The Real Lessons from The Oregon Trail

John O'Connor
3 min readAug 19, 2016

Hint: They have nothing to do with history.

If you went to elementary or middle school in the 1980’s and early 1990’s, you no doubt had the pleasure of playing some of the most fun and well-made educational video games ever created. “The Oregon Trail” was less of a game and more of a childhood bonding experience. We mourned the loss of our friends as they died of various ailments on the trail.

I found an Apple ][ emulator Online recently that came with a copy of The Oregon Trail. Feeling a bit of nostalgia, I decided to show Sean (my son) the game and how it works.

We were progressing along well until we ran out of food and dad got dysentary. Around the “Snake River Crossing” we lost our last family member.

Afterward my wife (Jessi) decided to play as Sean and I watched.

Watching as the team powered through broken legs, disease, thieves, and low supplies I had a sudden realization:

The real lessons of “The Oregon Trail” had nothing to do with history

Let me explain.

While there are certainly a historical aspect to the game, and it definitely sparked some conversation about history and traveling across the country, the real lessons from “The Oregon Trail” are not lessons about history.

Without further ado, here are the “The Real Lessons from The Oregon Trail”.

Planning Within Time and Budgetary Constraints

Sometimes in life you’re the banker, and sometimes you’re the farmer, but either way you can achieve the same lofty goal.

In the beginning of the game, you’re greeted with a screen that asks you for your origin. This determines how much money you start with, and therefore how many supplies you have. If you choose a “banker from boston” you start with a substantial budget. If you choose “a farmer from Illinois”, you start with a small budget.

The second choice asks you when you’d like to start the trip. Too early and you risk traveling with little food or water for your oxen. Too late and you get stuck in the snow and die. You have to figure out just the right mix of time, budget, and supplies to make it work.

It may seem obvious, but it’s easier starting off as a banker. You have more supplies, and at critical times in the journey you may have an advantage being able to purchase supplies or barter more effectively.

However, despite being more difficult, the game is still winnable as either a banker or a farmer.

The lesson here is that, no matter what your starting point, you can achieve the same lofty goals as anyone else. Your journey might be harder, and you might not have the safety nets that others will have, but you can still set out on a journey and achieve success without those. Success is more than just where you started.

Success Requires Perseverance and Luck

In the Oregon Trail, you can be the most well-prepared banker in the world and still die of dysentary. You can also be a small farmer that just happens to continuously find fruit on the trail and make the trip in record time with no casualties.

Success can often just be a matter of luck.

This is a lesson that I think many adults have a hard time remembering. We like to think that we’re masters of our own domains, in control of our lives and the events in them. But the truth is that all of the successful people in the world got there in no small part due to luck.

Luck plays a huge role in “The Oregon Trail”. Losing the trail for a few days at a critical time can cost you the game. Finding fruit at exactly the right time can also save your lives. There are events and situations that are out of our control, and those situations and events can affect our chances of being successful. The right director seeing the right actor at the right time can launch a career. Others may spend their entire lives and never make it out of the “actor currently working as a waiter” phase.

Failure does not necessarily mean you did anything wrong. Sometimes it’s just bad luck and that’s ok. Try again and work through the bad patch because you never know if there’s wild fruit on the trail just up ahead.

The next time you’re feeling worthless or unsuccessful, just remember to persevere and wait for the tides to turn and your luck to change. The longer you’re at it, the higher chance you have of succeeding.

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