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.

I don’t think I really understood the definition of teamwork until I got in a kayak with a perfect stranger and paddled through a winding, mangrove forest in total darkness.

While this may seem like the makings of a one-way trip, this excursion was part of a tourist attraction to see bioluminescent plankton in a bay just off the coast of Puerto Rico. As a vacation getaway spot, they don’t get as many single travelers as they do couples and families, so I was praying that some other brave, solo adventurer would board the pickup shuttle. Preferably someone who also happened to be a professional kayaker and part-time swim instructor.

You see, I already had a few reservations about this excursion going in:

  1. I’m a terrible swimmer.
  2. I’ve kayaked maybe three times in my life.
  3. The idea of being left behind at sea in utter darkness terrifies me.

After much cajoling from friends who had taken the same trek earlier on, I decided to sign up anyway. “It’s worth it,” they all said. “It was the best part of my trip.” “I’ll never forget it.” So there I was, on the 75-minute shuttle ride to some random bay in some random part of Puerto Rico without a working phone. Finally, Chiniqua boarded the shuttle. Also alone. Thus began a four-hour adventure I’ll not soon forget. And while the bioluminescent plankton was a compelling natural phenomenon to witness, the thing that stuck with me from the trip was the accelerated trust and collaboration needed with my new partner to get us there together. So, without further ado, I bring you the five steps of teamwork (as learned via kayaking with a stranger).


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.

There was only one problem: Chiniqua was equally anxious about water, kayaking, and her general athletic abilities. As a result, she looked to me as the team leader right off the bat. “I don’t want to make assumptions about your age, but I have a feeling I’m quite a bit older than you, so I’ll just say that you got this direction thing. Also: You just told me you did yoga this morning — so you just direct from the front, and I’ll follow suit.” That comment moved us quickly to step two…

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.

Like it or not, I was going to need to commandeer the navigational duties for our kayak. And in my case, this meant pushing my irrational fear of drowning aside to focus on the end game: Keeping us in line with the group and getting to our destination without capsizing. This meant that Chiniqua’s role was supporting me and backing me up where needed.

I knew she would be a good teammate when she said, “We’re partners now, and we’re committed. I don’t take these things lightly, so we’re all in.” Also when she starting singing, “Who runs the world? Girls!” as we paddled away from the sandy beach.

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.

We started off by having a lot of conversations like this:

“What are you DOING, Bethany?”
“I’m just trying to paddle faster to get us there! We’re falling behind the group!”
“Well, don’t just start on your own! You have to TALK to me before you start so we can be synchronized, remember? Otherwise, we’ll be working against each other.”

Then we advanced slightly to this stage:

“Right…right….RIGHT…RIGHT NOW!”
“No, LEFT!! LEFT!!”
“Paddling on the left makes us TURN right, remember?! We need to turn LEFT to avoid the — “ SMACK “…mangrove roots.”

By the end of our journey, we had fumbled together a mutual understanding of basic commands that I called out from the front while she backed me up with paddling power.

  • “Right” = “Paddle on the right side”
  • “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”

Our system of calling out each and every paddle stroke verbally worked for us in the end. While, on the way out to the lagoon, we were the ones causing traffic jams and getting turned around in roots, on the way back, we were the ones passing other kayaks in distress.

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.

We also learned that a more terrifying form of conflict was the kind where we would fall behind sight range of the group ahead and be forced to fend for ourselves as the new pack leaders…in total darkness. For those of you who haven’t been through a watery mangrove forest at midnight before, I’ll tell you what it’s like: You can see about three feet ahead of you at any time, and chances are, if you can see anything at all, it’s a giant tree trunk and by the time you see it, your kayaking path is fated to smack into it.

“Can you see what’s going on around the bend in traffic? That’s one thing I learned from being a bus drive — always look ahead.”
“I’m looking, I’m looking…”
“Can you see ANYTHING at all? We just need one of those red lights to guide us.”
“No, I really can’t see anything. It’s totally dark ahead.”
“Oh no, okay, so we should just stop. Let’s stop and wait. We can’t keep going like this.”
“We have to keep going or we’ll stop the whole pack behind us.”
“We should just wait. What if we’re going the wrong way?”
“Well, this is just a single canal tunnel, so in theory there’s only one way to go — out.”

A metaphor for life, really. Maybe everyone should be forced to paddle their way through a mangrove forest in the dark. Toward the end, it was Chiniqua’s whose “water nerves” finally hit a breaking point. By that point in the journey, we were both weary, water-logged, and finally within catch-up range to the rest of our group.

“I see the group ahead. Let’s catch up to them.”
“No, I see land and boats to the right. Let’s make a last ditch effort and veer right to head to shore.”
“I really think we should stay with the group. They aren’t far.”
“Bethany, this is one of those times in life where you just have to fend for yourself. We are out on water and the open sea is ahead. I don’t want to take chances.”
“We won’t go to open sea, we just need to stick with our group so they know we are here.”
“I would rather be safe on land than play by the rules. Let’s do what we have to do and cut right now. These waves can do anything, and I don’t want to get stuck.”
“Hey, it’s really important that we stay the course. It’s going to be okay. The water here is shallow, remember?”
“You won’t steal my life vest if we tip over will you? I mean, I’m pretty sure someone would rescue me and all, but that would be a pretty crappy move from a partner.”
“I promise I won’t steal your life vest.”

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.

“Are you going to call your mom?” Chiniqua asked from the lagoon.
“Sorry?”
“My mom is 72. I’m going to call her as soon as I get back and tell her about this. You should, too. I mean, this is something pretty major you just did.”
“Yeah, you’re right. I’ll call my mom when I get back.”

Of course, reaching the lagoon meant only half of our journey was complete. There was still the trip back through the mangrove forest in the same way we came. We repeated our quirky banter the whole way back, and when we finally stepped foot on solid ground, we each felt a little more connected and respectful of the other than we had just two hours earlier. A threw my hand out for a celebratory handshake. “Well done, partner.” No, that wasn’t enough. Hugs it was. Life jacket bumps and all.

Meeting a true teammate who’s as committed as you are at the task at hand can be rare but special. And when you do finally start to see the light of the (quite literal) mangrove tunnel, it’s good to know you didn’t have to go at it alone. Before she got off the shuttle at her hotel, she asked me for my number and email address. I gave it to her and soon received a text or redemption that she felt that same camaraderie too:

ur partner Chiniqua