What if the thing you’re afraid to do is exactly what you were meant for?
In this soul-stirring episode of The Counter Offer, host Tiarna McCormack sits down with longtime friend and global adventurer Lucas Chesterton. From Melbourne’s property scene to running a multi-country travel business, Lucas shares the true story behind Indy Escapes—how he risked it all, lost nearly everything, and still rebuilt a business rooted in purpose, connection, and exploration.
They discuss travel as transformation, the brutal reality of entrepreneurship, and why failure isn’t the opposite of success… it’s part of the journey.
Must-Hear Insights and Key Moments
The Risk That Changed Everything - Lucas opens up about walking away from a stable property career to launch his travel startup and why fear was his compass.
Losing Everything During COVID - With all trips cancelled, Lucas refunded clients out of pocket—plunging himself into debt. His radical decision reveals the ethics behind Indy Escapes.
The Five-Year Plan That Saved His Business - Lucas shares the pivotal advice that helped him rebuild post-pandemic with a clear and consistent roadmap.
Why Values Drive Growth - From contribution to connection, Lucas explains how aligning personal values with business decisions shaped Indy Escapes’ identity.
Words of Wisdom: Standout Quotes from This Episode
“I wanted more than just a 9-to-5 and a nice car. I wanted meaning.” – Lucas Chesterton
“Discomfort is often the invitation to do something brave.” – Tiarna McCormack
“Not everything that grows is meant to scale.” – Lucas Chesterton
“Travel is the tool. Community is the point.” – Lucas Chesterton
“It’s not about how many countries you’ve been to—it’s about how you felt in each one.” – Lucas Chesterton
“The freedom wasn’t just quitting the job. It was choosing what I cared about.” – Lucas Chesterton
“You can fail and still be proud of what you’re building.” – Tiarna McCormack
“Group travel can be transformative when the right people are in the room.” – Lucas Chesterton
“We’re not here to impress. We’re here to connect.” – Lucas Chesterton
“Purpose doesn’t show up fully formed. You create it by taking one step.” – Tiarna McCormack
About Lucas
Lucas Chesterton, founder of Indy Escapes, turned the challenges of solo travel into a thriving community for adventurers tired of waiting on others. After visiting 130+ countries, he created a way for like-minded travelers to connect, explore, and experience the world together without sacrificing spontaneity or meaning.
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