How do you leave everything behind for 6 months?

As I prepare to hike the Appalachian Trail, I’ve spent a lot of time visualizing the next five or six months. I think about the physical triumphs, the inevitable team failures, and the courage needed to persevere when the honeymoon phase ends.

But lately I’ve been thinking more about what I leave behind.

I will not pretend that my life is a disaster or that I am “escaping” a disaster. If I’m honest, my life is fucking great. I have a partner who supports me and constantly pushes me to be the best version of myself, two successful businesses that I spent years building from scratch, and a home that truly feels like a sanctuary.

So why leave?

It’s a fair question and I’m not sure I have a «logical» answer. But I’ve always found a strange comfort in the uncomfortable. When I started my mortgage company, it wasn’t just about the business; It was a deep-seated need to prove that I could do what was difficult. It would have been easier (and certainly more lucrative) to remain in the corporate positions he had held for decades. But the “what if” would have haunted me.

I’ve reached a point where I can finally step away from the daily grind and trade short-term career opportunities for a lifetime of stories. I’m willing to trade profit and loss statements for a package and a map.

Easton Factor

The most bittersweet part of this preparation has been the extra time I spent with my dog, Easton. He’s a rescued 11-year-old American Foxhound and, despite my provocative headline, he really is the best dog in the world.

Nothing gets your tail wagging like seeing me preparing my gear. He doesn’t know I’m going to Georgia; just think that we are going to take the greatest walk of all time.

Left to my own devices, I am a “mile maker.” I like to put my head down, find a rhythm and go the distance, a habit probably inherited from years of running businesses. But Easton won’t allow it. It slows me down in the best way possible. He insists on stopping to sniff every log and investigate every breeze. He breaks my rhythm, but in doing so, he reminds me to pay attention to the weather, the forest, and the moment.

As I prepare to head to the terminal, I try to take a page out of Easton’s book. I’m going to go out and cover the miles, of course, but also remember to stop and smell the trees.

(And for the record…I’m sure your dog is fine too.)

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