Solitude is sometimes a high-cost luxury and it is different than being "alone." Often the presence of another person diminishes the sense of wilderness, which is defined by the absence of human doings, not just human beings. If you can't find anyone who wants to go along, the choice is often to stay home truly alone, or go into Nature with only your thoughts for company and advice. Experience is sometimes only gained at the cost of lack of it. 

Perhaps "Don't go where a fall might be dangerous without being roped up" is more useful. He was comfortable in the wilds, and enjoyed it so much that he accepted the risks, knowingly or not. His experience made him bold, perhaps overly.

Enjoy the wilderness beyond this life, Jacob, where no harm can come to you, but no one goes without leaving this life behind. My sense is that you will not be alone there, but ironically experience the oneness with the universe you may have been seeking. We'll all see you on the other side of that river.