Our first dream-chaser was Chris Shultz, a Minnesota native who wrote the book on quitting your job and finding your paradise. Literally. It’s called Quit Your Job and Move to Key West: The Complete Guide. Shultz did just that many years ago, when he traveled to the quirky Florida getaway for a video shoot that was supposed to last two weeks. “Eighteen years later,” he says, “I’ve got a wife, a house, and a few bars.”
He started with The Porch, a craft beer and wine bar tucked inside the historic Porter Mansion in Old Town. He went on to establish a mini empire, eventually opening up The Other Side, the Waterfront Brewery, and 2 ¢ Restaurant. It’s all worked out amazingly well for Shultz, but he states right up front in his book that you shouldn’t expect Key West (and by extension, any coveted geographical landing place) to literally be paradise. There’s still loads of work to be done, appointments to be kept, and responsibilities to be met. Even if it’s 85 and sunny every day of the week.
He definitely hit rough patches during the transition. “All the time,” Shultz says. “Ups and downs were constant. I tried not to make the same mistake twice, but I still do that a lot. I’ve been broke a few times. But the best advice I ever got was, The thought of making the bed is worse than just doing it, so you might as well just do it.”
Sometimes, though, it helps to get a nudge from someone close to you. That’s what ultimately got Steven Baird to quit his accounts payable job at a New Jersey tech company and start pursuing something more… liquid. “I’m just not wired to sit at a desk all day,” he says. But with his wife pursuing an advanced degree and bills to be paid, Baird had little choice. Eventually, after his wife left grad school and the couple relocated to Brooklyn, she sat him down. “She told me that we would figure it out, and that should I quit the office job.”