• DD3 = Dear Third Daughter
  • DH = Dear Husband

DD3 vs. me

One of the byproducts of our more frugal lifestyle is that we stay in and do things like play board games more often. I tried to teach DD3, when we first ramped up the frequency of our Monopoly games, to DO something with her money. She would pass Go, collect $200 . . . and then just let that money sit there. She wouldn’t buy every property she landed on as I did. “You’ve got to buy more properties,” I explained, “to increase your chances of getting a full set so that you can put up houses and hotels. That’s how you win.” And when she finally did secure a full property set, she wouldn’t get houses as soon as she could afford them. I’d think to myself, She’s got all of those properties and all of that money, but it’s not doing her any good. For my part, I would max out in my house-buying, keeping just enough money aside in case I landed on one of DD3’s more dangerous properties. DD3, on the other hand, would take forever to spend $300 from her $2,000 stash for one house per space. Why not buy two? Why not three? You’ve got the money! I found it frustrating, but I kept my mouth shut. She would just have to learn the hard way.

My “bad luck”

Inevitably, things would go wrong. For me. The stash of cash I kept “just in case” would drain quickly in one unfortunate round:

  • A Chance card: “Pay poor tax of $15”.
  • The Luxury Tax space: $75.
  • A Community Chest card: “Pay hospital $100.”
  • The Go To Jail space (no $200 for passing Go this time). $50 to get out of jail.
  • Then – Arrgh! A landing  on DD3’s property with the house on it.

My cash already drained, I’d have to mortgage one of my properties. The beginning of the end for me. Just bad luck, I thought the first few times. But when bad luck keeps revisiting, you have to take a closer look. Maybe there was something to be learned from DD3’s stubborn insistence upon saving – her painfully measured way of spending. And maybe I needed to take a closer look at my own game. Why such a compulsion to spend as much as possible and to save as little as possible?

A close look at losing in real time

With a new awareness of DD3’s superior Monopoly wisdom, I played with her again a couple of times this past week. Same results! Only this time, I was conscious of each disastrous step in real time. Here are a couple of snapshots of my thinking:

  • Ugh! I didn’t buy a green property last time around, and here I am landing on one again. I’d have two now if I’d bought the first time. If I land on a green again next round, I’ll kick myself for not having taken advantage of this opportunity.
  • DD3 has 3 houses on each of her orange properties – and over $2,000 in cash. I have the advantage of owning more properties, but I only have $400. Still, I’d better buy some houses because I have to benefit from my property advantage.

In the end, I had to mortgage two of those green properties I felt compelled to buy. And when DD3 had hotels on her orange properties, I landed on one – cash strapped. Those houses I’d bought did nothing for me. It was game over.

Connections to my real money management?

I can see two connections between my modus operandi in Monopoly and my real life personal finances:

  1. My discretionary account is always bone dry by the end of each month. While DH manages to save a little from his discretionary allowance (exactly the same as mine) – to the point where he can go away for a week-end of snowboarding – I consistently spend it all, often cheating and borrowing from the next month before it arrives.
  2. My disagreement with DH last week stemmed from my greater desire to get rid of our money (in a positive way – by paying off debt) than to save it. I referred to our savings as “sucking my momentum”.

Soul searching

Mrs. Frugalwoods wrote an excellent post this past week about her former fear of spending. “Saving money isn’t the worst default position …” she noted. “The problem is that I was saving from a place of fear, not a place of strength.” If I try to identify the “place” from which I have rid myself of money throughout my whole life – clearly including the present – I would have to say it has been a place of panic. It’s even evident in my thoughts and advice on Monopoly.

  • “You’ve got to buy more . . . That’s how you win.”
  • I would max out in my house-buying …
  • … I’ll kick myself for not having taken advantage of this opportunity.
  • … I’d better buy some houses because I have to benefit from my property advantage.

These are not thoughts and words of calm confidence; there’s a tense compulsion to them. A fear that time and chance are going to pass me by. A dread that the future will provide no opportunity. Maybe I’ve got the youngest-of-5 syndrome? Make a mad dash to the counter to get a cookie before they’re all gone. I’ve got to mellow out. I’ve got to have more faith. More confidence that no mad dash is necessary – that there’s a cookie on the counter with my name on it, and it’s not going anywhere until I get there.

Looking ahead

We’re coming to a point in our “Total Money Makeover” (Dave Ramsey style), when savings will play just as great a role as paying off the mortgage – the last debt standing. There will be a hefty emergency fund to save. There will be greater investments towards our retirement. There will be short-term savings for cars, furnace, air-conditioning. All this in the face of soon-to-be greater expenses. (More on that later.) We will have to be measured in all aspects of our finances, and there will be no room for my panic.

Awareness is the first step to any positive outcome, and so I’m hopeful that I can get a handle on my money-ridding compulsion. I used to spend it all chaotically. In the last 3 years, I’ve thrown it against debt, hand over fist. I have to learn how to just hold it. Save it. Watch it grow. A few lessons from DD3, a few more games of Monopoly – it might just do the trick.

Does fear play a role in your management of finances? A fear of spending and a compulsion to save? A panic to spend and an aversion to saving? What’s your strategy in Monopoly? Your comments are welcome.




Join the Conversation


  1. Sounds like DD3 has learned a lot along the way. I’m the youngest of five and I never had fear of missing out, just the opposite. I was classified as spoiled by my older siblings. I think the only fear I’ve experienced related to money was not being able to provide for my family, but even that didn’t stop the debt cycle.

    1. Perhaps you felt that in order to provide sufficiently for your family, you needed to buy things that required you to go into debt. I would guess that the marketing machine had some influence there. Whatever it was that led you to debt, you seem to have freed yourself from its influence : ) Thanks for your comment, Brian.

  2. Monopoly really does offer great insight into how we view money–I’d never thought about it like that before, but it makes sense. I’m really thankful that I’ve finally moved past fear as the primary driver for how I approach money. It’s certainly a more liberating and peaceful way to live. I think it’s awesome you’re uncovering the root of your approach to money too–it takes courage to do that!

    1. “liberating and peaceful” – that’s what I’m after too, so I’m glad I’ve uncovered this panic. I’ve been accustomed to calling it “chaotic”, “scattered” or “careless” – but really, it’s fear. Speaking of courage, it was in strong evidence in your post too : ) Thanks for commenting, Mrs. FW!

    1. The question is, how is it that you influenced your children to play a better game whereas I am being influenced by my child to play a better game? Hmmm….

  3. There are only a few properties that I like to invest in. The oranges offer the best ROI, but Red is the most frequently landed upon property (due to the frequent ability of people to land in jail).

    Early in the game, I always buy Railroads and Utilities. The utilities are secret cash cows.

    My real secret though, is to never want a specific Monopoly so badly that I’m willing to sacrifice a trading position of strength to get the Monopoly (until I am cash rich, and they are cash poor of course).

    My family is a bunch of serious Monopoly players. We had a rule of no crying during Monopoly or everyone loses.

    1. OK, thanks for all of these Monopoly tips! I am going to apply them in my next game against my daughter – without telling her about them. At least, not for a few games. It’s quite something that you have to have the “No crying during Monopoly” rule in your household. That is some serious Monopoly!

  4. I save out of fear…..fear of not having the funds to take advantage of the perfect opportunity when it presents itself. Sure, lots of little things come along….a good movie, a chance to go out to a movie with friends. All things that would fit in the budget if we said yes to all of them. But Then along comes an opportunity of being asked by my brother-in-law to do a mud race with him – the registration fee is a little spendy….but because we’ve saved up, Vonnie and I decided the bonding experience with my bro-in-law and some others was well worth it. Tough Mudder, here I come! 🙂

    1. To me it sounds like there’s some anticipation mixed in with that fear. “Sure, this would be nice, but something better might be just around the corner…” I’m glad you were in a position to take the opportunity when it came. I hope that you bond and have an awesome time! (But what exactly IS a mud race?)

  5. I haven’t played monopoly in forever…this makes me want to start up a game now! There’s so many great lessons to be learned from it, plus it takes forever to play so it’s nice family bonding time 🙂 I somewhat have a fear, mostly fears that maybe we don’t have enough in savings. I didn’t have those fears until Little Miss came along though, I always think the worst case scenario is going to happen and what the results would be for us financially speaking. I’m working on not being so fearful though!

    1. There’s nothing like having a baby to make you more sensitive to fear. With your philosophy of simple living, I can’t help but think you’ll have plenty of savings before too long. I hope that you’ll have an opportunity to play Monopoly soon : ) Thanks for your comment, Christina!

  6. I love the monopoly analogy. My father was a successful property owner. I remember some of his soundbites: “Over expansion ruins many a successful business.” I always interpreted this to be “a bird in the hand” sort of philosophy – a way of balancing opportunity with risk. “Never bet more than you afford to lose” ; “Never spend your capital.”

    1. OK, this is timely advice for me. And I don’t mean in terms of my Monopoly game! Both DH and I have to learn to be enthusiastic about our savings and investments. We have so few – and we’re realizing that the reason why is that they simply don’t excite us. Way more exciting to buy. Way more exciting to kill off debt. I don’t know how to muster an enthusiasm for savings and investments, but somehow, I think that if I keep playing Monopoly, it will come : ) Thanks for your comment, Laurie.

    1. OK Kay, let’s form the Monopoly Improvement Society. We will report on our progress at the end of each month and fine-tune our game based upon results. First on the agenda: control purchase of properties. What do you think?

  7. I’m like DD3, taking my time to make purchases. The boys in our house buy everything & set traps with their hotels to take my money. Monopoly is not a quiet board game, that’s for sure.

    1. Who knew how intense Monopoly could be? My question is, who usually wins? You with your “taking my time” strategy? Or the boys with their “buy everything & set traps” strategy?

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