Courage Before Proof: The Leadership Skill You Need
Lisa Pagotto · May 18, 2026
Interview with Lisa Pagotto
Podcast: Dancing in the Discomfort Zone with Anne Bonney
May 18, 2026 · 34 min
What happens when everything you’ve built… disappears overnight? In this powerful episode of Dancing in the Discomfort Zone, Anne Bonney sits down with Lisa Pagotto, founder of Crooked Compass (https://www.crooked-compass.com/) to talk about resilience, reinvention, and the…
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About Lisa Pagotto
Founder & CEO of Crooked Compass, Guiding Personal Reinvention Through Experience
7 figures Scaled Crooked Compass globally12 minutes Shark Tank Australia appearanceAward-winning Travel brand founder2 ventures Crooked Compass & Crooked Compass by Air
Lisa Pagotto has built her career by navigating uncertainty firsthand, founding businesses, making high-stakes decisions without guarantees, and learning what actually holds when plans fall apart. That throughline runs from the companies she’s built to the conversations she leads about resilience, leadership, and decision-making when there’s no obvious right answer.
She is the founder of Crooked Compass, an immersive travel company created in response to how surface-level modern travel had become. What began with Lisa personally designing small, story-driven journeys into complex destinations grew into a multi-seven-figure business, later gaining national attention through Shark Tank Australia. From the beginning, the focus was never volume or convenience. Crooked Compass was built around depth, cultural respect, and the willingness to handle difficult logistics in order to create meaningful experiences.
That approach was tested when global travel came to a standstill. With her industry paused overnight, Lisa chose not to wait for certainty to return. Instead, she rebuilt — and expanded — the business in unconventional ways. During the pandemic, she launched a second venture, Crooked Compass by Air, sparked by a decision that made little sense on paper: using government JobKeeper support to learn to fly when commercial aviation had shut down entirely.
About this episode
What happens when everything you’ve built… disappears overnight?
In this powerful episode of Dancing in the Discomfort Zone, Anne Bonney sits down withLisa Pagotto, founder of Crooked Compass (https://www.crooked-compass.com/) to talk about resilience, reinvention, and the courage to lead when there is absolutely no clear path forward.
When the pandemic shut down global travel, Lisa’s entire business came to a halt for nearly three years. No revenue. No team. No roadmap.
Most people would have waited it out.
Lisa? She learned how to fly… and accidentally built a second business that saved the first.
This conversation is packed with real-world lessons on:
Leading before there’s proof (and why waiting is a trap) The truth about resilience (hint: it’s NOT “just push harder”) How to recognize burnout before it breaks you Why discomfort, travel, and uncertainty make you stronger The mindset shift that turns crisis into opportunityAnd here’s the truth most people don’t want to hear:
👉 Strength is not about endurance… it’s about knowing when to pause.
Whether you’re leading a team, building a business, or just trying to figure out your next step—this episode will challenge how you think about risk, growth, and what it really takes to move forward when plans fall apart.
Because the people who thrive aren’t the ones with the best plan… They’re the ones willing to move without one.
Want more from Lisa?
https://www.linkedin.com/in/lisa-pagotto/https://www.instagram.com/lisapagotto_/https://www.facebook.com/Crookedcompasstravel/https://www.youtube.com/@CrookedCompasshttps://www.crooked-compass.com/
Lisa Pagotto is the founder of Crooked Compass, an immersive travel company built on depth, cultural respect, and meaningful experiences in complex destinations. A business owner shaped by uncertainty, she speaks on resilience, leadership, and decision-making when there is no clear roadmap. Drawing from lived experience building, adapting, and reinventing through crisis, Lisa brings grounded insight on risk, reinvention, and what it
Guest: Lisa Pagotto
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5+ podcast & stage appearances. Remote or in studio, broadcast-grade audio.