What Playing Oregon Trail Taught Me About Building a Successful Brand

by | Branding

Benu Creative Branding And Marketing What Oregon Trail Taught Us About Building A Successful Brand

I’ll never forget sitting in class with eager anticipation in front of a small jet black screen as my teacher booted up the MS-Dos. 

Ah, those were the days! 

I waited patiently as bright green letters filled the black screen, and then….

…That synthesized country tune began to play, filling my heart with joy, letting me know my epic journey was about to begin. I was about to set out on The Oregon Trail

Years later I sat in front of a much bigger screen — absent the synth music — as I registered my business with the Oregon Secretary of State. A new journey had begun.

Along the way I discovered that running a business is a lot likeThe Oregon Trail — 

Sometimes you’re on top of the world, looking out upon a great expanse of possibilities, and sometimes you feel like you’re about to die of dysentery. 

In business, like The Oregon Trail, there are triumphs and wonderful things to experience, but there are also dangers and setbacks.

When you begin the game, you’re asked to choose your occupation, choose your supplies, and then there is one last choice to make…

when will you choose to set out on your journey. 

Many people believe the key to their success or failure is dependent on their circumstances or their resources, but this is not the case at all. 

It isn’t how many resources you have, but how resourceful you can be.

One of the most important components of resourcefulness is good planning. 

Looking back on my experience playing The Oregon Trail, this choice has always stuck out to me. It is one of the most important decisions one can ever make, and perhaps the greatest indication of success or failure.


In the game you are given this warning:

Set out too early and you’ll run out of grass for the oxen,

Set out too late and you’ll be trapped by the snow in the mountains,

But if you plan resourcefully you’ll likely make it to the end. 

In business:

If you market without a brand your message will leave your customers confused, your team directionless, and both will likely abandon you. 

If you strive for perfection you’ll be left spinning your wheels and you’ll be overtaken by your competition. 

But life doesn’t give the same upfront warning. Instead, we must look for signs to discern if we’ve made a wrong choice. 

Symptoms of not knowing your brand.

It’s not hard to identify when your business doesn’t have a strong brand. 

Unfortunately, many businesses see the symptoms, but don’t see the root cause. Instead, they react, attacking the symptoms, never truly remedying the core issue, and so problems prevail. 

There are some common symptoms of not knowing your brand:

  •  Fog around making business decisions
  •  Marketing strategies aren’t working 
  •  Poor audience reception
  •  Sales stagnate or don’t grow

If you’ve found yourself stuck it may be time to reexamine how you started. 

Eager to start, did you jump right in, and now you’re lost? 

Are you trying too hard to get your product or service just right so you can crush the competition, yet find you’re not really moving or gaining any traction?

Beginning too early

When I was in High School I was a short-distance runner.

One day I tried out for long-distance; I thought having a huge lead would give me the same advantage.

So when the gun fired I took off as fast as I could out of the gate. I left everyone behind, at least at first, but when I got about midway around the track I ran out of steam, and slowly, every… single… runner passed me.

Lesson learned!

Many people get excited about their business and want to jump right into the market, but this is a terrible idea.  

This is exactly why we advise business owners and entrepreneurs not to jump right into marketing without first understanding their brand

Marketing isn’t your message, Branding is your message.

Starting too early is often motivated by fear — the fear that one needs to get to market first to gain such a head start that the competition will never be able to catch up.

Believe it or not, the opposite is true. Taking the necessary time to establish your brand will give you a huge advantage. 

In fact, companies second to market were more successful than those who came before them in 35 out of 55 product categories.

Having what’s called the Second Mover Advantage allows one to see the pitfalls of other businesses and make resourceful branding decisions that can give them a huge strategic advantage.

You might have even heard of one of these brands — a little company called Apple. 

Beginning too late

Some business owners find that it’s not so much trying to get a head start on the competition that is their struggle, but instead it’s trying too hard to perfect their product or service. 

This is also fear-based motivation because they fear that if their product or service isn’t supremely better they can’t compete. 

When we asked entrepreneurs what fears held them back the most this ranked near the top. 

The truth is that companies with inferior products and services win over their competitors all the time because they have a clearer message and are able to convey that message more effectively.

What to do instead?

When setting out on a voyage you need to chart a course, otherwise, you’ll get lost.

If one does not know to which port one is sailing, no wind is favorable. – Seneca

If you wouldn’t start a recipe without checking the pantry to ensure you have all the ingredients, then why would you start marketing without the proper ingredients of a strong brand? 

If you take the time to create a strong brand presence you’ll build loyalty and trust with your audience and your people. 

Brand is your message — it’s what drives your company, it’s what you believe, why you serve, and how you communicate. 

Brand is your reputation — it’s how your customers feel about you, it’s how your team feels about you, and it’s the driving force behind whether or not they want to be a part of your movement. 

A good brand begins by knowing your mission and values. 

You can’t be successful externally without being successful internally.

Remember your brand touches every piece of your business so just as having loyal customers is important, building loyalty and trust with your team will not only ensure they don’t smear your name after hours, but they will be motivated to advance your business forward. 

I can’t tell you how many times I’ve heard an employee bad mouth the company they work for. This is terrible marketing for that company because essentially the employee has smeared their reputation and damaged their brand image. 


Setting out to market without a brand will leave you without a message to sustain you — your team will have no direction and your audience will have no idea what you’re about. 

Waiting until every piece of your business is perfect will leave you with nothing to offer and your competition will overtake you. It’s better to have an imperfect product/service with a clear brand message than have a perfect product/service with no clear way to communicate it. 

Taking the time to establish a clear brand identity will gain you the loyalty and trust of your team and your audience. 

Take a lesson from The Oregon Trail, if you plan your business just right, while you’ll still come across issues and setbacks along the way, you’ll develop a brand that’s strong enough to face them.


Feeling like you got off to the wrong start or just feeling stuck? 

I’d Like to Hear from You

Gabriel Shields Benu CreativeWhich camp do you fall into: Starting too early or Trying to perfect things first? I’d love to hear what you have to share so leave me comment below and let’s chat.


Key Takeaways





















































































Master Your Brand Workbook


master your brand workbook with plant upright

checkmark Better understand your true customer

checkmark Discover what they truly want

checkmark Demonstrate clear value

checkmark Learn what drives buying behavior

checkmark Build connections with your outreach