The Oregon Trail: 3 Crucial Traits of Successful Marketing Leaders

Cory Miller
Cory Miller / March 1, 2016
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Two years after Neil Armstrong became the first human to step foot on the moon and 20 years before the World Wide Web was introduced to the public, three unassuming men changed the world in their own way.

On December 3, 1971, Don Rawitsch, Bill Beinemann and Paul Dillenberger debuted their computer game, The Oregon Trail to an 8th grade history class. (P.S. you can play the original version online still.)

Maybe that’s a lot of hype for an HP 2100 computer game, but there was a time when The Oregon Trail was the single most important thing in my life. For me, it was Oregon Trail or die (of dysentery).

If you grew up sometime in the last four decades, I’d bet all of the buffalo meat I can carry (100 pounds, exactly) that you’ve hitched up a covered wagon on The Oregon Trail at least a few times.

It’s been 15 years since I last reached Oregon’s Willamette Valley, but the lessons I learned along the way still resonate today. Whether you’re a banker from Boston, a carpenter marketer from Ohio or a farmer from Illinois, how about we travel the trail one more time and see what lessons it can teach us about leading a successful marketing team.

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Good leaders ask questions and seek advice.

“You know how advice is. You only want it if it agrees with what you wanted to do anyway.” – Jon Steinbeck.

You need to learn something new every day. And the best way to learn is by asking questions.

Sure, experience is a valuable teacher, but it’s also costly and time consuming. Being a do-it-yourselfer is gutsy, but why make a mistake that could have been easily avoided?

Asking questions and heeding the advice of others is the only way to survive on the trail. It’s foolish to try going it alone. If you don’t bother to seek advice before leaving Independence, you can go ahead and start engraving headstones for your entire wagon party (Press 6!)

You’ve probably heard of the “10,000-Hour Rule.” It was an idea made popular by Malcolm Gladwell in his book, Outliers. The “10,000-Hour Rule” claims that the key to achieving world class expertise in any skill is a matter deliberately practicing the correct way for a total of 10,000 hours.

It’s an interesting idea that sold a lot of books and created an army of self-proclaimed “experts,” but it has its holes. What Gladwell didn’t account for (and what subsequent studies have pointed out) is that deliberate practice is only a predictor of success in fields that have super stable structure (tennis, chess and classical music, for example).

And like most creative fields, marketing is an amorphous discipline that has few rules of regulation. That’s part of its beauty and also the reason why “marketing experts” are dangerous. What works today has no guarantee of working tomorrow.

Good marketers (and professionals in general) know that information is a fundamental part of success. This lesson holds true in life and on the Oregon Trail. 

Should you attempt to ford the river, caulk the wagon and float it, take a ferry across or wait to see if conditions improve? I don’t know about you, but I can barely caulk a window.

It’s okay to trust your gut, but never discount advice from a valuable source. According to a study by the Harvard Business Review, once people receive advice, their most common mistake is to undervalue or dismiss it. Why? As the study points out, we're all biased, “For one thing, “egocentric bias” often clouds seekers’ vision—even when people lack expertise, they put more stock in their own opinions than in others’ views.”

It doesn’t matter if you’ve been practicing something for 10 hours or 10,000 hours, there will always be those who know more than you and those who have done something longer than you. 

Don’t be threatened by this. Regularly seek advice from your most trusted advisors when making decisions both big and small. Remember, information is power.

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Good leaders plan for plans to change.

“There is nothing so stable as change.” – Bob Dylan

Not even two days on the trail and a fire destroyed one set of clothing, one wagon axle and two wagon tongues. Why is it always the wagon tongues?

I clearly didn’t plan for this. I’ll also be the first person to call you a liar if you tell me that you routinely bought more than the recommended amount of wagon tongues.

If The Oregon Trail taught us anything, it’s that $#*! usually goes sideways and you need to adapt to survive. As actor, boxer and philosopher, Mike Tyson, famously concluded, “Everyone has a plan until they get punched in the face.”

And isn’t that the truth? Life will knock you to the canvas and Mills Lane isn’t running in to see if you’re okay. You’re on your own down there. Time to come up with plan B.

This isn’t to say you shouldn’t have a marketing plan (you absolutely should), but embrace the agile marketing methodology. Here’s how Forbes defines agile marketing, “Agile marketing drives long-term marketing strategies with short-term, customer-focused iterative projects that improve responsiveness and relevance. It allows for faster creative, more testing, smarter improvements and better results.”

So, whether a thief steals six oxen (how is that possible?) or Google drops a bombshell by releasing a new search engine algorithm, you have two choices – adjust or stay the course. 

The Oregon Trail rewards those who are willing to adjust their plan and buries those who are not (literally). Your editorial calendar might make you feel in control, but you’re not. Go ahead and use one, but make sure you keep white out and a red pen close by.

My role as leader of our marketing team doesn’t expose me to measles, cholera or typhoid, but there are minor disasters that I’m required to deal with nearly every day. On most Mondays I feel like a professional firefighter with a marketing hobby (that joke kills around the water cooler).

How we respond to these unpredictable challenges is what defines our character. Strong, confident leaders embrace uncertainty and are ready to answer the bell with decisive actions (seeking counsel when appropriate). Leaders that are too aggressive will uncompromisingly stick to their plan despite changing circumstances. Leaders that are too timid will play it safe and miss valuable opportunities.

You need to always be ready to press enter and size up the situation. Just look at the eight options The Oregon Trail gives you:
  1. Continue on the trail
  2. Check supplies
  3. Look at map
  4. Change pace
  5. Change food rations
  6. Stop to rest
  7. Attempt to trade
  8. Hunt for food
We’re all forced to make dozens of important decisions every day. You won’t always (or ever) know which buttons to press, but in simply recognizing that you have other choices besides “continuing on the trail,” you instantly become more agile.

Always have a plan, but plan for your plan to change.

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Good leaders protect their team.

“Difficulties are just things to overcome, after all.” – Earnest Shackleton

I’ve played TheOregon Trail hundreds of times, but it wasn’t until I started writing this blog post that I learned how scoring worked.

My philosophy was to go as fast as I could at all costs. “I don’t care about your exhaustion, Jeb. This wagon ain’t stopping!” I just tried to beat the game during the 35 minutes I had in the computer lab. I didn’t care how many headstones I littered the trail with.

As it turns out, this is the worst philosophy you can possibly have. Here’s how points were assigned once you made it to Willamette Valley:
  • 500 points * number of survivors – if you are in good health
  • 400 points * number of survivors – if you are in fair health
  • 300 points * number of survivors – if you are in poor health
  • 200 points * number of survivors – if you are in very poor health
  • 50 points for the wagon
  • 4 points for each ox
  • 2 points for each spare wagon part
  • 2 points for each pair of clothes
  • 1 point for each multiple of 50 bullets
  • 1 point for each 25-pound ration of food
  • 1 point for each $5 you possess in cash
What stands out to you? Sure, you might have enough ammunition to make Rambo jealous, but unless you take care of Mary, Jeb, Emily, John and all the others you’ll never make the leaderboard.

Good marketing takes a strong team but an even stronger leader.

And if you need an example of strong leadership, the story of Earnest Shackleton’s Endurance Expedition might be the best one there is.

In 1914, explorer and toughest dude on the planet, Ernest Shackleton set out on the Imperial Trans-Antarctic Expedition with the goal of being the first man to cross the Antarctic continent.

Like most things in Antarctica, the expedition went horribly sideways almost immediately. Before reaching Vahsel Bay (where Shackleton had planned to begin the 1,800-mile hellish trek to the other side of Antarctica), Shackleton’s ship, the Endurance, became trapped in an ice floe (and would eventually be crushed by the compressing ice).

The hardships that Shackleton and his 27 men endured are inconceivable. 

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Endurance in Antarctica, 1915 by Frank Hurley. Source: State Library of New South Wales, via Wikimedia Commons

They would spend the next 497 days hunkering down in the frozen ship, camping directly on the ice floe when the ship began to capsize and finally jamming into three lifeboats when the ice eventually broke apart before making landfall at Elephant Island.

With almost no food and limited supplies, Shackleton knew he needed to act quickly or everyone would die. He took five men and daringly set out on a 920-mile open sea journey to reach the nearest human settlement, a whaling station on South Georgia Island.

After 14 days of battling gale-force winds, devastating waves and frigid temperatures in a 22-foot lifeboat, Shackleton and his men reached the southern coast of the island. However, the whaling station they were attempting to reach was on the northern shore, so Shackleton led his men on a nonstop, 36-hour crossing of the treacherous and uncharted island.

On May 20, 1916, Shackleton finally reached civilization. It would then take another three months for the last member of Shackleton’s expedition to be rescued, but miraculously all 28 men survived.
You don’t need to be a heroic figure like Earnest Shackleton to be an effective leader, but you do need to keep in mind that you’re responsible for the well-being of your team.

You must observe, listen and be prepared to change course when necessary. Check in with your team. Keep tabs on projects and deadlines. Identify bottlenecks and roadblocks. Eliminate friction and promote comradery.

In routinely taking the vitals of your team, you are able to identify potential issues and take preventive action before fissures cause productivity to decline and your team to splinter.

On the trail, it's important to change your pace and food rations depending on your party's health, supplies and progress. While a grueling pace and meager rations might seem attractive, you will run your team into the ground. It's okay to sprint when a deadline looms, but make sure to slow down and catch your breath too. Remember, you can't be a leader unless people actually want to follow you.
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