Generally, the principles and values I learned as a Boy Scout have helped me in my life. But sometimes, unfortunately, I’ve confused the habits I’ve formed as a result of a lifetime of practice with the actual principles and values I’m committed to, as I did in getting ready for the AT.

In particular, the Boy Scout motto, “Be prepared”, is burned so deeply into my psyche that I now, out of habit, over pack for every trip. For example, when I go to Canada fishing I always pack two (and sometimes three) of everything piece of essential gear just in case I, or someone else on the trip, loses or breaks something. This has worked for me because I don’t have to carry any of this gear on my back.

But that’s not the case with the AT. All the food and gear I brought with me I had to carry. That meant those extra meals, shirts, pants, socks and underwear, the extra flashlight and bottle of stove fuel (and if I would have had room – extra shoes, hat, and a solar charger) were dead weight I carried every one of those 70 miles. I estimated it all added up to an extra ten pounds (or about 25% of my total pack weight).

Now ten pounds may not sound like a lot when one wants to “be prepared”, but in reality it was like carrying a gallon of milk, in addition to the rest of my gear, for 70 miles up and down mountains.

You see, with so many people on the trail, with towns, stores, hostels and roads dotted all along the path, the best way to be prepared is to know where you can get something if and when you need it. It’s why some people hike the AT with only 25 pounds of gear (a little more than half of what I was carrying). So the hard truth was, if I was truly prepared like a good Boy Scout, I would have known this about the AT and would have packed much lighter.

So what’s the lesson in all this? Do not confuse a motto, value or principle with its application. Memorizing a motto (Be Prepared) is easy. Learning a single way to apply it (over packing) is a mindless habit. But leadership requires the wisdom to know when a context is different, because different contexts requires different applications of those timeless mottos and values.

So how do I know this? Because, for seven days, I felt it deeply in my hips, shoulders, knees and back.