A very close friend de used to end his freshman year in Western Massachusetts by cycling home…

to Portland, Oregon.

In 1989.

So before cell phones, satellite phones, Strava, electrolyte powders, websites full of helpful tips, Google Maps…

He was likely criminally prepared and yet he says he had a great time. He mostly slept in the back yard of strangers and I vaguely recall that people offered him so much free food that for the entirety of the trip he spent about $35 and went through one giant tub of peanut butter (that he hauled with him). He got some sort of puncture-proof tires and never got a flat.

Skipping the dessert southwest helped avoid the risk of water shortage and she clearly got lucky and avoiding a variety of problems and it’s an n of 1, but it’s a data point saying one doesn’t have to plan to the nth degree.