Almost exactly two years ago today, I made my way to a campsite by the water for my first night in the van with a girl I had a big crush on. She came to visit and be with me as I was beginning the big new adventure that turned into a book last year. Get your copy here.

Little did I know, this day was part of my early introduction to the chaos that van life brings. As we pulled into the grocery store to get food and ice, my tire pressure light came on. Walking around the car, I heard a now familiar hissing noise. The patch in my tire came out.

Earlier that week, a very nice kid working at Walmart showed me how to patch tires. After the long drive across the country with a tire light on and daily air refills, I brought the van to Walmart’s tire center. There, a gentleman helped me find the culprit: a nail almost the size of my pinky finger. We made a plan. First, we would yank it out and then I’d drive over to the garage to get the patch. We got the nail out. As I drove over, the manager walked toward the van waving his arms wildly. That’s when I learned that their car lift isn’t strong enough for a van. They wouldn’t be able to help me fix it.

As I sat there racking my mind for another idea now that my tire had a gaping hole in it, the skinny tattooed kid working at the tire desk walked up to me. “You know you can patch a tire yourself. I can’t touch it, but I can talk you through it.” I was ecstatic. He showed me how and stepped in when I got frustrated. “Watch and make sure they don’t see me,” he said as I stood to block his manager’s view from the garage.

After the tire was patched, I gave him a tour. “I watch all the YouTube videos but I’ve never seen one in real life,” he said with excitement. As we talked more, I learned that he was a new Dad. He grew up around there, but wanted to show his kid a different life. Maybe a life with a view from the back of a van just like mine. “Don’t be scared to start,” I said. “Everything figures itself out.”

The Beginning Isn’t Always Magical

I didn’t have the same inspiration or motivation while I stared at the hissing tire, all while trying to keep my composure around the girl sitting in my front seat. I remember a whole whirl of thoughts. Few were kind. A lot of them were wondering why the hell I did this.

I feel a lot of similar things as I prepare to begin the next phase of van life in just 3 weeks. This time, the girl that once was a visitor will be taking this adventure with me. A dog, too. I’m sure the tires will find nails. Things will go wrong.

That’s the only thing I know to be absolute in this world: things will change. Break. We will have to start over. The finish line will move. The only thing I’m even more sure of? That the change will happen whether I like it or not – to my career, to my life, all of it. But I’m also more confident in my ability to begin again. And again, and again, and again.

So for this “New Year, new you” season I want to remind you that it’s ok to start all over. Beginnings make us better. Again and again.

Weekly Letters beginning