The Invisible List with Ravi Gupta

“Do not wait. Start now, because you just never know what’s going to happen.” — Ravi Gupta

What are the things you’ve always wanted to do—but keep putting off until you have more time?

After six years of building and running schools, Ravi Gupta found himself exhausted and disconnected from parts of himself he had put aside. At weddings, while reading, or simply watching other people pursue something they loved, he kept noticing the same thing: reminders of experiences he wanted to have, skills he wanted to learn, and passions he had never made space for. So he started writing them down.

That became his “Invisible List”—and the beginning of an experiment: choose one passion each year and commit to pursuing it. Since then, Ravi has taken on everything from surfing and tennis to novel writing, powerlifting, cooking, and even studying for the MCAT. Each pursuit became more than learning a new skill. It became a way of reconnecting with curiosity, challenging himself, and rediscovering parts of who he was.

In this episode of Leadership Story Talks, Ravi joins Jerome Deroy and Julienne Ryan to explore the ideas behind his book, The Invisible List: One Passion a Year, Every Year. Their conversation moves from burnout and identity to lifelong learning, the role of ritual and consistency, and how we might use AI without giving away the very thinking and creative struggle that help us grow.

You’ll Hear:

• How Ravi’s experience launching a school in North Nashville became one of the most formative—and difficult—experiences of his professional life.
• How burnout after starting six schools in six years led him to recognize his own “Invisible List.”
• Why writing down the things you’ve always wanted to do can be the first step toward actually making space for them.
• How different seasons of life call for different kinds of pursuits—from skills you can practice in spare 20- or 30-minute windows to immersive “skill-baticals.”
• Why Ravi decided to spend a year preparing for the MCAT as a kind of “mental marathon,” training memory, attention, curiosity, and problem-solving.
• Ravi’s approach to AI: struggle with the problem first, then use technology once you’ve reached the limits of what you can do yourself.
• Why he believes brainstorming and idea generation may be exactly where we should be most cautious about outsourcing our thinking to AI.
• How creating rituals around learning can make it easier to keep showing up consistently.
• A simple exercise for beginning your own Invisible List: one hour, a pen and paper, no phone, no Google, no AI—and permission to write down everything you’ve wanted to try.
• Why imagining the next decade of your life can create excitement and momentum long before those experiences actually happen.
• How Ravi’s pursuits are increasingly shifting from individual growth toward service—and why training as a firefighter may be next on his list.
• The reminder at the heart of Ravi’s message: there may never be a perfect time to begin, so don’t wait.

Resources:

• Ravi’s company, The Branch
• Ravi’s book, The Invisible List: One Passion a Year, Every Year
• Lost Debate podcast
• Majority 54 podcast
  

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