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How Seasonal Side Hustles Can Earn You Freedom to Travel

Fund this year’s vacation or become totally location independent — a seasonal side hustle can take you as far as you want to go.

How would you like to work for only nine months out of the year? Where would you go if you had the freedom to work in a different city every week? What if you didn’t have to choose at all between two passions or careers? 

Location independence—in other words, the freedom to choose where and when you work—is just another excellent reason you should start a side hustle

Working on your hustle fulltime for a season, instead of part-time year-round, can give you a huge boost toward earning financial and location independence.

Seasonal Workshifting

Seasonal work-shifting is the practice of changing the type of work you do base on the time of year. Traditionally anyone whose work depended on the weather (like farmers or builders) had no choice but to practice work-shifting. 

Today, even big corporations whose employees work almost exclusively indoors at computer stations often change their marketing, design, and production efforts based around holidays and cultural consumption patterns that shift with the weather. 

Seasonal workers whose jobs actually end on a certain calendar date are in one of the best possible positions for travel and hustling. If that’s you, then every single year, you’ve got a built-in chance to hit the reset button on your life to work on a passion project that could take you anywhere.

If you’re not a seasonal worker right now, that’s ok. You can start your hustle on mornings, nights, or weekends like just about everybody else to build confidence, skills, and cash for a year or two, then make the jump.

Choose your hustle and destination

Personally, I turned two hustles that I started to make extra cash during a service year into a hybrid career.

I work in the sun as a landscaper in New Jersey in the warm months. Then I pound the keyboard as a freelance writer in the winter from, well, anywhere I choose. Preferably somewhere indoors, toasty warm, and with plenty of good coffee to warm me up between snowshoeing expeditions.

I know others who hustle and travel seasonally; like my friend Ethan, a construction entrepreneur in New York who works as an Elk hunting guide in Colorado every winter; or Christi, who works at a thrift shop in the winter and as a law enforcement officer at national parks around the country the rest of the year. 

The possibilities are limited only by your own sense of adventure.

A friend of mine recently bought art by “Drawn There,” run by a sketch artist who turned a commissioned-art hustle into a life of full-time travel.

I met a guy named who went by “Grizzly” (a nickname probably earned by his fantastic beard) who quit his New England mechanic job. He leads off-road tours in Utah in the summer and backpack around the Southwest in the winter. 

A husband and wife team I know quit the professional concert circuit to live off-grid in the mountains in the summer. They run a home repair service out of their camper van in the winter. And their son is along for the ride.

I chose these examples because so many people focus on the highly popularized image of the “digital nomad”. When talking about location independence it’s usually a trendy twenty-something tapping on a keyboard in a hipster coffee shop or typing emails in a bikini on a white sand beach.

If you’re a trendy twenty-something and that’s your vision of freedom, that’s awesome. My hustles have let me live that vision, too (well, minus the bikini). But I want you to know there’s so much more you can do.

Plant in one season, harvest in the next

The key thing to remember here is that nobody just wakes up with their dream hustle. 

I started mowing lawns on the side to pay my rent. I took steps to grow that hustle into a highly profitable business. It then enables me to spend the less lucrative time necessary to build up the location independent, winter portion of my business as a writer. Grow it to the point where it can now support itself.

My friend Ethan, too, worked hard to start his own light construction outfit. He spent a couple of years learning the arcane skills of saddle packing, elk-tracking, and campfire-cooking-for-rich-guys before he could dependably look forward to serene pine-scented mountain grandeur, steaming coffee, and horse breath on snowy mornings, and thousand-dollar tips every winter — his version of the rich life.

Whatever your dream hustle, or your dream destination, spend a season working toward it. You’ll be amazed by how far you go.

Your next steps

If you want to learn more about using a side hustle to earn the freedom to travel, check these resources:

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