Thank you
, , and many others for tuning into my live video with !
If you missed our live session, you can now watch the recording right here.
and I pulled back the curtain on how PromptoberFest started, what’s new this year, and what to expect during the five-day event (October 20–24).We also shared some of the exact prompts you’ll get throughout the week and how to use them to write faster, think deeper, and sound more human than ever.
Top 5 Takeaways
PromptoberFest returns October 20–24
Four days of themed prompts: Content Creation, Copy That Converts, Humanization, and Integration, followed by a three-hour live Promptathon packed with demos, hot seats, and new prompts in action.AI is your creative partner, not your replacement
We talked about using AI to reflect your thinking and help you uncover what you’ve been avoiding, rather than letting it take over your writing.Humanization is the secret to standing out
Andy demonstrated how to kill the robot voice in AI output by layering emotion, contradiction, and imperfection into your prompts.Prompts are building blocks, not one-offs
When you chain prompts together into systems, they become powerful workflows that keep generating ideas and insights.Follow-up prompts create breakthroughs
When a prompt falls flat, don’t rewrite it—interrogate it. Ask questions like “What are you missing?” to find the missing spark.
AI Prompts Andy Shared
Content Creation
Ask me the question I’ve been avoiding.
Pretend a braver version of me hijacked this project. What would they say first?
Copy That Converts
The real reason I created this offer is…
Say it again as if you’re confessing it to a close friend.
Now rebuild this as a single fearless sentence.
Humanization
Write this paragraph the way an AI thinks a human would write it.
Now rewrite it like someone who’s had a terrible day but still cares.
Integration & Innovation
Use prompts as muscle memory—build suites and chains of prompts that create discovery, insight, application, and reflection.
Prompt Repair (Promptathon Preview)
What are you missing?
What assumption are you making about me or the prompt?
What are we missing that’s causing this disconnect?
Join PromptoberFest
PromptoberFest starts Monday, October 20.
It’s free to join and if you upgrade to VIP, you’ll get:
The full Promptathon recording
A curated list of every prompt shared
A 30-day action plan to put everything to work
Priority access to live hot seats with Andy
Custom Promptathon GPT with ALL prompts included
👉 Join PromptoberFest for free (or upgrade to VIP)
And coming soon… Andy’s latest book in his Humanizer series, Conversational Prompting. Get on the early release list here.
