New York Times Bestseller (and one of my all-time favorite authors) Robert Dugoni is on Guyset!!! I've been reading Robert's books for the past 4 years and this was an interview I dreamed of doing. I am endlessly inspired by his stories and I know you will be too. I'm so grateful to have had this conversation and I can't wait for you to hear it!

"I Didn't Want to Look Back and Say I Never Tried": Life Lessons from Bestselling Author Robert Dugoni

For guys in their twenties navigating career paths and life decisions, there's something uniquely valuable about hearing from someone who completely reinvented their professional life in pursuit of a dream. That's why I was thrilled to speak with bestselling author Robert Dugoni, whose winding journey from successful lawyer to acclaimed novelist offers powerful lessons about following your passion.

Robert's books have captured millions of readers (including my mom's book club, who first introduced me to his work with "The Extraordinary Life of Sam Hell"). His Tracy Crosswhite series has gone viral, his standalone novels have won critical acclaim, and his works are being optioned for film and television by major studios.

But Robert's path to success was far from straightforward. In our conversation, he shared insights on creativity, perseverance, and finding meaning that resonate far beyond the world of writing.

The Career U-Turn That Changed Everything

Despite knowing he wanted to be a writer since seventh grade, Robert followed the conventional advice most of us hear: get as much education as possible, have something to fall back on. This led him to law school and eventually a successful career at a prestigious San Francisco firm.

"I had the time of my life," Robert told me about his legal career, "but it was never my passion."

It wasn't until 1999—well into his professional life—that Robert and his wife made the bold decision that he would give writing a real shot. What followed was a rollercoaster of ups and downs that included:

• His first book published in 2004

• A five-book deal with Simon & Schuster

• Being dropped by his publisher in 2011

• Writing "My Sister's Grave" (the first Tracy Crosswhite novel) that went viral in 2013

• Finally becoming a full-time writer at age 50

For those of us feeling stuck on conventional paths or worried about making career pivots, Robert's story is a powerful reminder that it's never too late to pursue what truly matters to you.

The Creative Process: Discipline Over Inspiration

When I asked about his creative process, Robert didn't romanticize it: "My creative process is put your butt in a chair and go to work. I mean, that's my creative process."

This no-nonsense approach comes from years of balancing writing aspirations with real-world responsibilities. "I didn't have a problem working because I had worked as a lawyer," he explained. "I could sit at my desk for eight to ten hours. I still do."

But discipline alone isn't enough. Robert emphasized the importance of studying your craft—whatever it might be:

"The greatest artists that ever lived... what they were were great students. Michelangelo didn't just take a piece of stone and create the David. Michelangelo studied the human anatomy, ad nauseam until he understood it better than a doctor."

For his own development, Robert couldn't attend formal writing school, so he created his own education: "I gave myself my own MFA by going to the Elliott Bay Bookstore... sitting on the floor of the how-to section and reading books on the craft."

Finding Meaning in Your Work

Perhaps the most profound aspect of our conversation was Robert's reflection on finding purpose through his writing. While he never sets out to create profound meaning, his novels often deeply touch readers' lives.

"I get so many emails from people that were bullied when they were growing up," he shared about the response to "The Extraordinary Life of Sam Hell." "And they'll tell me how it hardened them, how it made them a stronger person... It's very humbling to have somebody email you and say, 'Your book changed my life.'"

This perspective on work—seeing it as potentially meaningful beyond just financial success—offers a refreshing counterpoint to how many of us think about careers in our twenties.

"I never thought about this as the opportunity to make a lot of money," Robert reflected. "I always thought about this as the opportunity to look back on my life when I'm an old man and say, 'You know what, I did it, I tried.' I didn't want to look back on my life and say, 'I never tried, I never gave myself a chance.'"

The Support System That Made It Possible

No successful career transformation happens in isolation. Robert credits several key relationships with helping him persevere through the difficulties:

1. His wife: "I had an incredibly supportive wife who just always believed in me and just always thought that things would work out for me."

2. His agents: "When I got let go by Simon and Schuster, Jane Rott-Rosen took me out for a drink and she said, 'Listen to me, I'm telling you right now, I've published dozens of bestselling authors and you will be successful. You will find an audience. Do you hear me?'"

3. His faith: "I'm a guy that has a very strong faith... I just am really grateful. And I try to give thanks as much as I can."

These support structures provided the foundation that allowed Robert to weather the inevitable setbacks along the way.

Advice for Pursuing Your Own Passion

Throughout our conversation, Robert shared insights that apply to anyone considering following their dreams:

1. Don't quit your day job (yet): "I'm not telling you to quit your job. I'm just telling you to find a way, find what you're passionate about and find a way to make a living at it. And in the interim, do the things that you're doing. Work full time. Take care of your bills. Take care of your families."

2. Remember Michael Colopy's advice: "Follow your dreams and the money will come. Follow the money and you'll lose your dreams."

3. Keep putting one foot in front of the next: "It's really more a matter of continuing to put one foot in front of the next... I never thought about this as the opportunity to make a lot of money. I always thought about this as the opportunity to look back on my life when I'm an old man and say, 'You know what, I did it, I tried.'"

4. Trust the process: "I think when I get done with one of my novels, I'm usually done with it. I'm like, 'For the love of God, just let me move on to the next thing.'"

When I asked what he would tell his 24-year-old self, his answer was simple: "Follow your dreams... Find your passion and then find a way to make a living at it. And then you never work a day in your life."

Practical Takeaways for Finding Your Path

For guys figuring out their next career moves or creative pursuits, Robert's journey offers several actionable insights:

1. Give yourself permission to learn: Whether it's sitting on a bookstore floor or taking online courses, invest time in building your skills.

2. Create a consistent routine: Success rarely comes from flashes of inspiration—it's built through daily discipline and showing up consistently.

3. Surround yourself with believers: Find people who support your vision and can encourage you when doubt inevitably creeps in.

4. Think beyond financial success: Consider how your work might impact others and create meaning beyond just a paycheck.

5. Embrace the journey: Recognize that most successful careers involve setbacks and reinventions—Robert wasn't an "overnight success" until his 50s.

Final Thoughts

What struck me most about my conversation with Robert wasn't his impressive success or growing fame—it was his gratitude and perspective. Despite the challenges along his path, he approaches each day with appreciation for the opportunity to do what he loves.

"Every day I get up and I come in and I sit at my computer here in my office, I feel incredibly blessed," he told me. "I thank God every day that I get to pursue my passion because I know that most people don't."

For those of us still figuring out our paths, that's perhaps the most valuable insight of all—the reminder that finding work that fulfills you is worth the journey, however winding it might be.

Want to hear the full episode? Listen to my conversation with Robert Dugoni on Apple Podcasts, Spotify, or wherever you get your podcasts. You can also follow along on Instagram and TikTok @theguyset for more content.

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Beyond Reasonable Doubt by Robert Dugoni is out everywhere today!

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