How My Road Trip Across the Country Ended in Boston and Why I Decided to Stay

I left California with half a plan, no place to live, and a tank full of gas. And if you were to have asked me why I wouldn’t have been able to tell you. (Read more on that story here).

Looking back now it feels like I was pulled to this city like a magnet. Boston.

My drive across the country was anything but a “vacation” by any sense of the word. Driving anywhere in the United States in the middle of a Pandemic, not to mention one of the most controversial election seasons in our history, was more like a pilgrimage than a “travel bug” getting the best of me.

Truthfully, I didn’t have an interest in “seeing the sights” or cramming as many experiences in one day as humanly possible (like you might on a vacation.) I spent much of my time in a hotel room hunched over my computer, on the road calling my clients, stopping for dinner and coffee and postcards wherever I could find a place.

It wasn’t your typical trip, but I suppose this isn’t your typical year.

By the time I got to Chicago, I knew I wasn’t turning around. The realization swept over me like a wave. I had just finished brushing my teeth and running a comb through my long auburn hair. As I tip-toed into bed and pulled the covers over my body I was greeted by an unforeseen thought standing audaciously at the doorstep of my mind.

“You’re not going home,” it said.

I tossed and turned and finally found rest on the left side of my pillow. A single tear escaped from the center of my eye. I knew it was true. I knew I wasn’t going back. And this was the first time I had come to realize and accept it.

I wasn’t afraid that I (still) didn’t know where I was going to live. That wasn’t it. It was the thought of leaving my life in California behind me: my friends, my community, and the place I had grown up and called home for so many years. I was grieving the loss of my life. My old life. It was this awareness that filled my entire body with immense sadness and discomfort.

As I challenged and argued my way through the complexities of this realization, I came to accept that my new life was waiting for me on the other side of Chicago.

And I had to keep driving, not knowing what would be waiting for me on the other side.

I traveled through New York, Pennsylvania, Vermont, and New Hampshire and finally arrived in Boston, Massachusetts on Tuesday, October 27.

I thought I was going to stay for two days.

What I didn’t know was this:

One week later I would stumble upon a woman’s Facebook post.

This Facebook post would lead me to a conversation with Emily.

Emily would tell me that she needed someone to take over her lease for a studio in Beacon Hill, one of the most beautiful neighborhoods in Boston.

My conversation with Emily would prompt me to walk down the street and up a winding staircase that would lead me to a beautiful light-filled apartment with tall glass windows and a marble fireplace.

I would stand there and smile and see glimpses of the future flash before my eyes.

I would sign papers and wire money and pick up keys.

I would move to Boston on Tuesday, November 10, exactly two weeks after the day I arrived here.

And now, in real-time, as I share with you the story of my move, I pause to consider the why of how I got here.

After 6,000 miles and dozens of cities, countless conversations, and enough new memories to last me a lifetime, I am calling Boston home.

How did I know? How did I know this was the right decision for me? Or that Boston was the right city to move to?

Intuition can’t always be explained in such a way.

What I can tell you is this: it was the same feeling that led me to Italy. The same feeling that told me to start a business, that brought me to Oakland, and away from Oakland. The same feeling that propelled me across the country, and the same feeling that told me I wasn’t turning around once I made it across the country.

It has never let me down. This voice, this feeling, this internal sense of knowing even when you don’t know.

Take heed with ears that listen. A heart that is open. Eyes unclouded by longing. May you move boldly in harmony with the ever-changing, ever-evolving reality of life itself.