From the “Planning is guessing” essay in REWORK:
Make decisions right before you do something, not far in advance. It’s OK to wing it. Just get on the plane and go. You can pick up a nicer shirt, shaving cream, and a toothbrush once you get there.
Marcel Uekermann noted that similarity and recently wrote about how he’s been applying Getting Real guidelines to his traveling habits for years. He breaks it down into three points. The first: Planning is Poison.
There is no need for pre-planned routes or pre-booked hotels. Get on the road and figure your way from there. I find the idea of not knowing where to stay overnight exhilarating.
Next up: The Less Principle & Avoid Preferences.
How many hours have you spent preparing your bag for every eventuality, packing too much stuff you did never touch while on the road. I once lived through 10 days just with just my hand baggage (My main baggage didn’t make it). Sure, I stocked up on underwear, a toothbrush and t-shirts but I imagined it far worse. I perfectly understand this doesn’t work for long trips or hikes, but you can believe me, I do no longer feel like I forgot something at home.
Along the same lines, “How To Think Like A Lightweight Backpacker” [The Ultralight Backpacking Site] lists some basic questions you should ask when planning a backpacking trip or looking at gear. Examples: How can I make this lighter? What lighter version can I carry? Can I leave this behind? What multiple-use items can I use to cut weight? Etc.
Ask of each item, “do I really need to bring this?” A small kettle can be used to fry things, in, so leave the frying pan home. Another question to clarify this is, “will I use it?” I carried a small chess set on more than one backpacking trip, but never found another player.
Simple, fast, light = freedom and agility.