore, unlike living and working on a ship where you unpack once per contract, working at Backroads you’re essentially living out of your suitcase. Every night or every other night you’re sleeping in a different bed.

In between trips, I stayed at the leader’s house in Berkeley. It was nice to have a free place to stay, but the house was so crowded and loud and oftentimes very dirty/messy. Maybe during my 20’s, I would have enjoyed this lifestyle, but now that I’m in my 30’s (so old, I know) it really wasn’t my scene. 

So, after talking it over with friends, I decided to quit. I felt really bad because I knew how much chaos that would create for the scheduling team, but I really truly dreaded going back and that’s not how I ever want to feel about a job. 

Your turn! Should you be a Backroads Trip Leader?

As I came to learn, good Trip Leaders are a special breed and I now understand (and respect) the fact that not everyone can be a good Trip Leader. It took me only several months to realize that I was not one of them nor was I ever going to be (or even wanted to be) an excellent Trip Leader.

I have some of the qualities – a great work ethic, good communication with coworkers, attention to detail – but I don’t possess the leadership skills that I saw in so many of my co-leaders – public speaking skills, charisma, emotional stamina, and desire to connect with every person on a deeper level day after day.

Most days, I just wanted to retire to my bed at 6 pm with a glass of wine and Netflix and not talk or look at anyone until the following morning.

So in an effort to help other potential Leaders not make the same mistake I did, I’ve put together a list of eight questions you should ask yourself before applying to become a Backroads Trip Leader.

This guide could actually apply to any adventure guide position because, at their core, they all require pretty much the same skill set and personality.

1. How much stability do I need in my life?

Being a Backroads Trip Leader pretty much means that you’re always on the go. You’re moving from one hotel or campsite to another either every night or every other night.

Time off in between trips can be a few nights at the leader’s house or a week off if you’re lucky. There’s no time (or point) to unpack. As such, any sense of stability can be hard to come by, especially if you’re a person that needs routine. 

On the other hand, if you thrive on always being on the go and don’t mind living out of a suitcase, you’ll fit right in! 

2. How well do I fare with the unknown?

A Backroads Trip Leader schedule can be the greatest thing in the world and it can also be the most epic disappointment. One month you can be working in the wine country of California and the next month you can be sent to Italy with only a few weeks of notice.

That may sound amazing to some people, but it can also be pretty jarring and stressful. Make sure you are open to anywhere you are placed at any given moment.

Remember, this is a job and Backroads will schedule you where they need you most, not where you want to go the most. 

3. Am I really, truly a people person?

This is where I failed. I like to think that I’m a people person – I do like people after all, but I’ve come to learn that I like people on my own time and in my own way. When you’re a Backroads trip leader you have to be a people person all time. In the morning at breakfast, on the bike during the day, when you run into guests in the lobby, at the dinner table, and all the times in between. So if you’re not really a people person, this probably isn’t the best job fit for you.

*I should note here that my job as a Wellness Specialist with Lindblad Expeditions is similar in terms of always being ‘on’, but I feel like there’s a lot more space and time to get away on a ship (ironic?) than there is on a Backroads trip.

4. How are my public speaking skills?

This was another area in which I struggled. Public speaking is unavoidable as a Backroads Trip Leader. Morning ‘route raps’ are given each day to go over the daily itinerary, toasts are given throughout the week for different purposes, points of interest need to be explained to the whole group… it’s not a deal-breaker, but if you’re not a confident public speaker you may struggle.

5. Am I doing it just for the travel?

The truth is, you may not actually travel that far, especially during your first year as a trip leader. The location you gain expertise in is very likely the place you will spend most of your season and the next. Italy may sound like a great place to work, but leaders call it ‘sticky’ because once you start working there it’s very hard to get scheduled somewhere else. 

Don’t go into this job with the idea that you’re going to be flying around the world, working in all sorts of amazing locations, living the dream of a global traveler. Most leaders only work in one or two destinations.

6. Do I need a lot of alone time?

My hand is raised, that’s me. I need a lot of alone time and I found it very difficult to come by as a trip leader. Hotel rooms are shared with your co-leaders, the leader houses are often packed, and you really have to work hard and be creative to carve out alone time. 

Unless you set up your cot in the middle of a Redwood grove…

7. Do I need a steady income stream?

Yes, you can make a lot of money as a trip leader (mostly in tips), but there may be weeks and/or months when the money stream is slow. As a first-year trip leader, you will be doing mostly support leading where you don’t receive as high of a percentage of the tips, and paycheck earnings can be a bit erratic.

Schedules can also be light. I had several two-week periods where I was not scheduled for trips and while accommodation is free at the leader’s house, bills still have to be paid. 

Also, first-year leaders don’t usually get the opportunity for winter (or year-round) work. You may make great money in the summer, but think about whether you’re ok finding a new job at summers-end. You’ll probably be rehired back as a second-year trip leader if you want it, but there are a good 5-6 months in-between seasons.

8. Am I a hustler?

Being a Backroads trip leader is a lot of work. I mean a lot of work. You have to hustle and if you don’t, you will receive the wrath of your co-workers. Be prepared to work your butt off and be prepared to do jobs that you don’t want to do.

I spend several nights washing sleeping bags at a laundry mat – definitely not my most glamorous hours. You have to hustle if you’re going to make it as a trip leader. If you think this job is just about sipping wine on the Italian Riviera and going for long bike rides in beautiful places, think again.

Final thoughts

So in the end, working as a Backroads trip leader can be an amazing and transformative experience, no doubt about it it. Some of the people I trained with have had incredible experiences as first-year leaders and I expect them to continue working for Backroads for seasons to come. 

But as an introvert and someone who honestly prefers to spend most of my time alone, it just wasn’t the right scene for me. I’m grateful for the experiences I had – especially the two-week training in Salt Lake City – but I’m humble enough to say that even though I wish I possessed the energetic and charismatic personality of a fantastic Backroads Trip Leader, I don’t. And that’s ok.