Unlock Personal Growth and Professional Success with Ryan Leak’s Leveling Up

Editor's note: Welcome to On the Books, your guide to titles that add value to your personal and professional ledger. In this series, we spotlight books like Ryan Leak’s Leveling Up, packed with actionable insights to help you grow, reflect, and succeed in life and work. From leadership to self-awareness, these reads offer practical strategies to help you balance the scales and move forward with purpose. Have a book that’s inspired or challenged you? Let us know—we’d love to explore it in future editions!

Ryan Leak, author of Leveling Up: 12 Questions to Elevate Your Personal and Professional Development, shares insights on growth, resilience, and achieving success. Photo courtesy of Ryan Leak’s website.

What’s it like to be on the other side of you?

Ryan Leak presents this as one of the 12 vital questions in his latest book, Leveling Up: 12 Questions to Elevate Your Personal and Professional Development. It’s a question that stayed with me as I read the book, prompting deep reflection on my own personal and professional life.

For Leak—an author, filmmaker, and keynote speaker—these aren’t theoretical exercises. They’re keys to unlocking a life that balances career achievement with personal fulfillment. This book resonates because it invites readers to ask tough, transformative questions that spark growth.

And Leak isn’t slowing down. Following the success of Leveling Up and his earlier work, Chasing Failure, Leak is set to release his next book, How to Work with Complicated People: Strategies for Effective Collaboration with (Nearly) Anyone, on March 4, 2025. His forthcoming book builds on his insights, offering practical tools for navigating challenging relationships in work and life.

How it happened

During the pandemic, Leak noticed a pattern among his high-achieving clients—Fortune 500 executives, NBA athletes, and others who were thriving at work but feeling unfulfilled in their personal lives.

“They’re crushing it at work. Yet, they’re lonely in their personal lives,” Leak told The Balance Sheet. “No point in growing a phenomenal career only to not have your children on speaking terms with you. What’s the point?”

This realization led Leak to write Leveling Up, a book that distills his insights into 12 transformative questions designed to foster self-reflection and growth. Released in 2023, the book offers a roadmap for navigating the complexities of work and life with intention and balance.

Leveling Up: 12 Questions to Elevate Your Personal and Professional Development by Ryan Leak provides practical insights to help readers unlock their potential and achieve success.

The Elevator Pitch

Leveling Up is more than a self-help book; it’s a framework for living a balanced, fulfilling life.

“I’m amazed at how many depressed multimillionaires I know,” Leak said. “I found myself trying to convince my clients to enjoy their lives. This book is about helping people find joy, even in difficult circumstances.”

Leak’s questions challenge readers to examine themselves, their relationships, and their priorities. Whether you’re a leader, a parent, or simply someone striving for more, the path to success starts with self-awareness—and asking the right questions.

The Bottom Line

Success isn’t just about professional milestones. It’s about balancing your “books”—ensuring your life reflects not just achievements, but growth, relationships, and fulfillment.

“Some would say, ‘You can’t have your cake and eat it too,’ but who buys a cake not to eat it?” Leak said. “You can level up in your career and in your personal life at the same time.”

Self-Leadership is the Key

Leak, also the author of Chasing Failure, emphasizes that the best leaders excel at self-leadership.

“They understand that their growth and development is their responsibility,” he said. “They’re not waiting for someone else to challenge them. They’ve figured out ways to lead themselves when no one else is around.”

However, Leak estimates that only 5% of leaders truly excel at both work and life, leaving most people adequate at best. And this reality isn’t limited to leaders—it’s a challenge many individuals face while juggling multiple roles.

Getting Unstuck

For anyone feeling stuck, Leak offers a simple but profound challenge: focus on getting better.

“It’s OK not to be the best,” Leak said. “Most of us won’t be. But we can all get better, and that’s something entirely within our control.”

He encourages starting with honest feedback: “Ask three to five people, ‘How can I get better?’ Then use their insights to guide your growth.”

The Power of Reflection

At the heart of Leveling Up are its 12 transformative questions. Leak believes these questions are more powerful than the answers they inspire. His favorite: What’s it like to be on the other side of me?

“We think we’re great to be around, but are we really?” Leak asks. “Self-reflection is the first step, but true growth happens when we ask others and use their feedback to improve.”

What About You?

Ryan Leak challenges us to examine ourselves with honesty and curiosity. Now, we’re passing the challenge to you: What’s it like to be on the other side of you?

Let’s talk! Share your reflections or the questions you’d ask to level up in the comments below or on social media using #LevelUpChallenge. We’d love to hear how you’re balancing your personal and professional books.