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In episode 68 Ross speaks with Journey with Jake, Ross Alcorn, the founder of Itinerary Boss, explains how he turns the travel ambitions of busy professionals into achievable plans. Drawing on years as the de facto trip organizer for friends while juggling a demanding healthcare-sales career, he built frameworks for everything from weekend snowboarding escapes to 17-day European odysseys. These systems now underpin his company’s service: stripping away the research overload and timing headaches that keep high-achievers from taking real vacations.

Alcorn’s method is rooted in personal experience with burnout, after a year of attending nine weddings without a single personal getaway, he saw how easily adventure slips down a packed priority list. His solution pairs practical strategy with a spirit of discovery: leveraging credit-card rewards, optimal booking windows, and streamlined planning so limited time yields maximum experience. The vivid stories he collects—soaring off a boat in Croatia, chatting with the Croatian president, shepherding quirky Amsterdam souvenirs through airport security, illustrate the lasting impact of stepping beyond routine, proving memorable journeys can coexist with demanding careers.

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Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.