Why Success Isn’t Safe: Lucas on the Power of Taking the Leap

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 MomentsThe 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.Building a Business Without a Business Degree - Tiarna unpacks how Lucas scaled a global brand without formal training—just curiosity, consistency, and community.Hiring His First Full-Time Team Member - Lucas reflects on leadership, loyalty, and what it takes to scale without compromising authenticity.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 McCormackAbout LucasLucas 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.Connect with Lucas Chesterton:InstagramWebsiteFollow The Counter Offer:⁠⁠⁠⁠⁠⁠⁠Susanna's LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠Tiarna's LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn Podcast⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠TikTok⁠⁠⁠