Should I Stay or Should I Go?


Have you ever clicked on a retirement website, just once, just out of curiosity?  A Best Places To Retire site? Or an Active Adult Community link someone shared on Facebook?  If you have, then you suddenly see many links, right?  Yay technology!

Many of the links point to developments designed for people 55+. Amenities often include no maintenance properties, single level floor plans, recreation facilities, hiking trails and golf courses. A lot of these places are in the Carolinas and Florida. 

My retirement strategy for years has been to stay where I am when I decide to retire. I’ve lived in Maryland for thirty five years and I mostly like it. Living in the DC suburbs means I’m less than an hour from all that the capital of the free world has to offer, like wide open spaces, historic monuments, awesome museums and a highly-regarded cultural and entertainment scene. In addition, I’m only three or four hours from the ocean or the mountains or Manhattan. I experience all four seasons here. I know my way around, I have an active local social life that’s years in the making and great access to outstanding medical facilities. That last one is a definite benefit for aging. 

On the other hand, I’ve always wanted to live on or near water. I’d love to watch a sunrise or sunset over a body of water every day, while sitting on a deck sipping coffee or wine. Oh, and I hate icy weather. 

I click on those links and picture myself living in one of those ‘active adult’ communities near the Atlantic Ocean or the Gulf of Mexico. 

Margaritaville, Del Web, The Villages. Ever heard of those?  All for ‘active adults’. Translation: planned developments for boomers who are aging but not old yet. (Boomers are 55 - 73 right now). 

There’s a strong temptation to check out these places. There are also many that are closer to where I am now, in coastal counties of Maryland and Delaware. We have friends with places there and we fantasize with each visit. 

I’ve often questioned why someone would want to pack up and start over right at that point of their life when familiarity, community and security are more important than ever to him or her. Then I see a picture of those physically fit, tanned, gray-haired golfers on the front nine in sunny Sarasota. Then I remember Florida has an abundance of heat, humidity, hurricanes and alligators. Then I see a picture of a beautiful Pensacola sunset as my road trip playlist starts playing Jimmy Buffet and Alan Jackson singing “It’s 5 O’clock Somewhere” and I can almost taste the sangria. 


The title of that 1982 Clash song keeps popping into my head. Should I stay or should I go?  The song isn’t about retirement or geography, by the way, and I don’t play golf. But you get the idea, right?

One thing I love about my current neighborhood is the generational mix of residents. A key to staying young is hanging out with the young. My local hangouts have a great balance of Boomers, Gen-Xers and millennials. 

As further evidence of my rationalization side, I’ll mention that my neighborhood also has several lakes; which means I almost live on water already. 

Another trendy retirement strategy is to be a “snowbird”.  Live in Maryland during summer and Florida during winter. Hmmm. 

There goes that song title again. 

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