
The Learning Leader Show With Ryan Hawk 276: Scott Belsky - How To Find Your Way Through The Hardest Part Of Any Venture
Sep 23, 2018
Scott Belsky, entrepreneur and bestselling author who co-founded Behance and served as Adobe’s Chief Product Officer. He talks about sustaining curiosity, carving out deep-work windows, and quirky rituals that trigger focused creativity. He explains navigating the messy middle of ventures, shifting from doer to manager while keeping it personal, and balancing big-company roles with side passions.
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What The Messy Middle Actually Is
- The Messy Middle is the volatile period of extremes between a project's start and finish filled with ambiguity and self-doubt.
- The book offers prompts to endure lows, find internal rewards, and optimize what works rather than a step-by-step formula.
Keep Management Personal With Regular Check ins
- As a new manager, keep relationships personal: hold regular check-ins focused on 'How's it going?' rather than impersonal reviews.
- Scott says management doesn't scale; you must know individual worries, family context, and career concerns.
Hire For Conversations That Keep Getting Better
- When hiring, favor candidates whose conversations deepen each meeting and who show initiative over pedigree.
- Scott interviews candidates multiple times to see if interactions become more interesting and build momentum.






