During DunCon 2025, I run a community building strategy workshop with @Screwtape. Going through the workshop gave me great insights into what I actually wanted out of my community and how to get there, so I figured sharing the session plan could be useful. If you end up following this plan, consider telling me whether it was useful!


Workshop plan

1-Hour Workshop Plan for DunCon 2025

Introduction (5 minutes)

  • Welcome and context about organizers
  • Concept: "Humans are not automatically strategic" - we don't naturally take time to think deeply about our goals and plans
  • Today we'll engage in deliberate, manual strategic thinking about our local communities

Workshop Flow: Manual Strategic Thinking (40 minutes)

Step 1: What Do We Actually Want? (10 minutes)

Prompts:

  • What specific elements from DunCon do you wish existed locally?
  • What's missing from your community that you value most?
  • If your local community were thriving in 5 years, what would it look like?
  • What does the perfect, S-tier success where your wildest dreams came true look like?

Step 2: Get Specific About Goals (10 minutes)

Prompts:

  • Drill down on your vision - what specifically would indicate success?
  • What's a realistic intermediate objective given your constraints?
  • What's your MVP version that could be achieved in 1-3 months?
  • What's a hard-to-fake, concrete thing you could measure? (Beware goodharting!)

Step 3: Strategic Planning (10 minutes)

Prompts:

  • What are 2-3 concrete steps that would move you toward your goal?
  • What obstacles will you likely encounter and how might you address them?
  • What resources and allies are available to you?
  • What could help you stay motivated?

Step 4: Execute First Steps (10 minutes)

Prompts:

  • Now we'll take the unusual step of actually implementing our first actions
  • Use this time to send messages, create events, or set up what you need
  • Don't let perfect be the enemy of done - take real action now

Participants actively complete their first actions during this time:

  • Write the 2~3 sentence version of the plan and share it.
  • Sending messages to potential collaborators
  • Setting up calendar events or Doodle polls
  • Creating Discord channels or communication groups
  • Scheduling follow-up calls
  • Drafting announcements or invitations

Conclusion (5 minutes)

Facilitator Notes

  • Encourage depth rather than breadth in thinking
  • This is not a discussion workshop until the final sharing - it's about creating dedicated space for strategic thought
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Not important, but: I clicked on this post expecting an essay about building physical islands outside of San Francisco bay.

Thanks for the feedback! It made more sense as en event title. I'll edit it

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