Entrepreneur Educator, Program Developer, Facilitator

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The time I told my biggest customer to go f*ck themselves

In business, breaking formality can lead to stronger connections

Seven years ago, my biggest project was a multi-year series of startup programs in Brazil. The U.S. State Department had given us a bunch of money to equip budding Brazilian founders with resources, create connections between the U.S. and Brazil startup ecosystems, and instill an American sense of confidence in these entrepreneurs. Little did I know, I was about to make a major blunder that would test the limits of our professional relationship.

My contact at the State Department was a lovely gent named Andrew. So far he had been responsive, on top of his work, and a committed partner in the project. I was in the middle of writing an email to him when my colleague Ali peeked his head in my office door. Ali and I knew each other well enough to talk crap to each other on the regular.  In other words, firing off insults at each other was standard. 

On this particular day, Ali cracked a joke at my expense. “Go f*ck yourself,” I countered with a smile.  

Which was no big deal. Except that I dictate emails using speech recognition software. And the microphone had been on. And I didn’t proofread the email before I hit send. And so when I told Ali to go f*ck himself, speech recognition transcribed what I said…so I had just told my biggest customer—the U.S. Government—a very bad thing.

Uh oh.

At the time, I didn’t even know what had happened. But Andrew at State had replied with a question that required me to review the thread. When I saw my words, my stomach dropped. There I was, a verbal Oppenheimer. 

Horrified, I fired off an apology to which he replied, “No problem—I thought it was just your cool startup style.”

Disaster averted. And a good reminder that if you do good work and treat people well, you will be afforded grace when you make a mistake.

What was more surprising was that this exchange increased the bond between Andrew and me. When I visited Brazil to lead sessions for those founders, Andrew picked me up at the airport and showed me his favorite spots. The accidental f-bomb breached a line of formality between colleagues—and the U.S. Department of State instructs its workers to maintain harsh lines—yet it brought the two of us closer together. 

In your own life, consider testing lines of formality every once in awhile. Doing so will give space for you a little more connection, something we can all use. 

I want very much to connect with others and for my writing to resonate. So from the bottom of my heart, dear reader, go f*ck yourself.

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Thanks to early readers: Kat Koh, Dominik Gmeiner

Photos from the Brazil program