I’ve been picturing this moment to myself for months now: sitting in the motel on the first night of the Ride and writing about the first day. When I imagined it, I kept thinking about how I would feel, what would happen that day, and where I would be. and of course, I feel very differently than I thought I would, different things happened, and I am not where I thought I would be.

First off, I thought I would be immersed in loneliness and guilt on the first night. I do miss my wife and kids and still have the urge to turn back and surprise them at home tomorrow, but the flood of excitement masks it all and the sense of adventure dominates. It’s only now that I realize the sheer magnitude and scale of this journey.

Secondly, my day did not involve any excursions in Amish Country, but rather a dropped bike, using the toolbox for the first time, a rough bilker bar, and some really nice bridges. Ride Of Your Life - Day One

The day started with saying good-bye. The kids gave me a big hug and went to Sunday school, then my wife followed me in the family van until we reached the Tappan Zee Bridge. We spent another hour or so together and then parted ways. I’ve never been away from Gili and the kids for more than a week, and both of us became very emotional when we said goodbye.

I left and headed west, and during the first two hours just felt very strange. Riding through New Jersey into I-78 and Pennsylvania was dull. But then after getting off the highway onto Route 222 I immediately saw what I’ve been waiting to see: vast corn fields ready for harvest, tall silos. The flatlands of Pennsylvania, a first glance into the many faces of the the real America. It was beautiful. Time simply stopped and for an hour or so there was no more navigation, no thoughts, just the miles humming along in a constant soothing rhythm.

Trained as a picture-taking dad though, I decided that I must document this moment and climbed to the top of a hill on a side road. The view was perfect and as I was getting off the bike I realized that with all the excitement I forgot to push the kickstand down. This motorcycle weighs about 600 lbs and has some additional 100 lbs racked on its back. It was impossible to pull it back up. All I could do is allow it to get to the ground gently. It almost felt like after putting it down I should have tucked it in and read it a story. Bike down

Long story short, some nice guy came in and help me pick it up. No damage, and I even used the toolbox under the seat for the first time, to fasten one of the mirrors that went loose. Boy, did I feel proud… This was an interesting experience. I wrote here before what I think about building strength – that it involves facing challenges of gradually increasing magnitude. I think that my journey should follow the Five Steps to Inner Peace; before I start reaping the benefits of mindfulness, flow, and all the other goodies I expect down the road, I must get accustomed to the road, study it, and adapt to it. When you throw a 40 year old dad out of his suburban habitat straight into a scene from “Easy Rider”, some stuff will happen. The good news is that these challenges build reservoirs of strength, so it’s definitely a good thing.

From this point on things took a few turns for the best. I accidentally found the Wright’s Ferry Bridge, a ruler-straight beauty crossing the Susquehanna River. On the west side of the bridge, right next to the water was a biker bar taken out of a movie scene. Solid doors and covered windows, cigarette smoke, poker tables, and pool tables. The real deal. when I asked for coffee or something else to help keep me awake they suggested “shots”. I took a Diet Coke, drank it quickly, and left. I am probably the only nerd this place has seen in decades.

Day one of Ride Of Your Life was packed and made me think about a lot of things. Tomorrow morning – Route 425 for the fun of riding, and then down towards DC where I will be speaking with best-selling author and coach Caroline Miller.

Here’s a little video with some bits of my first day.


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