'Now he's hinting that my performance slipped because I'm 'too comfortable'': Remote worker moves abroad to Portugal, doesn't realize that his boss is setting up a paper trail to fire him

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Jesse Kessenheimer • Writer and Editor
Nov 14, 2025 10:00 PM EST

Immigration is a complicated thing. At the risk of sounding boooring, there are taxes to consider, visa paperwork to file, and in many cases, a pesky language barrier that'll humble the most book-competent second-language learners. It's a whole ordeal. However, arrogant remote workers see their privilege to work from home as a privilege to work from ANYWHERE… Globally.

You'd think it would be common sense to look up labor laws in your future country of residence, since the answers to all your future questions are just one Google search away, but as we see in the next story, asking for forgiveness instead of permission seemed to be this worker's technique. A remote worker was thrilled their company offered the option for them to work from home, so they decided to move their 'home' somewhere a little cheaper and a little more exotic: Portugal. 

Like many "digital nomads" who once dreamed of the beaches in Lisbon or the mountains of Madeira, this worker was thrilled to head abroad and still keep their job in the USA, but as I mentioned before, it's not so simple as purchasing a flight. And once their boss caught wind that they were trying to pull a fast one on their company and the entire country of Portugal, they started laying the groundwork for a valid, swift, and final firing. 

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  • Remote man working on a terrace.
    via Truecreatives

    Image is representative only and does not depict the actual subjects of the story.

  • My boss thinks I'm on vacation because I moved to another country while working remote
    via voidtape_artists
  • I told my manager months ago that I was planning to work from Portugal for a few months since the company allows full remote. Flights were cheap, rent is half of
    via voidtape_artists
  • what I paid in Chicago, and I'm still online every day from 9 to 5. Last week he messaged me asking if I was "enjoying the beach" and if I
    via voidtape_artists
  • could "focus more on projects once I'm back from vacation." Dude. I've been working the entire time. My VPN logs literally prove I've
    via voidtape_artists
  • worked more hours than anyone on the team. Now he's hinting that my "performance slipped" because I'm "too comfortable." Meanwhile, I'm
    via voidtape_artists
  • shipping code at 11 PM local time. Do managers think remote means "working from a hammock with a mojito"? I'm this close to sending him a screenshot of my Jira board labeled "vacation mode: off."
    via voidtape_artists
  • throwRA0945.... Just email him what you did everyday so he cannt say you arennt doing anything
    via throwRA0945
  • ZombieCyclist Full remote doesn't mean other countries very often. There are work place legalities, insurance, oversight, a whole bunch of things. Did your company approve working in another country? Edit: plus probably on a tourist visa so shouldn't be working in Portugal either
    via ZombieCyclist
  • Man working remote in the tropics
    via TrueCreatives

    Image is representative only and does not depict the actual subjects of the story.

  • karmassacr People don't realize it but you can't just up and move somewhere while employed without telling your employer. It can get them in serious financial and/or legal trouble.
    via karmassacr
  • pHgirl ⚫ Just tell him you moved back and continue working remotely with a VPN that spoofs your location in Chicago
    via pHgirl
  • bedel99 I hope you're properly paying tax in Portugal. chramm This guy is skirting foreign labor laws and tax liabilities and pretending his employer is infinginging on him
    via bedel99
  • Cubsfantransplant Did you request to work from Portugal? Is your company authorized to employ people in Portugal? Are you legal to work in Portugal? Full remote does not mean work from wherever you want to.
    via Cubsfantransplant
  • PearlsRUs Yes, a lot of them do think that. Sounds like your manager is setting the stage to disallow you from working out of the country again. BrilliantHumble9560 man saw sunlight on your timezone and decided you're on sabbatical.
    via PearlsRUs
  • noclue9000. By going abroad and putting it in writing Op basically gave them legal reasons to fire him or her
    via noclue9000
  • dysonrules ⚫ "I'm remote, so I'm working in a different country." cringes in payroll tax My employer fired two employees for moving to different states where they were not set up to collect payroll tax. I'm baffled that people think it's just a matter of connecting to the internet and everything is fine. Dealing with international employment tax is a next level nightmare. Don't be this guy.
    via dysonrules
  • Man working remote in the tropics
    via TrueCreatives

    Image is representative only and does not depict the actual subjects of the story.

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