What are you still telling yourself you’ll do someday?
In a recent episode of Leadership Story Talks, hosts Jerome Deroy and Julienne Ryan spoke with Ravi Gupta, serial civic entrepreneur and author of The Invisible List: One Passion a Year, Every Year.
Ravi’s career has been full of ambitious, high-impact work. He has founded schools, led civic organizations, worked in politics, built media ventures, and launched new companies. But the idea at the heart of his new book did not begin with achievement. It began with exhaustion.
After years of building and running schools, Ravi found himself burned out, depleted, and increasingly aware of all the things he wanted to do but kept postponing. Salsa dancing. Writing a book. Playing sports. Learning things simply because they fascinated him. The list was there. It had always been there. It was just invisible.
The Week That Aged Him Ten Years
When Jerome asked Ravi about an experience that had shaped who he is today, Ravi went back to 2011 and the opening of his first school in North Nashville.
He was in his mid-twenties, launching a school in one of the most distressed neighborhoods in the country, with no prior educational experience. The school itself did not even have a permanent building. During the day, Ravi and his team used a Tennessee State University night school as their middle school campus, then had to transform the classrooms back again so the night school could operate in the evening.
Everything was new. Everything was hard. And many things went wrong. At the end of each day, Ravi and his team would gather at the whiteboard. They would list what had failed, divide up the problems, decide what needed to change, make the calls, visit the students, and begin again the next morning.
Ravi described that first week as the hardest professional experience of his life. He joked that he did not necessarily age physically, but that he gained about a decade of maturity in a single week. That experience became important not only because of what he built, but because of what it taught him about systems, iteration, learning, and responsibility. Those same lessons would eventually become the framework for something much more personal.
When Achievement Leaves Something Behind
Six or seven years later, Ravi had started six schools in six years.
By then, the accumulation had taken its toll. There were the operational challenges of running schools, the political challenges surrounding them, and the emotional burden of managing so many people. Ravi eventually left the work and moved back to New York in 2017.
Around that time, friends started asking him, “Are you okay?” He also began noticing reminders of a different kind. At weddings, he might watch people salsa dancing and think about how he had tried salsa a few times but always stopped. He would read something that reminded him of the book he wanted to write. He would see a sport he had wanted to learn but never made time for.
Again and again, he encountered versions of the same thought: I want to do that. But he wasn’t doing it.
The realization was simple. Ravi had spent years being responsible for other people, organizations, students, teams, and outcomes. Somewhere along the way, the things he wanted for himself had been pushed into an imagined future. That was the beginning of the invisible list.
Put It on Paper
Ravi’s first step was not complicated. He wrote it all down: every interest, every skill, every experience, every thing he had wanted to try but had postponed.
Then he borrowed a structure from his life as an educator. He decided to treat each year like a school year, with himself as the only student. Each year, he would select one item from the list and make it the focus.
The idea was not about productivity for productivity’s sake. It was not a new version of a professional development plan. In fact, Ravi often cautions people against making the practice too career-oriented. It was about learning, identity, curiosity, and reclaiming parts of life that had been pushed aside.
Instead of waiting for “someday,” he would give each passion a year.
You Have More Time Than You Think
One of the most familiar objections to an idea like this is time. Jerome raised it directly. Most people have demanding jobs, families, children, businesses, caregiving responsibilities, or some combination of all of them. How do you devote a year to something new without stopping everything else?
Ravi’s answer is to focus on flexible, nonprofessional time. That amount will differ from person to person, but there is usually some. The question becomes what we do with it.
In The Invisible List, Ravi offers different archetypes for different kinds of years. If life is unusually busy, an “anywhere, anytime” skill might be appropriate: something that can be practiced for twenty or thirty minutes wherever time opens up. If life creates more space through retirement, sabbatical, children leaving home, a career transition, or even a layoff, then that might be the year for what Ravi calls the “big one” or a “skill-batical”: surf camp, cooking school in Tuscany, or some other experience that requires real immersion.
The point is not that every year should look the same. The point is to work with the life you actually have.
Reconnecting With the Parts of Yourself You Thought Were Gone
Julienne connected Ravi’s idea to people she coaches who are going through major transitions. Many have spent years in demanding, all-consuming roles. When that role suddenly ends, they may still have all their skills and abilities, but their sense of identity is shaken.
Who am I without the title? What do I do with myself now?
Julienne often encourages people to return to hobbies or to remember what they used to wish they had time for when they were stuck in the office. Ravi sees something powerful in that instinct. He believes that trying new things can reconnect us with parts of ourselves that feel lost.
We often think self-discovery has to be deeply introspective. Therapy, reflection, retreats, journaling, and other forms of inner work can all matter. But Ravi offered another route: movement. Go do something. Pick up a racket. Learn to cook. Take the class. Write the chapter. Learn the language. Try the thing.
Sometimes action gives us access to ourselves in a way thinking alone cannot.
The Mental Marathon
When Jerome asked Ravi to choose one year from the book and talk about it, Ravi picked what he called the weirdest one. He decided to take the MCAT.
Not because he planned to go to medical school, but because he wanted a mental marathon.
We talk often about keeping our bodies young through exercise, running, strength training, or endurance events. But Ravi became interested in a different question: what would it mean to train the brain with the same seriousness?
The MCAT offered exactly that challenge. It required memory, sustained attention, analytical thinking, problem-solving, math, physics, chemistry, biology, psychology, and sociology. It required sitting through a roughly seven-hour test without a phone and forcing himself to become curious about subjects he had not studied in years.
For Ravi, the goal was not merely the final score. The year itself was the workout. He was training memory, attention, curiosity, analytical thinking, and the ability to sit with difficult material. He described it as one of the most fulfilling years of the entire experiment.
Don’t Outsource the Struggle Too Early
That MCAT year also opened a larger conversation about AI.
As Ravi was studying, new AI tools were becoming more powerful. He began experimenting with them, and the experience helped him clarify when he believes the technology is most useful. His instinct is restraint.
If he had asked AI to explain everything from the beginning, he believes he would have lost much of the value of the experience. Instead, he pushed himself first. He studied, struggled, made mistakes, reached the edge of his own understanding, and then used AI to help him understand what he could not solve alone.
That distinction matters. For Ravi, the struggle is not an obstacle to learning. It is part of the learning.
The same principle applies to writing. If AI generates the idea, the structure, and the substance from the beginning, the writer may produce something quickly but miss the experience of developing the idea themselves.
Ravi compared a more limited use of AI to “writing Botox”: perhaps the work is already ninety-five percent there, and the tool helps smooth a sentence or rephrase something at the end. The important thing is not to outsource the part of the process where your own curiosity, experience, frustration, memory, and originality have to do the work.
Your Ideas Need to Be Yours First
The discussion around AI led back to something central to Ravi’s philosophy. If you are going to use technology, use it after you have thought.
Do not begin the brainstorming process by asking a machine what you care about. The invisible list cannot come from an algorithm because the whole point is to uncover what has been waiting inside you.
What did you love as a child? What do you see other people doing and wish you could do? What book have you read and thought, I wish I had written that? Where do you have fun, even if you are not good at it?
Those answers are personal. They come from your history, your envy, your curiosity, your unfinished business, and your joy. That is precisely why they are valuable.
Take an Hour and Leave the Phone Behind
When Jerome asked Ravi where someone should begin, the answer was refreshingly low-tech: take an hour, bring a pen and paper, and nothing else.
No phone. No Google. No AI. No friends giving you suggestions.
Write down everything you wish you could do.
Ravi suggests asking yourself questions as you go. What did you want to do when you were younger that you gave up on? What do you encounter in daily life and wish you could try? What work inspires you? Where do you have fun? What skill have you always admired in someone else?
Do not edit the list too quickly. Just get it out.
The exercise is less about making a rigid ten-year plan than giving yourself permission to mentally travel into the future.
The Benefit Begins Before You Start
Ravi connected the invisible list to research on anticipation. When people book a vacation far in advance, they do not receive the benefit only when the vacation begins. They spend months looking forward to it, imagining it, planning for it, and enjoying the anticipation.
The same idea can apply to our passions.
If you know that next year might be the year you learn to surf, write a novel, study Italian, or take up ceramics, then part of that future begins to exist now. You start to imagine yourself doing it. You start to notice things connected to it. The future pulls a little closer.
That is the value of penciling the passions into the years ahead. The exercise is not about controlling the future. It is about making room in your imagination for a life that contains more than obligation.
Make It a Ritual
Jerome reflected on his own experience of blocking time in his calendar simply for himself. When work, children, and business all demand attention, it is easy to become the last person on your own list.
Ravi encouraged taking that practice a step further. Make it ritualistic. Create a place. Play a certain song. Light a candle. Say a mantra. Make the time feel different.
It may sound unnecessary, but rituals help communicate something psychologically important: this matters. The more distinct the space feels, the more likely we are to protect it and return to it.
A passion needs more than good intentions. It needs a place to live.
From Self-Development to Service
As Ravi has continued the invisible list experiment, something has changed. His earlier years were often more individualistic. That made sense. He had come out of years of public service and needed to reclaim parts of himself.
But over time, the list has begun bending back toward service.
His current year is focused on cooking, in part so that he can cook for friends and family. For next year, Ravi has tentatively booked a firefighting academy. The plan would require him to spend two and a half months training as a firefighter, with the possibility of later serving with a volunteer department or helping in wildfire response.
He is quick to say the plan could change. Life may intervene. But the direction interests him.
Learning does not have to be only about self-improvement. A passion can become a form of contribution. As Julienne noted, maybe it is not always about us. Maybe we can learn something extraordinary and give something back at the same time.
Do Not Wait
Toward the end of the conversation, Ravi spoke about a woman named Linda Elston, whom he profiles in the book.
Linda had used fitness and CrossFit as part of her fight against cancer. She continued learning, moving, and challenging herself while facing profound health difficulties. Ravi learned shortly before the interview that she had died.
Her story brought him back to the simplest message in the book: do not wait.
“Someday” can feel harmless. We imagine that the things we want will still be available when work slows down, when the children are older, when we have more money, when the timing is better, when we are less tired.
But time is not guaranteed.
The invisible list eventually has to become visible.
What’s on Yours?
Ravi Gupta’s experiment is not really about salsa dancing, MCAT scores, surfing, tennis, novel writing, cooking, or firefighting. It is about remembering that a life is not made only from duties and accomplishments.
There are parts of ourselves that become quiet when we are busy building careers, raising families, managing organizations, meeting deadlines, and taking care of everyone else. They do not necessarily disappear. They wait.
The invitation is to listen for them. Take an hour. Put away the phone. Write down what you still want to try. Do not worry yet about whether you are good at it. Do not ask whether it belongs on your résumé. Do not let AI tell you what your passions should be.
Write the list yourself. Then choose one.
Because one passion a year may sound small, but year after year, it can become a very different life.
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