An inflection point, an adventure, and and trying to see into the future.


In early September, 2023, my husband, Cortland, and I spent a weekend at a U.S. Forest Service campground near the Continental Divide in Colorado. We sandwiched our 17-foot trailer into a beautiful spot in the wilderness, delighted that it was small enough to fit.

We were at 10,000 feet. It was chilly at this altitude. The silence was interrupted only by the chirrups of chipmunks and the occasional bird. We felt autumn on the horizon, full of possibility. As is always true for both of us, getting out into the woods and mountains filled our souls. It allowed us to take deep breaths — physically as well as metaphorically.

The feeling of possibility was infectious. Cortland was planning to retire from his corporate job the following summer. My five-year-old podcast production company was still growing, but I felt rumblings of concern about the industry. Networks were canceling award-winning shows. Thousands of audio professionals had already been laid off, with more to come.

Sitting in our little fiberglass Casita, drinking coffee, we began asking big questions about the future. What possibilities would retirement open up for Cortland? What new adventures did we want to have? What purposes might there be to embrace, purposes neither of us had yet imagined? And what would his retirement, combined with the changing fortunes of podcasting and  journalism, mean for my career?

That morning, we hatched a plan: Could we live and work out of a tiny trailer for two months the following summer? It would be an adventure, a chance to live outdoors, to see old friends and family, and to live simply for a little while.

Over the next several months, Cortland sold our aging Casita, bought a newer and slightly larger camper, and asked himself lots of questions about what he wanted the next season of life to look and feel like.

I, too, was about to encounter several inflection points of my own. As 2024 wore on, the podcast industry worsened. By early spring, I was wondering: Did I want to keep my production business going? Did I even enjoy it any more? And if not, what would be next?

I was also facing a true empty nest. My son, who suffers from mental health issues, lived with us sporadically. He moved out permanently in May. I laid off my best and dearest employee, and told clients that I was pulling back from large projects to spend time teaching, consulting, and writing. I put my own podcast, Sound Judgment, on hiatus. An insomniac, I tried unsuccessfully to sleep.

In June, I spent a week at MEA (the Modern Elder Academy) exploring “finding my purpose” in a cohort of 25 other so-called midlife seekers ranging in age from 25 to 73. When I returned from Mexico, Cortland had reframed our trip from an adventure to a voyage of discovery.

Could we use this trip to expand our ideas about what our best lives will be in the future?

Farsighted is the chronicle of this voyage. Here, we explore questions from the practical to the philosophical: What is it like to live in only 150 square feet, with our dog, for so long? Will it test our marriage? How possible is it to work on the road? What unexpected sights and people will we encounter? What are people across the country thinking and feeling at this particularly challenging time in our country’s history?

And ultimately, how might this journey change us?

Farsighted is the story of a late-life love affair. It’s the story of traveling to ordinary and extraordinary places with curiosity, observation, and awe. It’s a wondering, out loud, about what the third season of life can look and feel like when all possibilities are on the table.

If you are at a crossroads, join us! Share your inflection points. Let’s navigate the adventure of life together.

Elaine Appleton Grant and Cortland Wolfe

Why subscribe?

If you are…

  • Contemplating your own adventure and keen to see how this works

  • Curious about living full time in a tiny trailer

  • Wish you could be traveling with us and want to join us in spirit

  • Thinking about downsizing and wondering how small you can go

  • Just love a good adventure read

  • And most importantly, hitting your own crossroads in life and want to navigate an intentional living journey with us…

  • Subscribe to Farsighted! You’ll get notified via email whenever we post updates on our trip. We plan to post frequently, but in keeping with the spirit and the practicalities of life on the road, there will be occasional spaces in our schedule. Internet connectivity, mountain hikes, and long talks with friends we haven’t seen in two decades are sure to interrupt us.

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A crossroads-inspired adventure in a tiny trailer, with a curious eye on the future and a spirit of curiosity, observation, and awe.

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Cortland is a retired telecom professional. Along with his wife, Elaine, and his reluctant dog, Liza, they are exploring the country in a 22ft fiberglass trailer.
Elaine Appleton Grant is a lifelong writer and audio storyteller. Her work has appeared on NPR and in Inc., Fast Company, AARP The Magazine, The Boston Globe, and hundreds of other publications. She runs on coffee.