How to Make Money

The Fun and Flexible Way I Funded My Travel Addiction for the Past 8 Years

Updated September 19, 2016
by Susan Shain
Senior Writer
seasonal jobs

Picture this: you’re riding a beautiful horse under a blue sky that goes on for miles. Mountains and streams surround you, and you feel like you’re in a watercolor painting. Riding alongside you are several new friends. As you describe the area and make jokes, one of them turns to you and says: “I can’t believe this is your job.”

That’s right: you’re getting paid to guide people on horseback rides under Montana’s Big Sky. You’d almost forgotten.

If this sounds like something out of a dream, you need to take a look at seasonal jobs. These jobs have allowed me to live around the country (and world), all while getting paid to do things most people only do on once-in-a-lifetime vacations.

What are seasonal jobs? And how can you find them? Read on to find out.

What Are Seasonal Jobs?

Just like they sound, seasonal jobs are positions held for a set amount of time. Though technically, working at Macy’s over the holidays is a seasonal job, we’re going to focus on seasonal adventure jobs.

I worked these types of jobs for almost six years after getting out of college. They allowed me to live a life of travel and adventure — all while earning money.

A good rule of thumb is that seasonal jobs pop up wherever tourists do. Which is great for you, because it means you’ll be working in places where others pay to vacation.

Think back to your last trip: Did you go on a guided tour? Did you chat with your hotel bellman? Did you eat out at a beachside restaurant? If so, chances are you interacted with a seasonal worker.

Seasonal jobs run the gamut from snorkeling guide to cruise-ship housekeeper to park groundskeeper, though the majority involve some sort of customer service. As for the seasonal workers themselves, they come from all different backgrounds, but they have one thing in common: they love the fun, adventure, friends and freedom that seasonal work provides.

The Pros and Cons of Seasonal Jobs

With seasonal jobs, I’ve been able to kayak in the Alaskan rainforest, ski a world-class mountain every day, explore new countries, and make memories and friends in amazing places.

Though I loved my time working seasonal jobs, they definitely aren’t for everyone.

In general, here are the pros of seasonal jobs:

  • Interesting jobs; no cubicles allowed
  • Opportunity to live in beautiful places
  • Housing is generally provided or subsidized
  • Short-term commitments; opportunity to live and adventure in many different places
  • Easy to travel during the off-season
  • Lots of new friends and experiences

As for the downsides? I’ve had to say goodbye to a lot of great people, I’ve never taken the time to hang pictures on the wall (since I move so much)… and I don’t have a dog. (That’s the worst part, if you ask me!)

In general, here are the cons of seasonal jobs:

  • Lower-than-average pay
  • Long hours during the season
  • Instability and up-rootedness
  • Tough to maintain relationships or have pets
  • Constantly on the lookout for the next job

Overall, I highly recommend this lifestyle — at least for a little while. You won’t be making a lot of money, but when you’re living in a community of similar people, you don’t notice it too much.

How to Get a Seasonal Job

Getting a seasonal job is surprisingly easy. Since they (generally) don’t pay a lot and are short-term, most people don’t give them a second thought — instead preferring the security of a more traditional position.

If you think they sound neat, however, here are five steps to getting your first seasonal job:

1. Take Stock of Your Interests

Think about what industry or region you’d like to work in. For example, if you love surfing, Hawaii would be a sweet option. Or if you’ve always been obsessed with Glacier National Park, start scouring jobs in the park and its surrounding towns. My favorite website to get ideas and find jobs is CoolWorks.com. (I list several other sites on my resources page.)

2. Research, Research, Research

Now for the fun part. Let’s take the surfing job in Hawaii as an example. First, Google the obvious: “surfing jobs Hawaii” and “seasonal jobs Hawaii.”

If you want to get more in-depth, think like a tourist — because that’s where the jobs will be. Start searching for “best surf spots Hawaii” and “surf shops Oahu,” and you’ll soon have a list of potential employers. Thoroughly read their “Employment” pages, and if someone on your list doesn’t have one, call. (Like this idea? Click to tweet it!)

3. Apply, and Apply Early

Seasonal jobs often get filled months ahead of time. If you’re applying for a job starting in May (summer season), get your applications in by December or January of the previous year. If you’re applying for a job starting in November (winter season), get your applications in by June or July. The best jobs fill up quickly.

In most places, it’s possible to show up before the season starts and find a job in-person — but for your first seasonal job, I’d recommend locking it down beforehand.

4. Take time with your application

A polished resume and well thought-out cover letter will give you a big leg up on your competition. Apply for several jobs, and let your enthusiasm shine through in your interviews.

It’s also important to get as much information as you can from your potential employer. Since you won’t be onsite to meet with them or see your working environment, questions are the next best thing. In addition to questions about the job itself, you’ll want to ask about housing, days off, fun things to do, end-of-season bonuses and cost of living.

5. Get ready for the experience of a lifetime

Have fun, get involved in your community and make some new friends. You’ll find that once you’re integrated into the seasonal lifestyle, finding your next job will be much easier.

With seasonal jobs, a world of opportunity and adventure awaits. What are you waiting for?

Your Turn: Have you ever worked a seasonal job? What type of job would you be most interested in?

Susan Shain (@TravlJunkette) has been working seasonal adventure jobs and traveling the world since 2008 — all on a strict budget. Follow along on her blog, Travel Junkette, to learn how you can do the same.

by Susan Shain
Contributor for The Penny Hoarder

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