I’m on The Back Nine of My Life, What’s The Legacy I Want to Leave Behind?

Craig Stanland
3 min readSep 14, 2022
The actual “keeping up with the Joneses” home.

“Keeping up with the Joneses.”

The term conjures up images of people displaying their prosperity through their homes, their cars, their clothes, their country club, and parties.

It’s a code term for materialism and flaunting your wealth, but underneath it lies a desperate need to fit in.

Keeping up with the Joneses is a constant comparison; it’s a race where the finish line moves further away with every step you take.

Enough is never enough if someone has more.

And if enough is never enough, how will we ever feel like we’re enough?

Externals will never fill the inner void; that’s like expecting snow in the Sahara.

Fun fact:

The Joneses were real people, and the house in the image is what created the popular saying.

In 1853, Elizabeth Schermerhorn Jones built a 24-room mansion for herself in Rhinebeck, NY, in the picturesque Hudson Valley.

The Gothic mansion had towers, gables, and arched windows; it was straight out of a fairy tale.

Even its name, Wyndclyffe, has a magical air about it.

The home was so beautiful and so opulent the neighbors began their furious quest to, you guessed it,

“Keep up with the Joneses.”

Unfortunately, the house fell into disrepair and is slowly falling apart; neglect, weather, and time it’s wrecking ball.

Before prison, my life was a constant comparison to everyone around me.

I looked at everyone the way the Terminator looks at people, sizing them up and coming up with a data set.

Only the Terminator’s data was accurate; mine was merely the stories I was making up about them based on their externals.

I was chasing the billionaires of Greenwich, CT, in a race I could never win.

Prison and losing everything ended the race, and I’m grateful.

I’m into the back nine of my life; I’ve got more years behind me than I do ahead of me.

Craig Stanland

I write about my journey from corporate success to federal prison and finding joy, mission, meaning, and fulfillment beyond professional and financial success.