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Home » Working Remotely » Remote Working Creates New Travel Opportunities
Working Remotely

Remote Working Creates New Travel Opportunities

Kyle Stewart Posted onApril 26, 2020September 13, 2021 17 Comments
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During the coronavirus crisis, nearly everyone learned to work remotely. As the world reopens new travel opportunities will arise as a result.


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Working Remotely

Anyone who can continue to work from home is doing so. Employers and employees are learning the importance of setting personal schedules, adding technology to their lives they otherwise wouldn’t use and keeping business moving without being in an office physically.

Many employers were less comfortable with working remotely than they otherwise should be. There was a stigma in some organizations that working from home was less productive regardless of whether the notion was factually based. But like it or not, all employers that could carry on from home had to give it a try and discovered it wasn’t the pariah it was thought to be.

Tim Ferriss discusses this in his kitschy but effective tome, The Four-Hour Work Week. It’s cheesy but delivers salient points around the topic of working efficiently and remotely.

Very Remotely

Work rules will change as a result of self-quarantine. Employers will likely be laxer regarding coming into the office in person. Those that don’t meet clients or manage in-person teams will find that they are able to continue working remotely, even very remotely.

Spend a month abroad. Yes, a month. Many that have stayed home have saved money over the last couple of months and may be able to extend their travel budget. Further, when you stay longer, especially in an apartment or home, you can shop at local markets, cook for yourself and spend little time getting to your destination with respect to the overall length of the journey.

Working remotely has completely reshaped Chiang Mai, Thailand. Inexpensive living costs coupled with exceptional weather in Thailand’s northwest rainforest has brought remote workers from across the world. Some struggle with work hour adjustments (opposite to US eastern time) but make it work for them and their employer.

Chiang Mai hotel
Chiang Mai hotel
Chiang Mai night market
Chiang Mai night market

It doesn’t have to be Thailand, maybe the time zone issue is a bridge too far. Airbnb lists condos in Quito, Ecuador for $500-700/month in the city center with views of the Andes.

Airbnb Quito
Airbnb Quito

One of our own readers owns this property, a luxury apartment in Guadalajara. Message him and negotiate a monthly rental, I am sure he would welcome the occupancy.

Airbnb Guadalajara
Airbnb Guadalajara

Selling Your Boss

The hardest part about working remotely, especially when it wasn’t a condition of hire, can be hard work. I have previously sold my boss on what we called “unlimited vacation” but was really the ability to work remotely as I saw fit. This is how I did it:

  • Never miss a call, meeting or email.
  • Maintain productivity at or exceeding prior levels.
  • Bear all of the cost of telecommunication with no additional work for the employer.
  • Request it on a trial basis, offer to abandon the practice if it’s not working.
  • Offer a reduction of vacation days (you won’t need them anyway.)

Conclusion

Working remotely for traditional office employees was a rare and limited option. Now that many have proven they can work just as efficiently from home, there is a new opportunity to work from abroad in a way that would have otherwise been unfeasible.

What do you think? Has working remotely the last couple of months changed hearts and minds at your employer? Have you worked abroad for an extended period of time before? What tactics worked when selling your employer on the concept?

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About Author

Kyle Stewart

Kyle is a freelance travel writer with contributions to Time, the Washington Post, MSNBC, Yahoo!, Reuters, Huffington Post, MapHappy, Live And Lets Fly and many other media outlets. He is also co-founder of Scottandthomas.com, a travel agency that delivers "Travel Personalized." He focuses on using miles and points to provide a premium experience for his wife and daughter. Email: sherpa@thetripsherpa.com

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17 Comments

  1. Eag Reply
    April 26, 2020 at 1:46 pm

    Why would you not still need your vacation days? That doesn’t quite make sense to me.

    • Kyle Stewart Reply
      April 26, 2020 at 3:40 pm

      Most people use their vacation days to travel away from their homes, but if you’re already abroad, they are less important and can be a valuable negotiation tool.

  2. Mike K. Reply
    April 26, 2020 at 2:15 pm

    Great article Kyle. And so spot on target. Thanks for mentioning my apartment in Guadalajara! That was a nice surprise to wake up to this morning. Many people are working remote. In fact, my current tenant originally booked it for 1 week and has extended now for the past 6 weeks as he finds it more comfortable than his house in the USA. He has been working remote since early March.

    I travel more than 100+ days a year and many times in Airbnb properties. The key is to always ask the owner/property manager what the Internet connection is like and what the speeds are like if you have to work. Some are really great and some are bad and it’s important if you have to work.

    I’m sure everyone can’t wait for things to go back to normal. Stay safe.

  3. Kory Reply
    April 26, 2020 at 4:01 pm

    If you work for a large firm, they won’t sign off, Permanent establishment rules and tax considerations, legal, HR, etc. will apply if an employee who typically works in, let’s say the US, starts working remotely in another country. This has already been considered at my large multi national firm and bigger companies will have policies in place already. There are business considerations that don’t make it as simple as just working on your normal day to day work remotely on US hours and getting the job done as you’ve always done. Plus as an individual there are your own foreign tax considerations to account for working remotely.

    • James Reply
      April 26, 2020 at 8:32 pm

      100% correct, there are legal and tax compliance policies that large organizations are subject to in that their employers must perform work in the country they are on payroll in.

      • James Reply
        April 26, 2020 at 8:33 pm

        employees*

      • Kyle Stewart Reply
        April 26, 2020 at 10:53 pm

        So, let’s pretend an employee for Deloitte is on a three-week holiday to Spain. One of her most important clients is unexpectedly in turmoil and requires her attention day and night. She takes phone calls, returns emails but as the situation is day-to-day, doesn’t return to the US. She works every single weekday of her holiday from dawn to dusk. What’s the tax implications for Deloitte and the employee?

        • MeanMeosh Reply
          April 26, 2020 at 11:32 pm

          So you’ll laugh, but I used to work at the accounting firm you used as an example, both in the expat services group and as an expat, so I’ve had personal experience with this.

          The answer: it depends, but if you work in a foreign country continuously for 3 weeks, there are countries where both the employee and employer can become taxable in that country. In India the threshold was just 14 days, with some exceptions if you were there exclusively for “training”. There are certain US states (cough…California…cough cough) who technically view you as an employee as liable for state income tax for doing as little as responding to e-mails at an airport in that state. It is fuzzier if you don’t physically work out of an office in that country, but never assume either you or your company are in the clear. I can tell you Deloitte took these issues VERY seriously and you’d have some explaining to do if they found out you were working remotely outside your home state/country without clearing it up with national HR. It’s been 7 years but I can tell you at the time I left, you wouldn’t have been granted permission for the type of remote arrangements you describe.

  4. Simon Reply
    April 26, 2020 at 4:55 pm

    I’ve done this previously. Worked in Europe for 2 months and other than a few people that called regularly and noticed my office line always forwarded, no one would have been able to tell outside of myself and my boss.

  5. Ed Reply
    April 26, 2020 at 6:14 pm

    I tried remote working in Bangkok for a couple weeks but had to keep US hours to answer emails and phone calls. As you mentioned, the time zone dilemma can be a challenge. I was aware of the situation before embarking on the trip. I kept the hotel room curtains closed to make myself less aware of the time when I was working and sleeping. Overall it was a fun and memorable experience living in a place where my day was night and night was day. I’ve been to Bangkok many times and knew there would be scare time to be a tourist. That’s the best way to approach any remote working plans. Be realistic about your need to be tied to your laptop in real-time and you wont’ be disappointed.

  6. Stuart Reply
    April 26, 2020 at 6:47 pm

    Brazil, where I have an apartment, is the best. Fairly time zone compatible, no jet lag, easy flight options to the U.S, thousands of miles of beaches, and a three bedroom apartment in S.P. or Rio with a full time housekeeper can be found for around $1800+ a month in the best areas (especially now with the exchange).

  7. emercycrite Reply
    April 26, 2020 at 8:14 pm

    LOL like this would even be a remote possibility for employees of most larger companies.

    • Kyle Stewart Reply
      April 26, 2020 at 10:54 pm

      I achieved it twice at two publicly-traded companies. It’s not as complex as it is made to be due to its informality.

  8. PM1 Reply
    April 27, 2020 at 8:27 am

    Hi Kyle, thanks for this timely article. I have been spending a few months a year in 2 week long spurts working in India for the past few years. My US VOIP phone is plugged in which allows me to receive the same calls and my phone plan (T-Mobile) allows me data and texts. It has been very nice spending time with family and friends. We also have an office in India with people reporting to me. I couple the trips to visit family and friends with a visit to the office (in a different city). Being in the same timezone also helps.

  9. Ak Reply
    April 27, 2020 at 10:08 am

    For some, this all is exactly right. For some others, who think they are being “productive at home,” the harsh reality will sink in when they are not invited back when the office reopens.

  10. Steve Reply
    April 27, 2020 at 11:13 am

    I work remotely (even pre-coronavirus) but have to travel to customer manufacturing sites about every other week. I know you travel with your young daughter, but my wife and I have a 3 and 5 year old and haven’t quite hit the hump where we feel like living/working remotely for a month would be less stressful than just being at home. But I think once they are a little older (in school), during the summer we’ll probably book a month somewhere remote, and I’ll just take 1-2 trips from whatever local airport to where I need to be. But this limits us basically to North America, I can’t be taking a trans-pacific flight to CA for a few days then heading right back :-\

  11. docntx Reply
    April 27, 2020 at 8:36 pm

    Excellent piece!
    Would this in some ways link to outsourcing the jobs overseas?
    Simply get a lower cost employee who can work from home, abroad. then you do not worry about having remote sites. Might this be a slippery slope?

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