How To Fall In Love With Teaching Again.
Step 1. Proceed to suck at something...
“Show me what you can do.”
“I told you, I don’t know anything.”
“Yes, but go ahead anyway. Show me the moves that you know.”
“...Ugghh…allllright…”
I gave a pathetic little laugh - more of a gasp - as I half grinned at the floor. It’s my standard response when I know things are going poorly. I was in a room with mirrors covering one wall while standing across from a petite Colombian woman with glasses. I was holding her hands in what I thought might resemble something to do with proper salsa etiquette. She was looking directly into my eyes waiting for me to begin a dance I didn’t know how to do.
With full knowledge of how stupid this must have looked, I started shimmying my hips while moving down to the floor. Had “apple bottomed jeannnns, boots with the fuuuurrr” been playing, I would have aced the test. She let go of my hands. She didn’t do it physically, but I could see her mentally rub her temples in frustration as she recalibrated her expectations of what kind of student she was working with.
Back in February, when I asked ChatGPT where I should learn how to Salsa, and the algorithm spat out Cali, Colombia, I didn’t question it. I messaged four different salsa schools in the city about their programs and one responded in English. I booked an Airbnb two blocks away from the school and four months later I showed up.
I knew my method of decision making wasn’t exactly common, but I guess I didn’t realize how weird my story truly was. When I told other dancers at the school how I ended up in Cali, Colombia, most of them were shocked. Ridge, a guy who became my best friend in Cali, told me he didn’t know a single person who had shown up to the salsa school without at least some kind of background in dancing.
Apparently, signing up for private dance instruction when you’re a true, know-nothing beginner was unheard of. Especially when you happen to be alone in a country where you don’t speak the language. When my poor poor dance instructor, Alejandra, truly understood that I didn’t have a fucking clue how to dance, I think she gasped in horror when she learned I had signed up for 30 hours worth of lessons.
“Theeeese iisss basico, Jiiilbert,” she said in her heavily accented English, as she moved in painful slow motion in an attempt to help me learn which foot was my left and which foot was my right.
Basic. Basico meant basic. I spent my first 90 minutes learning that first step.

Fast forward to 2 nights later and I was at my first legitimate Salsa club, El Rincon, and I was terrified. I was watching native born Calineans tear up the dance floor. Men moved women in blurring twirls, and then seamlessly transitioned into lightning speed foot work. The women moved with impossible finesse, performing never ending spins while somehow also catching eyes with their hip movements in every step.
I could barely fathom the fact that all the dancer pairs were making up the dances as they went. It was the grandest game of physical improvisation I had ever witnessed, and there was some idiotic ignorant version of myself back in February that thought I would be able to stroll into a Salsa school and learn this skill in a week or two.
My feelings of insignificance grew even worse when a bachata song would come on. The tempo would slow and the pairs moved in achingly sensual forms that left me in simultaneous awe of the beauty, and screaming jealousy of the men who had women who danced with them like that. I witnessed beauty while feeling belittled. All I could do was sit in my plastic chair, watch the show, and realize I would never be able to move like that.
Then a girl asked me to dance, and my heart sank into my guts.
Like me she was a tourist. Unlike me she was a damn good dancer. She was a blond beauty from Austria, moved like a native, and spent most of her time on the dance floor trying to avoid men who couldn’t dance. She moved her body in a way that said she had danced for years, if not decades. I had picked up and put down heavy weights in a gym for the entirety of my adult life. She was flowing water. I was rigid iron. There’s no way I could dance with her.
I tried to fend her off.
“I really can’t dance. I have no idea how.”
“That’s okay, come dance anyway.”
“No seriously, I know basico and an incredibly shitty correa.”
“Perfect. Come dance.”
She held out her hands expectantly to me. I considered digging in my heels and just giving a flat no. I didn’t want to make a fool of myself in front of all these incredible dancers. I didn’t want to look dumb in front of all these beautiful women. But then I also remembered something about who I was…
I am a goddamn teacher.
How many times have I asked a student to do something they have never done before? How many times have I asked a student to serve a volleyball when the whole class is watching? How many times has a kid said they don’t want to embarrass themselves? And how many times have I responded, “trust me, no one cares, and if they do, they’re going to forget all about it in 2 minutes.”
Even worse, 1 month ago I had spent an entire school dance yelling at the boys to get off their butts and go dance with the girls. Had I witnessed one of my boys turn down a point blank invitation to a dance from a cute girl they would have never heard the end of it from me.
This salsa club was putting me in the exact same vulnerable position I encourage my students to engage with on a daily basis. I was a high school kid again, and all the insecurities that came with seeing beautiful women and coming to terms with my own incompetence were rearing up in my face.
Thankfully, my mind started barking at me the same words I always yell at my kids, “That’s how you learn! Try. Fail. Try again. Fail better.”... “Yo, do you think you’re just going to be able to talk to pretty girls when the time is right? No! You have practice. You have to take the chances you get!”... “People think you’re an idiot? Who gives a fuck what they think. Who the fuck are they?”
I’ve never been a teacher who didn’t practice what he preached.
I realized I had to take this dance.
I gave the Austrian a grin, the same grin I always give when I know I’m about to make a fool of myself, and said, “well, I really hope you like basico.”
What was once a whim back in February - I wonder what it would be like to travel to another country and learn to dance - became a month-long obsession.
My daily routine eventually looked something like this.
8:30-9:00 a.m. Protein Shake, walk to the gym.
9:00-10:30 a.m. Get big or die trying
10:30 - 11:00 a.m. Go to my favorite restaurant and crush four empanadas. (Gracias, Maria)
11:00 a.m. - 12:30/1 p.m. Have Alejandra yell repeatedly “Jillbert! Otra vez!” during my individual instruction for salsa. In case you’re wondering, “otra vez,” means “again.”
1 - 2/3 p.m. Grab lunch with people from the dance school. Enjoy towering plates of food for less than seven bucks. Laugh, talk shit, make life-long friends.
3-6 p.m Go back to my Airbnb, nap or read or more often than not practice my shitty salsa moves in the mirror while blasting LA INDIA.
7-9 p.m. Go to a group Salsa Class at either La Topa, Sabaki Night, or anywhere I could. It was the best way to meet people.
9 - 10 p.m. Grab a bite to eat, usually with people who went to the group class
10 p.m. - 12/1 a.m. Find a salsa or reggaetón club, and dance my face off.
I put this day on repeat.
I had fallen head over heels for a culture obsessed with Salsa and all the people associated with it. I’d walk into the dance school, Arrebato Caleño, and the three school dogs would rush to greet me as I stretched out on the dance floor. The look of calculation Alejandra greeted me with in the first two weeks turned into a grin with a kiss on the cheek in the later two weeks. I’d talk shit with the dance instructor Sophia. She couldn’t speak a word of English and I couldn’t speak a word of Spanish, so when I say we “talked shit,” I meant we found ever more creative ways to give each other the finger.
Andres, the male dance instructor and the most agile 250 pound man you’ve ever seen in your life, would always greet me with, “Buenos Dìas Johnny Bravo!” on account of me always wearing black tank-tops, and I’d always sing out, “ChuuuChiiii!” To this day I have no idea what “ChuuuChiii” means but Andres always seemed to love it. The front desk guy at the school, Ridge, a guy who eventually became my best friend there, would constantly yell out, “hey Big Gilly!” and would interpret the Spanish directions Alejandra was jabbering at me when I really wasn’t getting it.
The people at the school loved seeing me get better. Particularly in my final week when salsa really began to click. There was one lesson where I learned 4 separate steps and linked them together to music at full speed with almost zero mistakes. By the time I got close to the end of the steps, I could feel Alejandra beaming at me as I twirled her around.
It was an expression I recognized. It was the sheer joy of a teacher witnessing true growth from one of her students. It was a grin that said she was proud of me, but also proud of herself, because she knew she had been an integral part of my dance journey. I may teach different kinds of movement, but I know that seeing your pupil’s success is some of the finest wine this world has to offer. I loved that my progress allowed her a deep drink from that bottle.
The whole process had made me fall in love with learning all over again. It reminded me of why I teach. The people I met, the conversations I had, and the communities formed over that trip never would have happened had I not embraced being a dumb rookie. Donning a Salsa white belt and humbling myself in front of better dancers repeatedly lead me to some of the best people I have ever met traveling. The friendships of a lifetime were rolled up in one intense month of trying, failing, and trying again. Otra Vez, Otra Vez, Otra Vez.
(Alejandra drilling me on move called the Cumbio. At least, I think that’s what it’s called.)
Perhaps my favorite moment came on the very last day of my trip. My plane left Colombia at midnight and I was determined to get one more night of Salsa in. I packed my bags and brought all of them to La Topa. The people at the coat check had a chuckle when I told them I intended to dance and then leave directly for the airport.
I salsa’d and laughed with the people I had become close to over the past month. I was so damn thankful for how lucky I was. To have met the people I met because a computer algorithm had suggested Cali, Colombia for salsa seemed impossible to me. I was also fighting the dread of leaving this world I had just discovered.
When the time came, I went to each of my friends and hugged them tight, telling them I had to go. One of these people was the Austrian girl I had met. She hadn’t gone to my dance school, but by the end of the trip she had become one of our crew. She was easily our best dancer and I had developed what people in the dance community would call a “dance-crush.” Anytime I danced with her throughout the month I felt woefully under-skilled and she continued to not give a damn and compliment me on my improvements. When I went to give her a goodbye hug she refused and held out her hands instead.
“One more dance.”
I grinned and accepted immediately. Airport security be damned.
We danced.
I was by no means good. But I was a world apart from the rookie who could only basico a month ago. My shitty “correa” was no longer shitty. I could pull her hand to my waist and smoothly spin her around my body. My “tunnel” followed by a “bloqueo” was fun and flirty. My two handed rainbow was still a travesty but we gave it a go anyway, and my feet were lightning fast in my “patineta” and my “latino.”
But best of all was the feel. Again, I was no professional, but I was feeling the music instead of thinking of the moves. I was laughing instead of silently counting the beats in my head. (uno, dos, tres, pause! cinco, seis, siete, pause!) I had made a brief leap from conscious incompetence, to unconscious competence.
For that one song I wasn’t dancing.
I was a dancer.
*4 years ago, I read Kevin Kelly’s article, “1000 True Fans.” The gist of it goes like this. Create a following of people who become fans of what you do. Be so damn good at what you do that people want to give you money so you continue doing it.
Here’s what I do. I teach, and I write stories about it.
If you’re in the position where you don’t mind becoming a paid subscriber, I hope you consider it… though if your initial reaction to that is, “fuck off, I’m just here to read,” then rock on.
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You crack me up! Now, in my life, PE teachers have despaired of my almost complete lack of coordination for anything more complex than well, walking. In my 20s, I took close to a year of tennis lessons—there was a federally funded program to promote tennis in the inner city of Durham, NC, something along the lines of $10 a month.
It came to an end when the coach called me into his office and said, “You are driving me to drink. I have tried everything I can to explain this game to you. What did you do as a child?”
When i replied that I read books and drew pictures, his reaction was as if I’d said I had traveled to outer space.
And this weekend, at a workshop on eco-friendlier etching (printmaking—still making pictures at age 70), I recalled the very first time I traveled to an art workshop more than 20 years ago. Nervous and excited. My husband dropped me off at Hartsfield Jackson airport with this admonishment: “Go make lots of mistakes.”
I was shocked and horrified at the prospect of doing so in the company of strangers, being taught by a very famous portrait painter, all the way up in East Fishkill, NY.
“How else will you learn?” he said.
I told my classmates this weekend that I thought I’d made every mistake there was in previous workshops on solar plate etching, a related technique. With pride! I learned new ways to screw up this weekend. With gratitude for the opportunity.
Flying to Colombia for a month to learn salsa at a random dance school is one of the most awesome things I have ever heard of.