Starting from Scratch - Looks Like Work, Season 1, Ep 13
What does it really mean to start from scratch—not once, but again and again? In this candid and thought-provoking conversation, Osnat Benari—co-founder of Dragons Can Fly and author of the upcoming Starting from Scratch—joins Chedva to unpack the art and grit of reinvention.
Together, they explore Osnat’s nonlinear path from corporate product leadership to entrepreneurship in Web3, and how each pivot, layoff, or spark of curiosity became a chance to build something new. Osnat doesn’t just talk about starting over—she’s lived it, documented it, and built a six-step methodology to help others do it too.
This episode is packed with wisdom on resilience, role models, imposter syndrome, and the quiet power of choosing your next move intentionally.
Key Topics:
Writing Starting from Scratch while living it in real time
Moving through tech, product, and startups without a straight line
Reinvention as a practiced skill—not a one-time event
Building a personal “board of directors” for your next chapter
Decoding imposter syndrome and the power of seeing it as a spiral
Exploring Web3 with curiosity (and no panic)
Launching Agatha—an NFT project that honors evolution and experience
Starting with sparks, not just survival
Knowing when to sit with discomfort—and when to leap
Osnat’s Powerful Question:
“Is this a spark or just a bad day?”
A powerful reframe for career decision-making that helps you distinguish between the need for reinvention and the discomfort of growth.Key Lessons:
Reinvention is cyclical—and you don’t need to get it perfect to begin
A learning mindset opens doors and builds resilience
Your “personal board of directors” should support and challenge you
Thoughtful outreach creates connection and community
Naming your past roles and “packing your baggage” creates clarity
Your identity doesn’t reset with every new job—but it can evolve
Curiosity-driven pivots feel different than panic-fueled ones
You don’t have to be your role model yet—you can become her
“Sometimes your role model takes two years to become. That’s okay.”
Listen to this episode on Spotify | Apple | Wherever you get your podcasts
Resources & Mentions:
Catch up on previous seasons of Looks Like Work wherever you get your podcasts: Spotify | Apple | Podbean
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