The Plan itself isn’t sound, but the supplementary strategy to execute The Plan seemed sound when I came up with it.

There is any number of ways to get from New York City to Chicago. I’ve always chosen to drive, but flying really is the way to go. The flight from JFK to O’Hare takes a little over two hours, but the time change crossing from East to Central time makes it seem like it’s even less than that. One could leave New York at 5 p.m. and arrive in the Windy City at 6:15p.m.

There is a different, much less efficient kind of magic to the drive. It takes 12 hours to make the Chicago run by land, and that’s under the best circumstances. If one takes all the right roads, stops only for gas, runs into no traffic, is not stalled by any construction work, is not deterred by police officers for speeding and can maintain a rigid mental and physical pace, it will still take half of the Earth’s rotation on its axis for that person to arrive in the Gateway to the West.

If I were smart, I would fly to Chicago. As it stands, I’ve always made the drive. I’ve justified it a number of different ways, each one more limp than the last. “It’s too expensive to fly,” I’ll weakly say to my parents, as they look at me sideways, clucking their tongues at their impulsive middle child. “The drive is fun” I’ll lie to friends who politely smile while calling me on my bullshit in their heads.

Truth be told, it is a little cheaper than flying, as long as you have three people riding with you and the gas gets split evenly between the squad. A solo drive would cost almost as much as a plane ticket, with none of the convenience. So that one is kind of a wash.

That line about the drive being fun, though? That one is complete bullshit.

The drive is mind numbing. It is a 700-mile trek across Pennsylvania, a state that is roughly the size of Russia and consists of nothing but shallow rolling hills and endless trees for the entirety of the 6.5 hours it takes to cross it. If beauty is what happens when you compare two things to each other, the PA stretch of the drive is the ugliest thing in America.

And yet, I drive. I am a romantic, I guess. I am not one of those people who read “The Road” when they were 15 and fell in love with the idea of traveling the world, drinking all the beer and doing all the drugs in whatever town I blow into, but I don’t deny that there is something to this cross-country ground travel. There’s a tangible effect that I find very appealing; it’s probably the same impulse that makes me buy records.

Beyond that, I’ve usually made the drive in good company. Girlfriends, friends, cousins and band mates have all made the drive with me. I always end up feeling closer to whoever shares the car with me, even if I want to kill them for maybe a third of the trip, due to proximity and endless miles (beauty, again).

It takes 12 hours in the best of times to make the drive, but with the right people, in the right light, at the right time of the day and with the right mood, a good hour in western Ohio can be worth 10 roundtrip flights.


So I am to drive to Chicago again this year. This is where The Plan comes in. It is a bad plan.

I am making the drive with three cousins, all of them veterans of this particular jaunt. Jared, Tom and Flynn. Outsides of my brothers, I am closer to no other family members. Out of all my friends, I count them among my best. It is a good squad to drive a long distance with. For lesser people, I would not make the kind of concession that lead to The Plan.

Tom works for a hedge fund in Manhattan. He has the kind of job that no one has, and yet, inexplicably, there he sits, hedge-funding in a Manhattan sky rise six days a week. Tom, for reasons passing understanding, be they cooperate strong-arming or personal obsession, cannot leave work, meaning he cannot leave for Chicago, until 6 p.m. Thursday night. We need to be Illinois by 12:30 p.m. Friday to see the start of Lollapalooza.

For those scoring at home, that means we have to leave Thursday night and embark on a 12-hour night drive through half of the continental United States.

And so; a 6 p.m. departure from the biggest city in the world at the heart of rush hour, bleeding into a death march through blasted hills of Pennsylvania so perilous that entering Ohio would seem like an accomplishment on par with getting one’s masters in a foreign language,

Initially, I was not on board. I was going to do it and I was going to do my damndest to try and have fun, but I was pessimistic about my odds of making it to Chicago with any kind of motivation to stand in the sun and watch an 8-hour rock concert.

If it were anyone else, I would have told them, “Tough luck. I can’t wait around for you all day. You’ll have to get to Chicago some other way.” It wasn’t anyone else.

And so The Plan was born: Jared, Flynn and I would pick Tom up from his job in Manhattan at 6 p.m. on Thursday. We would drive west, making as few stops as possible, and try to arrive in Chicago at 6 a.m. local time. We would then find my older brother Chris, who was staying at a hotel on the outskirts of the city, and sleep for a few precious hours before meeting the rest of our family and commencing wit the first day of Lollapalooza.

It was the hopeless nature of The Plan that led me to cook up The Supplementary Plan.

The Supplementary Plan was partially the brainchild of my friend Brett. Brett occasionally has to work nights. When this happens, Brettt will stay up until 3 or 4 in the morning, then sleep for as many hours during the day as he can. This adjusted sleep scheduled, partnered with coffee and a good attitude, allows him to be fresh as a daisy for his night shifts.

My scheme was to apply Brett’s move to my situation: on Wednesday night, I would stay up as late as I can by going to a rock concert in Philadelphia, driving to New York after the concert, picking up Jared and driving to Coney Island to see what the fuck that part of town looks like at 4 a.m.

On paper, this was a good Supplementary Plan: Jared and I would get to see a part of the city neither of us had ever seen before, we would be well-rested for our midnight drive, and the few hours of sleep we were able to get in the car ride and in Chris’s Chicago outpost would refresh us enough to rock out all day Friday.

Ah, the best laid plans.

I arrived in New York City around 11:30 p.m. I had consumed a Red Bull, despite the fact that they are toxic poison unfit for man or beast, and was feeling both awake and ready for adventure. I was determined, not only to stay up until sunrise, but to see if Coney Island, a small section of Brooklyn historically known for its mob activities and more modernly known for it’s general low-class minutia, was all it was cracked up to be.

Jared told me to meet him at the corner of Atlantic and Court in the Bay Ridge section of Brooklyn, but I could tell from our first phone call that the plan was in jeopardy.

“Nate Dogg … Meet me… at the CORNER of … of Atlantic … aaaaaaand Court. I’ll be a-at the corner of Atlantic and Court.”

I could tell by Jared’s voice that he was drunk. Normally, that’s no issue. However, he was the kind of drunk that only a person who works early day shifts in food service can be.

I worked in food service for a year, so I understand the mindset of working a 10-hour day then drinking for four hours, stumbling home, going to bed and getting up to do it again. From the outside, it’s wasteful at the least and a dangerous burning of both ends at most. When you are embroiled in service, however, it’s the only thing that makes sense when dealing with an entitled clientele for a living.

It was in the split seconds after that phone call that I knew the Supplementary Plan would have to change. The idea of staying up late would remain, but any hope of getting to Coney Island would have to die. So be it.

After a herculean effort by both Jared and I, he drunk and I directionally clueless, we found each other. Jared was indeed his particular brand of sleepy drunk; tired and weary, but smiling and desperately trying to be accommodating. It’s a very endearing mode, I’ll admit.

We hugged. We listened to rap music. We made crass jokes. We swapped quick family gossip. We drove back his apartment. I didn’t even mention Coney island. I knew that was a closed door.

We stopped at a fried chicken joint near his house so Jared could eat something before bed. The only thing worse than a 12-hour drive is a 12-hour drive with a hangover; you only make that mistake once. Jared had several pieces of fired food and I had an ice cream. We kept talking while we headed back to his place. If felt good to be with a friend.

It’s 3 a.m. right now and I’m in Jared’s kitchen, writing this very missive. I haven’t gone back to the bedroom Jared and I are sharing for the night, but I’m certain that he’s asleep right now. It’s for the best. The guy works hard, and he’s got a big day ahead of him.

If the Lord is willing and the creek don’t rise, I’ll fall asleep by 4 a.m. and sleep well into the afternoon.

As for that greasy jewel in southern Brooklyn, I’ll tackle it another time. Right now, exploration isn’t as important as being with people I love, going to a place I love, to spend time with them doing a thing that I love. If a 12 hour drive in the middle of the night means I get to have more of that, so be it.

Coney Island isn’t going anywhere. I, on the other hand, have miles to go before I sleep.