Wow - who'd a thunk that many people hammock solo. I wonder if, with a tent, you often share the load; one person has tent and ground cloth, the other has stakes/poles/rainfly. But my main experience is, you may be solo but that doesn't mean you are alone. Try climbing Mt. Hood "solo" one weekend. Or kayaking around the San Juan Islands, taking any published hiking trail. You will not be "alone". Of course you can go places where you will be alone, buy my point is, going solo doesn't necessarily mean "alone".
The only time I really learn stuff - what works, what doesn't, what I forgot that I should have brought, what I should have left at home, etc. is when I go out solo. When I'm with someone, I'm responsible for their safety and well being. If their comfort bar is higher than mine, I need to dial back on "primitive". But alone, I can forget stuff and suffer; with suffering comes learning (I won't forget that again, etc.).
With all that - when I do go out alone, especially when kayaking, I carry a SPOT signaling device. I press Check-in/Okay overnight at a campsite so those back home know where I am - right where I am. When on the water, I have real time tracking turned on so they can see my route over water.
I've read too many stories of "trouble" because there wasn't a way to let someone know where the outdoors person was. But I don't "let my guard down". There can be an assumption that if you get into trouble you will have your signaling device accessible. I used to feel competent because I carried spare batteries in a dry bag. But then the GPS ran out while I was on the water and the dry bag was up in the bow of the kayak. Now I carry spare batteries on me.
So I'm an advocate of "solo" as an opportunity to try new things and learn some lessons. But given that, there are times to put the lesson learning aside and share the scene/experience with another human (lessons to be learned there as well).
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