Leveling Up: 12 Questions to Elevate Your Personal and Professional Development

By Ryan Leak

10 min read

Why does it matter? Because the version of success you're chasing might not be yours.

At the end of a corporate workshop, a woman stood up during Q&A. No question. Just a confession. She'd grown up in a volatile home, clawed through a competitive college, learned one rule for climbing: pull someone else off the ladder. It had worked. And she hated who she'd become.

I sat in the back and didn't say anything. I recognized too much. Most of us never get that moment. We're too busy achieving to ask whether the person we're becoming is the one we actually chose to be. We absorbed our definition of success somewhere along the way — the timeline, the title, the right kind of recognition — and never stopped to check the label. Ryan Leak's twelve questions aren't about identifying your gaps. They're about discovering what's been running in the background the whole time. One of them is going to stop you cold. Not because you don't know the answer. Because you do. And you've been hoping nobody would ask.

The Life You're Optimizing For Might Be Someone Else's Dream

Before I could tell you what I actually valued, I could tell you what success was supposed to look like. I'd absorbed that definition from somewhere: school, the neighborhood, the cars in certain driveways. I never questioned where it came from.

Ryan Leak grew up straddling two worlds: a lower-income neighborhood and a private school across town where his classmates' parents held white-collar jobs and drove nicer cars. At around nine years old, he became convinced that one specific vehicle represented everything he wanted from life — a 1997 Chrysler Town & Country, a family minivan with wood paneling on the side and a VCR built into the back seat. A classmate's family owned one. Leak was so certain riding in it would change something that he was fully dressed and waiting at the window thirty minutes before they arrived to pick him up.

That's evidence. The longing was completely real, and completely assembled from context: what the other side of town had, what his neighborhood didn't, what a kid decided must mean something. He didn't choose to want that minivan. The gap between his world and his classmate's manufactured the desire, and the minivan happened to be the nearest object on the other side of it.

Leak's question is whether anything has actually changed. Is the desire for the newest electric car a different kind of longing, or just the same formation with upgraded status markers? Have unlimited cell phone minutes, which genuinely marked success in the early 2000s when your calling plan determined what time friends could reach you for free, just been replaced by frequent flier miles and business class upgrades?

The structure of the longing stays identical. Only the objects rotate.

Leveling up without interrogating what you're leveling toward just accelerates the problem. The benchmark is almost always external: someone richer, more followed, more credentialed. Hitting it just reveals the next one. Lottery winners adapted to their new circumstances and raised the bar rather than feeling happier. The yardstick is self-defeating by design: there is always someone with a better car on the other side of town.

The question almost no one stops to ask: is this definition of success actually mine? Not inherited from the neighborhood, the industry, the era, or the algorithm. Actually chosen.

You probably already know the answer. That's why it's uncomfortable.

Everyone Around You Has Already Read the Report You Haven't

A church board in Minnesota convened without their pastor to decide whether he could keep his job. They weren't debating strategy or budget. The complaints were about anger and abrasive language — enough that the board met in private before bringing him in. They agreed to retain him on one condition: a full year of counseling with a therapist named Fred.

Fred went to work. He interviewed everyone in Bob Merritt's life (staff, friends, family) with two questions: What's good about Bob? What's bad about Bob? They answered. When Merritt finally sat down with Fred, he was handed 225 pages of verbatim feedback. He read descriptions of himself as unapproachable, careless with words, poor at showing he cared. The line that stopped him cold came from his 15-year-old son: My dad is angry a lot. Merritt says publicly that what Fred handed him saved his career, his marriage, and his life. He had joined the church with 300 weekly attendees; he retired with 28,000.

That document already existed before Fred created it. The people in Merritt's life had been holding those pages in their heads for years. He just never asked.

Part of why we don't ask is that we've already written the story. Leak calls this self-serving narrative: we rewrite our own history so the failed project becomes "I wasn't given the resources," the frayed relationship becomes "they changed," the pattern of conflict becomes "I just have high standards." It's not dishonesty. It's the brain casting us as reasonable people in an unreasonable situation.

Tasha Eurich spent years studying self-awareness and found that self-insight and social perception don't travel together. You can be a gifted analyst of your own interior life and be completely blind to your effect on other people. You can read a room expertly and have no real compass for your own motivations. The people who can do both are rare.

Most of us can't. The gap between what we think we're projecting and what actually lands is where the damage accumulates — missed connections, quiet resentments, kids who decide to go sit on the couch.

The question Leak wants you to sit with isn't whether you're self-aware. It's whether the people closest to you would hand you 225 pages that contradict your answer.

The Feedback That Makes You Nervous Is the Only Kind That Works

Knowing those blind spots exist is not the same as finding them.

Most people, when they work up the nerve to ask for feedback, quietly select someone they trust to be gentle. A friend who'll say you're doing great. A colleague who needs something from them. The question gets asked, nothing changes, everyone walks away comfortable. That comfort is the problem.

Ryan Leak tested a different approach while writing his book. He texted his best friend, a lawyer whose previous candor had been honest enough that they didn't speak for a day afterward, and asked one question: How can I get better? What came back wasn't a list of flaws. His friend compared him to Matt Damon. Talking to Leak, he wrote, felt like sitting across from Matt Damon at a dinner party — you'd be desperate not to bore him. Leak's life is full of remarkable experiences; people around him quietly monitor for signs they're losing his attention, becoming oversensitive to whether they're interesting enough. Leak, who'd always thought of himself as a good engager, had no idea.

Leak called it spot on. His friend had put a name to something he'd never seen from the outside: post-event, drained and checked out, he was giving off signals he'd already moved on — and people read them. He now deliberately makes the other person's story more important than his own. Something a fan would never tell him.

That's the distinction. Fans help you feel good. The people you need are the ones almost reluctant to say anything — honest enough to name the thing, careful enough not to weaponize it. Their honesty also depends on how safely you receive it. If you've ever punished candor, they won't deliver it.

Leak treats the question as a practice. Not a performance review, not a crisis conversation. A text to three to five people, to reach the one whose answer makes you slightly nervous. Pull out a notebook when someone responds, he says. Not as a prop, but as a signal: I'm here to record, not argue.

The hard truth usually has an easy fix. You just need someone to name it first.

The People Most Worth Working For Are the Ones Who Give Credit Away

The same ego that makes honest feedback hard to hear also makes credit hard to give away.

What do you actually lose when you give someone else credit for something you did together?

Most people answer instinctively: something. A little standing. A bit of the story. The fear is that recognition is zero-sum — what you hand to someone else is no longer yours. Ryan Leak thinks this is precisely backwards, and he uses Allen Iverson to prove it.

Iverson is in the Hall of Fame largely on the strength of one move: the crossover. The quick fake, the ball switching hands, the defender left behind. His rookie-year use of it against Michael Jordan became one of the most replayed moments in NBA history. The crossover was Iverson's signature, the thing people quote when they say he changed the game. Except Iverson didn't invent it. His Georgetown teammate Dean Berry did. Berry spent hours studying film, synthesizing footwork patterns, and assembling the move from scratch. When Iverson kept getting beaten by it in practice, he finally asked Berry to teach him. Berry did. Berry went on to become an executive at a medical supplies company. Iverson went on to be Iverson.

Two decades into his Hall of Fame career, Iverson told the story publicly and handed Berry the credit. Leak's reaction: this was the Iverson thing. And giving it away cost Iverson nothing. He's still in the Hall of Fame. The story, if anything, adds to the legacy. It shows a player secure enough to tell the truth.

Leak's argument isn't moral. It's diagnostic. When he asks executive teams to each write down the percentage of credit they personally deserve for their group's success, the totals come back between 130 and 160 percent. There's only 100 percent to distribute. When he reads the number back to the room, he doesn't call anyone out. He just says: the math doesn't work, but everyone's number felt true. That's the point. Nobody is lying. The overestimation is structural, not malicious. Which means the instinct to protect credit is usually protecting something you didn't fully earn in the first place.

The people who give credit away freely tend to become the people everyone wants to work with, work for, and stay close to. That's not a soft benefit. It's leverage — the kind that compounds over a career in ways that hoarding recognition never does.

Doing Nothing Has a Price Tag Too

Think of caution as an insurance premium you never stop paying. The premium is your time, your energy, your presence, spent in small invisible installments every time you add another commitment, fill another hour, or optimize for a marginally better outcome on something that doesn't really matter. The policy never pays out. It just keeps costing.

Doing nothing is not neutral. Every lane carries risk, and waiting for the storm to pass is itself a choice with consequences. Sixteen million Americans were unemployed in July 2020, more than half because their businesses closed permanently, not from bad performance, but because staying the course turned out to be the riskiest bet they ever made. The same misread happens inside a life that looks successful. You think you're playing it safe by keeping everything moving, filling every hour, holding every commitment. But you're misdirecting the premium, paying it on things that don't matter.

Brian Dyson, who ran Coca-Cola Enterprises, made the cost concrete: imagine keeping five balls in the air — work, family, health, friends, spirit. Work is rubber. Drop it and it bounces back. The other four are glass. That's what the misdirected premium costs you. Most people have already dropped glass balls they didn't intend to, because they were so focused on keeping everything moving they never stopped to check what couldn't survive a fall.

Leak ran his own audit. He counted the Saturdays he has left with his oldest child before the kid turns 18. At time of writing: 564. That number doesn't motivate — it constrains. It reframes ambition as a scarcity problem: if this is all there is, what am I actually choosing to hold?

The answer isn't to stop taking risks. It's to stop treating glass as rubber.

You Can Win Seven Super Bowls and Still Not Be Yourself

Protecting your time is step one. Step two is harder: who are you actually showing up for, and what are you letting them see?

On an HBO talk show, Draymond Green — fined repeatedly by the league for saying what he thinks — sat across from Tom Brady. Someone in the room asked Brady if he'd ever wanted to pull a Draymond: take the hit, say what he actually means. Brady answered honestly. What he says and what he thinks are two entirely different things, he explained. Roughly 90 percent of the time, the words leaving his mouth aren't the ones in his head. He admires people who can do otherwise. But he avoids conflict. So he stays flat.

Seven Super Bowl rings. Over $290 million in career earnings. The most decorated quarterback in NFL history, explaining that he mostly doesn't say what he means.

Leak's read is brief and brutal: achievement at that scale still can't buy the freedom to be yourself. Brady isn't complaining. He's describing the terms of the deal. The rings, the money, the controlled image. And somewhere in that trade, the gap between what you say and what you think quietly widens until it's just normal. That's what inauthenticity costs. Not a scandal, not a fall from grace. Just the slow accumulation of a life where no one actually knows you.

Frank Warren has been collecting secrets for decades. PostSecret is his project. Anonymous postcards from people who've never told these things to anyone. One card is from a sports executive who describes his organization spending millions on mental health resources that players never use, because they're afraid it'll be used against them. "And it could be," the card reads. That's not paranoia. That's the correct read of the room.

What people can't say at work reads like a list Leak knows by heart: I'm about to file for bankruptcy. My marriage is falling apart. I have no idea what I'm doing and I'm terrified someone is going to find out. He's been in those rooms for years. The composed face across the conference table is carrying the same weight yours is. They're just practiced at keeping it there.

One of Warren's cards is from a lawyer who became one for a father who never got to see it. Read that twice. A career built on law school, the bar exam, and decades of work, chosen for an audience of one who wasn't around to notice. That's what unwitnessed achievement costs. You keep performing. The person you were performing for is gone.

Leak's answer isn't a public confession or a personality overhaul. It's deliberately small: one honest witness. Not a following, not a viral thread. One person — a spouse, a friend, a sibling — with clearance to see the actual ledger. The wins, the losses, the fear running underneath the achievement. Someone who actually knows the real version.

That single honest relationship is where the work actually starts. Not the next promotion, not the next stage. The question the whole book has been circling finally lands: who knows who you really are? If you can't name anyone, you're not there yet.

The Question Worth Asking Before the Week Is Out

All twelve questions eventually circle the same drain. You can reset the benchmark, give the credit away, count what's left of the Saturdays, ask the person whose honesty scares you a little — and still come home performing. Still carrying the ledger nobody else has seen. That's the gap achievement alone won't close.

The prescription isn't total transparency. It's smaller than that, and harder. One person. Someone who has clearance for the real version — not the polished one, not the composure you've gotten good at holding, but the actual accounting: what you've achieved, what it cost you, what you're still afraid of.

The last chapter follows a lawyer who spent twenty years becoming the thing his father wanted. His father died before he passed the bar. He'd been carrying it quietly until he finally told someone who was still alive to hear it.

That's where this begins. Not a transformation. Not a reckoning. Just someone who knows you. Start there.