3 Life Lessons from Playing Oregon Trail

Oregon Trail Picture - Dysentary is no Fun

Class, put your books away. It’s time to play Oregon Trail.

Was there a sweeter elementary-school-sentence? The promise of Oregon Trail would fill my little body with waves of excitement like I’d just caught the winning touchdown at recess, while simultaneously downing ten pixie sticks.

Oregon Trail - You Have Died of Dysentary Picture

The journey from Missouri to Oregon huddled around that gray, Apple computer was a glorious one. But as I look back, really, why were we playing it? Did we really need to learn that avoiding dysentery is a good idea and that we shouldn’t shoot too much buffalo because you can’t carry it all home?

But just like any good teacher, Oregon Trail was teaching us some vital life lessons and we didn’t even know it.

Three Oregon Trail Life Lessons that Apply Today

1) Planning Ahead Before you Start on the Trail is Key

I loathed going through the initial process of setting up our wagon, picking your profession, stocking up on supplies, and choosing the best time of the year to leave.  Just give me a gun and put me on the trial so I can start shooting squirrels.

Oregon Trail Planning Ahead Picture

But without fail my lack of planning would leave me stranded somewhere in the Rockies in the freezing winter without extra clothes and a busted wheel. (What 4th grader thinks about stocking up on wagon tongues?)

Most of my post-college experience has felt the same way. Just give me job, point me in a direction and I’ll figure it out from there. But how many times could I have avoided breaking down if I would’ve spent more time planning for what I’d really need for the journey ahead. Taking time in the beginning, saves lives in the end.

2) Sometimes a Grueling Pace WILL Kill You

In Oregon Trail you could choose the pace your wagon would go between slow, moderate, or grueling and I picked grueling every, single, time. If Martha or Frank couldn’t keep up and if a few oxen had to be left behind, so be it. We were going to get to Oregon as fast as possible – dead or alive (usually it was dead).

For us today, everything is on-demand and with a press of the button we can have dinner, our favorite TV show, our next date, two books and a lamp – all at the same time. And I think we want our “big future” to be delivered with next-day shipping as well. We launch into new projects, businesses, or relationships at a grueling pace and then wonder why in two months we find ourselves exhausted on the side of the trial unable to move forward. We won’t get to our destination in a month and if we try, we will kill ourselves and those who have hitched their wagon to ours.

Oregon Trail Picture Crossing River

3) Pay the Extra Money and Get Help

In Oregon Trail you had to cross many rivers, some five feet deep, some thirty. You could plow through it with the oxen, you could float your wagon, or you could hire a guide to get you across. But the guide was $30. Yeah right. I’ll take my chances with the 10 foot rapids.

And to my dismay, my 4th grade penny-pinching would leave my wagon sinking and send Jimmy floating away, never to be seen again.

We are such an independent, I can do it myself, back-the-frick-off, generation that we cross too many deep rivers without help. Pay that creative graphic designer, web programmer, marketing consultant, or sales assistant. There are so many talented people out there who will help you float across that river. Hire them. Cross safely. Your wagon, and Jimmy, will thank you.

book image small 101 secretsMore life lessons from playing Oregon Trail AND Where in the World is Carmen Sandiego are found in the glorious book 101 Secrets For Your Twenties. Check it out or risk being stranded in the twentysomething wilderness…

What did Oregon Trail teach you above life? And/or did you resonate with any of the life lessons above? Jump into the discussion below.


  1. Abby

    Re Oregon Trail–Even with the extra meat you’ll leave behind, sometimes it’s healthy to take a break from the quest and just go hunting!

    • admin

      Abby – I like it. You would’ve been my kind of wagon leader!

  2. April

    Wow, even just seeing those old screenshots filled me with glee! Playing Oregon Trail in class might have been some of the most focused moments I’ve ever had. (Those darn sneaky squirrels.)

    I think I could benefit most from the first lesson– about planning ahead. I get so impatient sometimes, and perhaps a touch overconfident, then jump right into the middle of things. Yikes.

    • admin

      April – I spent way to long looking at Oregon Trail pictures for this post. I was enjoying it too dang much.

      Yes planning ahead has always been the crack in my wheel. But I’m slowly learning that it’s better to plan ahead to help avoid all the potholes, instead of continually buying new wheels.

  3. Katie

    Paul- thank you (again) for so eloquently writing the quandaries of our generation! I don’t think you & I would have made good Oregon trail parnters though!! I was always the conservative one – and you can also perish along the trail being too cautious!

    • Paul

      Katie thank you for the extremely kind comment. I think we would have made great OT partners. We would’ve balanced each other out to actually make it to Oregon alive. Granted, we probably would’ve fought the whole way there and our teacher would’ve given us detention, but still…

  4. Kevin Thomas

    My strategy was to name every person in my wagon, except me of course, a name of a girl I liked or liked me in school. That way, by the end, when invariably it would be down to me and one surviving girl because the others had drowned or been kidnapped by Indians (did I just make that up?), I would know who I should be with.

    I’m not sure how that applies to real life now. I do wish I had planned ahead better though, in retrospect. Coulda saved a lot of drownings potentially. Oh well, live and learn, and Lacey Mast, welcome to Oregon.

    • Paul

      Kevin, your comment is hilarious, and creepy! Mainly because I did THE EXACT SAME THING! I felt it was God’s way of picking The One for me.

      Talk about an amazing reality show.

      “This fall, watch 1 guy, 4 girls, one wagon, and one epic trip from Missouri to Oregon. Rattle snakes, wild Indians, run-ins with charging buffaloes, river rapid crossings, and the possibility of contracting some of the most deadly diseases known to human kind. Which ever of the four girls survives will be greeted at the end of the trail with a wedding ceremony and 1 million dollars.

      Forget the Bachelor. This fall come watch the first reality show that truly is, ‘til death do us part.”

      • Becky Del Ponte

        Lewis and I would watch that show all the time!!

  5. Naomi

    Very good and hliarious as usual! I LOVE LOVE LOVE reading your posts. This one brought back memories of those after school days when I’d play this game as well as Carmen San Diego, and literally would sit there until I was dragged away by the teacher or my mom. Great stuff!

  6. Morgan

    Most Applicable Lesson Learned: Ration your food (=save money)

    Remember reading other people’s tombstones? I actually did the opposite as the guys did: I would name my Leader after the boy I liked that week because you could only write on the tombstone of the leader when he died. Then the tombstone would say “I love Brian forever!!!!! He’s the cutest!” Morbid…….. or brilliant?

    • admin

      Morgan! My head says “morbid” but my heart says absolutely brilliant!! Ha!

      Rationing has never been my best skill…great lesson….

  7. Markie

    Greatest lessons: 1. If you don’t take the fairy you will drown. 2. Spend as much time in town before the trail as possible. You will have separation anxiety and plus it will take up most of the class time. So when your friends ask you if you died, you can say no (they don’t have to know how far you got).

  8. Gilda

    Epic. This just made my day. I especially liked the “ask for help” revelation……..in addition to being one of our generation, I am also a first-generation American. My family is from Mexico and so I’ve been figuring everything out kind of as I go..I get grumpy about having to ask for help sometimes, because I get a little proud, I think, and so this was a good reminder.


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