Oregon Trail Lessons and Parents as Allies

“Class, put your books away. It’s time to play Oregon Trail.” “Everybody partner up and jump on a computer. It’s time for Where in the World Is Carmen Sandiego?”

Were there sweeter elementary-school sentences? The promise of Oregon Trail or Carmen Sandiego would fill my little body with waves of excitement like I’d just caught the winning touchdown at recess while simultaneously downing ten Pixy Stix.

Have you ever played? If not, I’m sure it exists online somewhere. Who knows, by the time you’re reading this maybe kids are playing this in class wearing AI glasses that place them on a dusty trail next to a covered wagon and they will actually feel the sting of that rattlesnake bite.

For me, the journey from Missouri to Oregon or jet-setting around the globe huddled around that gray Apple computer was a glorious one.

But as I look back, what did we really learn from playing these games? Were avoiding dysentery and knowing our limitations on how much buffalo we should shoot really necessary life lessons? Or did these games teach us something more? Maybe we learned complex and profound truths about how to be successful in our 20s that we can still benefit from today.

Sound crazy? I say nay.

SEVEN LIFE-CHANGING LESSONS OREGON TRAIL AND CARMEN SANDIEGO BESTOWED UPON US

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 trail so I can start shooting squirrels.

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 a 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) If on every crazy, confusing trip you can figure out just one piece of the puzzle, you’re making substantial progress.

Do you remember the clues you’d get playing Carmen Sandiego? Yeah, I don’t either. I couldn’t even decipher the words in the clue, let alone figure out what the clue was trying to show me. Either Carmen Sandiego was made for future Harvard grads or I wasn’t the sharpest sleuth in the agency. Probably a little of column A, little of column B.

Life in our 20s can feel the exact same way, can’t it? You know you’re getting all kinds of clues about where you should be going, but for some reason they just don’t make sense.

But if we keep our eyes open. Pay attention. Keep playing the game. At some point the clues will point us where we need to go.

3) 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 trail.

4) Sometimes you just have to keep going to figure out where in the world you’re headed.

Playing Carmen Sandiego was about learning how to take educated guesses. Finding that sweet spot where you were about 60–75 percent sure and just clicking “Go.” There was only one guaranteed way to find Carmen Sandiego.

Never stop looking.

There’s not too many “sure things” in our 20s. Sometimes we just need to find our “75 Percent Sure” and just go for it.

5) 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, stand-back-I’m-coming-through 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.

6) Carmen Sandiego was a beautiful enigma, and while she always seemed so close, she had an amazing ability to stay just out of reach.

7) If you’re going on a wild adventure there’s going to be proverbial casualties. No matter how much you prepare.

We all named people in our wagon for those we had crushes on. That way when, God forbid, a rattlesnake bite turned for the worse or dysentery ran its course, we’d know who we were supposed to be with by who was left at the end of the trail.

Life in our 20s is a wild, crazy, adventure, and even those people who you swore you’d be with at the end … come Wyoming some of those relationships might become casualties.

As kids, many of us saw our parents as completely perfect. The Mystique and Magic of Mom and Dad could do no wrong. As teenagers, many of us saw our parents as completely imperfect. The Disappointment and Disenchantment of Dad and Mom could do nothing right. As adults, we begin to see Mom and Dad not as perfect or imperfect, but as people—with their own dreams, fears, insecurities, flaws, and strengths. In our 20s we begin to know Mom and Dad for who they really are—one adult to another. Yes, living at home maybe there were times when things got a tad rocky. But when you’re all crammed in one boat and the waves start crashing in, things are bound to get a little tense. Now that you’re learning to sail your own ship, the last thing your parents want to see you do is drown. No matter the wars you might have waged in the past, your parents are your Always-Ally.