We Work Remotely — And You Can Too?

If the title of this post sounds like a bad infomercial, it probably is. Just kidding, it’s my cynicism for the recent onslaught of articles heralding how easy it is to travel the world while working remotely (related: if you’re the editor a travel magazine, call me. Let’s do lunch).

I’m here to dispel some claims and bring you back to reality.

Claim #1 — Get Permission to Travel!

Reality: The truth is, many companies still believe that remote workers are not as productive from beyond the confines of their desk. Remember in 2013 when Marissa Mayer recalled Yahoo’s remote employees? She believed that a successful day at work was “about the interactions and experiences that are only possible in offices.” Although we virtual freelancers and employees know that’s not the case, it’s hard to dissuade the decision makers (but not impossible).

Claim #2 — Any Job Can Also Be Remote!

Reality: Although there are sites that aggregate virtual job listings, not all jobs and lifestyles are created equal. Mental health care providers, hair dressers, librarians…sorry but you guys are out of luck. People with children, pets, or spouses with a career in a specific city are out too. Common telecommute jobs do tend to be tech heavy, but others include marketing, virtual assistance, teaching (pending proper credentials) and sales.

Claim #3 —Join a Remote Work Program!

Reality: There are some super cool startups emerging that facilitate the remote work/travel experience. The catch? You often have to shell out thousands a month to partake. Plus, they’re not remote job providers. The reality is that freelancing can be unstable. Client load ebbs and flows. People who travel with programs like Remote Year or Hacker Paradise need to ensure that they already have a steady income stream and make enough to cover the additional costs of travel.

Claim #4 — Remote Work Means Flexible Hours!

Reality: Time and time again, I hear freelancers and independent contractors talk about how much free time they’ll have to explore. In actuality, no work means no paycheck. When you take time off to travel, that’s time that you’re not earning a paycheck. Did I mention that my wife and I work odd hours? When traveling, we match our hours with our clients in the US. That means while in Europe, our work day starts at 6pm and ends at 3am (local time). We’d like to work from Australia eventually, but we know this means our work day will likely start at 2am and end around 10am local time (I’m tired just thinking about it).

Claim #5 — Rent Your Home for an Additional Income Stream!

Reality: Unless you’re already a homeowner or have an extremely understanding landlord, renting out your space is not a viable option. True story: we have a friend who put his rental on AirBnB to help feed his travel bug while he worked his way across Europe. Two months in, his landlord stopped by for a surprise visit! The story doesn’t end well — it concludes with an unhappy AirBnB guest, an angry landlord, and a nearly evicted telecommuter hurrying home as his revenue stream quickly dried up.

I can hear bubbles bursting all over the world. It’s not all doom and gloom and it certainly is possible to travel as a telecommuter — but it takes dedication and flexibility to make this dream a reality.

Step #1 — Apply, apply, apply: Dig for those legitimate opportunities. This step is no different than applying for traditional in-office jobs. If you find a job that calls to you, send a follow up email. If you don’t get the job, ask what you could have done differently. Send intermittent emails to virtual companies and get on their radar. Persistence is key!

Step #2 — Beware of Scams: I’m looking at you “my last month paycheck was for $15,000 dollars and all I did was simple online work from comfort at home for 3–4 hours/day.”

Step #3 — Budget: My wife and I planned to travel throughout Europe for 9 months. Everything has a budget — from our flights, to apartments rentals, to groceries and “fun stuff,” like local sweets and museums. The real kicker? As independent contracts, we have to set aside money for taxes, health insurance and travel insurance. Often these costs equate to 30%-50% of your income. Guess what? If you can’t afford an extra excursion, then you don’t go. It’s really that simple.

Step #4 — Plan for Everything: As I mentioned earlier, remote work can be unstable. If you didn’t follow the earlier link under claim #3, spoiler alert: my company with over 400 full time employees shut down overnight, with no warning. My wife and I immediately put our heads together and outlined a new budget. That, and we hustled to find new clients like it was our job (because it was). So include a contingency plan and have additional funds set aside to cover bills if things go wrong.

Step #5: Take a Moment: You’ve come this far — well done! You have enough income to pay Uncle Sam, cover transportation, housing, food, and some sightseeing. Take a moment to enjoy the new country that you’re in. Immerse yourself in the culture when you can.

Now, get back to work.


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