The game Spent has been making the rounds through the serious games and eLearning communities. In case you’ve been hiding under a rock (or don’t use twitter), the premise of this game is that you’ve lost your job, your house, and most of your savings. Your challenge is to make it through a month of difficult choices.
There are relevant facts about poverty woven into the storyline. However, I don’t remember those facts nearly as vividly as I remember not sending my child to a birthday party because I couldn’t afford the $10 present. The power of this game comes from the emotionally compelling decisions where there is no perfect answer.

Forcing the you to commit to these hard choices, rather than just throwing out facts, more effectively challenges your perceptions. With some of your decisions, Spent even questions your assumptions about your abilities to complete various tasks. Sure, you can commit to tutoring your child in math, but can you prove that you can actually solve a “two trains leave different stations” math problem of nightmares? (I actually like those types of math problems, but I’m severely nerdy.) Similarly, if you attempt to get a job as a temp, you have to prove your qualifications through a typing test.
Along these lines, I’ve been thinking about other “it’s difficult”-themed games and simulations I’ve played in the past. Here are three additional games and simulations that exist at least in part to allow the user to experience just how difficult something actually is.
3rd World Farmer
It lives here: http://www.3rdworldfarmer.com/
In this simulation, you take the role of an impoverished family in a politically unstable country. Do you plant resilient corn or take a risk with peanuts, which may yield a higher return? Do you send your child to school or keep him home to work? Do you buy medicine or livestock?

Despite your best intentions, this isn’t FarmVille, and disasters strike frequently. When I played, corrupt officials took my savings, guerillas took my livestock, and my well… well, it collapsed.
As you advance, you can invest in communications, infrastructure, a sympathetic representative and more, which help mitigate the effects of the disasters. In fact, the way to eventually win the game is to make all of these improvements. However, surviving long enough to save the required money is very difficult.
Peacemaker
It lives here: http://www.peacemakergame.com/
Okay, so perhaps most people don’t walk around talking about how easy it is to bring peace to the Middle East. However, this game does a superb job of simulating the complexities of trying to please multiple groups at once while working towards a peaceful resolution. In the screenshot below, you can see a few of the different groups that may approve or disapprove of any particular action (there are a bunch, and they like to disagree).

Making everyone happy all of the time is definitely not an option.
One of the key takeaways for me was that it’s really hard to make any progress at all, especially as the Palestinian president. I did manage to reach a peaceful, one state government (as the Israeli Prime Minister), but it was a long journey.
The Oregon Trail
It lives here: http://www.virtualapple.org/oregontraildisk.html
Speaking of long journeys, I played several versions of The Oregon Trail as a kid, and I can’t say that they were terribly effective at helping me remember locations or dates. However, the part I very clearly remembered was that traversing the Oregon Trail was just plain difficult.

If you go too quickly, you wear yourself out, but if you go too slowly, you won’t arrive in Willamette Valley before winter. If you don’t hunt enough, you’ll run out of food, but if you hunt too much, you risk depleting the critters available to you in the future.
And don’t even get me started about the diseases and other potential disasters. In my most recent venture down the trail using the above emulator, I was barely on the road before my iPhone family member died of dysentery.
Aside from often being terminally dry, textbooks can’t allow you to interact with history as a series of tradeoffs and dangerous propositions. Games can.
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With the exception of Peacemaker, all of the games/simulations linked to above are free (and PeaceMaker has a free demo mode)! Go make some difficult decisions!