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Used to plan everything 3 months ahead, now I book 3 days out

Back when I started nomading, I had spreadsheets for every city, hostels booked weeks in advance, and a rigid schedule. Then I got stuck in a rainy hostel in Medellin for 5 days because I didn't check the weather and had non-refundable bookings. Now I only book a place when I'm actually in the city and can feel the vibe. Anyone else find that overplanning kills the whole point of being location independent?
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butler.finley
I mean, yeah, I pretty much just wing it now too.
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