Retirement — Gangster Style

The Gangster in You

Mischief or Adventure?
A Sense of Style

You Have Skills

What's the Plan?
The Bounce

If you're retired, you know the feeling. It comes after you've cleaned the basement, fixed the deck, and put in time at the driving range. The feeling starts slowly and begins to eat at you.

Maybe it doesn't hit until the third cruise, or the fifth month baby-sitting the grandchildren. And they are good kids.

Then it hits. There has to be something more. Sure, it's nice to read the paper end-to-end, and the afternoon naps are great — but it's not enough. Working part time might be the answer. Though you don't relish dealing with old your boss and you can't imagine handling the latest crop of attitude heavy MBAs.

Adventure or Mischief?

It wasn't always that way.

Think back to summer vacations when you were growing up. The idea of no school shot you out of bed with a bounce in your step and a nose keen for the scent of mischief.

Summer time offered ball games, voyages on leaky rowboats, and secret trips to the local dump. You could boast about finding a turtle at the pond, but you also learned to keep other escapades to yourself.

Just Creative

It wasn't that the neighborhood kids were inclined to mischief. They were just creative. At the slightest hint of boredom, young minds would start spinning. The call, "Let's play tree tag," had us swinging like squirrels from the branches way too high for such a game.

Not all challenges got a warm response.

One quiet day, the suggestion came, "Billy went all the way through the drainage pipe (about a quarter of a mile long) and said the water was only six inches deep. We could handle that." Billy was somewhat of an urban legend. Feet shuffled until we were saved with, "Let's swipe a watermelon from old Harry's garden."

The adventures may have been seasoned with mischief, but they were mostly innocent.


Mike offered, "I remember when one of the kids showed up with a shovel. It caught us by surprise. Our minds were spinning. The cry, 'Let's dig a hole — a foxhole,' won the day.

We marched to the woods like Marines on a mission. Two hours later our first problem hit. The hole was too deep for the last digger to get out. The tale of Louie stuck in the foxhole was retold throughout the summer.

Okay, it was silly, maybe even stupid. We were lucky Louie didn't get buried alive, but those adventures filled the summer with a vitality I can feel today."

A Sense of Style

The neighborhood kids had rules though. Bullying was considered cheap, and blood always stopped a fight. Baseball caps were mandatory, and a pair of Chuck Taylor's boosted your status.

More importantly, the adventures required a sense of style. Simple tag was out, but playing tree tag up in the big oaks was cool.

In the summer's quest for challenges, we found that narrow path that let us mix imaginary missions, the hint of danger, and a flash of style. Maybe that's what's missing in retirement.

The Gangster in You

As kids, we weren't gangsters, but there were similarities.

We sought out adventures with flare, and the best ones could never be mentioned at the dinner table. We took risks and wore our bruises like badges of honor. We had a disdain for the ordinary and made every attempt to seek out the unusual.

Real gangsters, of course, are nasty people. The media, however, portrays them as flashy, full of life, and stylish. In their sanitized versions, gangsters are adult models of us in those old summer days.

The "gangster in you" image is an appeal to your sense of adventure and style. Okay, there may be a bit of mischief included.

You Have Skills

As enticing as those old days seem, you are a different person now. The old hijinks don't have the same attraction. Digging a hole or swiping a watermelon doesn't have the old allure.

Most of your changes are positive advances. You're more sophisticated, more capable. You can manage complex projects and can untangle complex decisions.

Your skills are key.

Success of the new adventures hinges on how well they utilize your abilities. Just as when you were a kid, the endeavors must offer a challenge, otherwise they feel lightweight and superficial.

Throw in a bit of mischief, and you have the recipe for a Gangster Style undertaking.

What's the Plan?

What type of activities fit a Gangster Style adventure? Let's start with the requirements.

1. Style
The endeavor needs style. There must be bit of swagger involved.

2. Depth
The adventure must leverage your talents. It should include tough decisions, logic problems, and an element of risk. Without a meaningful challenge, you'll be bored.

3. Mischief
Mischief isn't necessary, but what the heck.

4. Road Trips
You need to get out of the house. Road trips broaden your perspective and increase the mischief options 300%.

Initial Ideas

What are some options?

The game of billiards definitely has the swagger, though you might have to work on your Paul Newman smirk.

Handicapping racehorses gets you out of the house and provides an opportunity to wear that old plaid sports jacket. Picking winners by color is not allowed. "The gray horse to win," won't do. You will need your best analytic skills for trips to the track.

Poker could be the ultimate challenge. It requires discipline, analytic skills, and a sharp eye to be successful. What a lark!

A handful of "cultural" skills are essential if you are going to unlock the full potential of your road trips. This means adequate dance steps, a few drawing techniques, and the ability to write a tale.

Remember, style isn't just swagger and a leather jacket. It occasionally requires grace on the dance floor and the ability to turn a phrase.

Club games like, gin, chess, and backgammon round out the offerings. Thin mustaches and silk shirts are optional.

The Bounce

I can feel the bounce in my step already. These pursuits are not simple undertakings — they will certainly put your abilities to the test.

If that isn't enough, potential rewards from poker and race handicapping create a treasure hunt atmosphere (the ultimate summer adventure). With the right training and persistence, who knows what pot of gold you might uncover?

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