Intention-Obstacle Storytelling

A framework for crafting compelling stories by focusing on character intentions and the obstacles they face, based on Aaron Sorkin's storytelling principles.

Core Story Elements

• Every story needs two key components:
  • Character intention (what they want)
  • Meaningful obstacle preventing them from getting it
• Must establish both elements early to hook readers
• Should be able to pause at any moment and identify:
  • What the character wants
  • What's standing in their way

Creating Stakes

• Stakes don't have to be life-or-death
• Can create high emotional stakes in low-stakes situations
• Advanced technique: Making mundane situations feel important through:
  • Clear character motivation
  • Relatable obstacles
  • Emotional investment

Examples of Effective Stakes

• Personal stories about HOA conflicts
• Larry David using MAGA hat to avoid conversations
• Small daily interactions that feel meaningful
• Workplace conflicts and professional challenges

Story Structure Tips

• Start with the most important/provocative statement
• Don't bury the lead with background/context
• Create curiosity gaps to pull readers forward
• Use varying sentence lengths for rhythm
• Make the stakes clear early on

Common Mistakes to Avoid

• Starting with too much background
• Not establishing clear character wants
• Failing to create meaningful obstacles
• Making stakes too extreme or unrealistic
• Losing reader interest through poor pacing

Writing Style Elements

• Write like you talk
• Use short sentences by default
• Vary sentence length for impact
• Target 6th-8th grade reading level
• Remove unnecessary words and jargon

Resources for Learning

• Study comedians' storytelling techniques
• Analyze successful story structures
• Practice with personal experiences
• Focus on emotional connection
• Keep stories simple but meaningful