This story is based on an interview with Richard Woulfe, 63, a flight attendant from Fort Worth, Texas. It has been edited for length and clarity.
I have always been in the travel business. Starting out in 1986, I worked at an event management company that often organized employee reward trips for large corporations.
We offered VIP transportation, including meet-and-greets at airports, as well as luxury food and beverages.
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I enjoyed it very much, but I wanted to monetize my passion for scuba diving, which led me to become certified as an instructor at 19.
Around 2008, I moved into my second career selling scuba diving trips. They were mostly done through high-end dive shops and targeted at affluent customers.
I visited the Maldives more than 15 times
They wanted to explore countries like Papua New Guinea, Indonesia, and the Philippines. It was fun to accompany them to places like the Maldives, which I must have visited more than 15 times.
Courtesy of Richard Woulfe
Then the pandemic struck. My main markets shut down as destinations such as Thailand imposed travel restrictions.
I returned to the city of Chicago, where I grew up, and took a little time off, spending time with my mom and dad. Dad, in his early 90s, was quite sick, and I wanted to be with him as much as possible.
After I turned 60 in March 2023, Mom looked at me one day and asked if there was something wrong. I told her I wasn’t depressed, but I was feeling restless.
I texted my friend, who had been a flight attendant since 2018, for advice
She encouraged me to get back to work. Life expectancies are long these days — I could live for another 35 years — and I didn’t want to retire.
I read that some of the major US airlines were hiring thousands of flight attendants. I texted my friend, who had been a one since 2018, for advice.
His reply was two words long: “Do it!” he said. I’d been a passenger on countless flights and loved the transport industry since childhood.
As a kid, I was more interested in the process than the destination. How about I drew on my experience of travel and hospitality for a third career as a flight attendant?
Courtesy of Richard Woulfe
I applied to various airlines and had one face-to-face interview within 72 hours. However, there was a lot of back-and-forth in my personal life because of Dad, and it took me a while to make a solid commitment to a particular carrier.
At 61, I started the six-week training program in April 2024. Language is important to me, and I don’t like to refer to people as “Older than 50.” Instead, I call people like me “Better than 50.”
Gen X is willing to acquire new skills
I thought I was going to be the only “Better than 50” person. To my surprise, there were candidates ages 64, 67, and even 70.
I believe that Gen-X has maturity, flexibility, and a strong work ethic. We’re willing to acquire new skills to stay in the job market and make money.
Courtesy of Richard Woulfe
They also have life experience and the ability to listen. My mantra is to say, “I hear you,” whenever a passenger raises an issue. People want to feel heard.
The last two years have been amazing. I enjoy not knowing where I’m going next. It gives me an opportunity to learn about different locations.
Flight attendant work is not for everyone
I’ve been to international cities such as San José, Costa Rica; Guadalajara; Vancouver; and Montreal. Still, I’ve had fulfilling times in small, domestic places like Colombia, South Carolina, and Durango, Colorado.
Flight attendant work is not for everyone. Still, my message for anyone considering a lifestyle pivot is this: If something is calling you — something you haven’t done before — it’s worth taking a risk.
