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The Ultimate Guide to Seasonal Jobs

I remember when I landed my first out of state seasonal job after college. I announced to my family that I was moving to Colorado to work at a pizza shop in a ski town. They thought I was wasting my time and education. Seven years later, they probably still think the same thing. 

I’m currently working at my eighth seasonal job. My work has taken me to Colorado, Connecticut, Utah, Ohio, and Idaho. Generally I stick to jobs that are outdoor related, such as ski resorts, wilderness guiding, or jobs in mountain towns. 

It’s finally time to share the wisdom and let you guys know how you can do the same.

Once you get into seasonal work, it sort of becomes a way of life. It gets easier to pack up everything and move from place to place and to make friends in whatever town you happen to have landed. 

In this guide, I’ll cover how to find jobs, what to expect, how to manage your money, how to live with less material things, and the good and bad of making a lifestyle of working seasonal jobs. 

How to Find Seasonal Jobs

The short answer is find your jobs on CoolWorks.com and BackdoorJobs.com. I’ve found almost every seasonal job I’ve worked on one of those websites. I suggest you do the same.

If you’re pondering seasonal work, I’m sure you have an idea of where you might want to go or what type of work you might want to do. Do a search either by state or by industry. 

In terms of actually landing a job, it’s not that hard. If you’ve had a job of any kind before, you can definitely land a seasonal job. And once you’ve worked your first seasonal job, it’s even easier to get your next one.

Employers are mainly looking for people who are actually going to show up and fulfill their contract, not someone who’s going to bail on the job offer before the season even starts. If they’re a really good employer, they’re also going to be concerned with whether you’re going to be a positive member of their crew community. 

Before committing to a job be sure you get a clear idea of pay, weekly hours expected to work, your housing situation, dates of commitment, and if there’s a bonus for fulfilling your contract. 

What Kind of Seasonal Jobs are Available

There are so many seasonal jobs available. I’m an outdoorsy person, so I usually stick to that line of work. 

Ski resorts are typically the go to job for winter months. I’ve worked at two different resorts in Colorado, and I might be headed to a ski resort in Utah for the winter. The perks of working at ski resorts is that it usually involves a free season pass. Don’t worry if you don’t know how to ski or snowboard. I learned how to snowboard during my first resort job in Telluride, Colorado. 

If you’re not a winter weather person, don’t worry; there are plenty of jobs in warm places like Florida, Hawaii, and the Southwest.

In terms of summer employment, there are tons of options. Things that come to mind are mountain guiding or raft guiding. There’s always employment in national parks or major outdoor destinations. You could pick a cool town you want to spend more time in and work at a restaurant or hotel. There’s ranch jobs and summer camps. 

I got my seasonal start working at a summer camp in high school. This is the perfect option for high schoolers or college students because it will work with your school schedule and be a fun experience. 

For year-round outdoor jobs, wilderness therapy is a good option. I guided for a wilderness therapy company for two years cumulatively. It was good in terms of being able to stick to one cool area, have good pay and benefits, and have a long-term community of friends. 

There’s lots of jobs out there that are Ameri-Corp programs. I did a season of working on a trail crew in Colorado. Ameri-Corp jobs really don’t pay that well. However, they give you an education stipend at the end. While my paychecks were barely enough to scape by with, I did get about $1300 that I could put toward my student loans after just two months of work. 

A popular option for RVers is being campground hosts. Oftentimes you don’t get paid or you only get a small amount of money. But you do get to stay at the campground for free. 

If the outdoors aren’t your thing, there’s plenty of work available at resorts, retreat centers, and cruise ships. I’m not a part of that circle, but I imagine that warm weather chasers have their entire own repertoire of options. 

Another cool thing is that anyone can do seasonal work. I think there’s an image that it’s only for people in their early-twenties who want to screw around before starting a typical career. That’s definitely not the case though. I’ve met people in every age range. I’ve met people in their thirties and forties who quit their usual grind to do what makes them happy. There’s plenty of career seasonal people who having been bouncing from place to place for years. And I know retirees who want to get away from home for a season. 

Essentially, if you have a passion for any particular place or line of work, there’s probably a job out there you can do.  

The Pros and Cons of Seasonal Work

Pros:

  • Who hasn’t had the urge to drop everything and start a new life? You have the freedom to travel to different states and countries as you please. It’s a great way to see a new place and experience it like a local while also making money.
  • There’s plenty of time to recreate and explore. Think about it; you’re in a new town and have the ability to get the vacation experience without the vacation price. Living in my current location of Stanley, Idaho has allowed me to backpack in the Sawtooth mountains, have chill floats down the river and go on white-water trips, and go the the Thursday night street dances and learn swing dancing.
  • There are usually job perks associated with seasonal work. I’ve already mentioned free season passes at ski resorts. I’ve also gotten random perks like free white-water rafting, horseback riding, use of guest-exclusive hot springs, snowboard lessons, discounts on gear, and even free therapy. 
  • There’s a couple months between work seasons in the spring and autumn, so you can go travel or do whatever you want. What other career could you possibly have where you get about four months off of work every year?

Cons:

  • One of the hardest things for me is making amazing new friends then having to say goodbye after a few short months together. There’s times I see those friends again after lots of time apart. And there’s other people I’ve had a great summer with and have never seen again. 
  • There’s a lot of uncertainty in this line of work. While it can be liberating not knowing what I’ll be doing six months from now, it can also be hard living a life in constant motion. 
  • You have to be very responsible with money to make a lifestyle of seasonal work. Once a job ends, there’s usually one or two months until the next work season begins. You have to save enough money to get by until the next paycheck comes along. 
  • No benefits is another con of seasonal work. You’ll have to figure out your own situation in terms of health insurance and retirement savings. 
  • Don’t expect to go home for holidays. These are the busiest times for vacation destinations, and they’ll need you to work.

What to Expect from Seasonal Work

Housing

Most seasonal jobs come with some sort of housing. You might have to pay a certain amount of money in rent every month for your housing. Or your housing might be part of a package deal. The place I work right now in Idaho provides free food and housing, which is not the norm. However, my base pay is less than what I would typically work for. 

Get an idea of what your housing situation will be. Sometimes you get a studio room with your own bathroom, mini-fridge, and stove top. Sometimes you get a room with a shared living space. Sometimes you have a roommate. A lot of raft guides I know just get a space outside to put their tent. 

Do some math before committing to a job. Compare what your base pay will be with the amount of money you expect to make every month. Mountain towns can be expensive, so be sure the job you’re taking will allow you to live comfortably and save money for after the season. 

Corporations vs. Small Companies

I hate to say it, but big corporations can be hard to work for seasonally if you have any issues that arise. Like, you can typically depend on having good perks, a steady paycheck, and getting hired easily. However, if you have any problems that need to be sorted out they probably won’t care very much. If you’re one person out of hundreds of employees, they’re going to look at you as a disposable asset.

I once worked at a ski resort and had a creepy manager sexually harrassing me at work. I tried to talk to HR about it, and they basically didn’t care at all. Then the manager was angry at me for reporting him, and I had to deal with him being aggressive towards me. It was a miserable situation to be in, and it stressed me out that he was allowed to be a creep at work with almost no consequences. I like to think the mountain delivered consequences though because soon after he broke his arm snowboarding, and I still laugh about it.

If you find a smaller company to work for, they generally care a lot more about their employees and your managers get to know you on a more personal level. You do have to be OK with having a smaller number of people around to befriend. Like, I’m perfectly happy just having a few dozen co-workers around to hang out with. So I like working for smaller companies. 

Co-Workers

I’ve met so many cool people doing seasonal work. And often I find inspiration for future jobs and places through the stories of my co-workers. They basically become my family away from home for the season we’re together. I might even get a house for the winter with some of my co-workers from my current gig. 

There’s also usually a few crazy people that I have to deal with. I’ve had co-workers who seem to go for this line of work because they generally have trouble keeping a job. You might find yourself picking up the slack for people who just aren’t invested in their job.

For some reason, misogynistic middle-aged men also seem to like seasonal work. I think it’s because they can act like jerks and just leave at the end of the season or get fired and go find another job. 

Money Management

There’s a perception that you only do seasonal work if you don’t mind being poor. I don’t think that’s necessarily true. I’m usually able to save just as much money doing seasonal work as I am doing any other job. I mean, you’re not gonna get rich doing this, but you won’t be broke either if you’re responsible. 

Think about it. You usually have one flat rate for housing, so you don’t have to worry about paying utility bills like electric, water, and internet. They usually give you a uniform to wear or you can dress casual, so you don’t have to buy nice, new clothes for work. There’s no need to buy much stuff because you’ll just have to pack your life into your car at the end of the season anyway. 

You don’t have to pay for gas for your commute because employee housing is usually either within walking distance or there’s some sort of transportation for employees. I once lived in ski resort housing where I rode the gondola to work everyday. Right now I live in the main lodge of a ranch, so I literally walk downstairs to my job. 

Tips for Managing Money While Working a Seasonal Job

  • Change your mindset from how much you can make to how much you can save. Create a simple budget before accepting the job. Add up rent money and whatever bills you might have, like student loans or your phone bill. Add up monthly pay minus taxes. Will you still be able to save at least $500 a month or more? If so, you can probably afford to accept the job. Nowadays I don’t like to take jobs if I can’t save at least $800-1000 a month.
  • Get a job where you can earn tips. You know who vacations at resorts and mountain towns? Rich people. While it can be more stress free to take a job with a base pay where you don’t have to deal with guests, you’ll also miss out on some money. Servers, bartenders, and guides probably earn the most in tips. I worked at a ranch where we had a tip share split between everyone, and it typically doubled my paycheck. 
  • Start putting money into your saving account as soon as you start working. The season comes and goes quicker than you think. You’ll have a couple months of unemployment before the next season, and you need to have money to get by until then. Plus, you’ll need money to get to your next destination and possibly pay a deposit on housing. 
  • You’ll probably want some outdoor gear so you can recreate on your days off. Don’t pay full price for anything. Scope out Craigslist because people will be selling their old gear so they can buy new stuff. Check out the thrift stores in town because people often ditch their gear at the end of vacation so they don’t have to transport it home. If you work for a big resort, they often give pro-deals to employees and you can usually get 40% off. There are also plenty of websites that sell last season’s gear at a discounted rate. You don’t need the newest, best stuff. You just need stuff that will reliably get you outside. 
  • Don’t overspend on food and alcohol. I mean, treat yourself every now and then, and go have fun. But don’t eat out everyday or go to the bar every night. The quickest way to blow through your paycheck is by partying constantly. Scope out the deals in town at restaurants too. When I worked at a ski resort pizza shop we gave discounts to resort employees. The cheapest thing on the menu was cheese sticks for $5, and we would add toppings. All the lift crew came to the pizza shop for lunch. 

Live With Less Material Things

Over the years I’ve depleted my belongings down to what will fit in my car. I also have enough room to sleep in my car with all of my stuff in it. So yeah, I don’t own a lot of stuff.

Essentially, you need your clothes, any day-to-day stuff you might use, and outdoor gear to recreate with. 

The less stuff you have, the less burden you’ll have to deal with. I usually leave a small amount of stuff at my parent’s house. I have friends who keep a storage unit in whatever town they like to return to between jobs and adventures.

If you own a lot of stuff that you’re not too attached to, you can just sell it. I came back from Nepal once almost out of money, and I sold a bunch of my outdoor gear that I no longer used. I made about $500 without putting a lot of effort into it. Additionally, I often just donate the clothes that I hardly ever wear. 

I’ve made an effort to be more eco-conscious as well. I try not to buy new clothes from stores. I usually check out thrift shops first or go to discount stores like T.J. Maxx. If I do have to buy something new, like outdoor gear, I’ll research the company first to see if their stuff is made ethically. Once you start being a responsible consumer, it really limits the number of places you can actually shop. 

What to Do With the Off-Season

As I’ve mentioned before, you’ll probably have a couple months of free time between seasonal jobs. I hope you followed my advice and saved your money because you’re definitely going to need it. 

There’s been times I’ve gone back home to Ohio to visit friends and family between jobs. This is a cheap way to get by because I stay with my parents. Plus, I often have to work during Thanksgiving and Christmas, so I like to have an opportunity to catch up with people while I can. 

I also have my car set up so I can live out of it. It’s great for road trips across the country because I never have to pay to stay anywhere. I just sleep in Wal-Mart parking lots. Sometimes I just road trip around and visit friends across the country. This is a great way to see a lot of friends in a short period of time. Also, the more seasonal work I do, the more friends I have all over that I can go visit. 

I’m also a big fan of traveling internationally. I usually only go to countries where I can get by on a budget. If you find a good deal on a plane ticket, it’s often cheaper to travel internationally than it would be to stay in the USA during your time off. 

Whenever I save up a lot of money, I take an entire season off from working and travel long term. So far, I’ve been on a 4-month long trip in 2015, an 8-month long trip in 2017, and another 4-month long trip in 2019. Plus, I’ve gone on shorter international trips in between. For real, find some good flight deals and you can make it happen. 

Get Out There and Find a Seasonal Job

Don’t be afraid to go to places you’ve never considered before. Some of my best memories are from living in towns I’d previously never heard of like, Salida, Colorado; St. George, Utah; and Stanley, Idaho. 

I’ve generally been disappointed when trying to live in uber-cool destinations. I spent a miserable winter in the Denver area working for a resort call center. It wasn’t worth the free ski pass because traffic was so bad to and from the mountains during ski season.

Take the leap and give seasonal work a go. You might miss home, but you can always go back afterwards if you want. Or it could be the best thing you’ve ever done and be the launching point for a life of adventure.

If you could drop everything and spend a season anywhere, where would you go?

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