How Australian businesses can improve their strategies by thinking like Monopoly players
Want to succeed in business? Then perhaps you need to go back to the most basic of basics and think like a Monopoly player, writes ‘Mr. Monopoly’ himself, Philip Orbanes.
Without a strategy, there is no plan of action to achieve your goals, be it in a game, life or business.
Monopoly is like that. Sure, itโs about real estate, finance and monopolisation, but fundamentally, itโs about strategy – and you wonโt win without it.
My love for the game and the strategy played out. I successfully centred my career around game design and Monopoly. However, Iโve also been an executive for more than 40 years, and I believe my success, in part, can be attributed to the game-like fashion in which I approach my work.
Lewis Carroll said, โIf you donโt know where you are going, any road will get you thereโ. Without an end goal, you just flounder aimlessly. Your strategy enables you to master distractions, identify opportunities, and even ignore whatโs irrelevant.
Thereโs a lot to be learnt from the strategies you adopt to win at Monopoly that translate to the business world. Iโm excited that I have the opportunity to present these strategies and more during the Cascade Strategy Fest.
The success of Monopoly lies in the rules, simple yet ambiguous enough to allow for individuals to play their game. In gameplay, as in business, when there is structure, responsibility and objectives, people have permission for their imagination, creativity and skills to move them toward the objective. The synergy is in what individuals have to offer to get there.
The dice dictate the speed to which you get around the Monopoly board after you leave โGoโ, just as time ticks by in business, and this is where key strategies help you win or lose.

The words โGo to Jailโ have instilled frustration into Monopoly players for over 80 years, but itโs not always a bad thing. Time for pause is important for strategy. Going full-throttle for the duration wonโt work. Being sidelined offers a two-faced predicament: youโll need to strategise when to engage, or not.
Speed to market is critical (early in the game, winners pay to get out), then as your journey unfolds, a slow and steady rhythm kicks in, and being on the sidelines can offer security. Letting the competition play out around you, while you collect on your investments with no major outgoings, can afford the opportunity to re-strategise.
Unsurprisingly, most of the best players are business people. They know that just collecting $200 every time they pass โGoโ to amass great cash reserves alone is not going to make them a winner. Itโs about the investments made along the way, maintenance and improvement costs, and diversifying your assets.
You canโt win Monopoly by owning just luxury properties. Diversify to ensure you have a wide range of assets, so when somethingโs underperforming, your other assets are doing the work. You need to invest in your current assets, and with the rhythm kicking in while watching your competition, youโll identify where that investment will be better placed. If thereโs no potential, donโt waste your money; minimise your risk.
Monopoly trains your brain to recognise opportunity and make fast-paced decisions during competition – which is exactly what business leaders do. Best-laid plans get interrupted by distractions that canโt be ignored.
In Monopoly, a few wayward rolls of the dice – and the Chance and Community Chest curveballs – can teach you that sometimes the universe refuses to play your way, and not all opportunities are good ones. Leveraging your intuition and assessment skills can decrease the time it takes to make important decisions in life and business.
In life, and in the game, a strategy requires negotiation skills and good relations – even with your competition. Bad behaviour and leadership that offers no benefit to the big picture strategy will grind the game to a halt and send a business bankrupt.
So, while itโs vital to have a strategy to reach your goal, you also need to be adept and flexible to deal with obstacles that block progress. Most of the better-than-average players have a plan to โsometimesโ win, because in business, as with Monopoly, thereโs always an element of luck.
You can catch Philip Orbanes as a keynote speaker at the global Strategy Fest on June 21.ย
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