Sitting on my daughter’s bedroom shelf, in a line of childhood books, many years long forgotten, is the story of Brother Bear in the book Inside Outside Upside Down.

For those not familiar with the popular line of children’s books, the Berenstain Bears are a family consisting of the burly carpenter Papa Bear, the wise Mama Bear, and their children, Brother Bear, Sister Bear, and Honey Bear.

Inside of each book is a simple life lesson taught by Mama and Papa Bear.

In the simple book, Inside Outside Upside Down, Brother Bear happens into a box that makes its way to town on a truck. The box falls off the truck in the town, the bear comes out of the box, walks back home, and proudly announces at the end of the book, “Mama! Mama! I went to town. Inside, Outside, Upside down!”

Inside of each story is a lesson.

The lesson I want to relate is something I am sure the authors, Stan and Jan Berenstain didn’t intend, but your Kickass Entrepreneur has found a wise life story for his fellow entrepreneurs looking for some inspiration.

You see, I have a theory about this book.

Inside the book, the bear happens to make his way into a box that gets put on a truck. The truck starts driving, and midway through the drive, the box happens to fall off the truck near the town. The bear “escapes” the box and walks home.

The authors don’t mention how or why the bear got into the box, but here’s my theory.

Brother Bear knew that he wanted to make his way to town, so he crafted a plan.

He knew that this particular box would be picked up by the truck driver. The bear had a goal. He wanted to make his way to town and was perhaps too lazy to walk all the way there himself. So he schemed his way into a box that he knew would drive to town.

He knew when to “fall off” the truck.

Was he successful in accomplishing his goal of making his way to town?


You see, this bear was quite smart. He had a goal and a vision. When he woke this particular sunny morning, he awoke with the goal of making his way to town. He also knew that he would have to make it look “accidental,” otherwise his mama would be upset with him.

So he made his way into a box. The box traveled to town. He knew when to fall off, and he walked home.

Adventure success.

The Bear With a Goal

This bear had a goal. He knew what he wanted. He accomplished his goal.

What is your goal?

I am sure that most of our goals are much loftier than making our way into a box and getting driven to town, but so many of us don’t even have a goal in the first place.

At least Brother Bear had a goal.

The bear knew what he wanted and went after his goal. He knew what success looked like.

What’s Your Goal?

Is business success your goal?

What does success look like anyway?

For many, owning material things like a luxury car, large beach house, Rolex watch, and fancy vacations are the definition of success.

For others, it’s all about having more money, and for some, it’s all about the health and well-being of their family.

For some, it’s all of the above.

And for some, maybe it is as simple as making your way to town, just like the bear did.

Unfortunately, many people write their goals down in a book and don’t look at it again for many years. And for some others, they have no idea where they’re going and/or what their priorities and goals are.

There’s an expression I learned when I was in high school. It’s one that has resonated with me since then. It’s an expression I think about often.

“If you don’t have a dream, you’ll never have a dream come true.”

So What Is Your Dream?

The new year often brings New Year’s resolutions, but dreams and resolutions aren’t something that you can jot down on a napkin and look at once a year.

The first step toward accomplishing your goal(s) is to have a goal in the first place.

The second and equally important step is to break each goal (dream) into smaller, more actionable steps.

If your goal is to have a million dollars next year, or to make your way to town, it’s important that you know what you’re going to do, each step of the way, that will get you closer to accomplishing the end goal. For example, what will you need to have done by the end of next month that will get you closer to having a million dollars next year?

Perhaps you need to find your box?

You Need to Start Somewhere

I speak with a new entrepreneur at least once a week. The conversation often starts with the entrepreneur asking me for some help with sales, marketing, cash flow, or some other business-related question or issue.

They’re stuck and don’t know how to grow their business, cash flow, sales… and as we dive further into the topic of helping the entrepreneur, I often ask the following questions:

– Where are you hoping for your business to be in the next one, two, and five years?
– Where are you hoping to be in the next one, two, and five years?

Many often struggle through these answers.

If you don’t have a very clearly defined goal, you’ll never know when and whether you’ve reached that goal.

As we head into 2019, use this opportunity to ask yourself whether the direction you’re headed in is really the destination you’re intended to go. Do you love what you’re doing? Do you know where you’re headed?

My Journey to Town

My life changed in 2017 when I started doing my 2017 planning. I recognized at that time that I wasn’t enjoying where I was headed and what I was doing.

I asked myself the question:

If today were the last day of my life, would I want to do what I am about to do today?

The answer was no.

As a result, in late 2017 I sold my business. (You can read more about that here.)

In early 2018 I decided that I wanted to be a best-selling author. By mid-July, my book was number one in’s business and non-fiction sections. You can read more about that here.

Each year, I have a new set of goals.

Earlier this year, after my book was number one on Amazon, I stepped back and recognized that I wasn’t thoroughly enjoying what I was doing. I had a set of goals, but I wasn’t loving life, so I took a page out of Stephen Covey’s The 7 Habits of Highly Effective People and wrote my personal vision statement. You can read more about that, and my new personal vision statement here.

So as we move into 2019, ask yourself some of the questions I noted above.

Ask yourself, how am I living?

Ask yourself those questions, and it just might be for you—like it has been for me—life-defining.

So let’s all take a message from the Berenstain’s Brother Bear: develop our plan, find our box and truck, and make our way to town.

Enjoy the journey.


Do you know the steps required to get your new business off the ground?  Read this blog post: The 5 Steps You Need to Take to Get Your Startup From Paper to Launch and Then to Infinity and Beyond

I write two blog posts a week on entrepreneurship, how to grow your business, and ultimately, create wealth. You can subscribe here.

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