Schedule Space For Serendipity

A discussion about how successful people should intentionally create space in their schedules for random opportunities and serendipitous encounters, rather than filling every moment with planned meetings.

Core Concept: Creating Space for Luck

• Need to intentionally create a "landing spot for luck" in your schedule
• The more successful you get, the busier you become by default
• Must actively carve out space rather than letting calendar fill completely
• Goal is to allow for unexpected opportunities and connections

Implementation Examples

• Brad Feld's "Random Day" approach:
  • Set aside one day per month for random meetings
  • 15-20 minute slots in a coffee shop
  • No warm intro needed
  • Open to meeting anyone
  • Created brand value as being accessible

Benefits

• Prevents getting stuck in your bubble
• Allows meeting people outside your normal network
• Creates opportunities you wouldn't find through normal channels
• Helps maintain connection to broader community
• Can lead to unexpected business opportunities

Key Principles

• Allocate 1-2% of time for randomness/serendipity
• Remove normal barriers to access (like requiring warm intros)
• Keep meetings short to manage time investment
• Choose public/casual settings like coffee shops
• Maintain ability to end unproductive meetings quickly

Warning Signs of Need

• Only meeting pre-vetted people
• Calendar completely full of back-to-back meetings
• No space for spontaneous opportunities
• Limited exposure to new ideas/people
• Operating entirely within existing network

The key is being intentional about creating unstructured time, rather than letting your calendar fill completely with planned activities.