Some Things I Learned in 2019


2019 deserves a medal. I think it’s one of the first years in a long time (since 2014 to be scientifically accurate) where Americans took inventory of their lives just before the clock struck midnight and thought “Well, except for the diapered mouthbreather in the Oval Office doing all sorts of damage to our long-term future, this wasn’t a bad vibe.”

I have to agree. For me personally, it meant taking the second biggest investment in my personal well-being and spending the summer in Tuscany and Florence, understanding what’s important physically, emotionally, and spiritually alongside a partner who did so much heavy lifting to make that a reality.

That’s not to say it didn’t have painful or introspective moments. We lost my Uncle (also the monumental responsibility of being my godfather) to a heart attack, and the moment I found out nearly broke me. He had a curious mind, being fully immersed and learning all there was to know about botany, religious studies, genealogy, and most importantly, human kindness.

My best trait is that I’m blessed with his curiosity. And I’m working, however slowly, to adopt his temperament. In that vein, I hope to share both emotional and factual things I learned in 2019 in hopes that one of you reads this, goes on Jeopardy one day, and gets a question about Lorenzo de Medici in the “Final Jeopardy” round.

  1. Italians are off the entire month of August. The entire month. There’s no Italian Gary Vaynerchuck telling the shop owners to wake up at 4 and “get to the grind.” They leave the city and take a holiday with their families in the north and away from tourists. I spent part of August fantasizing that it was July and that our favorite panini maker would magically open back up. He did not. And I love him for that.

  2. Florence remains the best city on this planet, but it’s not because of Cosimo I or Lorenzio Il Magnifico. It’s because the family’s final heir, an painfully depressed Anna Maria Luisa de Medici, had the foresight to hand all of the Medici assets to the people of Florence after being unable to bear children. No bulldozing and building skyscrapers to knock down the Palazzo Vecchio, no awful Starbucks, no digital display units on the Duomo. In the centuries of stories of women not getting their fair shake, Anna Maria Luisa has to be Top 10.

  3. I learned I work best in solitude and in silence. This runs contrary to the energy I seek out from my friends and family. It turns out, however, that outside stimuli isn’t much help to any of us trying to get into a flow and do deep work.

  4. There are thousands of churches in Italy, but one of the most religious experiences I had in the country was at a four-hour wine tasting at Accademia del Buon Gusto from its owner, Stefano Salvatori. I won’t link to the thousands of TripAdvisor reviews about this incredible human, but will just say that I teared up more than once talking to him about the pursuit of happiness. It wasn’t the wine. Alexa’s given me so much in our time together, but perhaps one of the most memorable was meeting Stefano.

  5. I learned that one family is essentially responsible for much of the progress you see in the world today. (We’re back to the Medicis.) They commissioned Michaelangelo, Leonardo, Vasari, Verrochio. Catherine de Medici, even though a bit prickly, is responsible for French cuisine and the communal dining experience. (No one in France thought to ever sit together to have dinner. They would just bring the men their food and watch them eat it. Not on Catherine’s watch.)

    The Protestant-Catholics Wars and the rise of Protestantism? That’s the Medicis. Pope Leo X – one of four Medici popes throughout the ages – was so corrupt that Martin Luther decided to write 95 theses and nail them to the church door. How corrupt? He was selling forgiveness of any form of sin to rich lords for 30,000 florins since his appetite was eating into the funds of the Papal bank.

    Oh yeah…and Galileo. The guy who theorized that the Earth wasn’t the center of the Universe and later called a heretic when his benefactor, Cosimo II, lost a bit of power and couldn’t defend him? Bankrolled by the Medicis.

    If you want to read one of the best books written in the past few years, pick up Paul Strathern’s book about them creatively titled “The Medici,” which you can imagine I’ve read at length.

  6. I learned that the Emilia-Romagna Italian State (Parma, Bologna) is the best for food, tourists don’t visit it much, and it’s unbelievably affordable.

  7. I learned that the most important book written for every person on this planet in 2019 was published in the 1980’s and written by Neil Postman. It is the only legitimate work that lives up to the hype of a Matrix-like”red pill” , and will be the reason I never watch political debates or television again, and substitute those things for detailed policy papers or biographies on a candidate.

  8. I learned that Brunello is 100% Sangiovese and must be aged five years with a minimum of two of those years in oak. It’s exclusive to Montalcino.

  9. I learned that Tuscany is enormous and when people ask for a Tuscan wine they probably think the region is far smaller than it is. The climate and terroir in Chianti vs. the climate and terroir in a Montepulciano or Montalcino is different, and there’s a two hour drive between the former and the latter.

  10. I learned that you miss your best friend a lot when they move away. Even if it’s only temporary.

  11. I learned that a place named Condom, France exists, and has an exceptional Italian restaurant.

  12. I learned that loving someone – having grown out of my need to constantly entertain other people or be mentally stimulated 30 hours a day, 8 days a week – is on another level of rewarding.

Here’s to more lessons learned for us all in 2020. And to smart leaders helping us learn them.

About the author


Matt DeSiena's the Head of Strategy at The Winston Project, a marketing collective based in NYC. He's also held senior strategy roles at Bold Move, TBWA\Chiat\Day New York, and Saatchi & Saatchi Wellness, and served on the board of the Cobble Hill Association.

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By Matt