Personal, Stories Told

Monopoly money: A story from my new book, A Place to Start

This story is in my book, A Place to Start

I don’t naturally see the bright side. I have to work at it.

Blogging has given me a way to work at it. As I push through challenging things in life, I write about it looking for the silver lining, the lesson learned, the happy ending.

What you tell me in the comments is that you find my stories to be encouraging. I find that to be encouraging!

Today I’m launching my book, A Place to Start. It collects the best stories and essays from this blog’s first two years. I was recovering from a divorce, trying to build a new life, working to be a good dad to my sons. I worked very hard to find the good in everything — it helped me keep my head together.

If you’d like a copy of my book, here’s how you can get it:

This story is in the book. It first appeared here on August 30, 2008.


I was feeling good about my financial situation as I headed into the summer. I was rapidly paying down debt and had built up some savings. But then August was unexpectedly expensive. I replaced my car’s transmission (and rented a car for two weeks while it was in the shop), replaced my refrigerator when it conked out, and had some medical and veterinary bills. Bam! Within a few weeks, my savings was gone and I had even gone a little more into debt.

I know that everything that cost me was just a matter of chance. Cars break down, 20-year-old fridges die, dogs and people get sick. It was better to spend savings on these things than to have borrowed to pay for it all. You might even say that God took care of me, providing for me through these misfortunes. But I’ve been angry about it just the same. It really hurt to get a little bit ahead only to lose it almost all at once.

On Wednesday, the boys and I broke out the Monopoly board. My youngest is starting to understand trading and can now stick with a long game, and so our play is starting to become vigorous. We’d made some trades and we all had monopolies — my older son had the violets, my youngest son had the neighboring oranges, and I was just around the corner with the reds. When we started improving our properties, it became hard to move along that side of the board without somebody collecting.

My youngest son landed on my Kentucky Avenue. With two houses, the rent wasn’t terrible, but having spent all his cash on houses he hocked most of his property to pay me. He weathered that with good humor, but he next landed on Go To Jail and so would make another trip down Death Row. His next roll put him on Community Chest, but then he landed on Indiana Avenue, which by then had four houses and was much more expensive to visit. Cash-strapped and hocked to the hilt, he had no choice but to sell most of houses. He was ticked. And then a few tears ran down his face. And then he buried his face in my shoulder.

The irony did not escape me as I hugged him and told him it’s bound to hurt when you build things up and get a little ahead only to have bad luck take it all away.

When I woke up the next morning, I didn’t feel so bad anymore.

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Last updated on 21 November 2020 by Jim Grey

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13 thoughts on “Monopoly money: A story from my new book, A Place to Start

  1. Love this and also love Monopoly. I used to play it with my boys too … since I remarried (which was many, many years after a rather shoddy divorce) my new husband started playing with us. Now this was brutal! He was ruthless and my “don’t worry darling I’ll lend you some money to keep you in the game” was poo-pooed! How we love it! The shrieks and laughter … They’re all grown up now and yet I hope we’ll play it again next time they come to visit. In the meantime, I totally understand about the real money aspects – yup I’ve been there too. Hang on in there … it passes. Very best wishes, Katie

    • The family I grew up in, we were all big Monopoly players. So naturally I taught my boys. They’re grown and gone now, and I’ve remarried. I’ve played with my new family exactly once, and I freaked them all out the first time I wanted to trade properties! My wife described my play style as “cutthroat”! Apparently her family *never* trades.

      • Ha! I love that … we also occasionally play Risk, but with a military husband he seems to win each and every time. I seem to have problems both attacking and defending – maybe it’s a multitasking issue I don’t know, but I must confess to taking the game far too personally when he invades my territories … Pathetic I know!

    • Hardcover is tricky with print on demand. The only place I know that does it for a book like this is IngramSpark, but they appear to sell only in quantity to bookstores and libraries. I could try uploading this to Blurb or something but I’m sure at 200+ pages the cost would be scandalous.

  2. A great story. We never played a lot of Monopoly when the kids were young, not sure why. They seem to have developed good financial habits anyway.

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