What Kayaking Through a Mangrove Forest at Midnight Can Teach You About Teamwork

This week marks my two-year anniversary working at Union Square Ventures. In my week in between jobs, I took a solo trip to Puerto Rico, where I braved a late-night kayaking trip through a mangrove forest to see bioluminescent algae. It was terrifying, but I made a friend along the way. While I wrote about it immediately afterward, I never published it. Here is the story of this epic adventure in teamwork. Or, as Chiniqua describes it: “Uncharted Territory: Where No One Man Has Successfully Gone Alone, but Two NYC ‘Gritty’ Chicks Have Conquered all in the Name of the Pursuit of the Shine.”

For those of you unfamiliar, mangrove trees grow in shallow waters with their roots splayed atop the surface like a mess of tangled noodles. While beautiful during the day, kayaking through a scene like this can be particularly treacherous late at night. Image via Google.
  1. I’ve kayaked maybe three times in my life.
  2. The idea of being left behind at sea in utter darkness terrifies me.

Step 1: Get to know your partner.

Before you can establish trust in a relationship, it’s important to know who you’re dealing with. As it turned out, Chiniqua and I had one commonality to draw from right away: We were both from New York City. It put us both at ease knowing we shared a little bit of that “New York grit” you need to push on in tough situations. In the city, Chiniqua drives the #22 cross-town bus in NYC and is gunning for a promotion to move onto driving trains. Another plus. Someone who knows how to navigate traffic patterns and directions would be a valuable asset in a kayaking trip. Finally, I observed her outgoing, friendly attitude as she took the time to meet other travelers on our tour and even remembered another little girl from a previous trip a few days earlier. Also a positive. A good attitude and a friendly face goes a long way in a teammate.

Step 2: Assign your roles.

Clear role definition isn’t only important for high-growth tech companies. Even in a two-person kayak, if you don’t know who’s calling the shots and who’s following, you’ll wind up going in circles. Literally. If only it were so easy for business to tell when you steer off course.

Step 3: Figure out an approach that works for both of you.

As with any relationship or business setting, this “figure out how to make it work with the people you have” step is the one that can typically take months, if not years, to refine. Unfortunately for Chiniqua and myself, we had about 45 minutes to leave it all on the floor before we arrived at the bio bay. The cost of failure was also pretty high: If you don’t keep up with the group, you fall behind and can’t see anything in the dark. If you can’t see anything in the dark, you run the risk of catching your kayak, your paddle, or even your head against the hard roots and thick trunk-like vines of the mangrove trees. Also: You ruin things for everyone else by messing up the traffic flow in the one-lane mangrove canal and causing general mayhem in the dark. No pressure.

  • “Left” = “Paddle on the left side”
  • “Coast” = “Stop paddling”
  • “Mangrove root on the right” = “Paddle on the right side LOTS OF TIMES NOW”
  • “ACK WAIT” = “Slow down or we’re going to hit the kayak in front of us”
What we were doing was just like this. Oh, except that it was 10 p.m. and you couldn’t see ANYTHING in front of you… (Image via Google.)

Step 4: Learn How to Resolve Conflict

Getting your kayak wedged in between the tangling trunks and roots of mangrove trees is kind of like getting your bumper car wedged in a corner. You have about 10 seconds to get out of there before the other kayaks come crashing into you — wedging you in deeper and possibly turning you around the face the wrong direction. Unfortunately, the first time this happened, I felt my mind jump back 15 years to the same “you can’t do this” attitude I used to feel in middle school gym class. My fight or flight instinct kicked in: I wanted to flee. An impossible demand to meet in a water-logged forest. So I started panicking and squirming. But then my teammate chimed in from the rear.

“Don’t panic. Just remember what they told us and keep paddling. Don’t rock the boat. We have to get ourselves turned around. It’s going to be okay.”

Her patience helped set us right. Whereas my instinct was to flail wildly and hope the instructor would come rescue us, Chiniqua calmly and dutifully talked us both through the way to untangle ourselves.

Step 5: Celebrate Successes Together

Perhaps the most important aspect of a teammate is celebrating successes together. Once we finally arrived at the lagoon through the mangrove forest, the payoff was great. Overhead, we could see the most brilliant constellations and detail of the celestial sphere. Orion’s belt and sheath, Taurus the bull, the Big Dipper, the Pleiades, the shifting colors of Sirius, the brightest star in the sky, the quiet. Then below, in the water, the plankton seemed to take a note from the stars above and twinkle themselves when you dipped your hand in the water. This was not a place accessible to just anyone. It took hard work and blistered palms to get here, so we were going to enjoy this moment.

GM @USV, alum of @StackOverflow and @NorthwesternU, board member at @CompSci_High and @NUalumni, co-founder of #BeyondCodingNYC

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