The Unscheduled CEO

This personality trait 1000% decides your level of happiness and success

Oct 28, 2025
Dive into the fascinating trait of openness, a strong predictor of success and enjoyment in life. Discover how this characteristic can be measured and even increased through experiences. Jonathan contrasts cultural differences in openness and shares how it affects entrepreneurial success. He reflects on how open individuals foster creativity and innovation in dynamic environments. Plus, get insights on managing relationships with varying levels of openness and the exciting details about his new creative retreat.
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ANECDOTE

Surprising Early Demand For Area X Retreat

  • Jonathan launched Already There and expected slow, cautious interest for a niche creative retreat called Area X Expedition One.
  • He was surprised that qualified signups exceeded venue capacity from minimal marketing like a podcast and an email.
INSIGHT

Openness Predicts Creative Success

  • Openness is a measurable Big Five trait that predicts curiosity, creativity, and willingness to try new experiences.
  • Jonathan Courtney argues high openness correlates strongly with entrepreneurial success and life satisfaction.
ADVICE

Choose Open People For Brainstorming

  • Prioritize spending time with people high in openness when you want expansive ideas and opportunities.
  • Avoid relying on highly closed people for imaginative brainstorming about big career or creative changes.
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