In this “Dear DSO” episode, I respond to a story from John—a newly separated man wondering if it’s time to ditch the 9-to-5 life, buy a van, and find himself on the open road.

Is this a classic midlife crisis, or the adventure of a lifetime? Let’s talk about what it means to "lose yourself" in the family machine… and whether it’s ever too late to start over.

👊 Want to share your own story? Submit it at deardso.com and maybe I’ll feature it on a future episode.

👉 If you're a man looking for support, connection, and direction, check out The Brotherhood.