🔵 Compass Guidebook: Run a Successful Online Challenge PART 1

the 3 things my failing challenge was missing

Author

Joshua Hale
March 03, 2025

Estimated Read Time: 6min

Hey Future Challenge Creator!

When I first launched the challenge... I almost quit. FOUR times.

I had poured my heart into launching my 28-day AI challenge—aaand... crickets. No sign-ups. I tried again. More crickets.

Cue the self-doubt soundtrack:

  • "Maybe no one cares."

  • "Maybe this was a terrible idea."

  • "Maybe I should just stick to what I know..."

But instead of giving up, I tried 5 more things. One of them was I reached out and landed a podcast interview, and talked about AI's impact. And suddenly… momentum.

My goal was 20, and I ended up with 63 participants! That's right - more than TRIPLE my original goal.

Truth Bomb Time

Here's what nobody tells you about challenges: Your first attempt will probably flop. Your second might too.

But here's the thing - people are HUNGRY for structured guidance. They're drowning in information but starving for transformation. A well-designed challenge delivers exactly that.

Why Challenges Work When Done Right

  1. They solve the "where do I start?" problem
    From my intake forms: "Too many new tools, too much information, analysis paralysis." Sound familiar? That's what your audience is feeling.

  2. They create momentum through small wins
    One participant wrote: "I always knew AI had potential, but until I started this challenge, I wouldn't have had the tools to get going."

  3. They build community around shared growth
    My Signal chat became the unexpected MVP. People weren't just following prompts—they were sharing breakthroughs, helping each other, and going beyond the daily tasks.

The 3 Critical Elements My First Challenge Was Missing

After face-planting on my first attempts, I discovered what was missing:

1. The Right Traffic Source

My breakthrough? Getting on Jack Spirko's Survival Podcast. Suddenly, I was talking to the right people who trusted a source they already followed.

Smart Move: Identify where your ideal participants already hang out. Guest on podcasts, collaborate with aligned creators, or tap into communities where you're already known.

2. A Crystal-Clear Time Commitment

My winning pitch: "Build Your AI Confidence 10 Minutes a Day— with your Morning Coffee".

No ambiguity. No overwhelming promises. Just a specific, doable commitment that busy people could fit into their lives.

The #1 objection from my intake forms? TIME. People aren't afraid of your content—they're afraid they won't finish it.

3. Instant Gratification Mixed With Long-Term Vision

Here's the formula that finally worked:

  • Day 1: A stupid-simple win they could get in minutes

  • Week 1: Practical skills they could use immediately

  • By Day 28: A transformation they couldn't achieve alone

One participant told me: "There's no going back for me now!" That's the reaction you want.

Your First Challenge Action Plan

Ready to create your own challenge? Start here:

  1. Define your challenge concept - What transformation can you promise in 7, 14, or 28 days?

  2. Identify your ideal traffic source - Where do your people already hang out? How can you get in front of them?

  3. Create your minimum viable sign-up page - Keep it simple: the transformation, the time commitment, and what they need to join.

  4. Map out your first 3 days of content - Start with quick wins that build confidence.

Here's a prompt to help you nail down your challenge concept:

Drop this in your fav language model, (ChatGPT, Claude, whateva) 

Design a compelling challenge that attracts participants and keeps them committed. Ask user for information to create the clear promise below. Ask each question in order one at a time to refine the concept. Guide them through a structured transformation over 7, 14, or 28 days by identifying a repeatable process that leads to success.

Help users craft a clear promise:
"In [7/14/28] days, I will help [specific group] go from [current struggle] to [desired outcome] so they can [bigger goal]."

Ensure the challenge moves participants from:
Confused → Confident
Overwhelmed → Systemized
Beginners → Advanced

Create five engaging headlines for a sales page that highlight:
✅ Clear transformation: "Go from [pain] to [outcome] in [X] days."
✅ Time commitment: (e.g., “Just 15 minutes a day.”)
✅ Requirements: (e.g., “A ChatGPT account + a simple worksheet.”)

Plan three quick-win tasks to build momentum:
✅ Day 1: A small, high-impact action (e.g., "Use AI to draft an email in 60 seconds.")
✅ Day 2: Reinforce success (e.g., "AI helps you write social posts 10x faster.")
✅ Day 3: Introduce the next step (e.g., "Use AI for brainstorming and content planning.")

Tomorrow, I'll break down exactly how I structured my 28-day challenge for maximum engagement and completion (including the daily framework that kept people coming back).

Until then, hit reply and tell me: What challenge are you thinking about creating? I'd love to hear your ideas.

Let's build something amazing,

Joshua

P.S. Your first launch might fail. Your second might too. But when you find the right message for the right audience, you'll create something people rave about. Like this feedback from the challenge: "This would have taken forever to do by hand, but it took a short time to do with ChatGPT... There's no going back for me now!"

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