9: Writing with Heart: How Douglas Weissman Crafts Stories That Stick

I'm really excited to take you on a journey into the world of storytelling with someone who understands that great writing isn't just about plot, it's about connection. Meet Douglas Weissman, a travel writer and novelist who's turning personal experiences into compelling stories.

But his story? It's not just about writing books. It’s about crafting experiences that stay with readers long after they’ve turned the last page.

From Ordinary Moments to Narrative Gold

What if our most powerful stories are hiding in the moments we overlook? Douglas believes your life is a treasure trove of storytelling potential. From a random conversation with a stranger to a missed train, every moment has the potential to inspire extraordinary stories.

Actionable Tip: Start a story collection journal. For the next week, write down one unexpected moment each day. What made it unique? What emotions did it stir?

Bonus: Choose one of these moments and write a 500-word scene exploring its emotional core. Don't worry about perfection. Just dive in and see what emerges.

Breaking Free from Creative Paralysis

Most writers get stuck because they're chasing some mythical "perfect story." Instead of waiting for the right moment, Doug embraces the messy, real, and raw. Your first draft doesn't need to be a masterpiece. It needs to be honest.

Actionable Tip: Set a timer for 20 minutes. Write without stopping, without editing. Let your story spill out onto the page in its most raw form.

Bonus: Read your unedited writing out loud. What surprises you? What feels most authentic?

Navigating the Small Press Landscape

The publishing world isn't just about big publishers. Douglas has carved a path through small presses that celebrate unique voices. These publishers aren't looking for cookie-cutter books—they're looking for stories with heart.

Actionable Tip: Research three small presses in your genre. What makes them different? How do they support emerging writers?

Bonus: Reach out to one small press. Ask a genuine question about their publishing approach. Build a relationship, not just a submission strategy.

Writing in the Age of AI: Staying Human

AI can generate text, but it can't generate soul. Douglas sees AI as a tool, not a replacement. Your lived experiences and unique perspective are what make stories shine.

Actionable Tip: Use AI for brainstorming, but write your actual story in your voice. Compare the AI-generated ideas with your authentic story.

Bonus: Write a scene both with AI and on your own. Which feels more alive?

The Vulnerability Advantage

Don't be afraid to share your most vulnerable moments. They're the ones that connect most deeply with readers and make the best stories.

Actionable Tip: Write about a moment you've been hesitant to explore. What makes it uncomfortable? What does it reveal?

Bonus: Share this writing with a trusted friend and ask for input. Sometimes an outside perspective helps us see our story's true power.

Marketing Your Work Without Selling Your Soul

Douglas believes in building genuine connections to sell his books. Your marketing should feel like an invitation to connect, not a sales pitch.

Actionable Tip: Instead of just sharing links to your book on your newsletter, share your writing journey. What's happening behind the scenes?

Bonus: Host a small online writing workshop or class. Give value before asking for anything in return.

Key Takeaways:

• Your life experiences are your greatest storytelling resource
• Embrace imperfection in your writing process
• Small presses can be powerful platforms for unique voices
• AI is a tool, not a storytelling replacement
• Vulnerability creates the deepest connections

Your Story Deserves to Be Told

If you've been holding back in your writing, now's the time to take action. The world needs more stories with heart. Yours could be one of them.

Ready to Level Up Your Creative Career?

Visit TheStandoutCreatives.com to book your free strategy session.

📌 Note: I keep these sessions limited so I can give each person my full attention—so don't wait too long!

Recommended Books:

Big Magic by Elizabeth Gilbert and On Writing by Stephen King