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It isn't necessarily fun, but Charles believes it's incredibly important to prepare for every contingency possible. This is the type of "game" that all preppers, a subculture made famous by National Geographic's TV show Doomsday Preppers, take part in. A game of chess, says Charles, where winning or losing means life or death.
Unlike other preppers, many of whom live in less populated areas, Charles has to contend with one major obstacle to surviving any apocalypse: living on the island of Manhattan.
"The biggest problem is getting off this rock," Charles told Business Insider from his Harlem apartment. "People in a town or a landlocked city can just walk out. We can't. And you can't swim off the island unless you are an Olympic swimmer."
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In the event of a catastrophe, Charles' first move is to grab his wife, kids, and dog, as well as their respective "bug-out bags," a prepping term for a bag loaded with everything needed to survive for a week or more. Charles keeps these bags stocked at all times and in an accessible area in his apartment.
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"If we can take the car even five or ten blocks, we will take it. On a long haul, you want to save as much energy as you can." Harrison Jacobs/Business Insider
The family will then make the hike to the West Side of Manhattan with the intention of crossing on foot over the George Washington Bridge or through the Holland or Lincoln Tunnel.
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Charles has a solar and handcrank-powered radio to hear any reports over the airwaves. He also has a solar-panel charger for his cell phone, in case cell reception is still active.
If they hear reports that the bridges and tunnels are already closed, they will head to the water. Charles has two heavy-duty rafts in his pack which they will use to cross the Hudson River.
"We have two rafts that attach: one for us and one for our gear. Our goal is to get across the Hudson River at high tide," explains Charles.
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Once they land across the river, hopefully as north as possible, Charles and his family will continue hiking as far and as fast as they can into a wilderness area, where they can set up a protected camp for the night to rest. In the following days, they will continue hiking north, with the intention of getting as far from population centers as possible. Harrison Jacobs/Business Insider
While Charles has thought out this plan a hundred different times, he recognizes that in the heat of the moment, it's unlikely anything will go according to plan.
"There are so many variables to a 'bug-out' situation. You expect things to go from A to B, but instead they go A to Z. It's a crappy game that you have to play. You have to be smart and resourceful," says Charles.
To test those different variables, Charles and the NYC Preppers will frequently go on bug-out weekends in the wilderness to test their gear and survival skills, as well doing bug-out walks to test evacuation scenarios. It's during these tests that Charles has realized a few extra wrinkles to his plan:
1. If you are traveling in a large group, break up into groups of three and space out your evacuation by thirty minutes or so. "Having twenty or thirty people traveling clumped together is dangerous. For looters or marauders, it would be like shooting crabs in a barrel," says Charles. Instead, if one smaller group is attacked, the others a couple miles behind will be able to see it in the distance and react with a plan.
2. Test your equipment. "People find out all the time that a backpack didn't hold up, a sleeping bag wasn't warm enough, or a pack was too heavy. You've got to test to get a feel for what you need," says Charles.
3. Worry about crime. "We have high crime rates in New York. That rate will go up when society breaks down. All the people who thought about doing crime will start doing crime and that's on top of the criminals already here," says Charles.