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Stay a Remote Worker Permanently – Here’s How

by Kyle Stewart

Many of us have gotten a taste for the remote worker lifestyle and we aren’t going back to our offices. Here’s how to stay remote even after the pandemic is over.

Convincing Your Boss you should stay remote

Perhaps the best thing to come out of COVID-19 and the crushing global pandemic is that companies have reorganized their business strategy outside of the office environment. Now more than ever, employers are more likely to allow employees to work from home full-time. In fact, many businesses are planning on fewer employees (if any) coming into the office even when the pandemic comes to a close and are downsizing their office plans.

But that doesn’t mean workers won’t still have to convince their employers that working from home is better for everyone. Is the company still getting the same return on investment as it was with the employee in the office?

Tim Ferriss in his landmark book, The Four Hour Workweek, Ferriss describes a process by which employees can prove themselves more valuable located virtually than in-person.

The key is to demonstrate productivity over presence. The impetus is on the employee seeking to work from home to measure their productivity away from the office against results when in the office. Regardless of the position of the employee, if their work is possible from home, one should work to deliver the same if not better results to management to send the right message.

For reluctant employers, make a trial proposal: Let’s try it for a month and compare. If my productivity decreases, if I miss meetings or appointments, I’ll come back to the office – no questions asked. But if I am just as productive or more so, then remote working should be available until the unlikely event that productivity levels drop.

Agree on metrics in advance. If you’re in sales, demonstrate you make the same number of calls, submit the same number of proposals (or more.) If you’re in tech support, demonstrate that the same number of tickets have been successfully closed. If in a management role, show that you have been keeping tabs on your employees and they are succeeding.

Preparing Your Lifestyle Change

Working remotely doesn’t have to mean working from home. The freedom of remote work isn’t limited to avoiding the commute to work (though that’s nice too), it’s being freed from a geographic location entirely. If a remote worker with reliable connectivity is available and productive during work hours, does it really matter where the worker is based? I’d posit that it does not.

I grew up in Nebraska which has four full seasons including a very, very cold winter. If I had the opportunity to live and work in Mexico (much of the country is in the same time zone) who wouldn’t trade snow shoveling and gray clouds for palm trees and tacos?

Here are some things to consider when remote workers become very remote:

Long-term rentals

Living in a hotel isn’t sustainable for the long haul but is a good place to land when newly remote workers first move to a new location or country. Workers should seek out long term rentals but perhaps not through the traditional channels.

a pool with a view of a city and a skyscraper
Work from the Park Hyatt Bangkok

My wife and I moved to Thailand for an extended period of time. We found our home after shopping them on Airbnb and ultimately visiting them in person when in our destination city. For our stay, we found an apartment that was a two-level duplex penthouse with an ocean view (minutes from the beach) and negotiated for a six-month stay. The longer duration gave us more flexibility to achieve a price point suitable to our budget and gave us a strong negotiation position.

Pro Tip: If the home owner lives nearby, arrange for an initial one-month rental and then pay upfront for the next month in cash direct to them, saving the expense of cleaning fees and commissions to third-party vendors.

We were able to secure our duplex for the six months of our stay for 65% off the nightly rate bringing an $1800/month apartment to just over $620.

Renting out your own property

Many may be concerned about their own apartments or homes. What should a remote worker do with their property while they are away? Luckily, services like Airbnb and VRBO make it possible to rent out homes easily. While some valuables and personal effects might need to be placed in long-term storage or with relatives, many business seek rental homes for executives moving into a new area.

These arrangements can be 3-12 months and require the home to be furnished. The best part about corporate rentals is that customers pay on time and will offer a premium as they do not have to rent furniture for their housed staff.


Every new worker should seek out opportunities for arbitrage. Find a place where your money goes further while continuing to make US dollars at home. This allows the remote worker to maximize their happiness and their bank account.

Consider Portugal, a six-hour time difference from the East Coast of the US. Work days start later (feel free to sleep in) as 8AM in New York is 2PM in Lisbon. Remote workers will have to work later (10/11PM local time) to accommodate their co-workers at home, but for a seaside view and Portuguese sausage it’s worth it. Another option is to request an earlier start and finish to the day.

For workers that can focus on tasks that do not require collaboration earlier in the day before their peers arrive into the office may be able to curtail hours that extend into the night. Meanwhile, the lower cost of living in Portugal will quickly add up to savings and a better experience for the employee.

a plane taking off from a runway

Major cities may not offer the comparative cost advantages over US cities, but heading to the coast or smaller cities will create a financial arbitrage that is addictive and highly advantageous.

Utilize the Movement’s Momentum

It’s been more than 13 years since Time Ferriss published The Four-Hour Workweek. His seminal piece outlined how to work remotely and free yourself from the bonds of the office. Now, the world has embraced the movement and businesses are seeing its advantages. Utilizing the momentum that remote work has built is essential.


There has never been a better time to be a remote worker. There’s never been an easier time and manner by which to achieve it either. If you want to work from home, from the beach, from Mexico or Siberia, now is your moment. It’s also a good time to reconsider what you need or want for yourself and your future. It’s entirely practical and now possible to never go back to the office again, so give it a try.

What do you think? Will you stay a remote worker permanently?

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Dan November 16, 2020 - 8:01 am

I’m never going back to an office again. I had already made that call in Jan 2019 when I left my in-person job to work for a fully-remote company but I’m certainly not going back now

Mary November 16, 2020 - 8:11 am

I’m curious to hear your tips on how you deal with health care when working/living remotely.

The C Boarding Group November 16, 2020 - 9:04 am

I think it depends on where you go. If you stay domestic, it’s like you won’t have any serious issues – perhaps some out of network challenges depending on your plan. Internationally, however, could be an issue, but we would recommend following the same methods that digital nomads use for health when traveling abroad.


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