the Stateside Wanderer

Artificial Intelligence (AI) is transforming how we create, communicate, and explore the world. From generating comedy scripts to crafting travel itineraries, AI tools like ChatGPT, Claude, or MidJourney are only as powerful as the instructions we give them. As a novelist (Chasing the Mic, The Stateside Wanderer), stand-up comedian, and storyteller, I’ve learned that mastering the language of AI—through precise, creative prompts—is like directing a talented but literal-minded actor: you need to be clear, specific, and a little imaginative to get the performance you want. In this article, I’ll share practical strategies for writing better AI prompts, drawing on my experience crafting stories that blend humor, travel, and cultural insight. Whether you’re a writer, entrepreneur, or curious tinkerer, these tips will help you unlock AI’s potential—and maybe inspire you to explore my books or podcast for more storytelling wisdom.

What Is Prompt Engineering?Prompt engineering is the art and science of crafting instructions for AI models to produce useful, accurate, or creative outputs. Think of it as a conversation where you’re the director, and the AI is your collaborator. A vague prompt like “Write a story” might yield a generic tale, but a detailed one like “Write a 500-word comedic short story about a backpacker in Panama facing a language barrier, in the style of Jack Kerouac” can produce something vibrant and specific. My novels, Chasing the Mic and The Stateside Wanderer, taught me the power of precise language—whether I’m writing a punchline or a travel scene—and that same principle applies to AI. Why does this matter? In 2025, AI adoption is soaring, with over 50% of businesses using generative AI for content creation, marketing, and more, according to recent web insights (Forbes, 2025). But the quality of AI outputs depends on the user’s ability to communicate intent clearly. Let’s dive into five key strategies to write better prompts, with examples inspired by comedy, travel, and storytelling.

1. Be Specific and ContextualAI thrives on specificity. Vague prompts lead to vague results, much like asking a comedian to “be funny” without a setup. Instead, provide context, goals, and constraints. For example, when I wanted to brainstorm ideas for a podcast episode tied to Chasing the Mic, I used this prompt: “Generate 10 ideas for a 30-minute podcast episode about free speech in comedy, aimed at aspiring comedians aged 18-35, including one guest suggestion and a humorous anecdote.” The AI delivered tailored ideas, including a guest comedian and a funny story about a heckler, because I gave it a clear framework.

How to Do It:

• Define the Goal: What do you want? A blog post, a script, a data analysis? Specify the output type.
• Set the Audience: Who is this for? Beginners, experts, or a niche group like travel bloggers?
• Add Constraints: Word count, tone (e.g., witty, professional), or style (e.g., “like a TED Talk”).
• Include Context: Mention relevant details, like your industry or purpose.

Example Prompt: Instead of “Write a travel guide,” try: “Write a 300-word travel guide for budget backpackers visiting Costa Rica, focusing on cultural experiences under $50/day, in a conversational tone like The Stateside Wanderer.” This ensures a focused, relevant output.Try This: Next time you use AI, add one sentence about the audience and one about the desired tone. You’ll notice a sharper result.

2. Use Examples to Guide the AI. AI models learn from patterns, so providing examples in your prompt can steer the output toward your vision. When writing Chasing the Mic, I honed my comedy by studying specific punchlines. Similarly, I give AI examples to mimic. For instance, to generate social media content for my podcast, I prompted: “Write 3 Instagram captions for a comedy-travel podcast, each under 50 words, in the style of this example: ‘Lost in Panama, found a punchline!  Join my podcast for more tales.’ Include hashtags #ComedyPodcast and #TravelStories.”How to Do It:

• Provide a Sample: Share a sentence, paragraph, or format you want the AI to emulate.
• Highlight Key Elements: Point out what makes the example effective (e.g., humor, brevity).
• Specify Variations: Ask for multiple outputs with slight tweaks (e.g., “3 versions, one serious, one funny, one inspirational”).

Example Prompt: “Write a 200-word blog intro about stand-up comedy, mimicking the conversational style of this excerpt from Chasing the Mic: ‘The stage was a sweatbox, but the laughs made it home.’ Emphasize the emotional highs of performing.” The AI will mirror your voice, enhancing authenticity.Try This: Include one example output in your next prompt and note how closely the AI matches it.

3. Iterate and RefinePrompt engineering is rarely a one-shot deal. Like editing a novel or tweaking a comedy set, you often need multiple rounds to perfect the output. When I used AI to brainstorm travel itineraries for The Stateside Wandererreaders, my first prompt—“Plan a trip to Panama”—was too broad, yielding generic suggestions. I refined it to: “Plan a 5-day itinerary for a solo backpacker in Panama, focusing on offbeat cultural sites, with daily costs under $100.” The second version was spot-on, with hidden gems like a Boquete coffee farm.How to Do It:

• Start Broad, Then Narrow: Use an initial prompt to explore ideas, then refine based on what works.
• Ask for Feedback: Prompt the AI to critique its own output (e.g., “Is this response accurate? Suggest improvements.”).
• Test Variations: Request multiple outputs (e.g., “Give 3 versions of this blog post”) and pick the best.

Example Prompt: “Write a 500-word comedy script. If the output lacks punchlines, revise it to include at least 5 punchlines inspired by Chasing the Mic.” This ensures iterative improvement.Try This: After receiving an AI response, prompt it to “revise this output to be 20% more concise and add one specific detail about [your topic].”4. Leverage Tone and StyleAI can mimic any tone or style, from formal to irreverent, but you must specify it. My comedy background taught me that tone sets the stage—whether it’s a deadpan quip or a heartfelt travel tale. For a blog post promoting my podcast, I used: “Write a 400-word blog post about free speech in comedy, in a witty yet respectful tone like a stand-up comedian addressing a mixed audience, linking to Chasing the Mic.” The result was engaging and aligned with my brand.How to Do It:

• Choose a Tone: Funny, serious, conversational, academic, etc.
• Reference a Style: Compare to a known voice (e.g., “like Bill Bryson” or “like a TED speaker”).
• Test with Context: Tie the tone to your audience or purpose (e.g., “motivational for aspiring writers”).

Example Prompt: “Write a 300-word travel story about a Costa Rican market, in a vivid, humorous tone like The Stateside Wanderer, appealing to adventure travelers.” This ensures a consistent brand voice.Try This: Add a tone descriptor (e.g., “humorous”) and a style reference (e.g., “like a travel memoir”) to your next prompt.5. Automate and Scale with Prompt SystemsFor businesses or creators, prompt engineering can streamline workflows. I’ve used AI to generate social media content for my podcast, saving hours. A systemized prompt like “Generate 5 tweets about comedy and travel, each under 280 characters, with hashtags #ComedyPodcast and #TravelStories, posted weekly” creates a consistent stream of content. This approach is ideal for entrepreneurs or writers scaling their output.How to Do It:

• Batch Prompts: Create a set of prompts for recurring tasks (e.g., weekly blog posts, social media).
• Automate Delivery: Use tools like Zapier (free tier) to schedule AI-generated content.
• Test Scalability: Prompt AI to produce multiple outputs (e.g., “10 email templates for book promotions”).

Example Prompt: “Generate 5 newsletter ideas for a comedy-travel podcast, each with a 100-word summary and 3 bullet points, to be sent monthly to 1,000 subscribers.” This streamlines content creation.Try This: Create a prompt for a recurring task (e.g., weekly social posts) and schedule it with a free tool like Buffer.

Tying It All TogetherMastering the language of AI through better prompts unlocks endless possibilities. Whether you’re generating comedy scripts, travel guides, or marketing copy, specificity, examples, iteration, tone, and systems are your tools for success. As a storyteller, I’ve used these techniques to brainstorm podcast episodes, promote Chasing the Mic and The Stateside Wanderer, and even pitch speaking gigs on AI and creativity. Want to dive deeper? Check out my podcast on Spotify for more on blending comedy, travel, and storytelling, or grab my books on Amazon to see these principles in action.

About the Author: Patrick DiMarchi is the author of Chasing the Mic, a novel about comedy and free speech, and The Stateside Wanderer, a tale of wanderlust in Central America. A stand-up comedian and AI enthusiast, he shares insights on storytelling and technology. Visit PatrickDiMarchi.com or follow 

@PatDiMarchi on Instagram.