​​​​Rebelle Part of the Story

A Work in Progress excerpt from my book “The Rebrand”

Brynne Henn
The Startup
14 min readOct 11, 2019

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Before him, I like to imagine myself as fearless. Give me a challenge and I would take it on — convinced that I was always the right person for the job, even if the reality was I was 18 years old and full of hubris. That gall took me to Uganda, it led me to a major I would struggle to succeed in, to a wild group of kids just bold enough to believe that living in a van for 6 months showing movies could bring down a war lord.

​​There’s a side effect of trauma though, or maybe of age, where an imposter syndrome creeps in. What once felt like I could jump first and fear later, was now a task too daunting. If I took it on, at what point would they realize I was incapable? When would they learn that I couldn’t just figure it out along the way and succeed? And when they did, how much would it ruin me to learn I was found out? Whether it was studying for the LSAT, taking on jobs outside my normal scope, leap frogging careers, or even, marriage, this nagging uncertainty and voice of doubt always filled my mind.

​​And when your partner sees the truth but denies it — when he sees you taking on challenges and succeeded despite the odds, notices you getting raises, taking on responsibility, building a friend group — he makes sure any voice of confidence is stifled. It was small things — honestly, I didn’t notice them until long after he left, but he’d been giving voice to my doubts and asking me to negotiate my worth for years. From questioning my story when I reported sexual harassment by my CEO at my first real job, being embarrassed when the Washington Post wanted to do a profile on me and my PTSD therapy, or the one that made me finally take notice — refusing to celebrate my promotion and raise that finally brought my salary above his.

​​He brought my confidence to a point that the Brynne who I am today wants to find the Brynne I was then and carry giant red flags and place them on every moment — a glaring siren flashing “Stop, Don’t listen. This is utter bullshit.” And what’s odd is that, sometimes actions just spoke so much louder than words. It was the lack of acknowledgement, not the direct attacks, that tore me down the most. Because when I needed it most, my partner wasn’t there to quiet the imposter voice in my head, to hold up a mirror and show me reality. `

​​​​I fought that voice for months after he left. The feeling of being lost and a failure sometimes so strong, it was all I could do to get up and go to work and keep fighting and looking for some sign of me growing stronger.

​​In the midst of my deepest doubts, I was given an opportunity. A strange, not-remotely-close-to-my-comfort-zone challenge. I was asked to compete in an 8-day, 2,000 kilometers, off-road rally — with no GPS, no phones, just paper maps and a compass to find my way with one partner from Tahoe to the Mexicali border.

​​A year prior, my company sponsored this race called The Rebelle Rally. To be honest, it felt like an odd fit given that we were an all digital company supporting an analog race. But, my job was to support it — handling the daily social updates following the race, the blog, and emails. I was entrenched it in for over a week, and was slowly enraptured by what I was seeing. For eight days I cheered as I saw women from all walks of life voluntarily locking up their technology, leaving their “sensible sedans” and “grocery getters” at home, to hop behind the wheels of Jeeps, Toyota Tacoma’s, and a stunning sky blue vintage Ford Bronco to try their hand at this competition — testing not only their driving skills and ability to navigate with just a map and compass, but also challenging the very image of what I’d come to understand as grit, endurance, and strength.

​​When the Rally came to a close, my CEO, Eric, pinged me on Slack, having fallen in just as much awe of this race as I had, and told me, “You’re doing this next year.” I really, really hoped he was kidding. These women were awe-inspiring to me, and I felt like the polar opposite. I was the wife with the sensible sedan, and I used my GPS on every trip I took, even though I’d lived in DC for almost five years and it is less than 10 miles square. Anytime I had the option, I felt much more comfortable in the passenger seat. Most of me hoped he would forget, but a small part of me wanted to know if I could prove even myself wrong and cross that finish line one day.

​​​​When I brought the idea up to R, he crushed even the ember of the fire I had to give it a try. He laughed at the very notion, and suggested that I start training right then and there if I had any hope.

​​​​So a few months after we separated and the founder of the Rebelle came to speak at a company event, I was surprised at my reaction. I found my self dying to try my hand at the wheel after hearing her talk. During her presentation, my soul quieted the doubting voice for just a moment, and I went from “I hope they forget they asked me” to “There’s no way I’m letting Eric forget.” What I didn’t realize then, is that the Rebelle would become a beacon for me — something that if I could just cross that finish line I’d prove to myself that I was stronger than I thought.

​​My first challenge came just a week before our first training. My partner dropped out, and I needed to find someone else to join me. I sent Slack messages and reached out to friends at work I knew, but few people wanted or could fit it on their schedule. When my manager suggested Karen, I knew little more about her then a photo on our website — and I was about to ask her to spend eight, 12+ hour days in a car with me, without a cell phone or music to escape.

​​After a walk around the block, where she asked the most intentional questions about how I handled stress, what our communication styles were, and any similar experiences we had Karen agreed. We trained twice before the Rebelle, one weekend in August where we honed our off-roading and navigation skills, and one in September where we learned how to drive in the dunes. We did our best to fit in mapping and plotting practice and compass skills into our schedules when we came back, but if I’m honest I crammed as much as I could the two weeks before the Rebelle.

The rally is structured like this: It’s not a race for speed, but one of skill. Each morning we were going to have to wake in the dark somewhere in the high deserts of Nevada, and be handed 20–22 coordinates of checkpoints. We had just about one hour to plot them all before we had to be at the starting line. We’d be driving to each checkpoint completely off-road, navigating our rented Jeeps through puddles, up rocky terrains, and skating across sand dunes.

​​Before we knew it, it was October and the teams my company sponsored — Karen and I, and Amy Lee and Paige — were on our way to the rally. To say I was nervous is an understatement. I was feeling the weight of the challenge just on tech inspection day, where rally books looked like foreign math problems and the maps were four times the size I was practicing on.

​​That imposter voice was screaming at me — I was a Honda Civic driver standing among women who built their own cars. I worked for a mapping company, but up until a few months prior didn’t know how to read a coordinate. I convinced the company to send all four of us on this journey, and suddenly realized the weight of the cost and expectations if we failed. But time was up, I had to put my concerns away when we pulled #2 and found out we were second off the line on day one of the 2018 Rebelle Rally. Like it or not, I was going to be like the women I admired just a year prior.

​​The night before the rally kicked off, Karen and I headed back to our hotel room. Karen calculated our multi-page roadbook of turn-by-turn directions to our first base camp, and I plotted our first 6 check points. We tripled checked our luggage and talked about what we hoped we’d accomplish. Looking back, we definitely underestimated the difficulty of the journey we were about to embark on when we said we hoped to be in the top ten.

​​I did a final review of my belongings — making sure I left no warm clothing or map ruler behind, when I shifted my clothing and saw a note from my boyfriend at the time, Ben. In it he sent me words of encouragement, noting how proud he was of me, how he knew I could do it, and how I was stronger than I realized it. The thougtfulness of it blew me away, but it also showed me how far I’d come when just a year before I believed R when he told me I had no business being there.

The first two days went well. I fell easily into the schedule of waking up at 4:30 am, attempting to throw on some makeup in a freezing cold tent, waiting for the cowbell to “awake” us all at 5 am when we could grab our maps and checkpoint guides for the day ahead. We had until 6 am to plot what we could and then depending on our position in the starting line we could do a few more, or we’d hit the rest later on the trail. I loved driving — amazing myself by how quickly I learned the feel of the car, what I was comfortable taking it over, and how fast I could navigate over washed out terrain. Navigating was a bit more of a challenge, but even on Day 2 we were finding our black checkpoints (the hardest because they had no flag, we just had to read the map and compass correctly) and getting some points.

​​But by Day 5, the demands of the rally begin to pick up. This was hard. It wasn’t just a fun ride in unique places across the American West. It was a test of a new skill with no chance to distract yourself in another task or project, or a minute or two on Instagram. It came to a head for me on that day. Karen and I alternated between driving and navigating every other day. Day 5 was my third day of navigating, and it was hard. We were in Johnson Valley, where the terrain alternated from wide open sand, to rocky creggs, to small mountains. Reading the terrain was complicated, with such variety it was hard to distinguish the contours on the map with what I was seeing in the real world. And to make matters worse, the ground was cut up from a recent event with giant rally trucks that left wave like patterns in the straight passages of the terrain. Meaning, if I took a little bit longer on a checkpoint, Karen couldn’t make it up in speed without one of us snapping our necks with the constant whiplash.

​​Half way through the day, I navigated us to our first chance at a black checkpoint. We missed the other two — having been unable to locate a reference point on the first and then checking our tracker in the wrong order on the second. But on this one, I had it. I checked my back bearing and the compass was perfectly aimed at the flag behind me, I confirmed my front bearing, and knew we traveled exactly .79 km. I was confident — we were in the bullseye of a black checkpoint. I’d done it. I’d navigated us to the exact coordinate we’d been given that morning, and possibly our first full point black. I was so excited and proud of how far I’d come.

​​That was until I heard Karen’s voice from the car, calmly asking if I was sure I plotted it correctly. I could hear the trepidation with which she asked, the voice of someone who knows they’re delivering bad news. It took only one glance to realize I was wrong, I’d placed the ruler on a county line, not the latitude line. Meaning I was literally standing on the wrong side of the map.

​​The voice of my ex-husband telling me that “I suck at driving” and that I had no hope in doing this race exploded in my ears. Had I come this far only to prove him right, after everything? It broke me in that moment and the tears began to well up. I was exhausted, more competitive then I knew, and faced with a type of failing I wasn’t ready to accept. I needed a second to walk away, and cry in the desert. I oscillated between being disappointed in myself for crying, and the realization that if one of the camera crews came by I’d look hilarious — my hands atop my Jetson’s sized white helmet trying to calm down as tears streamed down my face.

​​Here I was a full year later, thinking I was one of the women I had admired on Instagram and instead I was in the middle of the desert faced with realities of this race. It was testing me to my fullest. I had a choice, let 18 year old me return and convince myself to just keep moving, or allow the imposter syndrome I’d listened to for years convince me of the realities of how out of my depth I was. I turned to Karen, not needing to say a word, her kindly understanding my exasperation. She helped me fix my mistake, showing me where I went wrong in my plotting, and we eventually got to what we thought could be the checkpoint. Then I had to figure out what to do next — put myself together and navigate us to our remaining 10 checkpoints or convince Karen to let me drive and put her with the task of finding our way. I knew I didn’t want to do the former, but the later meant giving up. I turned to my teammate, hoping she could give me the grace in my failure that I had not given myself.

Karen, someone I barely knew before, knew exactly how to keep me from giving up. She helped me correct my mistake, finding our way to the correct black checkpoint, and speaking to my strengths with the compass where she was good at reading the maps. I still wanted to drive. She asked me to get us to the next check point, and the next one, and the next one after that — as we approached each green and blue flag she helped me slowly quiet the self doubt and realize that mistakes happen. As Rebelle Operations Director told me later, “There’s a reason the rear view is smaller then the windshield.”

​​This was the essence of the Rebelle — each day we woke at that ungodly hour and worked together to figure out our next steps. We got enough down on the maps as we could, thinking we knew our route and we’d adjust it on the fly. We’d set out in the morning, maybe not so much refreshed but at least excited and renewed, crossing terrain I’d never seen before and watching sunrises few get to appreciate. Each small win felt monumental — when the odometer read exactly what I measured as we pulled up to a blue flag, I felt like a true Marco Polo. When we spotted a tiny bit of rebar just in the distance, it was really like finding a needle in a haystack. We grabbed the points we could, and reflected on the fly how we could improve on points we missed. There was no room for egos — mistakes compound and can ruin an entire day, or worse, get you lost in the desert. To fail fast, I had to whole-heartedly trust the person next to me. And honestly, I never thought I’d be able to do that again.

​​As Karen and I crossed the finish line on the final day, we made our first connection to the world by desperately scanning satellite radio for something akin to “We are the Champions” or a belting Kelly Clarkson, but gave up and settled on “God is a Women” by Ariana Grande. I jumped from the passengers seat, took off my Jetson-like helmet, and danced like no one was watching.

​​​I looked at Karen, a perfect stranger grown teammate into friend, knowing we had pushed ourselves to our very limit and come out stronger. With tears in our eyes, we both were greeted by Emily Miller and her incredible team who understood this accomplishment and greeted us with the same joyful tears. The smile on my face was not forced, the pure elation was brimming from my uncleaned pores, and I instantly realized I was with my people — women willing to find out what they’re made of, unafraid to be both competitive and compassionate in the same day, willing to step away from the world of responsibilities to try something new and return home a better person.

​​For me, though, there was one more layer to this journey. At the final closing gala, I watched a recap video they made. When I saw my face on the screen, strong and determined as the words “I am not afraid” played in voice over in the background it was all I could do to stay composed. The team number we’d been assigned was 180, and that’s exactly where I was in this moment. My life had changed so much. It was so much more than a journey from Tahoe to San Diego, more than an endurance rally, I had found a path back to me. The person I was a year ago could not have done this, but for the first time in over nine years I wasn’t afraid. I wasn’t limited. I wasn’t broken — I was free.

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