Ask Jack: A Young Man Traveling Without Commitment?

“It should not be denied… that being footloose has always exhilarated us. It is associated in our minds with escape from history and oppression and law and irksome obligations, with absolute freedom, and the road has always led West.” —Wallace Stegner

Got an unusual question via email the other day. It comes from a young man who will be familiar to you but whom we will not explicitly identify. He was once a writer, once an editor, and now a financier, having achieved escape velocity from this ragged, scuttling business into the security and prestige of grown men’s endeavors. There was a time that he worked for me, and a time that I worked for him. It seems difficult to believe that we met eight full years ago.

Anyway, in the course of our various conversations, this Canadian fellow (we’ll call him “Bo”) happened to mention his upcoming travel plans and his need for some companionship along the way, preferably of the short-term, transaction-oriented variety.

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