Life Lessons from Monopoly

Monopoly taught some great life lessons

Growing up, we used to play a fair amount of board games. I love board games for a number of reasons – a topic I’ll touch on later this year. They were great times to bond as a family, even if I lost more than I won.

One of our favorites was Monopoly. Pretty much everyone’s familiar with Monopoly – especially now that there’s so many dang versions of it! Chances are you either like it or you hate it – I’ve met few people who are neutral about the game.

Regardless of your personal thoughts on it, here are a few lessons I picked up from my years of playing.

Free parking is FREE

Alright first off let’s get this out of the way: if you’re the type of person who puts money in the middle for if you land on “Free Parking” you are the worst kind of person.

I half joke. Half.

It’s called FREE parking, not We Pay You To Park!

If someone is giving you something for free I assume they’re generally doing it out of good will. Instead of taking advantage of that to the tune of having them pay you, just be thankful that you’re not landing on New York Ave (my brother’s favorite monopoly) with a Hotel on it.

Sure sometimes there will be some sort of catch, and it’s important to see those when they happen in real life.

Property > Cash

Every now and then we used to play a game for fun where one person would start with all the money and the other person would start with all the property.

Of course as a kid, you think “Oh man!!! Look at how many $500 bills I have, there’s no WAY I could lose!” The game would drag on for a while until you realized that your inevitable demise was approaching quicker and quicker as your opponent built his real estate empire.

Here’s the thing: All the cash is awesome. It makes you feel flush and secure.

But cash doesn’t earn you money. Cash doesn’t win the game.

Investing that cash wins you the game. Properties win you the game. And without those investments, it’s impossible to get ahead.

Likewise in life, if you’re sitting on a ton of cash, it may feel nice to have some extra cushion. After all, we’re entering a recession soon, right? Some may tell you to stop investing and hoard all of your cash.

But without investing you aren’t going to win. It’s unlikely you’ll be able to hit your financial goals unless you invest. Sure the market may tank the day after you put money in. But guess what?

Historically it’s always bounced back. Depending on your timeline you may want to choose something slightly less volatile to help soften the blow. Volatility when you have a short time horizon can be crippling.

If you don’t invest though, your cash is guaranteed to slowly be eaten away. Better to get started sooner than later. Even if it’s something simple like contributing more to your 401(k) at work, it’s at least a step.

Jail Makes Everything More Difficult

Unless you had a ton of properties, time in jail sucked. It was perhaps nice to delay your doom if you needed to play it safe for a while, but winding up in jail almost never was a good thing.

I always get out of jail ASAP if it’s early in the game; losing out on the ability to purchase properties because you’re behind bars just puts a bigger delay on your investments. Time is a great ally when it comes to Monopoly – the sooner you build up your properties the better position you’ll be in.

Make Beneficial Deals

The art behind Monopoly is making deals with other people playing the game in a way that you perceive as advantageous to you. Most of the time these deals involve swapping one or two properties for another.

If you make a deal that gives someone else a monopoly but doesn’t give you one, it’s probably a bad deal. You need to weigh the pros and cons of all exchanges, of course. When the goal is to be able to build houses and wipe your opponent out, though, you need to make sure that the agreement you’ve reached is beneficial for you.

Passing Go Won’t Win The Game

Each time you pass Go you get $200. It’s nice – it’s like a little paycheck for your endeavors. At the beginning of the game especially this is the majority of the money you bring in.

Hopefully though over time your properties will start to bring in money. Maybe it’s semi-infrequent and maybe it’s not as much as passing Go.

But when you reinvest the money you get from your properties, you can start to build houses and/or hotels. This is like reinvesting dividends in your portfolio to help you earn more money more quickly.

Passing Go is always nice – but it’s never going to win the game by itself. It’s like having a paycheck but never investing it, and hoarding it all in cash or spending it all.

If you want to not rely on that Go money, you need to invest it.

Luck’s Not All

Sometimes luck is on your side – sometimes it isn’t. Those that are prepared for the worst and who can make a plan even when things go awry tend to do better overall.

The Chance cards always made me nervous. Sometimes they’d be okay but a lot of them were not great. It was always easier to deal with the bad Chance cards, though, when you had some sort of moderate cash cushion. It wouldn’t save you from every catastrophe but it at least would be a good first line of defense.

Enjoy Your Time

Monopoly was a game we played to have fun – not to really learn anything. It was about enjoying the experience and getting to talk with the family.

Sure it was nice to win but what’s the point of going through a game if your only goal is to win and not enjoy the company of others? What’s the point of life if not to live the one you enjoy?

We can pick up some queues from silly board games, but at the end of the day you need to enjoy your time here on this earth. Sometimes it’s not about winning or losing – it’s about the journey and the connections you make along the way.


What were some of your favorite games growing up?

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  1. Ahhh Monopoly… we had an after school care game of monopoly go for almost 3 weeks straight, played in 1-2 hour increments. Lesson learned: patience can win you a lot of things. Many kids just gave up and walked away by day 3. I learned I don’t have that kind of patience… maybe we should bust it out again and see if that’s changed with time.

    1. Hahaha I’m surprised by the dedication to let a single game stretch out so long! Most of the time if we couldn’t finish it in two sittings we’d call it quits.

      Patience is a great lesson here too. Nice!

      I’m a huge fan of board games (a topic I’ll touch on later) and would happily play again! Still not paying anyone to land on Free Parking though, that’s BS!! 🙂 🙂

  2. Hi Dave. Fun post! I really enjoyed this one. I like your Property > Cash section. Just yesterday we had the 401k meeting at work. A colleague sitting next to me leans over and says “Yeah, this is great until you lose it all.” I said, “You won’t lose it because there is no money in your 401k, only shares of companies.” Up or down it’s the same share of the same company. But it’s hard for people to internalize that.

    1. I feel like people who have had a bad experience in the past are super prone to this mindset. For example if you started investing in something like penny stocks – or any stock that tended up going down for that matter – and you didn’t diversify, I can see how that’d leave a bad taste for investing in the future.

      It’s a shame, because proper diversification pretty makes this a moot point as long as your time horizon is sufficient.

      1. Agreed :). I will say that I put my life savings into some Vanguard funds in 2006. I remember the pain of watching it go down 50%. I did not sell – lucky. Things have changed now, and I have earned more money, but I try to hang onto that feeling as a reminder in the next round.

  3. Great post, I grew up in Baltimore City so the best piece of advice I ever got was “don’t go to jail!” But where I grew up that was a common thing, thankfully I avoided it.

    And as far as Monopoly, I always banked big scratch on Park Avenue. That was my money-maker.

    1. We’ll be flying into Baltimore early next year to visit some friends actually! 🙂 Love the advice though lol

      I was a huge fan of Park Ave for sure. But I also liked some of the lower-priced monopolies since it was easier to get a little bit of cash flow from them to build up. The big guys did the work of bringing down your opponents though!

  4. I loved Monopoly for a long time, but I have more difficulty enjoying it now, mainly because of the game Cashflow. Cashflow is just a better (not perfect, but better) approximation of real life and, for me, that makes it even more fun. It’s a hard game to get people to want to play (mainly because you fill out a personal P&L / Balance Sheet and some people think that’s nerdy or something) and there is still an element of luck, but it gives a deeper understanding of the value of investments.

      1. I read your post today about mapping out your income and expenses by hand and not using a tool and I think the same applies here… the first few times you play, scoring your own Income Statement and Balance Sheet teaches you the relationship between the decisions you make and how they impact your financial situation. Ultimately, that’s the whole point of the game.

  5. I loved monopoly as a kid and it definitely taught some financial life lessons. The big one for me is to invest in average to get wealthy, not the moonshot. Ie buying boardwalk and park place may win you the game by luck. But odds are higher with more diversified monopolies at more moderate prices.

    1. Great one to add to the list! The big ones always seemed so dang expensive to build up too and a lot of the time by the time you could afford to put hotels on them, you’d be wiped out by other smaller ones that consistently hit you in the wallet.

  6. Haha I liked this one Dave, property and assets are much better then cash! I have to stay away from monopoly when I see the family get way to competitive and sending your siblings into bankruptcy shouldn’t feel so good.

  7. Love it. Being a landholder, property owner is one of the most ancient and proven paths to wealth in human history. Monopoly does a pretty good job of laying out the basic premise – compound your gains as you grow your empire.
    Mr. Moneybaggz

  8. When I was in my younger teen years, a game with family friends turned unfriendly… we had a (the?) monopoly ‘incident’ where we ran for cover, me shielding my sister & brother as houses and hotels were thrown, the board was flipped, monopoly money everywhere! I don’t think I’ve played the full game since then. Monopoly junior, sure.
    I often aimed to own utilities, and a few moderate priced properties. The chances of landing on park place and board walk were usually slimmer than a run of the yellow or green.
    I do like your lessons though.

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