Most of what I read today on remote work is persuasive in nature. In fact, sometimes I’ll read an article so vociferous I fear that if I don’t go remote immediately, the author will kidnap me and force me to code on a beach in Bali until the sun melts my body into a puddle of Arjun Soup. While this passion is great (clearly there’s something to remote work), I thought it’d be helpful to write something that helps you think things through for yourself and decide if remote work is for you. 

We’ll do this by looking at 3 common reasons people want to go remote: to save money, to travel, and to improve their work environment. We’ll examine each in-depth so that you can decide whether remote work really is a good move for you.

Common Reason #1: To Save Money

Cole, a software engineer at Google, comes home to his studio apartment in the heart of SF. After a long day (10 am – 4pm) of eating free snacks, napping, walking, and fabricating stories for stand up, he decides to relax by crunching some numbers.

“Hmm,” he says to himself, “I’m paying $3k per month in rent for this place. That’s $36k per year. I wonder how much I’d save moving to somewhere cheaper.”

He’s heard great things about Brazil, so he checks out Airbnbs in Rio de Janeiro. 


“A nicer studio in the most expensive part of Rio costs $800 per month?” He’s in disbelief, his mouth starts salivating, and his eyes roll back as he runs through the numbers in his head — 


“I’d save $26,400 per year on rent living in Rio.”

He thinks to himself that maybe his place in SF is too expensive — what if he got a bunch of roommates and paid $1,700 for rent in SF? He crunches the numbers again.

*Softer Gasp* 

“I’d still save around $11,000 per year on housing in Rio, except down there I’d live like a king, not a college student.”

So far he’s only considered rent. In SF his monthly cost of living would be at least $3,700 per month (with $1,700 spent on rent) whereas in Rio his cost of living would be around $1,500 per month (NomadList). That means he’d save around $2,200 per month and $26,400 per year living a more affluent lifestyle in Rio.

Cole starts sweating and opens up the compound interest app that’s on the front page of his iPhone. Quickly, he realizes that if he spent one year remote and put that $26k into an index fund that tracks the S&P 500, he’d have close to $110,000 after 15 years.

While this is certainly exciting, there are other factors that Cole hasn’t considered yet. For example, by going remote it might be harder to get a promotion, make connections, and be invited to interview for jobs. It may be possible that he’d save $26k, but give up more in terms of earning potential over the course of that year.

I haven’t found much data on whether it’s harder to get a promotion if you’re one of the only remote members of your team, but I’ve personally seen remote workers thrive at my company and on my team despite most of the organization being in-person. The key to their success is that they consistently communicate their increased productivity (we talk about this strategy here) and have incredible results. There probably is some disadvantage to not being there in person, but I think if you master remote communication, it’s possible to mitigate this risk.

If you’re leaving the epicenter of your industry (SF for tech) to work remote, then you’ll definitely miss out on opportunities to make connections, which are incredibly valuable. Losing out on networking is even more costly than you think because of how networks operate. If you meet one additional person, your network is likely to expand far beyond that one person as he or she will introduce you to five or ten others. While you can master remote networking, it’ll take more effort and will likely be less effective than connecting in-person. It’s hard to put numbers on this loss, but it’s really important to consider these factors as you come to your decision.

If you’re looking for a new job, then you should note that it’s likely that fewer recruiters will be interested in hiring you if you’re out of the country. One strategy to de-risk this would be to leave your location on LinkedIn as the city you currently live in and then explain to recruiters that you’d be happy to interview for a remote position or you’d like to start by working remote and then transition into an in-person role when it fits your timeline.

Common Reason #2: Travel

Cathy loves reading books set in foregin countries, following travel bloggers, and spending hours on r/digitalnomad each day. 

It’s a Monday in her office in Austin and she’s still a little hungover from the weekend. She went out with her college friends and they had the same conversations with the same strangers at the same bars they’ve been going to for the last five years. In the middle of a one hour meeting with absolutely no agenda, she opens up her computer and sees this:

“I’ve gotta get out of here and see the world,” she thinks to herself.

Cathy isn’t alone — the desire to travel is a huge reason that many people want to work remote, but when you push people on why they want to travel, they often struggle to come up with compelling answers. Partially, this is because traveling is a highly emotional experience and it’s hard for the intellect to catch up with the subconscious’ reasons for this desire. However, spending time exploring these reasons will lead to an enhanced, more fulfilling travel experience.

Do you want to travel because you’re discontent with your job? Being unhappy at work is a plague that requires thoughtful treatment. In this case, converting your current job to a remote one likely won’t get at the root issue. However, if you’re looking to switch careers entirely, you may want to consider quitting your job and taking some time off rather than going remote. Such a trip may give you a respite from an unpleasant occupation and the chance to explore other fields of interest so you can decide what you want to do upon your return. For example, you could travel to Japan to take a short course in design, then go to Colombia to teach English for a few months, and then spend a few months teaching yourself to code in Argentina.

You also may want to travel because you’re dissatisfied with the place you currently live — maybe the guys are corny, you’ve outgrown your friends, it isn’t intellectually stimulating, or something else. In this case, working remote while traveling could give you the chance to sample widely and find out what you like about living in different cities so that you can find a more suitable location once you’re back. Throughout your trip you should note what you like about different places and use the common threads to decide on a better place to stay long term. It also may be worth planning for a couple of months at the end of your trip to test out the experience of prototyping living in cities that you could see yourself settling down in.

Did you just go through a hardship? Traveling can be a great way to shake things up, but it may make sense to realize this is the catalyst behind your departure and that you should dedicate time to explore yourself and what you went through. It’d be a mistake if you spent the entire time distracting yourself only to come back to an unresolved wound.

Do you want to impress others? To answer this question, you can simply ask yourself, “would you travel if you couldn’t tell anyone about it?” If the answer is no, then you should spend some time examining why this matters so much to you — it’s very likely that social media is at the heart of it.

These are just a few of the more common sly reasons that can influence us without our awareness and some ideas for how to address them. It’s worth spending a few more minutes questioning yourself on why you want to travel so you can adjust your plans to maximize the benefit to your life.

Common Reason #3: Work Environment

Alfred’s doing that thing where he sucks the Cheetos powder off his fingers again, so John fires up his noise cancelling headphones. As he starts to get focused, Alice taps him on the shoulder to ask him a question. He gets back into the zone after 20 minutes and then his friends come by his desk to grab him for lunch. The heavy Indian meal sits at the bottom of his stomach like an anchor and he becomes so fatigued that he has to physically pry his eyes open in order to continue working. He barely gets anything done and heads over to the gym once the clock strikes five. It’s absolutely packed.

Many people are discontent with the modern work environment and over 40% of remote workers say that the best perk is that they finally get to have a flexible schedule. Additionally, many remote workers find that they have more time for focused work, and thus, really start to enjoy their craft. Others, however, find it hard to get motivated and need to see other people in the flesh every day. 

The only way to figure out if the remote work environment is better for you is by trying it for at least a couple of days per week while following our best practices and constantly reflecting on the experience. Does this feel like something you could do every day? What are the biggest problems and are there ways to address them? What are the biggest upsides and do they outweigh the negatives? Keep in mind that if COVID-19’s lockdown was your first time working remote, you’ve experienced a skewed version of it with few upsides and many downsides. Therefore, you’ll want to give it another shot to get a more accurate picture of what remote work is really like.

In Conclusion

As you can see, there are many factors to consider as you’re making your decision. Additionally, some roles (managers) may have more drastic downsides than other roles (designers or engineers).

While there is far more exploration to be done, hopefully this gives you a starting point in thinking about if remote work is truly right for you.