How Monopoly Teaches You Everything You Need to Know About Quitting Your Job

For many of us, Monopoly was the only financial education we had growing up (further discussion on this is coming in a future blog post!). The depression-era Parker Brothers (now Hasbro) board game was based on an even earlier game called The Landlord’s Game, designed to educate the players about taxes. Monopoly takes it a step further, educating the player (I was always the battleship or car) on cashflow, taxes, financial ups and downs (Chance!) and…jail.


As in life, in Monopoly the name of the game is assets. To quote from a well-known financial literacy advocate, an asset “is something that puts money in your pocket.” This includes stocks, real estate, or a business. To Quit Your Job, you must have assets. Let’s say you’re hired as a retail employee. You are paid a low wage because your only asset is your time. If you move up, or get hired into management, your assets include your time and skills or knowledge.

To break away from this, you need assets that generate income irrespective of your time. Stocks, for example, are an easy asset to obtain. Stocks can go up in value. Even better are dividend stocks, which pay out money to those that hold shares on a regular basis.

Real estate is also an asset. It retails value, the value can go up and then the real estate is sold at profit, or you can charge rent to put money in your pocket. This is the backbone of Monopoly — green houses and hotels. Both generate money for you as your car or thimble roam the board. In real life, you can purchase real estate to rent to create monthly cash flow. You can also purchase REITs (Real Estate Investment Trusts) and collect rent dispersed as dividends.

Businesses are a third type of asset. Represented in the game as utilities (Water Works, Electric Company) and railroads, businesses are a way of generating income (aka ‘cash flow’). A business is the ultimate asset — it can grow in size, become an excellent source of cash flow, and is tax beneficial. Even better, you can continue to collect your $200 GO! salary as a business owner.

To Quit Your Job you must have assets. Saving up a bunch of money and then quitting will only give you a long vacation. Eventually it ends with you having to go back to work. Bills don’t end — even if you own your home 100%, you still have taxes and insurance and maintenance costs. You still need to eat. Life also likes to come knocking at the door. You need income — and assets provide it.

At the start of the game, every player has some savings and a job (this is what GO! is, where you collect your $200 salary). You must balance your income (salary) early on while acquiring property and utilities. You can also save your income for later purchases. For those who don’t have a drive to Quit Their Job, they happily move around the board, trying to get to GO! as fast as possible – to collect their $200. Money is spent on things like Luxury tax and the occasional Community Chest mishap. They are happy not taking any risks with property and thus never get anywhere. In the context of the game, they will eventually be wiped out by landing on a red hotel at some point.

The winner of Monopoly is the one that ends up with all the assets.


Is cash an asset? Technically, cash can put money in your pocket through interest. However, in this day and age, most bank interest rates require a microscope to see and inflation easily wipes out any gains. But to Quit Your Job, you must have cash readily available.

Cash serves two purposes:

  1. Protection. In real life, you’ll inevitably flip that random Community Chest or Chance card. Hospital fees. School fees. It will be someone’s birthday and you have to give them $10. Also referred to as an Emergency Fund, you must have cash on hand when you Quit Your Job. Not having an Emergency Fund will require you to go into debt for sudden expenses, or sell assets like stocks to pay for it. Loss of assets or going into debt leads to going back to a job.
  2. Preparation. If you have cash, you can be ready to strike at any time. Imagine having a cash reserve when the 2008 crash started. Stocks and real estate (assets!) severely went on the cheap. By having cash at opportune times, it enables you to acquire assets at low cost. This is another facet of Monopoly: when another player is in desperate need for cash and looking to auction off a property, those with cash can scoop them up. Or if you already own Park Place and land on Boardwalk and not having the cash to purchase it. You just missed out on the biggest monopoly and biggest potential for cash flow because you didn’t have cash handy.


You want to stay out of jail both in the game and in real life.

It’s scary to think about how in the game, when you have nothing and you’re behind, that the best place to be is in jail. I’m not going to wade into the ‘poor people and jail’ arguments made online or in sociology circles, but there is an eerie correlation between this component of the game and real life.

Other Lessons

Overall, Monopoly is a great education in life. In addition to what’s been mentioned above, Monopoly also teaches about negotiating and compromise. There’s the wheel-and-deal component to it when it comes to trading properties and utilities. It’s also about accepting the randomness of life (I don’t expect to ever randomly win second place in a beauty contest) and the inevitable things ($75 Luxury Tax).

There is a reason Monopoly has been popular for 80+ years. The game is competitive, as is life. ‘Getting ahead in life’ is part of life. Whether it’s trying to get promoted, pay the bills, or Quit Your Job, Monopoly is the early childhood education in doing so.

And for all the realism in Monopoly, there’s always one thing that never happens: