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Working Remotely / Digital Nomads

Owned by Nathan Wailes
Last updated: Oct 25, 2023
5 min read

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How do people make the money-side happen?




How much do people make?


How do people like it?

  • 2013.02.27 - Scott Hanselman - Being a Remote Worker Sucks - Long Live the Remote Worker
    • This guy's website seems to be all about working remotely. I should definitely check it out.
  • 2013.09.12 - Alex Pszczolkowski (Blog) - How I thought I wanted to become a digital nomad.
    • HN discussion

    • "...there are some major drawbacks to this kind of lifestyle, that I’d like to share. They mainly involve two recurring, significant problems that I found I was facing: 1) Limited types of projects, you are able to tackle while on the road; 2) Illusion of freedom of choice concerning your location;"

    • "knowing that you’re on a constant move, quite often facing unpredictable internet access quality and desire to make the most out of your traveling experience you just can’t be doing some substantial, challenging work, that involves hours of analysis, discussions and complicated programming. There are just too many distractors around and too much stuff to see after (and sometimes during) work."

    • "working with a team of people that are more experienced and smarter than yourself is crucial for your development, and as a freelancer, doing minor gigs involving some MVC/CRUD application programming, you just miss out on a world of possibilities to grow and learn."

    • "creative, meaningful work, requires some routine"

  • 2014.06.06 - Working remote, 3 months in
    • she doesn't say anything that new to me
  • 2015.11.04 - VICE - Living as a 'Digital Nomad' Is Like One Super-Long Vacation
  • 2016.08.15 - HackerNews - Ask HN: Did some of you try the digital nomad lifestyle and not like it?
    • levelsio: "What many people do is travel then think "this is it, I want to do this forever", then travel, isolate themselves from their home communities, live in cheap places, make some money, share cocktail by the pool photos on Instagram with a hashtag #nomadlife and then get clinically depressed. Then they return to their home countries after 3 years, but they've lost touch with their old communities. And everything is expensive. And it's cold. Now they're worse off than before they left! That's not the way to go. (...) I did it, and it was fun for about a year until it got VERY tiring. It shouldn't be black and white. Digital nomad stuff should show us that we can have more freedom in terms of location. That means, deciding "I want to live/work in X for the next 3 months". And going for it. Then coming back home."
    • I need to go through the rest of the thread and look for the main ideas.

Are people as productive?

Interviewer: The gains in technology make it easier to live and work far from an office. Yet big cities have grown and become even more vital. Why is that?
Bloomberg: Fifteen, twenty years ago, when telecommuting was going to be big, I kept saying, “No!” Skype didn’t exist back then, but being on a conference call isn’t the same as standing at the water cooler. It just isn’t. And I think you gotta go to work. And I think people should be next to each other to the extent possible.

PLAYBOY: The promise of the internet was that we’d all be working remotely from hammocks somewhere and ordering pizza with a click of a mouse. But your company culture demands that employees show up and stick around.

HSIEH: We’ve always taken the view that we have to physically be together from an employee perspective. People don’t work as well remotely. The author Steven Johnson writes about something called the “adjacent possible”—this notion that great ideas bubble up from unexpected places and random interactions over time. We want employees all in the same physical space to have more collisions. In fact, we’ve done weird things to prioritize collisions over convenience.


What issues do I need to take care of when preparing to move abroad?

  • 2014.08.23 - TypicalProgrammer - How I work as a digital nomad
    • Get your banking set up.
      • Getting paid, paying bills back home, and getting money in a foreign country can get complicated, so sort that out before you go, because it’s close to impossible to open a US bank account remotely.
      • Open a bank account that won’t charge you crazy foreign transaction or ATM fees.
        • I recommend the Charles Schwab Investor Checking account.
      • Get a backup credit card that doesn’t charge foreign transaction fees.
    • Get your tax residence set up.
      • You might want to change your state of legal residence to a state that doesn’t have an income tax.
    • Get your mailing address set up.
      • You will need a mailing address in your home country. I use Traveling Mailbox.
    • You may want to get a lawyer in your home country and give them power of attorney, in case you need to have something signed and notarized.
    • Get your health insurance set up.
      • You can buy a travel insurance policy for catastrophic problems.
    • Get your immunizations.
      •  In some countries, such as Thailand, immunizations are advised but not required for entry, and it’s cheaper to get them once you’re here.
    • Take photos of important documents and back them up on Dropbox or a similar service.
      • passport, visa, prescriptions, credit cards, birth certificate

Bank issues

Receiving physical mail

  • 2014.08.23 - TypicalProgrammer - How I work as a digital nomad
    • You will need a mailing address in your home country. I use Traveling Mailbox. For a small monthly fee you get a US mailing address, scanning and online mail management, forwarding (including overseas), depositing checks, and package receiving. Many expats use parents, family, trusted friend for handling mail. You may want to get a lawyer in your home country and give them power of attorney, in case you need to have something signed and notarized. Sending documents back and forth by FedEx is expensive and you will have to go to a consulate or embassy to get notary service.

Processes for working remotely

  • When you need to step away from your computer:
    • set your Skype status to 'Away'.
    • update your 'Mood message' to explain where you're going.
    • bring your phone.
  • Whenever your boss tells you to do something, create a JIRA task for it, and use that to track and prioritize all of the things you've been told to do.
  • Use Notepad to track daily / smaller tasks.

Misc articles

World citizens / offshoring / renouncing US citizenship

Articles / videos

Paying US taxes while living outside the US

Nice places to work from

  • Starbucks
    • Deal with visual distractions.
      • Sit facing a wall.
        • Explanation: This may help you not get distracted by having people enter your field of view.
          • Explanation: I suspect people have a reflex to look at any person who enters their field of view, to make sure it isn't someone who may try to hurt you. At least, I've noticed this tendency in myself.
    • Deal with auditory distractions.
      • Wear earplugs, and then listen to music through headphones that you wear over your ears.
        • The idea here is to drown out "unexpected" sounds, which are what I find distract me the most.

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