
Founder & CEO of Crooked Compass, Guiding Personal Reinvention Through Experience

Creativity Under Pressure with Lisa Pagotto
Sustaining Creativity Podcast
Jul 2026

Courage Before Proof: The Leadership Skill You Need
Dancing in the Discomfort Zone with Anne Bonney
May 2026

The Flight of Authenticity: How Lisa Pagotto Leads with Humor in the World's Most Extreme Destinations
Humor In The C-Suite
May 2026

Authentic Leadership in Business with Lisa Pagotto, Founder of Crooked Compass
Sales POP! Podcasts: Insights from Top Experts in Sales, Marketing, Leadership & More.
Apr 2026

How Travel Is a Personal Reinvention, Not Escape as We Age
This Travel Tribe
Mar 2026
Latest video

Digging Deeper with Crooked Compass - Episode 1
Latest episodes
Key topics
How to design a small-group tour that doesn’t feel like a bus tour in disguise
Most group travel fails in predictable ways: generic itineraries, awkward group dynamics, and cultural experiences that feel staged. Crooked Compass counters that with deliberately small groups (2–12), careful accommodation choices that reflect place, and local partnerships that keep experiences grounded in real community. Lisa can explain what “thoughtfully crafted” actually means operationally-how you reduce friction, protect authenticity, and still deliver comfort.
Retirement travel that doesn’t feel like a slow goodbye
A lot of retirement messaging quietly shrinks people’s lives-safer, smaller, more predictable. Lisa’s alternative is “you think you’ve lived?” travel: adventures designed for educated, curious travellers who still want challenge, learning, and stories worth retelling. She can talk about matching ambition to ability (without patronising anyone), choosing destinations that stretch the mind, and why “active and young at heart” is a better travel metric than age.
The business lessons you only learn after a catastrophic yes
Some of the most dangerous failures arrive disguised as validation-big names, exciting deals, momentum that feels impossible to slow. Lisa has lived through that moment, nearly losing everything, then being forced to reinvent during a global shutdown when her entire industry effectively disappeared. She can unpack how ego, social proof, and urgency distort judgment, and how true resilience looks less like “bouncing back” and more like rebuilding from first principles when there’s no playbook left.
View all topics →
Latest video

Digging Deeper with Crooked Compass - Episode 1
Latest episodes
Key topics
How to design a small-group tour that doesn’t feel like a bus tour in disguise
Most group travel fails in predictable ways: generic itineraries, awkward group dynamics, and cultural experiences that feel staged. Crooked Compass counters that with deliberately small groups (2–12), careful accommodation choices that reflect place, and local partnerships that keep experiences grounded in real community. Lisa can explain what “thoughtfully crafted” actually means operationally-how you reduce friction, protect authenticity, and still deliver comfort.
Retirement travel that doesn’t feel like a slow goodbye
A lot of retirement messaging quietly shrinks people’s lives-safer, smaller, more predictable. Lisa’s alternative is “you think you’ve lived?” travel: adventures designed for educated, curious travellers who still want challenge, learning, and stories worth retelling. She can talk about matching ambition to ability (without patronising anyone), choosing destinations that stretch the mind, and why “active and young at heart” is a better travel metric than age.
The business lessons you only learn after a catastrophic yes
Some of the most dangerous failures arrive disguised as validation-big names, exciting deals, momentum that feels impossible to slow. Lisa has lived through that moment, nearly losing everything, then being forced to reinvent during a global shutdown when her entire industry effectively disappeared. She can unpack how ego, social proof, and urgency distort judgment, and how true resilience looks less like “bouncing back” and more like rebuilding from first principles when there’s no playbook left.
View all topics →