710: Ravi Gupta - The Anti-Dabbler's Guide to Mastering One New Skill Every Year, Why Presence Isn't Enough, Bourdain's Masterclass in Humility, and Pairing Reasonable Goals With Delusional Ones

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My guest:

Ravi Gupta is the founder of RePublic Schools, whose flagship Nashville schools became the first in Tennessee to rank in the top 5% statewide for both growth and achievement. He co-founded Arena, which trained more than 7,000 political staffers, worked on the first Obama campaign, and wrote speeches for UN Ambassador Susan Rice. Today he runs The Branch, a media company fighting polarization. His new book is The Invisible List: One Passion a Year, Every Year.

Key Learnings

One new passion a year, every year. When Ravi left his job running schools, he decided to treat every year like a school year with himself as the only student. He's done it for seven years. Surfing, tennis, screenwriting, a novel, Italian cooking.

Be an anti-dabbler. The seductive version is a little boxing, a little salsa dancing, a little cooking. You get fifteen years of sampling and none of the skill. Pick the thing, commit to the year, see it through even if you come to regret the pick.

The rule that makes it work: no new thing midyear. You can maintain old passions. You cannot start a new one.

He broke his own rule and learned why it exists. Bored one day and avoiding his cooking, Ravi walked into a Muay Thai gym on his corner. He loved the class, walked out, and told himself it was off the table until January 1. The pull wasn't interest. It was the rush of early wins, and that rush is the most convincing form of procrastination there is.

Trying something and quitting can be worse than never trying. Once you've tasted it, you start seeing it everywhere, and you replay the version of your life where you stuck with it.

Pair a reasonable goal with a delusional one. Ravi almost always hits the reasonable one. He almost never hits the unreasonable one right away, but he often gets there eventually. The pairing is the point.

Tim Ferriss's observation on why that works: there's less competition for big crazy goals, because so few people think that way anymore.

December is the meta-learning month. Thanksgiving to New Year's, Ravi wraps up the current year and pulls together the next one: the books, the experts, the sequence, what it actually means to be great at the thing.

Don't start researching it in August. He has next year's candidates in his head by late summer, but he refuses to buy books or line up coaches until December. Planning next year's passion is an elaborate way to avoid this year's.

Output goals need a skill set attached. Example: hiking an outrageous number of national parks. Ravi's counter: keep the output goal, but build the skills underneath it. Pitching a tent, starting a fire, navigation, survival prep. Then the year leaves you with something beyond a number.

Each year becomes a chapter. 2020: surfing. 2021: tennis. Childhood is memorable because it's divided into grades with names attached. Adult years blur into one undifferentiated stretch, and Ravi thinks that blur is part of why peop