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I left Boston with two carry-on bags and a suitcase, intending to live in London for six months before returning home.

Four years and twelve countries later, I’m in Portugal, still living out of those bags…minus the suitcase. This arc of my life had a very defined beginning, but so far has had no definite ending.

This is the story of my past 1500 days.

  • Part II
  • Part IV

Going remote

As it would happen, the organizers of Movers and Shakas were unprepared for the volume of applications they received: for a pilot group of 50, they got over 90,000 applications. Bonkers. They decided to create a sort of ‘overflow’ group of 200, who would be more loosely connected to the program but would not be involved in core activities. Astoundingly, I was accepted into this overflow group. I’m not entirely certain what tangible effects it proved to have, but that acceptance instilled my migration with a sense of affirmation and welcome, and I’m certain my experience would not have been the same without it. Even now, only a few years removed from it, I struggle to recall how vividly alone I was; it’s the sort of thing I can only infer from how intensely I remember the healing of those islands.

Those islands. That time. I cannot describe it, but I will anyways.

When I first arrived, it was March 2021, a full year after my world shut down. I had never been there before, and to my COVID eyes the city of Honolulu felt absolutely bustling. I hadn’t expected tourism to still be going on, and I didn’t like it. Neither did Summer: we agreed that we’d stay at our Airbnb in the city (it was really a hotel that was looking for ways to make money when hotels were supposed to be closed) for only as long as it took to find a place to live away from it. We’d come with a few areas in mind already, on the northeastern edge of Oʻahu. It took us a whole month, but we eventually found an older couple in the wealthy beach town of Kailua who were renting out parts of their house while they checked off a bucket list item and moved into the city. It was a great deal for us: an open plan studio half the size of a small house for something like $1950/mo, within walking distance of the beach and town center, a short bus ride away from the mountains, and commuting distance from the city.

Around the same time that we moved to Kailua, my company started hinting about plans to reopen the offices. My stomach sank, but I’d known it was coming, and I was still confident in the decision I’d made before moving: it was time to find another job. It sucked. It royally sucked. I had been in a new position for just over a year now, on a new team, and I loved the folks I worked with and the new challenges I faced each day. And now I was going to leave it, because where the company could employ was at odds with where I had chosen to live. I hate leaving something before I’m finished with it.

But how to begin the job search? This was a time when the idea of remote work was not very mainstream yet: sure, the entire world was working from home, but not by choice and mostly with only the grudging acceptance of our employers. Sure, I’d been working for a Boston office while living in London for half a year immediately before COVID shut the world down, and so I had a bit of a head start on the whole dynamic; but the idea of intentionally hunting for a remote job felt very foreign to me.

Amazingly, FriendBnb came to the rescue for a third time: one of my good friends was also a former colleague, and when I told him about my situation, he presented me with the opportunity to join his company. He’d just been promoted to head of his engineering department, and needed to backfill himself on his old team; and he thought I’d be a great fit. The company was a startup, but it was also a remote-first organization, and they were willing and able to let me work anywhere I legally could, as long as I could overlap at least half the working day with the east coast USA. Plus, with the director of engineering as my referrer, my interview was ceremonial at best.

It was perfect. And the folks met during my interview day seemed interesting enough. With an offer in hand, I now needed to tell my boss I was leaving him. That was rough, and I did it over text on a weekend like a shitty boyfriend; I couldn’t stomach the idea of breaking up with him face to face, not the initial telling at least. I could tell it was a big blow to him, but he understood my reasons. He put some legwork into getting the company to offer up a counter offer to keep me, even though he knew I wouldn’t take it. I had managed to negotiate a later start date with my new employer, so that I could give my team a solid month to prepare for my departure. I remember sitting on the ground in the early morning, in the little sideyard of my studio in Kailua, having my final one-on-one with one of the more senior guys on my team in San Francisco; and I remember him saying

…Well this sucks. But good for you, man. Hit me up if you ever make it out to Cali.

The next week, I started my new job, and officially became a remote worker.

*  *  *

This is part of a longer reflection.

~ Daniel.
17 hours ago