#17: ''You're Driving Down The Road 100 Miles An Hour In Life, And You Can't Read Every Billboard'

Ryan from Illinois has spent much of his life moving between newsrooms, mountain towns, rural communities, nonprofit work, and the world of regenerative agriculture. But in this episode, he shares something even more personal: the lessons he would offer his younger self about discomfort, trade-offs, community, empathy, and learning to make peace with the life you're actually building (rather than all the speculative futures you daydream about but might never actually experience).

In this episode, I talk with Ryan about what it means to keep growing as a human being without demanding perfection from ourselves. I really appreciate Ryan's honesty about the choices we all make: the doors we walk through, the ones walk past, and the wisdom that comes from finally giving ourselves permission to accept the path we've chosen.

Ryan shares how his parents helped him learn the value of being uncomfortable, how working in journalism shaped both his empathy and his sense of detachment, and why cause-driven work can be both meaningful and heartbreaking. He also reflects on the communities that formed him — from Aspen and Lake Tahoe to Chicago and rural America — and what it takes not only to live somewhere, but to truly belong.

His story is a reminder that life is full of trade-offs, but those trade-offs don't have to become regrets. We can learn from our younger selves, offer kindness to the people we used to be, and share what we've learned with someone who needs encouragement for the road ahead.

Sincere thanks to Lee Williams for his fantastic production of this and every episode of Perennial Pen.

In this episode, we explore:

Ryan's reflections on what he would tell his younger self How being uncomfortable helps us grow, change, and keep moving The importance of surrounding ourselves with good people when life feels difficult What cause-driven work can teach us about heartbreak, humility, and persistence Ryan's reflections on journalism, empathy, listening, and learning when people need help or simply need to be heard The trade-offs that come with choosing one life path over another What Ryan learned from living in mountain towns, rural communities, and cities Why strong communities require ownership, contribution, fun, and belief in one another How reconnecting with nature can help us loosen our grip on control Reflection Question

What's one lesson you'd want to give to your younger self? And who in your life might need to hear that lesson this week?

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