“Where the hell you going with that?”

The captain is blocking my path on board. A white shirt stretches over his puffed chest. Biceps flex like cannonballs. A seagull shrieks and flies away. The air is thick with tension like before a duel in an old Western. But I’m not in a dusty frontier town. I’m on the edge of Manhattan taking a ferry to New Jersey.

I pretend that my baggage isn’t out of the ordinary. Nothing to see here, folks, just a nice day to hit the Shore with my bike, which isn’t really mine. It’s a rental Citi Bike. It can’t leave the city.

The sun is packing high-noon heat at 9:00 a.m. It feels like one of those August Fridays when people take a long lunch and never return to the office, ending up on a restaurant patio packed with tables and chatter. Phones vibrate with work emails, but attention fades with every sip of refreshment.

Weekend vibes take over.

The attitude on summer Fridays at Elite 1 was mercifully on this same wavelength. We got out early at 3:00 p.m. Otherwise, we worked from nine to six without a break. Lunch culture was grabbing a sandwich to eat at our desks in a windowless room, pecking away at projects and brushing crumbs off the keyboard. So at three o’clock on summer Fridays, I’d skip down the stairs and throw up my hands in delight. Sunshine. Air. Freedom. Monday morning seemed so far away.

What if I had a life where I looked forward to Monday? I’d been thinking about taking a Citi Bike across America for more than a year, and today I’m turning those thoughts into action. I’m launching myself into uncharted waters to see what else is out there. Nobody has tried leaving NYC quite like this.

Suddenly I miss the security of a routine. At 3:00 p.m. on Fridays, I’d Citi Bike down the Hudson River Greenway to yoga in Tribeca to de-stress from the week. At three this Friday, I could be doing poses for a mugshot. What happens now determines how far I’ll get on my journey. California is the goal, but I’ll settle for safe passage to New Jersey.

The captain calls my bluff. He’s built like a statue and stands stone-faced with bronzed skin. He demands to know why I’m taking this bike on the boat. The waves quiet down to hear what I have to say. Oh God, where do I start?

“Hey man, relax, just a day trip to the Shore…I’m coming back later,” I say with a smile.

Silence.

“Are you kidding me?”

“No, I am coming back later,” I insist. I have evidence. “I’m an annual member. See, here’s my key.”

“These bikes can’t go to Jersey. No-ho way,” he howls.

“I…I’m just…going for…for the day.” Choking on my own lie, I fumble for words.

The captain’s tattooed forearm swings forward. He grabs the handlebar. “That’s grand larceny,” he barks.

“No…no, you don’t understand, I—”

“I’m calling the cops!”

Worst case scenario. I always brace for it. Expecting the worst helps me avoid disappointment, but not since jumping out of a burning building has my worst-case scenario been as bad as getting arrested.

Thankfully, I’m not. None of the doom swirling around my mind is happening in real life. There is no burly boat captain. The ticket taker is a skinny guy with spotty skin who has no reaction as I roll the bike aboard. Nobody says a word. Nobody calls the police. Nobody cares. It’s New York. It’s summer. It’s Friday. A horn blasts and motors gurgle. Relief at making it on board turns into stress about getting off. What if I’m arrested in…New Jersey? Yes, that’s it. I’m going to get arrested upon landfall. The story will go viral. My name will be smeared online. I’ll never get a desk job again. My nerves shoot higher than Manhattan skyscrapers. I’m on a ferry to New Jersey with a bicycle that belongs in New York.

Excerpted from “West of Wheeling: How I Quit My Job, Broke the Law & Biked to a Better Place,” by Jeffrey Tanenhaus ’02 (Houndstooth Press). Reprinted with permission.