Remote Roving And Digital Drudgery, Part 2

Yet another post with tips, tricks, and thoughts bout being a digital nomad. Part 1 is here.

I’m not sure how humanity got into a position where pensioners are traveling and young people are writing.

It used to be the other way around, Descartes would spend his youth collecting knowledge from around Europe and the dusk of his life would be caught up in philosophy.

Dumb advice is often given about compounding interest, investing 100$ now will yield 1000$ when you’re 60.

But what will 100$ buy now compared to 1000$ when you’re 60.

No amount of money will fix damage to the 6 stumps jutting out of your torso, and 1000$ wheelchair is a poor replacement for 100$ hiking boots. I leave coarser analogies to the reader.

Anyway, where was I?

iv — Booking

Accommodations are the most expensive part of your travels.

Sadly enough you can’t really skimp on them, especially if you plan on working from home rather than in a coworking space.

Hostels are great for full-time tourists but horrible for people working 6 hours, 2 out of which are spent in zoom calls.

A common myth I see is that you can go to a less developed country like Thailand or Vietnam and cut your rent to 1/4th of what it was. I’m not sure if it’s a lie or just a selection effect for people with very low standards of hygiene blogging about nomading.

I expect a few things from my accommodations:

  • No bugs (especially no bedbugs, lice, mosquitos, and ticks)
  • Running hot water with low-enough volumes of lead and rust to be safe for washing dishes
  • Air conditioning
  • A reasonable amount of space with a nice desk and couch for working

This will lead to a surprising leveling-out of prices across the world. This is not to say that you can’t find some pretty sweet deals, especially if you are used to big city pricing, but don’t trust anyone that’s telling you you’ll get away with paying less than 1k/month for accommodations.

There is a paradox: you can probably stay in “normal” rented apartments for cheap in countries that are middle of the road in terms of income (think Greece, Jordan, or Georgia), but not in poor ones (e.g. Nepal, India, Peru, or Morocco).

Past a level of poverty, you essentially need 4 or 5 stars hotels to get a reasonable level of service, and these are expensive.

There are 2 main booking aggregators, and

Your main issue will be finding trustworthy listings. Reviews only get you so far, especially since all of these platforms have low-quality control and no incentives for good reviews.

The standards of are better, at least in-so-far as they don’t remove reviews and allow you to easily filter on ratings. But there are fewer apartment listings and higher prices.

A basic checklist for me is:

  • Don’t be dubiously cheap
  • Above 8.5 stars for booking or 4.7 stars for airbnb.
  • More than 30 reviews.

Once you’ve decided on a place based on website filters, take a look at the actual photos and description for clues that something might be off.

But booking and aribnb are expensive and if you’re looking at anything beyond 2 weeks in a moderately well-off country they aren’t your best bet.

You should search for deals through Facebook, local rental websites, or by literally walking up to accommodations and bargaining, the last approach is how I found some of the best apartments I’ve rented.

This method will yield substantial savings compared to booking online, we’re talking 2–3x here.

If you are planning a stay in the 2–6 month range, “normal” rent-seeking websites are also an option.

The scam avoidance checklist is simple:

  • No “deposits” or pre-payments through anything but a booking website. No cash, no paypal, no bank transfer.
  • If you are paying the merchant directly, ask to see the place first, and pay half (or all) the money when leaving or, at least, mid-way through the stay. This applies to 5-star hotel chains and random dudes from facebook equally.

Renters will understand your suspicion and not mind it. They may make a show of it, but they won’t feel insulted, it’s just a custom, same goes for bartering prices.

v — Speedrunning airports

I must have taken at least 100 flights in the last 4 years, maybe more. How much time could that waste? Let’s assume the following:

  • 3 hours per flight
  • getting to the airport 2 hours before take-off
  • 1 hour getting off the plane and grabbing your luggage
  • 1 hour transport between apartment and airport

That could be 900 hours or 50 waking days of my life, over 4 years that’s quite significant. How do you cut this down and make it more pleasant?

First, keep in mind that Dan Carnegie-style speech actually works on the vast majority of people, even if to you it sounds cringy, these people include all the staff in the airport and airplane.

Second, get the poor man’s first-class, front seat, or wing seat. This gives you extra legroom and a no-baby guarantee.

Check-in counters close, at the most early, 1 hour before take-off.

As long as you arrive 1 hour in advance, airlines will be obligated, for the sake of PR, and in many cases by law, to let you check-in.

Many airlines don’t have a dedicate per-flight check-in counter. But if you find a representative or go to the business-class check-in and tell them your flight is in 1 hour they will wave you through if there is a queue, or they might even be explicitly calling people for your flight in front.

Again, you may be legally entitled to this, or at least entitled by company policy, so most employees will be fine helping you.

This not only means you get to spend only 1 hour and a few minutes in the airport but more importantly, that your baggage will be last in, which usually means first out.

Once you’re past check-in there’s no way to speedrun security, and boarding fast doesn’t help, I prefer sitting and writing until the last people are boarding, this way you are optimizing for time spent on your laptop or kindle doing focus work or reading.

If security takes very long, don’t worry, the plane will wait for you to a point… as surprising as that may be. You can also politely elbow your way through to some extent, though I myself have never done this.

You can also speedrun disembarking.

You should already be seated close to front, aim to get off first, then:

  • If there are buses waiting, take the one that seems to be getting full right as the driver prepares to leave, position yourself next to the door which will end up facing the airport entrance (sometimes hard to tell, then either take a gamble or sit in the middle)
  • If the plane is connected to the airport, speed-walk as fast as you can, and politely call out passengers in front to give way if you must.

Why? Because a lot of airports have dedicated immigrations (+ covid bureaucracy check) for a flight, and even if they don’t, they have so few flights it’s usually de-facto dedicated for the flight. This can take literal half-days if you are unlucky, and on average it can take 30 to 60 minutes if you are towards the end of the queue. Obviously works much better at the airports in Sapporo and Granada than those in Tokyo and Madrid.

But if you are among the first dozen, it’s almost instant, and you’re done just about the time when luggage starts rolling in.

You were among the last to check-in, so your luggage is probably the first.

You can further optimize all of this if you fly on weekdays, use airlines that don’t have a lot of flights from the respective airport, and fly from small airports.

vi — People

By far the oddest thing about traveling is that you are doing it alone, or at most with two people. I’ve tried both ways, traveling alone for about 3 years and a half, and together with my girlfriend for the last half a year.

If you are even considering a digital nomad lifestyle, let alone if you’re doing it, I expect you to be pretty odd in terms of how you relate to others, so I’m taking advice here with a grain of salt.

First, I recommend calling friends and family or at least texting them often, maybe having a few group chats. Getting into the habit of doing this for no reason will make it less awkward, and you’re constantly traveling to new exotic places, so surely it’s easy enough to keep a 20 minutes social call interesting.

Setting something semi-periodical helps, for example, I have 2 periodical~ish paper discussion groups with friends, and it helps a lot.

Second, I recommend relishing in work calls, using them as an opportunity to socialize, grab a coffee, stroll through the park, and pay attention to what people are saying. Not only is this helpful for work, but it also helps fill in the socializing gap.

This helps with “grounding”; Not hearing your native language or speaking with people that known you for more than a few weeks can have unpleasant effects on your psyche if it goes on for too long.

I find this much less important now that I’m traveling in two, but traveling in two brings up the other weird dynamic of having only 1 conversation partner for 90% of your thoughts. I tried this twice and it also brings up oddities of its own, so I’d still recommend the above even then.

Meeting locals is the other side of the coin, and it puts traveling in a whole new light. I “feel” like I get countries much better if I’ve had in-depth conversations with even one or two residents, rather than just visiting, reading Wikipedia, and talking to tour guides.

That’s not to discourage you from getting tour guides, a good tour guide that gets together 2 or 3 visitors and shows them around is a top-notch way of both getting to know some people and getting to know about the place. I include things like Airbnb experience and such here.

Beyond guided tours, you can try making small talk with taxi drivers, baristas, and the like, but there’s an art to doing this in a way that’s not very awkward when and it only stretches to a certain level of unfamiliarity with English.

Then there are facebook groups for expats and “nomads” where you might be able to find people that have been living there for a while, both to stave off the insanity caused by the lack of face-to-face interactions, meet some interesting characters, get intros to actual locals, and get their take on the place.

Finally, you’ve got more socializing-focused apps and forums (including Facebook groups) which can be split into roughly 3 categories:

  • Meetup apps… easy to find groups for physical activities and maybe some lounging + discussion groups, but these might be surprisingly hard to find outside large cities, and the language barrier will be an issue in many places.
  • Dating apps… for 1–1 meetings with whatever sex you are interested in, potentially hard to find people if you’re a guy, potentially dangerous if you’re a girl, but low involvement and getting along with English is much easier outside a group setting.
  • Couchsurfing apps… very few people on there, but if you can find people that want to hang out it’s the triple-whammy of talking with someone that’s weird, a local, and “international” enough to avoid serious communication difficulties.

But by far the best way to meet people is to just go to people that you already know, even if you know them briefly.

I’ve previously visited random people from Mindsdb’s community slack, coworkers that I had barely ever spoken to, distant acquaintances I hadn’t met in half a dozen years, and the likes.

This doesn’t always work, but often enough someone new coming to town is enough of a break

And then, of course, you should get creative. Is there a blogger you enjoy in a specific town or country you’re visiting? Mail them!

Are there meetups or conferences for some sort of community you’re vaguely part of? Go there!

Ever heard of someone that’s vaguely interested in the area? Find their contact details, and propose grabbing an impromptu coffee for whatever reason.

Traveling around the world is the easiest way to meet all sorts of interesting characters and they will be the fixtures of your journeys as much as the places you go to. But it’s so easy to get too busy, or too stressed, or too social anxious and not do this… which is a shame because it takes away the ultimate purpose of wandering, the friends and enemies you make along the way.

Had I been more introverted about prompting people to meet I wouldn’t have ever met four people which became my good friends, and one who became my girlfriend.



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