When we left Mobile, Alabama this morning we didn’t know where we were going to be sleeping tonight. This is fairly common for us. I have an Excel document with our route plans and some notes, but more often than not in the “Sleeping” column it just says “Off Road”. Which basically means “fuck if I know, I’m sure something will work out”. Tonight, like 99.9% of the time, something worked out.
As dusk was approaching we biked past a woman who was walking on the same trail as us. She was probably in her 60’s or so. She flagged us down and asked about our ride and, after a little bit of small talk, she said that we could camp on her land. Her father just died and she is in the process of selling all of his belongings and preparing the house for someone else to live in. We chatted with her a bit before she left us alone with the house, giving us free reign to shower, power our things, use the kitchen, and sleep.
If we decided to plan every moment of our ride we would miss out on these serendipitous moments. If we stayed in hotels or reserved camping spots, then our rides would be about travel instead of adventure. Our decision not to worry about little things like where we are going to sleep or how we are going to get where we want to go have allowed us to live fuller, richer lives filled with interesting people. And, I like to think, by living a little unconventionally we add something to other people’s lives as well. Life cannot, and should not, be planned too strictly. Sometimes it is best to just walk out the front door and see where your feet take you.
Wandering Oak 
I’ve always wanted to try something like that!