& Not To Yield — Leading from behind
By: John Dila
Tags: Short Story, Lead From Where You Are, Helping Others, Self-awareness, Leadership

For high school graduation, my parents gave me a great gift, which taught me some valuable lessons about being on a team, and what leadership can mean.

This gift, among other things, offered me the chance of rising at 6 AM for 30 days in a row that summer. Upon rising, me and 11 other lucky souls, got to run 4 miles around a rocky island off the coast of Maine, where fog and chill in the air were almost guaranteed. The finish line was a dock on the south side of the island, where we lined up as we finished the run. First finished, first in line! But we had to wait for all twelve of us to be in line before we got to do the next thing, which we all had to do in order to have the privilege of eating breakfast: We had to jump off the end of the deep water dock into the harbor, which hovers at about 49 degrees in the month of June (lobsters love cool water).

I was sixteen years old, five-foot nine-inches, and weighed 143 pounds. I was skinny. Not much fat. Which made the Atlantic water damn cold.

I was at Hurricane Island Outward Bound (HIOB) for a 30-day wilderness sailing program for kids eighteen to twenty years old.

Did I mention that we all had to jump off the dock? Yeah, so here’s the way it worked:

When you arrive at HIOB, you’re assigned to a watch, which is a team of 12 sailors and two instructors. You do everything with your watch, either as a group of twelve, or sometimes in pairs. It’s all for one, and one for all. And no man or woman gets left behind. And no one eats breakfast until everyone in the watch completes the run and jumps off the dock and swims ashore. Only when the last soul has hauled him or herself out of the drink, does the watch head to the mess hall for breakfast.

This happens every day for 30 days except when you spend the night on the water, in which case you swim ashore, run in soggy shoes, and then jump back into the water to get to the boat, where breakfast is made (by the watch).

I was among the first three to get to the dock and strip down to our skivvies for the jump on day one. We waited, and waited, and waited as the rest of the watch trailed in. Nine. Ten. Eleven. Eleven. Eleven. Where’s 12? And we waited, and waited. A general annoyance began to rise among the ranks of hungry sailors. Eight minutes went by before I stepped back into my shoes and headed back along the trail. I ran for about 7 minutes before I came upon 12, who was walk-shlomping along the trail, long hair wet and sticking to her face, sobbing loudly.

My annoyance subsided immediately when I saw the struggle. She was heavier than I was, and she looked flat-footed, and I noticed a bad scrape on one of her knees, and mud on her butt.

Ok, 12, I’m going to help you.

No, I can’t make it. Go on ahead. I’m going to go home. I hate it here.

No, no, no, I said. We have to make it. Otherwise the rest of the watch doesn’t get breakfast! (If she was able to hear this through her struggle, it must’ve added to her stress, which was not my intention.) Come on, 12, you can do this! We’re almost there. I’ll help. Look, there’s one final hill, and I’ll push as you run. We can do this!

For the final 50 yards, she leaned into the slippery hill trail, and I got behind and literally pushed her back side as hard and evenly as I could to help her get to the top.

The rest of the watch caught sight of us as we crested the hill, and ran back cheering and encouraging 12 along. We made it to the dock and fell into a pile of laughter and hoopla.

Jumping in was a whole other story, because that morning the tide was out, and the height from the dock to the water was about 20 feet. You actually had to endure the chilly marine air screaming in your ears for a couple seconds as you rushed toward the water. But we all did it, and we all ate breakfast. A lot of it!

The next morning when the first three of us got to the dock, we didn’t bother stopping. Instead, we circled back, running past the rest of the watch, all the way to the end, where we helped 12 along.

The next day we didn’t have to run as far to find her.

By the end of the week, number 12 became number 11.

Leading from behind begins with realizing you’re part of a team. Having an all-for-one-and-one-for-all mindset is where leadership begins. Helping others learn how to become their best self can be done from the front, middle, or end of the line. Leading from behind is about empathy and walking in someone else’s shoes, and then helping from there.