As I mentioned in my annual review, I recently took the plunge and went full “digital nomad” mode: Selling most of my stuff and dropping my apartment lease. Since then I’ve been bouncing around from place to place, learning a ton about my preferences for traveling and environments in general. These preferences have started to inform a set of “rules” that I’m going to apply to future travel.

I’m a big fan of rules in general. They reduce cognitive load from decision making and promote discipline in important areas. As phrased by Atul Gawande in The Checklist Manifesto:

“And the reason is increasingly evident: the volume and complexity of what we know has exceeded our individual ability to deliver its benefits correctly, safely, or reliably. Knowledge has both saved us and burdened us.”

There is a lot of surface area to navigate when choosing how to travel. Lots of decisions to be made. These are the rules I’m using to automate as many of those decisions as possible:

On booking trips

Be willing to pay more for flexibility to make spontaneous changes

  • Avoid booking the next flight until 1-2 weeks before expected departure
  • Book one-way flights whenever possible
  • Book cancellable housing whenever possible

On where to go

Favor going somewhere totally new if traveling alone

  • If traveling solo: Go abroad if you have the chance
  • If staying in the US: Go somewhere you want to meet up with others

On where to stay

Settle into your own place if staying for awhile

  • If staying somewhere a week or longer: Book an Airbnb or apartment
  • If traveling abroad solo: Book a hostel
  • If both of the above points: Stay in an Airbnb during the week and hostel for weekends

On when to move

Stay for a few weeks and play it by ear

  • Start with 2-3 weeks and extend as needed
  • Schedule travel days for Thursdays or Fridays

That's it! No laundry list of things to check or think about. Just a handful of standards that I prefer to default to. Just my preferences, these may or may not be helpful for you.

It's also worth noting that these are always in flux — It's inevitable that things will be tweaked and added and removed. But for now, I feel quite good about this list. See you on the road.

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