A boomer finds a new way to retire

Baby boomers lead the field in finding new ways to retire … or … to remain blissfully unretired. That’s what Howard Kaplin of Suffern, New York, has figured out. It’s what he writes about in “Welcome to the Conch Republic.”

As I turned 64 last March, my office moved from 10 minutes away from my home to 50 minutes away through New Jersey traffic. I thought to myself, now is the time to make a change, but retirement wasn’t the change I had in mind. I was able to transition my workplace to the bedroom that my children had slept in when they were infants. This took some coaxing and hard persuasion to get my wife to see my way of thinking; she thought it would be the end of her life as she knew it. But the idea that I am the majority breadwinner finally took hold and my home office became a reality.

Howard Kaplin

Howard Kaplin

That Fall, our daughter went off to college and all of a sudden we were able find the time to go places during the school year that had inhibited us before.

With today’s technology, I was set up with a remote office phone which operates over the internet. This now allowed me to work from anyplace that a router existed, which meant I was able to tap into the internet.

It seemed that this freedom of movement, coupled with the freedom of a moveable workplace, had limitless possibilities.

I spent three weeks on Cape Cod as a test run to see if I could really be as productive as I was in my home office. Although an upgrade in the computer I have at Cape Cod was needed, I was able to stay focused and work well. Still, the great beaches beckoned, and so before my work day started, I was able to satiate my love of being there with early morning walks.

The next idea was to work from another better place, and in my mind, that place should be tropical.

Key West is as tropical as one can get and still stay in the mainland U.S. and have reliable internet service.


So off we went to a rental house in mid-January to settle in to a new community that we had only visited in the past.

It is now late winter, and my moveable office has been a success, and a point of envy for my friends and clients up north who have suffered with an exceptionally harsh winter.

A new life in a new community certainly has its challenges, from where I can legally park my car, to how to parlay our food shopping into discounts on gasoline. A parking ticket here, and a tow away of our car there, have taught us quick lessons.

But through these minor tribulations, what I have been able to do is successfully combine the ‘idea’ of retiring to a better place, to putting that off so that I can be in the place, and still stay active and productive, and continue to earn an income instead of wondering how I am tofill my time in early retirement.

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  1. Ah, the wonders of retirement in the digital age. Well done, Howard, and I can say my husband and I have done the same (but as we both work, that means it’s double computers, double printers etc everywhere for us, in the city and the countryside). We’re very happy with our system, we never stop working and we’re always in touch…

    But wait, that can be a problem too. You know what? I dream of a good long vacation on a desert island with NO internet connections!

  2. Thank you Howard, now you have given me something to really think about and explore. Your office set up looks a lot like mine, OK so yours looks a bit more modern, but taking it on the road has such interesting possibilities.

  3. Congratulations! Sounds like the possibilities are endless. My son and his family just returned from a month in Oaxaca, Mexico. He worked remotely while there, limiting his work week to three days (nice employer!) and was able to enjoy the different culture with his family. I hope you’ll share your future adventures.

  4. Good for you Mr. “Boomer” Kaplin for escaping the winter up north for a winter in Key West and then writing to inform others of the possibilities of a moveable workplace in retirement. Key West is a magical place if you can afford the rents and tows…LOL

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