Thriller author Robert Bailey is here to talk about his new novel "The Boomerang” a page-turner that will have you guessing until the very last chapter. Whether you're a thriller fan, looking for your next summer read, or just love books that keep you hooked from page one, this episode has something for you.

We dive deep into Robert's writing journey, from his early aspirations to getting his first book published, and what a typical day looks like for him as an author. Get an exclusive behind-the-scenes look at his writing process, how he sits down to create these nail-biting stories, his daily writing habits, and the rituals that keep him motivated.

Robert opens up about the inspiration behind "The Boomerang," sharing how this particular story hits close to home and what he hopes readers will take away from it. We explore the highs and lows of the writing life, his favorite aspects of the creative process, and the challenges that come with writer's block.

Robert discusses how to separate yourself emotionally from your work, the bittersweet moment of finishing a book, and how his life has changed since becoming a published author. Plus, he shares his favorite books, career-changing advice he's received, and his best tips for aspiring writers.

This episode is perfect for anyone interested in writing or just wants to hear an engaging story about pursuing your passion. Tune in for practical writing advice, honest insights into the author's life, and discover your next favorite book.

What You'll Learn From Robert Bailey:

• The daily habits and rituals of a successful thriller writer

• How to push through writer's block and creative challenges

• The story behind "The Boomerang" and its personal significance

• Practical tips for aspiring authors

• Book recommendations from a master of the genre

Book: "The Boomerang" by Robert Bailey, available everywhere now

More: From Lawyer to Bestselling Author: Robert Bailey's Blueprint for Career Change

How a practicing attorney followed his dream to write 12 books—and what his journey teaches about taking risks in your twenties

When Robert Bailey finished law school, he had a clear path ahead of him: successful legal career, steady income, predictable future. But there was one problem—he couldn't shake the feeling that he was meant to be a writer.

Today, Bailey has published 12 novels, including his latest thriller "The Boomerang," all while initially maintaining his law practice. His journey from courtroom to bestseller list offers powerful lessons for any guy in his twenties wrestling with whether to pursue his passion or stick with the "safe" choice.

The Spark That Changes Everything

Bailey's writing journey began in college with a single creative writing class during his final semester at Davidson College. "I wrote four short stories, which were probably terrible," he admits, "but I got enough good constructive criticism that I thought there might be something there."

That "something" didn't immediately lead to a career change. Like many of us, Bailey followed the conventional path—law school, legal career, building a practice. But the idea for his first book came during law school, and it wouldn't let go.

The Lesson: Sometimes your passion finds you through a side door. That random elective, weekend hobby, or creative project might be showing you your real calling.

The Two-Track Approach: Passion + Stability

Here's what sets Bailey apart from the typical "quit your job to follow your dreams" story—he didn't. Instead, he developed a system that let him pursue both:

• 4:30-7:00 AM: Writing time, every morning before work

• Full days: Practicing law and supporting his family

• Weekends: More writing when possible

"That was really the only time I could do it," Bailey explains about his early morning writing sessions. "We had young kids, and that was the only time I could carve out."

The Lesson: You don't have to choose between financial responsibility and creative passion. Build a bridge, not a cliff jump.

The Reality of Rejection

Bailey's path to publication wasn't smooth. He queried 100 literary agents for his first book. Thirty wanted to read it. Eventually, he got two offers and chose one. Then came another year of publisher rejections before finally landing a deal.

The process taught him a crucial mindset: "Writing and so many other endeavors—it's the land of a thousand no's. But it really only takes one yes sometimes to change your stars."

His first manuscript was 800 pages long. "Nobody would have read it except my wife," he laughs. After learning the industry standards, he had to completely revise.

The Lesson: Rejection isn't personal—it's data. Use it to improve and keep moving forward.

The Power of Persistence and Preparation

One breakthrough moment came when Bailey needed a blurb from a famous author. He reached out to Winston Groom (author of "Forrest Gump") with the same query letter he'd been sending agents, just slightly personalized.

Groom said yes—and that blurb ended up on the cover of Bailey's first published novel.

"A lot of the authors did respond that I reached out to," Bailey notes. "You just never know what somebody will do for you unless you ask them."

The Lesson: The worst someone can say is no. And sometimes, they'll say yes in ways that change your life.

Building Momentum: The Daily Practice

Bailey's writing routine evolved as his success grew. Now writing full-time, he typically writes:

• 5:30-8:00 AM

• 9:00 AM-1:00 PM

• Plus evening sessions when he's near finishing a book

He's learned that showing up matters more than hitting arbitrary word counts. His to-do list used to say "write 1,000 words." Now it just says "morning session, mid-morning session, afternoon session."

"If I check those three boxes, normally I'm going to get more than a thousand," he explains. "I might get 2,000, but I'm not thinking about a thousand."

The Lesson: Focus on the process, not just the outcome. Consistency beats intensity.

Dealing with Imposter Syndrome

Even after 12 published books, Bailey still battles self-doubt. "There is a bit of imposter syndrome that never goes away as a writer," he admits.

His solution? Keep showing up. "I try to be a little easier on myself once I feel like I've put everything I've got into it."

He finds comfort in knowing even literary giants struggled with the same feelings. He mentions John Steinbeck's journal entries while writing "The Grapes of Wrath," where Steinbeck expressed the same doubts every writer faces.

The Lesson: Imposter syndrome doesn't go away with success—but you can learn to work through it.

When Personal Experience Fuels Your Work

Bailey's latest novel, "The Boomerang," draws from his family's experience with cancer. His wife battled cancer at 40, and his father died from stage four lung cancer—both experiences informed the emotional core of his conspiracy thriller.

"All of the steps that Eli and Bella and Dale walk along the way, those are steps that I walked," Bailey explains about his characters' cancer journey.

Writing about personal trauma was challenging, but it added authenticity and emotional depth that resonates with readers.

The Lesson: Your experiences—even the painful ones—can become the source of your most meaningful work.

The Transition: From Side Hustle to Main Hustle

Bailey didn't wake up one day and quit law. As his books became more successful, his legal practice naturally scaled back. He transitioned to mediation work, which complemented his writing schedule better than trial law.

Last year, he officially retired from practicing law and now writes full-time while doing occasional mediation work.

The Lesson: Career transitions don't have to be dramatic. Sometimes the best approach is a gradual shift that aligns with your growing success.

Advice for Your Younger Self

When asked what he'd tell his younger self, Bailey's answer was surprisingly simple: "Relax a little bit more and be a little bit kinder to myself. I would just tell my younger self that this is gonna be okay."

He admits to being a "worrywart" who sometimes focuses so much on results that he forgets to enjoy the journey.

The Lesson: Success isn't just about the destination—it's about becoming the person who can appreciate the journey.

The Bottom Line

Bailey's story isn't about choosing between security and dreams—it's about refusing to accept that you have to choose. He built a sustainable way to pursue his passion while meeting his responsibilities.

His approach required discipline, persistence, and a willingness to work harder than most people are willing to work. But it also allowed him to transition from lawyer to bestselling author without risking his family's financial security.

For guys in their twenties wondering if it's too late to start something new or too risky to pursue their passions, Bailey's journey offers a middle path: Start where you are, use what you have, do what you can.

The dream you have today doesn't need to be put on hold until "someday." It can start tomorrow morning at 4:30 AM with a blank page and a commitment to show up.

As Bailey learned from Stephen King's advice: "Read a lot, write a lot." Replace "write" with whatever your passion is, and the formula remains the same.

Your breakthrough might be just one yes away.

Want more stories about guys who figured out how to chase their dreams while staying grounded? Subscribe to Guyset for weekly conversations about navigating your twenties with purpose and authenticity.

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