The fun in an adventure doesn't come from the things you know about. It's not in the things you plan for. The fun in an adventure comes from discovering new things, even if they're only new to you. No matter how well you prepare, life will find a way to share something new with you.
I did a LOT of preparing for my most recent loose surface adventure. I had everything I needed for every situation I could think of. I had my water treatment system, an extra fuel bottle, several days worth of freeze dried food, etc. There was still a box of stuff I thought I should take, but couldn't figure out how to pack, sitting on the floor of the garage when I left.
I was ready. I was too ready.
Setting aside my ill-advised decision to try to keep up with purpose built adventure bikes on my glorified street bike, the over preparation was the biggest problem I faced on the trip. The top case broke clean off of the bike mostly because it was overloaded. It was full, and then had stuff strapped on top of it.
After a couple of hours of riding careful to protect the strapped down top case, it occurred to me that I could whittle down my gear. I'd wanted to repack, putting the stuff I didn't need in the top case, and finding someplace to ship it home for me. If you find you can do without stuff, do without it. It's more fun to have to figure stuff out any way.
We were never more than 150 miles between fuel stops. With the sort of riding we were doing, I have 180-200 mile fuel range. So the fuel bottle, which never got filled, was just wasted space and weight. For the same reason, the water treatment system was a waste. If you can find fuel, you can probably find potable water.
I don't know how many air-pumps we had in the group. At one point I'm pretty sure there were 3. You don't need to carry an entire expedition's worth of tools and supplies on a single bike if you're traveling with others. Take the time to get together before your adventure. This is everyone's opportunity to reduce their pack load, and increase safety. Sure, some bikes have panniers big enough to live in. Do you really want to pick that bike up when you've filled every bit of space on it? I don't. I don't like picking up my bike, with it's little Givi V35s, fully loaded.
Work as a team, spreading those items which are essential to the group, but not to an individual, among the group. Be open to surprises. You may have to puzzle through something that would have been easy if you'd only packed the flux-capacitor, but that's why you're going out into the world. To experience new, unexpected, and exciting things. Where's the fun in having everything go exactly to plan? Where's the fun in not having to figure anything out?
Besides, if you over pack, the world will find a way to demonstrate that to you. Then you'll have to puzzle through how to deal with whatever carnage ensues from being too prepared.
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