Awhile back I posted a link to Highway2Health Walk, a planned thru-hike of the Florida Trail from Orlando to Key West. The other day I revisited the Trail Journal of the hike’s organizer, one Steve Silberberg, the brains behind a would-be backpack-guiding company called “Fitpacking.” Steve’s ardor for the outdoors is unquestioned, but his business sense is, well, questionable. From his opening Trail Journals entry:

Anyway, successful business people always judiciously release only certain information in order to maintain their image. I, on the other hand, typically wear my heart on my sleeve, and talk frankly about problems and issues, which I’ve observed is about the worst thing you can do in a business (next to sodomizing some co-worker in the conference room).

Way to set the tone, there! As one might surmise, Steve is like the last person on earth suited to leading strangers on stem-to-stern hike of the Sunshine State. Trolling through his journal entries is like a watching a bad reality TV show minus the presence of Donald Trump. From the first day of his hike:

Despite one of the most stressful days of my life, where everyone seemed to hate me, I was on the trail, having started off 2007 backpacking. Yay!

So he’s trying to stay upbeat. It doesn’t last.

I am failing to keep people happy, therefore, I am a failure and should give up. Funny, that’s the same conclusion I had as a programmer. People complain a lot about me. It’s kryptonite to me. If I’m around supportive people who love me, I can and will do anything, but if I’m not, I probably spiral them down into a pit.

This reminded me of the central character of Dostoyevsky’s “Notes from Underground,” a guy who revels in his status as the lead architect of his own misfortune.

It’s true I’ve cherry-picked the most priceless complaints from Steve’s journal, but there are more slightly less juicy ones for those who are into this sort of thing. His entries do trail off after awhile … I suspect one of his contacts back home told him people were actually reading his journal and perhaps he’d like to either tone it down or cheer it up. Which is a shame, because it was so entertaining to see somebody tell it like it is, at least through his Prozac-deprived perspective.

Normally I’d feel a twinge of guilt at having a few laughs at another hiker’s expense, but somehow I expect Steve wouldn’t want it any other way.