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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 III
  • Part V


Summer soon joined a coworking space with a surf club in Town (the local name for Honolulu city) and began commuting over the mountains every day and surfing after work. I joined her occasionally (in the commute, not the surfing) but I preferred to stay in Kailua most of the time: things moved more slowly there, and I loved it. I worked from home a few hours each week but mostly I worked from cafés, as had become my habit in London: most places on the island were “open” by this point of COVID, with mask mandates in place. I quickly established my place as a regular at a few of my favorite spots and began growing my own community. I eventually became light friends with the married owners of a new Singapore café that opened up shortly after we moved there, and I came to look forward to their company throughout the week.

On most afternoons, I would be walking through town to my next work spot, and would invariable encounter the one I called ‘Kailua man’: a clean but scraggly middle-aged man with a long unkempt beard, walking around in a flannel shirt, cargo pants, and incredibly worn backpack; he could usually be found on the bench outside Whole Foods, watching the people and chickens, sometimes doing sudoku or crosswords. We never spoke, but we would often make eye contact with each other.

In the evenings, Summer and I began learning how to surfskate, and we’d spend a brief hour after dinner most nights skating down our street in the fading light. Sometimes we’d walk to the beach and watch the waves instead. Our beach was quite long, very local, and well-taken care of; the only trash you ever saw were the microplastics that would wash up to shore, and there was never a crowd, just small gatherings of friends and family with plenty of space in between. I wouldn’t call myself a beach person, though. I enjoy them, but I don’t seek them out. I’m mountains, forests, and rocks guy, and Hawaiʻi has plenty of those natural beauties, too.

All too soon, Hawaiʻi ended for us. We were there together for only six months (I was there longer on my own) but they way we were living, the place, that time…It seemed we’d been there for a year, at least. But after six months Summer returned to school in London, and for the second time I stayed behind to finish out our apartment lease before following.

This time, though, I was not eager to leave, and not eager to arrive, either. It was October, and I’d experienced life in London during the winter: if Summer hadn’t been there, I wouldn’t have ever thought of moving back. And this time, we wouldn’t even be living together: she had found a community of grad+ students to live with, basically a dorm unattached to any particular university, and I’d encouraged her to live there; it seemed like good soil for a grad school experience, and I’d figure out my own living situation hopefully nearby. So it’s perhaps unsurprising that I figured out a slight workaround to moving to London for the winter again.

While chatting on the phone about what we could do for the Christmas holidays, Summer brought up the idea of heading to Lisbon, in Portugal. We’d tried to go there for Christmas the last time we were in London together, but our airline went on strike the day of our flight and so that didn’t happen. I liked the suggestion, and began working through the logistics in my head, and that’s when I realized I didn’t have to move to London immediately: I could move to Lisbon first! There was absolutely no reason I was moving to London except to be with Summer, but we weren’t even going to be living together, and she was about to get 120% absorbed into grad school life; odds were good we wouldn’t be seeing that much of each other for awhile, even if we lived next door to each other. On the other hand, if Summer wanted to go to Lisbon for Christmas, I could just go there first, directly from Hawaiʻi, stay there until at least the new year; she could come stay with me for the holidays, head back to school, and then I could figure out how to move to London. And skip out on most of the winter dread!

It seems cute to me now, but at the time my mind was mildly blown by the realization that I could actually do that. This decision is where I would point to as the true beginning of nomadic life for me. Yes, I’d technically been working outside the confines of an office, in multiple geos, for two years at that point; since the autumn of 2019. But that just isn’t the same thing, like working from home isn’t the same thing as working remotely: each move had a well-defined end and expected return to the office and home in Boston. Except for Hawaiʻi, but even that move hadn’t been taken with the intention of being nomadic: everything about it I had characterized in my head as a ‘move’, a full-on changing of homes; and even though I had decided ahead of time to find a new job once my then-employer asked me to return to Boston, I was honestly expecting to find a local job, in Hawaiʻi. I still imagined the nomadic life as being the realm of freelancers, and thus out of my reach.

But Summer encouraged me to do it. To move to Lisbon first. She was excited for me to explore this new freedom I’d found. I was excited too, but nervous, and reluctant to continue our separation. For whatever reason, being on the other side of the world feels the same as being a train ride apart: we’re not occupying the same space, the same life, and that makes the distance feel infinite.

I decided it would feel mostly the same level of suck whether I lived in London or Lisbon. So I started looking for housing in Lisbon. I don’t quite recall which Slack group it was, but by this point I had joined two community Slack groups as a result of beginning my remote work journey: one was the Hawaiʻi Slack community, which I was brought into via the Movers and Shakas program; and the other was called Nomadlist, which I’d bought my way into and contained a community of digital nomads. I think I asked around in both groups for living recommendations in Lisbon, and someone named Hollie pointed me to something called a ‘co-living’. ‘Co-‘ standing for ‘community’ or perhaps ‘communal’, it was something that seemed like a dorm…but for adults? And without bunkmates? And without anything obvious bringing them together. I didn’t know what to make of it, but the personal recommendation, combined with the look and feel of their website and Instagram, made me feel something, was giving off vibrations that pulled me towards it.

The community was called SameSame, their statement:

Same same—but different. We invite you to be here with us, to rest, create, and linger.

Definitely sounded like my kind of attitude.

I didn’t even bother looking anywhere else. I booked myself a private studio at SameSame for two months, December ‘21 and January ‘22, and began making my preparations to leave the island. It was such a bittersweet thing…. I really, really didn’t want to leave Hawaiʻi. And I was also very excited to move to Portugal, if only for eight weeks. Thinking back, I realize I made a conscious effort, every time I’ve moved since then, to approach it the same way I had approached Hawaiʻi, regardless of how long I was going to be living there. My first experience traveling ‘abroad’ while working and living had been that six-month excursion to London; and I had undertaken that experience as a ‘trip’, a temporary thing, that somehow existed outside of real life. Basically like a vacation, but without the permission to relax. I didn’t try to truly be there, I just tried to live through it.

This time, and every time after, I was determined to be there. To show up.

*  *  *

This is part of a longer reflection.

~ Daniel.
16 hours ago