For those of you who have hiked the AT before, you know that the southern terminus of the trail officially starts at the top of Springer Mountain in Georgia. Springer Mountain is a tall mountain, and somewhat difficult to get to. Most hard-core AT hikers will start at Amicalola Falls, which is a hard days hike from Springer, all of it up. Some slack packers will hire a shuttle to take them up to the top of Springer, but I think this is cheating. I’ve always found it interesting that you have to hike a hard day to get to the beginning of the AT, but that’s fitting considering the breadth and depth of the trail.

Getting from the Brazos Valley to Harpers Ferry today was my approach trail, and a very interesting day. The two flights up to DC were uneventful. After 3 subway rides, I made it to Union Station, which is a massive building beautifully designed. I had several hours to kill so I bought a half a sub sandwich and sat down on the lower level to people watch.

I didn’t have to wait long, because a man ran up to the subway counter, stole some money and ran off. Several seconds later four cops passed by running to go catch him.

When I finally got on the train, the real fun began. If you’ve never read the book A Walk in the Woods, by Bill Bryson, you really should pick it up. You’ll laugh so hard your sides will hurt. Anyway, there’s a character in the book named Mary Ellen. The guy I sat next to, let’s just call him James, was a male Mary Ellen. He was obviously a train spotter, and launched into a detailed description of the trains that he had when he was a kid, how he worked at a hobby store and bartered for trains rather than take money, and how he used to steal coils of wire from houses to wire up the trains that he collected. He peppered me with a little known facts, such as Roger Clemens went to his high school, but because he never went to class they were disqualified from winning any games. He was also a Scoutmaster, and so that was something we had in common. He told me detailed descriptions of at least five different trips that they took with the scouts. A real boor. After 30 minutes of this, I politely excused myself to go to the restroom. When I got back he was leaning over the seats in front of us and talking with those folks whom I’m sure he had never met before. He remained in that position for at least 20 minutes talking to them, about what I don’t know, his butt-crack just visible over the top of his waistband. That was the longest hour and 15 minutes I’ve ever had in my life.

Getting to Harpers Ferry, I was picked up by my Airbnb hostess Rei, who is a delightful woman with NOWLS experience. Her bed and bed breakfast is well worth visiting if you’re ever in Harpers Ferry. I’ve unpacked my pack, redistributed, everything to be more efficient, packed my go-home box for tomorrow, and I’m sitting here on the porch of the house looking at the overcast sky to Maryland Heights across the river. In the morning, I’ll start day one. Yes, today was an eventful approach trail.

I posted my first trail package this morning. Using the “hold for pickup” service, you can post a package to a U.S. post office which will keep it for you until you get there. In this way, you can stage boxes of consumables to be picked up during your hike. It’s a bit of a balancing act. You have to allow for variations in your hiking schedule, delivery time, and even the hours the post office is open. You don’t want to show up at 10 am to a post office that doesn’t open until noon. Arriving late could mean that you have to spend the night close by and essentially waste a day hanging around when you should be moving.

Mama Bear will post the next three boxes when the dates get a little closer. She will add tortillas just before mailing – they are a great luxury on the trail. Knowing that she is back home, holding down the “fort” and thinking of me is a great comfort, a connection to the real world. I can imagine getting the boxes she sends, perhaps with a little note in them. My father taught me the greatest thing you can give to another person is to wait for them. My boxes will be waiting for me somewhere up ahead. Mama Bear will waiting for my return somewhere behind.

Carl Philipp Gottfried von Clausewitz is often misquoted as saying, “No operational plan extends with high certainty beyond the first encounter with the main enemy force.” In fact, it was not von Clausewitz, but rather Helmuth Karl Bernhard Graf von Moltke who said that, even though it’s a fair restatement of the battle philosophy of von Clausewitz. What does this have to do with hiking?

I have a plan. The plan is to cover 271.4 miles in 29 days. But my return flight home actually leaves 33 days after I step off in Harpers Ferry, WV. Experience has taught me to plan for the unexpected. Delays, setbacks, distractions, coincidences, and opportunities will change the plan, almost certainly from the start. I wouldn’t be surprised if I got back a week later than planned, or didn’t finish at all. In any case, I’ve resigned myself to the fact that I’m not completely in control of this hike. The trail will teach me what I need to know, one way or the other.

Which brings me to the point of this post. Dealing with the unknown, i.e., being comfortable in an uncertain situation, is a trait known as “tolerance of ambiguity.” Project managers are good at assessing ambiguity, usually phrased as complexity and uncertainty. In fact, any project manager worth her salt knows that the first step to controlling uncertainty is to acknowledge it. Then a “band” of uncertainty is applied, usually with statistical tools. By defining the boundaries, PMs can gain some level of comfort.

It turns out that TOA is a key characteristic of many leaders. It is negatively correlated with neuroticism and positively correlated with openness to new ideas. As I’ve gone through my career, I’ve coached many managers to examine their level of comfort with ambiguity. When they reply that uncertainly makes them anxious (not usually in those words), I point out that ambiguity will exist regardless of their feelings. But if they want to feel better, be prepared.