Standout Creatives: Business, marketing, and creativity tips for solopreneurs launching their ideas - 9: Writing with Heart: How Douglas Weissman Crafts Stories That Stick

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

02/12/25 • 97 min

Standout Creatives: Business, marketing, and creativity tips for solopreneurs launching their ideas

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

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

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

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

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

Previous Episode

8: Creative Career Success: How Self-Published Authors and Creatives Can Build a Thriving Business with Russell Nohelty

Meet Russell Nohelty, the self-publishing maverick who's cracked the code to turning creative passion into a sustainable writing career. With nearly a million dollars raised through crowdfunding and a proven track record of breaking through the noise, Russell offers a step-by-step roadmap to help authors transform their writing from a side hustle into a thriving business.

Conquer Perfectionism

Why Imperfect Writing Wins Every Time

Perfectionism can be a creativity killer. Russell’s game-changing approach? Treat your first draft as raw material, not your masterpiece. Perfectionism becomes your superpower when combined with radical self-compassion and a commitment to continuous improvement.

Actionable Tip: This week, aim for messy but meaningful progress: draft 1,000 words in one sitting without editing.

Bonus: Pick one chapter you've been stuck on and finish it within the next week, imperfections and all.

Build Your Community

How to Network Like a Pro

Self-publishing doesn’t mean going it alone. Russell emphasizes the power of building a community of fellow writers, beta readers, and a supportive network that amplifies your reach and credibility.

Actionable Tip: Join one writing group or online community specific to your genre. Contribute meaningful feedback to at least three other authors this month to build genuine connections.

Bonus: Propose a cross-promotion with an author in your niche. Think joint newsletter or shared promotional event.

Amplify Your Unique Voice

The Secret Weapon for Self-Published Success

In a sea of endless books, your unique voice is your greatest asset. Whether you write niche sci-fi, unconventional memoirs, or genre-bending fiction, your perspective will attract dedicated readers.

Actionable Tip: Identify the three most unique elements of your writing style or story that set you apart in your genre.

Bonus: Share a provocative social media post showcasing your unique angle. Invite readers to engage with your story’s world.

Monetize Your Writing

Earn More While Staying True to Your Vision

Authors have more monetization options than ever before. Russell’s approach focuses on creating multiple revenue streams. Having multiple revenue streams allows you to support your creative vision, not compromise it.

Actionable Tip: Audit your existing work. Could you bundle books, offer special editions, or create bonus content for your readers?

Bonus: Develop one additional product related to your book: a workbook, online course, or exclusive behind-the-scenes content.

Share Your Authentic Story

Build Reader Trust by Sharing Your Journey

Your most vulnerable stories are often your most powerful. Being transparent about your writing journey can forge deep connections with readers.

Actionable Tip: Share one behind-the-scenes moment from your writing process. It can be a challenge, breakthrough, personal struggle, or something similar.

Bonus: Create content that showcases your authenticity. Share your inspirations, writing rituals, or the spark behind your story.

Key Takeaways:

Embrace imperfection as part of the creative process.
Build a supportive community around your writing.
Leverage your unique voice as a marketing tool.
Create multiple revenue streams from your writing.
Connect authentically with your readers.

Your Career Transformation Starts Now

It’s time to turn your passion into a profession. The world is waiting for your unique voice.

Ready to Take the Next Step?

Visit The Standout Creatives to book your free one-on-one strategy session today.

Note: Don't wait. I limit the number of strategy sessions to ensure I can give my full attention to each person.

Links referenced in this episode:

Next Episode

10: The Business of Creativity: How to License Your Art, Overcome Blocks, & Navigate Burnout with Lizzie Clark

What transforms a creative passion into a sustainable career? For surface pattern designer Lizzie Clark, the journey started with a love for collage and evolved into a thriving business in licensing and textile design. With years of experience navigating the creative industry, Lizzie has built a business that blends artistry with strategy—proving that with the right approach, creativity can be both fulfilling and financially sustainable.

From Passion to Profit: Making Art Work for You

When does hobby art become a viable business? For Lizzie, the breakthrough came by reimagining her collage work as repeating patterns, ultimately finding her niche in surface pattern design.

Actionable Insight: Look at your current creative work through an entrepreneurial lens. Could your existing art live in multiple formats or markets?

Bonus: Research three brands or retailers that license artwork similar to your style and explore their submission guidelines.

Find Creative Freedom Through Diversification

Building a sustainable creative career isn't just about creating multiple income streams—it's about creative autonomy. Lizzie has strategically built her career by exploring various artistic opportunities and revenue channels.

Actionable Insight: Brainstorm potential ways to sell your creative work. What unexplored avenues might complement your current practice?

Bonus: Identify one new revenue stream (such as licensing, teaching, or collaborations) and outline three steps to start testing it.

Overcome Creative Blocks & Burnout

Creative roadblocks are universal. Lizzie’s approach involves strategic disengagement, seeking inspiration in unexpected places, and maintaining artistic flexibility.

Actionable Insight: Recognize when you need a creative reset. Design personal strategies for reconnection and inspiration.

Bonus: Create a "creativity restoration" toolkit with five things that help you recharge—whether it’s a playlist, nature walks, or a different artistic medium.

How to Navigate Copyright, Art Theft, and AI

Our digital world is changing rapidly so it's essential to understand intellectual property. Lizzie shares pragmatic insights about protecting her creative work in a complex and evolving landscape.

Actionable Insight: Proactively research and implement digital protection strategies for your work.

Bonus: Learn about one legal tool (like watermarks or copyright registration) that can help protect your art.

Align Your Art & Business with Purpose

Understanding what motivates you creatively provides a lot of clarity. Lizzie emphasizes aligning your business practices with your artistic values.

Actionable Insight: Talk about the deeper purpose behind your creative practice.

Bonus: Write a one-sentence mission statement that captures why you create and share it with your audience.

Key Takeaways:

✅ Creative careers evolve through adaptability

✅ Diversification enables artistic freedom

✅ Strategic breaks prevent creative exhaustion

✅ Intellectual property protection is essential

✅ Authentic motivation sustains creative work

Turn Your Creativity into a Thriving Business

Want to make your art work for you? Book a free strategy session at TheStandoutCreatives.com to take the next step.

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

Standout Creatives: Business, marketing, and creativity tips for solopreneurs launching their ideas - 9: Writing with Heart: How Douglas Weissman Crafts Stories That Stick

Transcript

00:00:00.160

Creativity is a muscle. We have to flex it, we have to stretch it, we have to exercise it. And we find different ways to do it. But we have to. Coming back to that idea of showing up to do it, like if I'm not at my table or my desk writing, it's not going to get written. Sometimes there is

00:00:16.719

a block. Not terms of writer block specifically, whether you believe in it or not, but a block just in terms of I don't know where to go right now. S