On this installment of our advice segment, we address a question about making a huge life change. A listener named Where Am I Going writes of his disillusionment with his corporate job, and shares his dreams to live a nomadic lifestyle. But taking the leap feels reckless to him — and would almost certainly mean ending his long-term relationship.
"How can I identify with confidence what is going to make me the most happy in the long term?" he asks.
When Olivia Round set off on a cross-country bicycle trip, she told people she was doing it to have an adventure, or to take a semester off school. But her real reason was more personal, more urgent: she wanted to overcome a paralyzing fear. A fear of men.
On this episode, Olivia shares the story of one particular night on her journey. It's a story about a surprising encounter she had in the mountains of Colorado — and about what's actually possible when it comes to overcoming our deepest fears.
Jen Kinney wanted to be a strong, independent woman. She had just split up with her long-term partner, and she felt a powerful need to prove that she was capable — that she could make it by herself — that she could meet her own needs.
So she decided to take herself backpacking. Alone.
She picked a 50-mile stretch of the Mountain To Sea Trail in North Carolina, and began planning meticulously. She worked through all the logistics, assembled her gear, packed everything she would need to provide for herself.
But what happened to her out in the mountains did not make her feel strong or capable. At least not right away.
The trip might not have been what she bargained for. But it left her with an important life lesson — a new understanding of what it means to take care of yourself.