Fantasizing About Retirement

When my father retired from the real estate business, he didn’t close his office. He kept it intact for a year, as a contingency plan. He worried that he might be so bored in retirement that he would need to go back to work. That’s not surprising for someone who had to start working at age ten in the depths of the Depression.

Me, I’m ready for retirement. Emotionally, not financially. Don’t get me wrong — I love my work. But after more than 30 years doing the same thing, I’ve started to yearn for the next thing, even if it’s the last thing I’ll ever do.

I’ve harbored this fantasy about retirement for quite a few years. I’m not sure it’s logistically possible — especially since I haven’t convinced my wife of its viability — but it keeps singing to me in the middle of the night.

I want to take 10 years and spend each year in a different city. I enjoy long weekend trips to new places — I can see enough to figure out if I want to come back. But to become really part of the city, to know it like a citizen, that takes some time.

Admittedly, there are problems with this plan.

Problem #1. My list (in no particular order) has more than ten cities on it: 

  • Sydney
  • Auckland
  • London
  • Venice
  • Vienna
  • Florence
  • Boston
  • New Orleans
  • Vancouver
  • Montreal
  • Kona
  • Munich
  • Seattle
  • Casablanca

Problem #2. My wife probably has a completely different list of cities (although I’m sure that Venice and Florence would be on hers too).

Problem #3. The timing will be tricky. For greatest efficiency, I should pick the ten years immediately before I’m ready to go into a retirement home. That way, I can sell the house and divest myself of all my stuff before I leave on the great adventure. Or, in the alternative, find a really big storage locker.

Problem #4. I would have to give up pets. Emotionally, that’s the hardest part of all. Our current kitties are six, and could be with us another 10 years or more. I’ve found that adopting pets about every six years helps you through the passing of the older ones, but to put this plan into place, I wouldn’t be able to do that.

Problem #5. I would have to have the financial wherewithal to manage such a venture. That’s the biggest obstacle of all. As with so many boomers, this starting-and-stopping-and-starting-again downturn has put a crimp in another kind of kitty, the retirement kind. Instead of spending a year in each of those cities, I may have to limit myself to a week. Which seems counter-productive to the whole idea.

So, my fantasy has some problems. But my working life has had its challenges: capricious bosses, magazine shutdowns, layoffs, low-paying gigs, technological nightmares, and other vivid memories. I just need to be as creative and disciplined in my retirement as I am in my work.

Which, unfortunately, makes retirement sound like taking on a whole new career.


About middleagecranky

The Middle-Age Cranky blog is written by baby boomer Howard Baldwin, who finds the world, while occasionally wondrous, increasingly aggravating.
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6 Responses to Fantasizing About Retirement

  1. lois says:

    Fantastic idea! You might have to pare down your list of cities and perhaps try renting an apartment in each for a week or two to further define your choices. “Untours” offers you apartments and support for a week or two in many cities….they are a great outfit or just go online..
    You have my blessing and good wishes.

  2. Sondra Newman says:

    Try a slightly watered down, more economical, but still fun version: Go live in one of your favorite cities for one month and do that for 10 years straight. That’s do-able, right? You choose 5 cities, and M. can choose five — and send me a postcard from all of them!

  3. Miles says:

    I do recommend Auckland. It is a nice city.

  4. Pingback: That Mirage Off In The Distance … Is That Retirement? | Middle-Age Cranky

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