At 63, Richard Woulfe Found a Third Career in the Skies

Woulfe’s professional journey began in 1986, long before he traded corporate logistics for the cabin aisle. His background in high-end travel, which included leading expeditions to the Maldives, Papua New Guinea, and Indonesia, provided a foundation in hospitality that proved transferable. When the pandemic halted international tourism and personal family obligations brought him to Chicago, the transition to his current role was sparked by a simple two-word text from a friend: "Do it!"

He entered a six-week training program in April 2024 at age 61. Far from being an outlier among younger recruits, he discovered a cohort of peers in their mid-60s and 70s. Woulfe rejects the "older than 50" label, preferring the term "better than 50" to describe a generation he believes brings essential maturity, flexibility, and a refined ability to listen to passengers. By applying his mantra of "I hear you" to resolve customer grievances, he has turned a life of travel experience into a functional service role. He now balances international layovers in cities like San José and Montreal with domestic routes, proving that a professional pivot is possible well into one’s seventh decade.