🔵 Compass Guidebook: Run a Successful Online Challenge PART 2

The blueprint that turned 63 strangers into raving fans

Author

Joshua Hale
March 04, 2025

Estimated Read Time: 6min

Hey Challenge Creator!

Picture this: Day 28 of my AI challenge, and participants are literally begging for MORE.

Not gonna lie — it feels pretty damn good. Especially considering I almost quit multiple times before getting traction (as I shared yesterday).

But here's the thing: These results didn't happen by accident.

Street Knowledge: Most Challenges Fail Because of Poor Architecture

Listen, I've seen too many challenges that are just thrown together—random content dumped on people daily with no thought to the participant journey.

That's like building a house without a blueprint. You'll end up with a weird-ass structure where nothing flows and people can't wait to escape.

Let me show you the framework that not only kept 70 people engaged for 28 days but had them asking for more when it ended.

The Challenge Blueprint That Actually Works

1. The Perfect First Day

The first day of your challenge needs to deliver a stupid-simple win that makes people think, "Holy crap, this actually works!"

For my ChatGPT challenge, I didn't start with theory or history. I gave them a prompt that would instantly solve a real problem they had.

One participant messaged me: "I'm an attorney. I made sure to get citations for everything, then had ChatGPT draft a letter. It only took me 10 minutes—normally, that's at least an hour of my time. This is amazing."

That's Day 1 energy right there. They immediately knew this wasn't going to be some theoretical BS.

2. The Weekly Theme Structure

Instead of random daily topics, organize your challenge into themed weeks:

Week 1:
Foundational Skills Theme: Confidence Booster
Master the “magic words” that get ChatGPT to actually do what you want. Get Wowed.

Week 2: 
Home & Life Theme: Level Up Your Life
Personalized meal plans? Budget-friendly home upgrades? Scheduling hacks? Let ChatGPT be your life sidekick.

Week 3: 
Work & Productivity Theme: Office MVP
Fire off emails that sound pro (and actually get replies). Brainstorm big ideas. Plan projects in half the time.

Week 4:
Upgrade Your Life Theme: Self-Discovery
Build goals, habits, and decisions that stick. Yes, ChatGPT can even help you figure out the next steps in your career or side hustle.

3. The Daily Formula

Each day follows the same structure:

  • Hook: Why today's prompt/activity matters (keep it to 2-3 sentences)

  • Context: A super brief explanation (1 paragraph max)

  • The Action: EXACTLY what to do, step by step

  • Share Value: Encourage them to share their experience in the community

  • Tomorrow Teaser: "Tomorrow you'll discover how to..."

Keeping It Simple: My daily text were around 250 words. That's it. People are BUSY, and they want to get to the action.

4. The Secret Sauce: Community Engagement

This caught me off guard: The Signal chat group became the most valuable part of the entire challenge.

Participants weren't just following prompts—they were sharing results, helping each other troubleshoot, and coming up with ideas I hadn't even thought of.

Your challenge community isn't just a nice-to-have; it's essential. This is where the magic happens.

5. The Strategic High Points

Plant these throughout your challenge to maintain momentum:

  • Day 7: A slightly more advanced technique that wows them

  • Day 14 (Halfway): A celebration + reflection activity

  • Day 21: A surprising application they hadn't considered

  • Day 25-28: The "Holy crap, I never thought I could do this" finale

Keeping It Real: Lessons From My First Challenge

What worked:

  • 10-minute daily time commitment (realistic for busy people)

  • Signal group for real-time interaction (beats email-only)

  • Daily accountability with clear, copy-paste instructions

  • Strategic difficulty curve (starts easy, gradually increases)

What I'll improve next time:

  • Add short video walkthroughs for complex topics

  • Create separate tracks for beginners vs. advanced folks

  • Host a Q&A session

  • Add more structure to the community discussions

Your Challenge Structure Checklist

Ready to blueprint your challenge? Make sure you have:

✅ A day 1 activity that delivers an immediate win
✅ Weekly themes that create a logical progression
✅ A consistent daily structure that respects people's time
✅ Community component where participants can share and support
✅ Strategic high points to maintain motivation
✅ Realistic time commitments (be honest about what's required)

Tomorrow, I'll show you how to turn challenge participants into paying clients and customers with a value ladder that feels natural, not pushy.

Keep building,

Joshua

P.S. Hit reply and let me know: What's going to be YOUR Day 1 quick win that hooks participants?

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