Dreaming in The City that Never Sleeps

New York can’t be simply summed up in a word.  It is all the world’s languages mashed into a living and breathing creature.  It is serendipitous and terrifying, beautiful and gruesome.  I’ve spent a lot of time there, not just visiting, but as a business owner.  I look back on those days with great nostalgia.  Many of the people I met and worked with were native to NYC and had an absolutely beautiful and optimistic view of their hometown.  

Many of these friends have reached out more recently to talk about a different subject—  How to get the hell out.  They don’t dislike the city, instead they desire something which is elusive in New York.  They yearn for a second act, a new chapter set in a peaceful not boring, private but not solitary, slice of heaven.  Many of the things that make NYC such an exciting and energetic place are also what make it exhausting and stressful.

I decided it would be interesting to do some research and uncover a few people who quit New York.  Remember, you can’t simply take a few months off from New York, you have to quit it completely.  Anyone from NYC knows that it’s the only place like itself on earth.  Agreeably, every other place on earth will be as drastically opposite.


Many people are familiar with this storyline— Big city executive slugging through the rat race gives it up while visiting a tiny tropical island.  I myself hold this fantasy in high esteem.  There is something truly magical in the realization that we could escape at any point and with any level of stakes.

escape-supply-company-03Don’t Stop the Carnival: A Novel
by Herman Wouk

The story of Norman Paperman, a New York City press agent who, facing the onset of middle age, runs away to a Caribbean island to reinvent himself as a hotel keeper. (Hilarity and disaster — of a sort peculiar to the tropics — ensue.)

escape-supply-company-02Where Is Joe Merchant? A Novel Tale Paperback
by Jimmy Buffett

In his debut novel, Jimmy Buffett cooks up an irresistible gumbo of dreamers, wackos, pirates, and sharks, as he leads Trevor and Frank on a wild chase through the Caribbean Islands to a place where anything can happen . . . and everything does.

Screen Shot 2015-09-24 at 3.18.33 PMFlirting with Mermaids: The Unpredictable Life of a Sailboat Delivery Skipper
by John Kretschmer

Over the course of twenty years of delivering sailboats to far-flung quaysides, John Kretschmer has had innumerable adventures, both humorous and terrifying. in Flirting with Mermaids, he recounts the most memorable of them.

escape-supply-company-04The Rum Diary: A Novel Paperback
by Hunter S. Thompson

The Rum Diary is a brilliantly tangled love story of jealousy, treachery and violent alcoholic lust in the Caribbean boomtown that was San Juan, Puerto Rico, in the late 1950s. Exuberant and mad, youthful and energetic, The Rum Diary is an outrageous, drunken romp.



There are quite a few examples of people who documented their travels away from the big city.  Each person who writes about their exit has a unique perspective so I would encourage you to go through all of them to learn why and how they made their escape.

Noelle Hancock (Twitter)

Robert Herzog (Twitter)

Arin Greenwood (Twitter)



Hopefully the links above will give you the gift of inspiration, and help you visualize your second act.  Please use the comment area below to share suggestions or inspirations you may uncover.