Skip to content

What's Your next Adventure?

Wildflowers in Crested Butte

What's Your next Adventure?

Crested Butte What's Your next Adventure?

Your first day punching the clock for any new job is like punching in for a new adventure.  With our careers taking up the majority of our lives, we owe it to ourselves to make sure that adventure is fulfilling and enjoyable. 

I sat down with CBMR’s Human Resources Manager, Jessica Caskey, to discuss the perks of working here (as if I didn’t already know).  Jessica is also the master mind behind Living Seasonal, a resource website for folks looking to live that seasonal dream.  She has the professional chops to share her advice on “living seasonal”, having worked seasonally for about 7 years.  Let’s take a look at what your seasonal career with CBMR could look like—the perks, the difficulties (that are actually just “opportunities”, to quote Jess) and the adventure you’ll embark on when you start a seasonal career.

“Anything from a front desk agent, to an HR manager, to a transportation director, to payroll, accounting, ski school. . . “

Jessica has worked in a spectrum of positions, in locations such as Denali National Park to ski resorts along the I-70 corridor in Colorado.  In her tenure as a seasonal employee, she has worked as a Human Resources manager, snowboard instructor and bus driver—the beauty of seasonal work is getting to dip your toes into numerous career tracks. 

Nearly every position you’re interested in can be found in a seasonal avenue, as Jessica states above—it’s not just about guiding adventure outings or teaching people how to ski.  You can take your college education and still craft a career in the area you studied in college while having the perks of a seasonal lifestyle.  Like that one time I scored a 4 month internship with the Alaska Department of Fish & Game, which landed me in a tent in the back country of Kodiak, AK, studying salmon and chasing off 10-foot bears.  A dream for an environmental studies and biology student.

 So what are the benefits of seasonal employment you ask? 

“I’m not one to live vicariously through people, I want to be the one having the adventures.”

Jessica and I have had a conversation or two about traveling and she certainly has the bug.  Seasonal work is unique, in that typically the places you find seasonal work are destination vacation spots for the full-time, year-round folks. 

While seasonal work is sometimes difficult and the hours long, that’s balanced by clocking out for the day and having numerous adventures right out your front door.  I write this from my office in Crested Butte, CO, where thousands of tourists visit throughout the year.  I spend my lunch breaks mountain biking or snowboarding, my weekends hiking and backpacking—all from a step outside the door.  I wake up in a place people choose to spend their blessed 1-2 weeks paid vacation—have I made my point yet? 

If the opportunity to travel and make a living in beautiful destinations throughout the world doesn’t tempt you, perhaps this will: seasonal work is temporary work.  Which can be unsettling for some, but for others, it’s the light at the end of the tunnel.  Not everyone wants the year-round salary and health benefits—perhaps you’re scared of commitment, and prefer signing up for stuff 6 months at a time.  If you’re prone to boredom, you can politely escape through the back door after your 6 month work commitment if things “just aren’t working out”. 

“People don’t get burnt out. . .because they’re not doing the same thing over and over again.”

After your work commitment ends, you have that blessed 1-2 month reprieve from obligations before the next season starts—what we call “shoulder seasons” in the resort industry.  If you’re anything like Jessica, you’ll jump ship and find yourself with a passport full of nearly 20 stamps.  That travel bug?  It’s alive and well.  So if you’re looking for an adventure in your career (working in travel destinations) or fueling your dream to travel the world, seasonal employment might be for you.

“I have met some of the coolest people on this earth working seasonally.  Anywhere from individuals who have literally walked the entire length of the Mississippi river, to individuals who are professional hobos jumping trains across the country.”

Seasonal workers have been places, seen and experienced things that people who work and live in one place typically do not.  When you work in an environment like this, you’re likely to rub elbows with people who will inspire and change you—and talk about the networking!  As Jessica points out “I can travel just about anywhere in the United States and have a couch to sleep on.”  Seasonal workers are a rare breed of folk in a tight knit community—once you’re in, your personal and professional network expands to include people you’ve never met.  Forget Facebook, this is a friends list that actually serves a purpose in the real world.

“It’s breaking apart from tradition, It’s breaking apart from the norm and going out and doing something completely different that people just don’t understand.”

Beyond the glory of seasonal work, there are downsides—like the confused look friends and family will give you when you discuss your new job.  This kind of work is not typical, but many people make a living with a seasonal career. 

You will make sacrifices pursuing this lifestyle.  You’ll occasionally regret your choices.  Like I did, as I watched the floatplane I rode in on, takeoff during my internship in Alaska.  Leaving me with all my gear, green as can be in my Extra-Tuffs in the remote Kodiak backcountry.  I cursed myself as I thought about the mother bear and cub I spotted during landing, ambling up the path from the cabin that was my destination.  The pilot advised me to “make loud noises” as I hiked—the fear on my face likely a source of laughter as he pulled the plane away.   

Homesickness will find you when you realize how far away you are from family and friends.  Thank goodness for care packages and pen-pals. 

Loneliness will certainly sink in when you arrive some place new, filled with people you don’t know.  Which is actually a blessing in disguise—these moments build character (as my Dad would say).

But your true character will show when you overcome these moments of despair and arrive at the end of your seasonal gig more independent, adventurous and confident—and ready to take on the next seasonal job you can find. 

If you’re ready to “just jump off and give it a shot”—as Jessica says, head over to our open jobs page and apply for 1 (or 3!) positions that interest you.  Still not sure?  Have a peek at Jessica’s pro’s & con’s list below to weigh your options!  Know someone who would make a perfect seasonal-living buddy?  Make sure they see this.


  • Relationships: Meet true characters and visionaries from around the world, while expanding your network—you’ll have friends for life.
  • Location:You work where people vacation—the most unique and beautiful locations around the world. Then, move on to the next amazing destination—your Instagram followers will be so #Jealous.
  • Time off:You work hard and make good money for 4-6 months, then have 1-2 months at the end of each season to go play, travel, and rejuvenate.  You’ll have the time and resources to truly see the places you travel to, instead of rushing through the standard 5 day vacation.
  • Simplifying: You take everything you own and consolidate to make frequent moves easier—or, if you’re like Jessica, you make everything fit into a Subaru and call it good. You learn to appreciate things—like running water when you live in the remote backcountry.
  • Bettering Yourself:You go through the loneliest and happiest moments of life and get through it on your own. You’ll grow up, learn independence and have some pretty enlightening experiences.


  • Relationships: Love can be difficult to find when you’re moving frequently, its also difficult to convince a partner to pick up and move every 6 months.
  • Loneliness: Moving to a place where you don’t know anyone is incredibly difficult if you’re not a social person—but what an opportunity to branch out and challenge yourself!
  • Stability:Moving frequently prevents growing roots to a place, and your life can feel stressful and unsecure at times.
  • Work Environment: Seasonal work can be very busy and stressful. It could mean working long hours and many days in a row, which can be draining.(Stay tuned for next week’s blog post on Snowmaking for insight into this particular seasonal position!).
  • Finances:Saving money can be difficult during off-season, especially when you’re traveling the world. However, creating a budget that includes travel and a bit of saving can make all the difference.