Monopoly® is, undoubtedly, one of the most iconic modern board games of all time. The game involves 2-8 players with 16 Community Chest Cards, a pack of Monopoly money, 32 Green Houses, 12 Red Hotels, 8 Tokens, 28 Property cards, 16 Chances, 1 Speed Die, and 2 Dice. Basically, you win the game by collecting rents on your property. The bigger the cash flow (collected from rents) the longer you can prevent yourself from going broke.

The game teaches a variety of financial lessons, much of which has been widely discussed, nit-picked, and scrutinized by entrepreneurs and financial planners before. Robert Kiyosaki, the author of Rich Dad, Poor Dad, said that Monopoly teaches you the only thing that matters in financial planning: Grow your assets (Get as many red hotels you can).

Yet beneath all the obvious strategies you can pick up from the game is a preview of your would-be behavior given the pretend-play presented to you. For instance, given $1500 at the start of the game, don’t you feel a bit more powerful holding that much cash (although they’re not real, but still….). In your head, you’re itching to make your first purchase, don’t’ ya?

Based on years playing Monopoly, I know for a fact that you can increase the probability of winning the game if you have good control of your emotions. Ultimately, the growth of your emotional intelligence with the game can cross-over to similar experiences in real life.

So here are some bunch of behavioral lessons I picked up from Monopoly.

Self-Control

In Monopoly, you’re a tycoon. You’re basically sitting with a lot of cash. You’re guaranteed $200 every time you pass by the corner marked “GO”. What could possibly go wrong? Well, when you wantonly spend your cash, that’s what. Be prudent when spending your money. Control your urges. Think carefully about the properties you buy. Be more careful in auctions where the urge to outbid your opponents becomes more important than the long game.

But Time the Gratification

Delaying gratification in Monopoly is a good start for any player. However, if that’s your only strategy, you’ll miss out on opportunities. I understand the principle of delaying gratification is to save money and survive the marathon. Saving money just for the sake of it is textbook Loss Aversion. If you hoard money and not spend it on building your asset, and you’ll be out of the game before the spend-drifters. That’s true with this game as well in real life. A better way of looking at this is timing your gratification right. Spend money on assets so the money will work for you (through rent, that is).

Plan Ahead

The fun part of Monopoly is not knowing what will happen and see where your luck takes you. Of course, you can’t do that in real life, unless you’ve gone bonkers. Professional players of Monopoly (and yes, they do exist) have fun with the game with a set strategy and let it play out against the opponent’s strategy. For the most part, that’s the optimal route to success in Monopoly and in life

But be Wary of the Cautionary Tales here.

Holding on to a set of strategies carries a number of cans of worms you need to be wary about. Professional players tend to lose to less-experienced players because of overconfidence with their game plan.  Other players lose simply because of Hindsight bias—or that tendency of people to overestimate their ability to predict an outcome.

Toughen Up

Monopoly relies on the old formula of chance luck. Despite how good you are and how many strategies and adjustments you take, bad breaks and jail times are inevitable. With a game that could run as much as an hour or two, be prepared to get tripped, ripped off and screwed on. It’s not how many windfalls you get in the game that wins it, it’s your grit and your ability to handle a stream of losses that forges players into real tycoons. So don’t give in, saddle up, and seize opportunities to survive the gamut of rent payments across the board. Turn your luck into a behavioral skill.

But don’t be so tough with Other Players

Monopoly was born in a time when Tycoons gobble each other up when the opportunity arises, bringing with them the cycle of a dog eats dog world. If Monopoly teaches the old world some new tricks, it is that new would-be Tycoons need to cultivate relationships with other tycoons to negotiate a good deal. Bad behavior will only get the player with bad deals with others. In the real world, entrepreneurship is about establishing a productive relationship with advisers, professionals, and suppliers, as they will help the business grow.

However, don’t forget that you’re still playing the cutthroat world of Monopoly. In the end, it’s your goal to send your opponents to bankruptcy. Play it safe by playing it cool with intent. You win the game if your opponents never read your behavior or saw you for what you really are—a shark.