Why I’m Proud to Be the King of Second Tries
Three books can change your Thursday. One book can change your world.
Hello,
Over the years, I’ve sat around dinner tables, in writing circles, with friends and colleagues—and the same question often comes up:
What’s your superpower?
Some people say empathy. Others say grit, discipline, or humor. I always pause when I hear it. Not because I don’t have an answer, but because mine isn’t flashy. It doesn’t wear a cape or arrive with fanfare.
My superpower?
I’m the king of second tries.
Which is a poetic way of saying—I’ve failed. A lot.
I bombed my first MCAT. Landed in the bottom 25th percentile. That one hurt. I’d studied, thought I had done enough. I hadn’t. But I didn’t walk away. I regrouped, changed my strategy, and sat again. Second time? 90th percentile.
When I first applied to medical school, I was rejected. That kind of silence can shake your identity if you let it. I gave myself two years. Earned a master’s degree, gained new experience, and reapplied. That second try? I got into my first-choice school.
During my intern year of emergency medicine residency, I was told—I was near the bottom of my class. It was honest, and I took it seriously. I dug in. Studied harder. Showed up early. Asked better questions. By my third year, my evaluations described me as a leader—calm, capable, confident.
My first business collapsed after six months. The second—Rosh Review—grew to support hundreds of thousands of medical learners around the world. It started small. A laptop and the will to get it right this time. I moved slower. Thought more clearly. Chose better partners. The second try changed everything.
If I had accepted the verdict of my first tries, my life would look nothing like it does today.
Here’s the truth: most first tries aren’t failures. They’re drafts.
We’re conditioned to celebrate people who get it right the first time. But real life? It’s rarely that neat. Almost every meaningful thing in my life—medicine, business, school—got better the second time around. Why? Because the second try comes with experience. With humility. With a little scar tissue.
Second tries are underrated.
They’re quiet. Unceremonious. They don’t come with applause. They come when no one’s watching. They show up when it’s easier to walk away. They arrive with less ego, more patience, and a deeper understanding of what truly matters.
And maybe most importantly—they come with belief. The belief that the next version of you might be stronger, wiser, and more capable than the one who stumbled.
Because second tries don’t start from scratch.
They start from experience.
So if you’ve failed recently—good.
If you’ve stumbled—good.
If the path’s been harder than you expected—welcome to the human experience.
If you’re sitting on the other side of a first try that didn’t go as planned—good. It means you’re alive. It means you’re learning. It means you still have a second swing in you.
There’s a quote I think about often:
“The best time to plant a tree was 30 years ago. The second-best time is today.”
Take a breath. Gather yourself. Get up.
Try again.
That second try might just be the one that changes everything.
Welcome to this week’s Three Book Thursday.
1. Memoir
The Pursuit of Happyness
Summary
Before it was a blockbuster film, before Will Smith turned it into a cultural touchstone, The Pursuit of Happyness was a story that most people would’ve never believed. A single dad, homeless, sleeping in subway station bathrooms with his toddler son—who somehow went on to become a Wall Street success story. It sounds like a fairy tale. Except it’s all true.
Chris Gardner didn’t grow up with privilege. He grew up with pain. An absent father, a violent stepfather, a system that offered more obstacles than opportunities. But what he lacked in stability, he made up for in determination. Not the kind that screams and postures. The quiet kind. The kind that shows up, day after day, even when the world tells you no.
That’s what makes this book so powerful.
It’s not just about the grind—it’s about grit. About showing up in a suit for a stockbroker internship with no salary, while carrying your entire life in a duffel bag. About being told no over and over, but still knocking. About protecting your kid’s future, even when you’re not sure what yours looks like.
Gardner doesn’t write like someone trying to impress you. He writes like someone trying to survive. His voice is raw, honest, and filled with the kind of wisdom that only comes from being forced to figure things out the hard way. He doesn’t sugarcoat the journey. There are no easy wins. Just relentless forward motion.
And that’s what stuck with me.
This is a book for anyone who’s ever been told they’re not enough. For anyone who’s been knocked down so hard they weren’t sure they’d get up again. For anyone who’s had to chase a dream with nothing but belief in their back pocket.
Chris Gardner’s story is proof that your circumstances don’t get to write your ending—you do. That sometimes the gap between rock bottom and the life you imagined is just one more step forward. That success isn’t always about brilliance. Sometimes, it’s just about refusing to stay down.
And maybe that’s the most powerful kind of success there is.
Favorite Quote, Insight, & Principle
Quote: “The world is your oyster. It’s up to you to find the pearls.”
Insight: The world will often whisper you’re not enough. Your job is to roar back with everything you’ve got.
Principle: The secret to success is to find something you love to do so much, you can’t wait for the sun to rise to do it all over again.
Author: Chris Gardner
Themes: Memoir, Living a full life
2. Memoir
My Life
Summary
In college, I was a full-on Bill Clinton fan. Not in a casual, “I like the guy” way—but in a “watch every speech, quote his lines, debate his policies” kind of way. His presidency overlapped with my college years, a time when I was forming my worldview, trying to figure out who I was and what kind of life I wanted to build. So when My Life came out, I didn’t hesitate. I bought it on the first day. And I devoured it.
This book is massive—both in size and scope. Clinton doesn’t just cover his presidency. He takes you all the way back—to his childhood in Hope, Arkansas, to the complicated relationship with his stepfather, to the teachers, mentors, and moments that shaped him. You see the full arc: the ambition, the setbacks, the improbable rise, the decisions that defined a generation, and the personal failures that nearly undid it all.
What makes My Life worth reading isn’t just the politics. It’s the humanity.
Clinton is deeply reflective in these pages. He doesn’t shy away from his missteps. He owns them. And while he remains a politician—careful at times, strategic in how he tells the story—you also get a glimpse of something rarer: someone wrestling with the complexity of being both powerful and flawed. Someone who knows what it’s like to carry enormous responsibility while still being deeply, painfully human.
There’s something for everyone here. If you’re an entrepreneur, you’ll recognize the fire of someone who believes in vision and outworks everyone to get there. If you’re a medical professional, you’ll resonate with the tension between public service and personal sacrifice. And if you’re simply someone trying to live with purpose, you’ll see how often we are shaped not just by the big moments, but by the small decisions we make when no one is watching.
My Life reminded me that growth is never linear. That ambition and idealism can live alongside doubt and regret. And that leadership, at its best, requires heart, resilience, and the willingness to learn from your own mess.
It’s not a perfect book. But it’s an honest one.
And for me, it was a reminder that no matter how far you rise, the real work is staying grounded in who you are, owning your story, and continuing to grow—even when the whole world is watching.
Favorite Quote, Insight, & Principle
Quote: “I wouldn't piss in his ear if his brain was on fire.”
Insight: Your life is shaped by the opportunities you turn down as well as by those you seize
Principle: Will you be someone who defines yourself in terms of who you aren't or who you are?
Author: Bill Clinton
Themes: Memoir, Politics
3. Patient care
A Not Entirely Benign Procedure: Four Years As A Medical Student
Summary
There’s something about medical school that never fully leaves you. No matter how many years have passed or how many shifts you’ve worked since, you can still hear the echo of those first white coat days—the thrill, the fear, the constant sense of not being enough.
That’s what makes A Not Entirely Benign Procedure such a timeless read.
Perri Klass takes you right back to those formative years with a clarity and honesty that only someone who’s lived it—and processed it through reflection—can provide. The book isn’t about heroism. It’s about humanity. Klass captures the raw, unpolished moments of learning how to become a doctor while still trying to hold on to your sense of self. She’s brilliant without being boastful, vulnerable without being performative, and deeply observant about what happens to a person when they’re immersed in a world that constantly asks more of them.
Reading this brought back so many memories: the early mornings, the weight of responsibility, the moments where I questioned if I had what it takes. But also the awe. The privilege of being with people during the most fragile, powerful, and intimate moments of their lives. Klass doesn’t sugarcoat it—she honors it.
And what makes this book resonate beyond medicine is the larger message: the tension between becoming and belonging. Between doing the work and staying connected to who you are. Between mastering the system and not losing your soul in the process.
If you’re in medicine, this book will feel like a mirror. If you’re outside of medicine, it’s a rare window into a world most people don’t fully see. And if you’re in any profession where the stakes are high and the journey is long, you’ll find pieces of yourself in these pages.
Because becoming who you are—whether that’s as a doctor, a leader, a parent, or a person—is never an entirely benign procedure.
It leaves its mark.
And if we’re lucky, that mark becomes something meaningful.
Favorite Quote, Insight, & Principle
Quote: “Uncertainty is the central fact of medicine, though it is the last thing the public wants to hear.”
Insight: Medical school is a journey of discovery: you learn about medicine, but you also learn about yourself.
Principle: The terror of incompetence is the universal terror of medical school; it is what drives us to study until the library closes and beyond.
Author: Perri Klass
Themes: Patient care, Medical school, Residency, Medicine
First tries get all the attention. They come with anticipation, with pressure, with the bright shine of potential. But it’s the second tries—the quiet ones, the gritty ones—that often carry the most weight.
Chris Gardner didn’t find his purpose on the first swing. He found it in the darkness—homeless, broke, scared—but still showing up in a suit for an unpaid internship because his son was watching. The Pursuit of Happyness isn’t just a story of success. It’s a story of refusal. Refusal to quit. Refusal to let the first try define him.
Bill Clinton’s My Life reminds us that even when the whole world is watching, you’re still just a person figuring things out. That growth isn’t a straight line. That after every triumph and every mistake, the work of becoming never stops.
And Perri Klass shows us that becoming a doctor isn’t just about passing exams—it’s about surviving your own doubt. About coming back after long nights, hard critiques, and the fear of not being good enough, and still choosing to put on the coat and try again.
The thread between them—and maybe between all of us—isn’t perfection. It’s persistence.
Because the truth is, most of life is made in the second tries.
The ones that don’t look heroic. The ones that start quietly, with no guarantees. The ones that happen after the applause has stopped.
That’s where the real stories live.
And maybe that’s the invitation this week: to let go of the myth that greatness happens on the first attempt. To see your stumbles not as signs to stop, but as signals that something better might be waiting—if you’re willing to keep going.
You don’t need to be brilliant the first time.
You just need the courage to try again.
Always ❤️📚💡
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