Last night, I booked a one-way flight to New York.

It was the second time in two months that I’ve done that. This time, I have absolutely no idea when I’ll return “home.” I don’t even know which airport I’ll fly back from. I got a good price on the ticket, and it will bump me up to the next frequent flyers level. But what’s the deal with the one-way thing?

A few years back I wouldn’t have been able to live with so much uncertainty. I would have no idea what to pack. But my status as an empty nester and mid-life digital nomad finally sunk in, and I’m getting much more comfortable with the unknown.

What are my (few) worries?

As I learned back in 8th grade, every free-floating moment of anxiety can be cured by simply asking myself, “So?” In my corporate life, we called it “worst case scenario planning,” and the more negative and alarmist people on my team always liked doing it, because they could bring up every scary and doomsday-like scenario. We then had to create “contingency plans” on how we would deal with awful stuff. When you break it down, no challenge is so daunting that it doesn’t have a solution.

So, in this case (my one-way trip to NY), I asked myself:

FEAR: “What if I don’t pack appropriately for the weather in New York?” 

CONTINGENCY: I think they may have some stores there where I can buy what I need.

FEAR: “What if my friends/colleagues cancel our plans and I’m left all alone?”

CONTINGENCY: I’ll wander the pop-up shops at Bryant Park or visit a day spa. I’ll spend more time at the gym, or if the weather is nice I’ll walk the city and see the tree (like a tourist)  At night I’ll treat myself to dinner at one of my favorite restaurants (Hillstone or The Smith) and I’ll sit in my hotel room and write/knit/read/watch TV and otherwise entertain myself.

FEAR: “I won’t be able to return when I want to return.”

CONTINGENCY: It won’t be the first time I’ve been stranded somewhere. Hurricanes and snowstorms have thwarted other travel plans. I’ll just take a deep breath and deal with it.

The upside of one-way travel far outweighs the downside. I have ultimate flexibility in what I do, where I go, who I see (and when) and — to a great extent — when I return.

Frankly, one of the toughest parts of free-form travel is that other people seem to be more uncomfortable with it than I am. They want to know the details of my trip when I don’t even know them myself.

I missed that “gap year” and a trip through Europe when I was in my 20’s, so this phase of my life has become a version of that. I carry a rolling suitcase instead of a backpack and I probably won’t be sleeping in hostels, but traveling this way fuels a sense of adventure that we often lose as we age. Reconnecting with old friends and relatives on the road can be reaffirming too!

Not quite ready to buy that one-way ticket? You can always follow my adventures vicariously on social media!

Have you taken any one-way trips? I’d love to hear about them in the comments!



  • Nancy A Shenker

    The Silver Hair Playbook: How to Be a Bad Ass >50™

    Nancy A. Shenker is a marketing innovator, brand builder, writer, speaker, and self-proclaimed rule breaker. Over the course of her 40-year business and marketing career, she has been a C-level executive, an entrepreneur, and a mentor to hundreds of small businesses at all stages. Founder of theONswitch marketing, Nancy was formerly a senior executive for major consumer and business brands, including Citibank, MasterCard, and Reed Exhibitions. She has written four books, and publishes a women’s entrepreneur community (, as well as AI/machine learning/robotics site and travel and lifestyle site She also wrote a column for called Bots & Bodies (about the human side of tech) and is a contributor to a wide range of consumer and business media. She recently won the "Killer Content Award" for a major project for a fast-growing technology company.