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Lisa Pagotto

Lisa Pagotto

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

EntrepreneurLeadershipExecutive CoachTEDX Speaker
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Lisa Pagotto Podcast Episodes

This Travel Tribe

This Travel Tribe

How Travel Is a Personal Reinvention, Not Escape as We Age

March 5, 2026

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About this episode

If you're an empty nester, nearing retirement, or craving something deeper than another European highlights trip, this episode is for you. I sat down with Lisa Pagotto, founder of Crooked Compass, to talk about travel in retirement, or what I like to call the "what's next" phase of life, and how this season can be the perfect time to explore beyond the usual bucket list destinations.

Lisa Pagotto Podcast Episodes

Humor In The C-Suite

The Flight of Authenticity: How Lisa Pagotto Leads with Humor in the World's Most Extreme Destinations

Humor In The C-Suite

May 2026

Sales POP! Podcasts: Insights from Top Experts in Sales, Marketing, Leadership & More.

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

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Latest video

Digging Deeper with Crooked Compass - Episode 1

Digging Deeper with Crooked Compass - Episode 1

Latest episodes

Humor In The C-Suite

The Flight of Authenticity: How Lisa Pagotto Leads with Humor in the World's Most Extreme Destinations

Humor In The C-Suite

Sales POP! Podcasts: Insights from Top Experts in Sales, Marketing, Leadership & More.

Authentic Leadership in Business with Lisa Pagotto, Founder of Crooked Compass

Sales POP! Podcasts: Insights from Top Experts in Sales, Marketing, Leadership & More.

View all episodes →

Key topics

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.

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.

Building a life where ambition doesn’t require self-abandonment

Most high-achieving people quietly accept a split between who they are and what they do, then wonder why success feels hollow. Lisa’s path shows how alignment is built in real time—through asking for help before you feel ready, making bold requests visible, and letting community replace lone-wolf mythology. She can talk about the real cost of choosing coherence over approval, how support compounds when you stop hiding the struggle, and how ambition actually accelerates when it’s shared instead of shouldered alone.

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