Life Lessons Learned from Oregon Trail

oregon trail wagon

Oregon Trail might be the finest educational piece of software ever created.

Okay, that may be a slight exaggeration, but I do remember the sheer joy of finding out we had “45 minutes of computer lab” once a week back in grade school.  Although we could play other educational games on those old computers, we always chose Oregon Trail – a game that (allegedly) taught us students about pioneer life back in the mid 1800s.

In this gem of a game you control a covered wagon starting from Independence, MO and proceed along a 2,000 mile trail to Oregon.  Throughout your journey you are faced with various catastrophes: cholera, typhoid fever, your oxen drowning, winter, and perhaps worst of all, shooting 1,000 pounds of buffalo meat but only being able to carry 200 pounds back to the wagon.  For shame.

As I sat at my computer the other day, Oregon Trail popped into my head out of the blue. Although I might not have learned much about pioneer life back in the 1800s, I did learn a boatload (cart-full?) of things about how we can improve our lives.

Feel free to listen to Old Crow Medicine Show on repeat while reading.

Playing on easy is for wusses


When you first start out in Oregon Trail, you’re given a choice between three starting characters:

  • Banker ($1600 in starting cash)
  • Carpenter ($800 in starting cash)
  • Farmer ($400 in starting cash)

Now obviously the first time you play through, you pick the Banker – he’s got the most money, can buy the most supplies, and he gives you the easiest path to success.  HOWEVER, once you figure out that you receive a bigger ending bonus for picking the tougher starting characters (3x final score multiplier if you win as a Farmer), you realize that the more difficult path can actually lead to a far stronger score at the end.

So you ask yourself, “Am I up to the challenge? Am I good enough without the extra starting money?”

Life is no different.  Some people get to start out as Bankers: they won the genetic lottery, their parents bought them everything growing up, and they never had a hard day’s work in their life.  You, on the other hand, might have had to struggle for everything in life.  You’re overweight and losing weight is a tremendous challenge for you.  You might wonder why the Bankers get to play life on easy, and you’re stuck playing on hard.

That’s life on the Oregon Trail, my friend.  But don’t worry, it all balances out in the end.  Although you’re playing on a harder difficulty, it makes the reward that much sweeter when you manage to succeed.  So yes, it might take you a few months (or years) to lose that weight and achieve the look you want, but when you get there, you’ll have such a greater appreciation than those who never went through that adversity.

Be thankful for the harder difficulty – you’ll be a better person because of it…Seriously, psychologists are now discovering that those who faced and overcame adversity are stronger versions of themselves and more able to cope during the next challenge.

Alright, Mr./Ms. Farmer, load up your wagon, grab your family, and let’s get started.

Grab your supplies and start

lego covered wagon

Once you’ve decided your profession and named your family members something inappropriate (“BOOB” and “BOOGER” were always class favorites), it’s time to fill up your wagon with the supplies you’ll need for your trip!

Now, you can spend the entire 45 minutes of your computer lab time analyzing how many wagon wheels you think you might need, how much food is the perfect amount of to bring, and if you should bring five oxen or six. Or you can realize that once you hit the trail, all of that planning goes right out the window!  So what happened? You did you could, you made an educated guess of what you thought you’d need, and then got started.

You also get to pick your starting date.  If you wait too long to leave, you’ll get stuck in the winter months and never make it to Oregon! So less thinking, more walking!  Yeah, you might run low on food earlier than expected or you break one too many wheels and you need to barter for another, but you figure it out as you go.

Are you an underpants gnome?  Whether it’s with fitness, diet, your job, or any other aspect of your life, do you overanalyze? Do you try to make everything perfect: pick the perfect plan, worry about if you’re eating too many calories or not enough, consuming too much protein or not enough fat?  Maybe you’re trying to start your own blog or book a trip, but you spend weeks getting every tiny detail right and never actually “hit the trail.”

The best plans become obsolete the second the “battle” begins.  So stop worrying about the perfect plan, just pick one and START.

Have a trail to follow

oregon trail mapImagine you’re a pioneer back in the 1840’s, and you want to go from Missouri to Oregon.

How would you get there?  Would you head west and hope for the best?  Would you put a blindfold on and hope you got there?

Simple: You have a map, with a trail to follow, and landmarks on that trail that can tell you if you’re on the right path and how close you may be.

“Okay I should hit Fort Laramie after ____ miles, and then I should hit the ______ River after another 200 miles.”

It amazes me how many people don’t bother to put together a fitness trail to follow.  “I want to lose weight” is the Oregon Trail equivalent of heading west and hoping you somehow find Oregon.


  • Where are you now?  Take a picture of yourself, and perform some basic fitness test (how many push ups or how fast you can walk/run a mile).
  • Where do you want to be in six months?  Down 30 pounds? Down 15% body fat? Doing sets of 10 pull ups? BE SPECIFIC
  • What would your landmarks be?  If you want to lose 30 pounds in 6 months, then you should be losing five pounds a month.  After a month is up, judge your performance and adjust accordingly!

The more specific you can make your map and the more frequent you can make your landmarks, the easier it’ll be for you to assess your position to course-correct!

Take care of your own

family guys

It’s a long journey to Oregon, and you’re left with three choices for how quickly you progress:

  • Hare pace (strenuous)
  • Walking pace (regular)
  • Turtle pace (slow)

The goal is not only to get to Oregon as quickly as possible, but as ALIVE as possible.  It’s no good if you arrive and both BOOB and BOOGER have died, your oxen have croaked, the wagon’s on fire.  Travel at the proper pace for you and the family so you all arrive safe and sound.  Push your oxen too much and move too quickly, and you’ll be susceptible to disease, injury, hurt oxen, broken axels, and who knows what else!

It’s not a race for you to get to the finish line in real life either.  I would MUCH rather you lose a pound a week, get slightly stronger, make a small adjustment to your diet, and build one tiny habit compared to crash dieting, starving yourself, running on a treadmill for four hours a day, and hating yourself until reach your goal.  Like with Oregon Trail, too strenuous a pace will leave you more susceptible to injury, illness, and failure.

So take your time! Build momentum. Always be taking one step forward, no matter how small.

Big Game Hunter

cute buffalo

Everybody knows the best part of Oregon Trail is hunting.

Your character (made up of like 6 pixels) would spin around in a circle and fire bullets at various amorphous blobs, only somewhat resembling animals. You had to shoot these blobs in order to bring enough food back to your family to survive.  Sure, it was fun to take aim and see if you could hit the tiny, fast-moving squirrels. However, if you wanted the most bang for your buck (literally), you’d aim at the heavy, slow moving buffalo.  They were easy to target and provided the most meat.

Efficiency for the win!  Of course, we couldn’t help but shoot 1500 pounds of meat, even though we could only carry 200 pounds back to the wagon – shame on us.

Are you a big game hunter in life?  This is one of Ramit Sethi’s favorite things to rant about: “stop saving on lattes and go for big wins!”  Tim Ferriss took this “big win” principle, the 80/20 rule, and wrote three Life Improvement Books about it!

Stop chasing squirrels and go for the buffalo:

  • Instead of freaking out over 10 calories here and there, eating reduced fat brownies, and suffering through sugar-free ice cream, go after the big wins. Cut out processed carbs from your meals, clean up your diet, and then every once in a while eat REAL brownies or ice cream.
  • Instead of forcing yourself to run on the treadmill every single day for hours, spend 30 minutes three times a week strength training and put your effort behind fixing your diet!
  • Instead of creating a complex email and productivity system, focus on getting three important things done and then go home earlier to spend time with friends and family.

Don’t sweat the small stuff and stop devoting hours to unimportant tasks. By focusing on the big wins you’ll make changes that will have the most lasting impact.

Sh** happens

broken wagon wheel

Everything that can go wrong in Oregon Trail will probably go wrong for you:

  • “BOOB died of dysentery.”
  • “Six oxen drowned in the river”
  • “Your wagon caught fire.”
  • “Your wife MRMCGIBBLETS died of exhaustion.”

No matter how much you plan, and how prepared you think you might be, you’re going to run into some sh**y situations – hell, all of your people might even die two weeks into the trip and you have to start over!  If there’s a possibility for something to go wrong, Oregon Trail will make sure it happens.

This leaves you with two options:

  • Don’t play.  Sure you won’t have any fun, but then you won’t have to worry about what could go wrong or how you could fail.
  • Play. Accept that sh** happens.  Accept that you might fail.  And have a damn fun time figuring it out how to succeed.

The choice is yours, pioneer. 

But remember: Failing is awesome

Sh** happens sometimes. You’re going to hit roadblocks on your journey to a leveled up life – a torn ACL, a sick family member, the black plague, a broken leg, getting laid off from work, or a jacked up spine. As Alfred tells Bruce Wayne, “Why do we fall Master Wayne? So that we learn to pick ourselves up.”

Here’s the truth – in life, we’re all farmers; there ARE no bankers.  We all have problems that we’re dealing with and it’s how we deal with those problems that make us who we are.

So when your wagon falls apart, fix that broken wheel, dust off your britches, and get back on the trail.

Enjoy the Journey

Oregon Trail Box

Whenever we had computer lab, it was a race to see if we could beat Oregon Trail before our 45 minutes were up.  

Sometimes I would win, but other times I would come up a few hundred miles short before having to return to math class.  Sometimes I barely made it out of Missouri.  Sure, I was bummed that I didn’t reach the end goal, but I still had a damn good 45 minutes along the way.

Life is one big multiplayer game that’s meant to be enjoyed – it’s the journey, not the destination, that makes it worth playing.

Sixty years from now when your great grandkids are playing Oregon Trail 65 on their PsWiiBox 7200’s, you can look back and say, “I lived a life worth living.  I took care of my family. I had a lot of fun. I went on this great adventure, and I was a big game hunter.”

Good luck on your Oregon Trail.

What’s YOUR favorite lesson learned from playing Oregon Trail?


TODAY’S REBEL HERO: BENJAMIN L., motorcycle racing extraordinaire!

Benjamin Racer

From Benjamin: “My personal hobby is amateur motorcycle road-racing.  Last year I set to the goal to compete with renewed vigor in the 2012 race season by training hard at my skills, but also vastly improving my conditioning.  I changed around my eating habits, joined my local crossfit gym, and watched as my concentration and stamina improved with every race weekend.

 I am proud to say that thanks to your motivation, humor, and all around awesome nerd-ness, I achieved my goal and have won the 2012 ASRA Semi Pro Amature Thunderbike Championship.  Enclosed is the picture to prove it at the Daytona Race of Champions.”

Now, I’m not going to say that Benjamin’s Nerd Fitness shirt was the reason he won…but I’m not gonna say it wasn’t the reason either 🙂

*Have a great photo of you in your Nerd Fitness battle gear? Submit it to so we can make you the next Rebel Hero!


photo source: Covered Wagon, farmer toys, lego covered wagon, broken wagon wheel, cute buffalo, oregon trail map, pioneers

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24 thoughts on “Life Lessons Learned from Oregon Trail

  1. Oh, Steve – you are truly my new hero.  I literally JUST downloaded Oregon Trail onto my iPad on Sunday and have been playing it an embarrassing amount of time this week.  This article is so perfect.  Thank you!  

  2. Another awesome article!  I was thinking about how to plan out my goals over the next year and this helps a lot.  Thanks also for sharing Benjamin’s story!  Really inspiring for me!This padawan is learning much, she is. Stay groovy, Yoda!

  3. What does Oregon Trail teach us? That everyone you’ve ever loved will die of snake bites, broken limbs, and cholera.

  4. The only time I played was in school, in the 1970s! That’s a long time ago. What I remember is having friends around me meant we could pool our knowledge. They knew the game more than I did and their insight helped me play longer.

    Same IRL.

  5. Nerdy, informative, relevant = brilliant article! I remember playing this when I was younger, although I didn’t understand much, I was kind of at the age where I’d just click and hope for the best, so being tactical wasn’t on my priority list.. From what I can remember, it was a newer version of the game, so I didn’t have to suffer from the six pixel dilemma, and I learnt that patience and attention was key in hunting game! 

    To be honest, I couldn’t agree more with you, going for the buffalo is definitely the better option, and you don’t have to know people that well before you know what choices they generally make, which is helpful in choosing the best associations you can! 

  6. Awesome article Steve! Oregon trail was one of the first games I ever played on the old Apple llE along with Super Bunny. Little did I know at 8-9 years old I was learning such valuable life lessons. Doing my first 6 week Challenge now, love your site. And my 3 year old loves your 18 month travel video. She calls it the exercise movie and wants to watch it whenever she sees me on the computer.

  7. F’ing brilliant 🙂  I used to love the green screen version we got to play on elementary school computer days, kept a 1993 Apple well into college because it had my family’s version of the game and just downloaded the iPhone app for nostalgia’s sake.  

    Way to go, pulling so many great lessons out of such a fun game!

  8. Don’t name your party members after real people!

    Seriously: If things are going badly in a developing situation, you need to step back and think, strategically and fast.  Picking that moment to wallow in your feelings is counterproductive.  Get yourself out of trouble first – there will always be time to grieve.

    “The Fellowship of the Rings” (2001)
    ARAGORN: Legolas, get them up.
    BOROMIR: Give them a moment, for pity’s sake!
    ARAGORN: By nightfall these hills will be swarming with Orcs! We must reach the woods of Lothlórien… On your feet, Sam.

  9. I used to LOVE Oregon Trail. That was back when there were barely any computer games to choose from, so I’d sit there for hours playing that one. 

    I also used to name all the family members after boys I had a crush on in elementary school, which is incredibly embarrassing now that I think of it. Should have gone with BOOB instead!Anyway, great article, and good lessons learned! 

  10. This is one of the most awesome blog posts yet on Nerdfitness Steve!

    The hardest path can be the most challenging and it really really sucks, but you come out the other end a better person, or at least you should be! Coming out of such struggle can change someone, gives people perspective on life and perhaps new goals…

  11. Fantastic post, though I do have to point out that it was Bruce Wayne’s father that said that quote. Not Alfred.

    I can’t help myself I’m a nerd >_>

  12. Hahah brilliant article. Hopefully the first of many “life lessons from old school computer games” articles. I’d like to see The Secret of Monkey Island written up…

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