We've probably all had that one friend from high school or college. The one who talked the big talk. The one who always tried to get a hustle on everyone. The one — who when we were young and impressionable (or perhaps just more impressionable than we are today) inspired us with the way they carried themselves and carried out their business.

I mean, the way they even talked back to the teacher — we knew they were going to be something after school.

And then, years later, we find out via Facebook or some other type of social network that keeps us at a familial distance to acquaintances of our past life we see that they actually didn't amount to what we thought. Not to say they didn't end up successful, but that they didn't strike out on their own and enterprise some entrepreneurial endeavor. They got that quiet office job donning a title that makes them seem important enough.

Then of course there's the other friend from high school or college that pulled off a total one-eighty. They were considered by most at the school to be an "eff up." They never did their homework, they were constantly in detention, and they barely graduated. Against all the odds, however, when you look them up on the web, you see that not only have they made something of themselves — but they've drastically blown you away.

The individual from my telling of this story goes by the name, Greg. I had a chance to catch up with Greg recently (after almost twenty years) and was fascinated by his journey. Greg barely graduated high school, and in 2012 started cleaning office buildings to make a living. He kept grinding and turned his solo venture into a business that cleans commercial offices across the Midwest with offices in Chicago, Detroit, Minneapolis, and Milwaukee.

During our catch-up, I wanted to know how he was able to defy the odds. We talked a lot about mindset and the mindset of a street smart individual. What you'll find below are questions that will help you identify if you or someone you're dealing with is faux street smart or not…

First off, what do we mean by street smart?

Because in today's world, it can take a few different definitions. Our world and economy are changing at a rapid pace. A 2017 study conducted by McKinsey predicts that by 2030, anywhere from 400 to 800 million jobs worldwide are going to be replaced due to automation. The bulk of these replaced jobs are going to be repetitive in nature.

Plain and simple — machines are capable of performing remedial tasks way better than humans.

The study goes further, however, to note the demand for creative jobs as we head forward into the future. The ability to optimize, utilize, and enterprise human creativity is going to drive our economy and species forward.

So, the plainest definition I'll give us with respect to this article is this,

Street smart: The ability to be creative, innovative, think "outside the box", and provide value — rather than follow instructions.

Now, that we've got that out of the way, let's return to our friend Greg and pick his brain on how he has been able to utilize and develop his beautiful street smart mindset. To uncover the answers, we're going to label some different philosophical questions and then provide answers: one leaning towards being street smart, and the other more towards a repetitive, routine-driven output.

Question One: "Who holds your future?"

This question dives into the psychological concept of locus of control. Locus of control refers to how strongly people believe they have control over the situations and experiences that affect their lives. In education, locus of control typically refers to how students perceive the causes of their academic success or failure in school.

In an economic sense, it questions how you're going to going to make a living:

• Is the control of your future in your hands?
• Or is it in the control of your employer?

Greg had it hard after high school. Not that many people wanted to hire a deadbeat (his words). Many of us have been given the, "you have to get good grades, join these clubs, and partake in these extracurriculars to get in that school that will help leverage attaining those jobs."

But when you're like Greg, or at least you make decisions akin to Greg, it's not so easy. In Greg's mind — his entire future was entirely in his hands. If he was going to end up face down in a gutter somewhere, it was because of his doing. Conversely, if he were to actually make something for himself (like he ended up doing), it would be on him.

Of course with perhaps a sprinkling of luck as well.

Question Two: "How do you make money?"

Seems it seems pretty simple right? For most people, they answer,

"I make money by getting a job and getting paid [hopefully] a salary."

I have "hopefully" in brackets because many people in the workforce have to settle for an hourly wage.

And I have "settle" italicized because. Well, never mind… If we dive further into the nature of the question, we can find a more important distinction worth uncovering. When thinking about making money are you making it through a salary or hourly wage (i.e. trading your time for money) or are you making money through the value you create (i.e. sell the benefit for what you create)?

Our friend Greg, being a street smart as the rest of them, has not only been able to make money via the value he's created — but he's also been able to multiply his benefit-selling efforts by expanding on his reach and maximizing his capital.

Greg understands that there's a need for business owners to keep organized, fresh, tidy office spaces. He provides value to their business owners and exceeded his time constraint (performing a role in exchange for income) by investing in a bigger team. While he isn't reinventing the wheel by cleaning office spaces, he used his creativity and "out of the box" thinking to offer a better service compared to his competition.

Question Three: "How do you solve problems?"

The modern school system is an amazing and innovative institution.

If you're a young individual being groomed for factory work in the 1940s…

Hyperbole aside — there are pitfalls and clear and present failings plaguing the American public school system. One that stands out in favor of our case is the insistence to train people to perform a task rather than foster ingenuity and industriousness. The American school system is a breeding ground for drones. As the world matures into a creativity-driven economy, that's the last thing we need.

There are two ways we can traditionally answer this question:

• "I wait for instruction and follow the guidelines to solve a problem."
• "I decide for myself and proceed how I think the problem should best be solved."

Now, if you've been following along — you can probably identify which answer would most correspond with being street smart and our paisan, Greg.

Our world is beset with problems — many of which can and should be addressed through creativity and entrepreneurialism. Of course, we can do what is often done and wait for instruction from some authority or, we can roll up our sleeves and get to work — doing it our way.

Question Four: "If you need to increase your income — what do you do?"

This is an important consideration for all of us. As the years go by — housing prices will rise, inflation will kick in at a quicker rate, and we'll find ourselves wanting to consume more because, well — we're human. All of these factors will help contribute to our need to make more money.

How will we go about doing that?

One way of answering this question is, "Well, I'll work harder. I'll put in more hours. When my boss finally sees what I'm contributing, I'll ultimately get a raise."

Another way is, "I'll work smarter. I can take these skills and abilities and market them to an audience or customer base. I'll monetize these skills via a side-hustle. I'll leverage that side hustle into perhaps adding an extra 20% in income. Hell — maybe I'll even make enough to out-earn my current job!"

Now, before you tell me the second response isn't that simple, I know. I'm with you. But again, we're talking about mindset.

If we dig a little deeper, we can see two different mindsets coming out of these responses. A mindset of working harder and a mindset of working smarter, respectively.

The world is changing and it's changing at a rapid pace.

It's funny — I like to think sometimes about the progression of technology over the decades. Being born in 1989 I think about how much the world changed from 1990 to 2000. I think then about how much it changed from 2000 to 2010 and finally from 2010 to 2020.

When I look back — 2000 and 2010 don't seem too different. When I think about the next ten years, I'm blown away by what technology has changed.

It makes me think very hard about the aforementioned McKinsey article that was cited in this article. 2030 is only nine years away. How different is this world going to look a decade from now?

While he didn't change the world like the Zuck's or the Elon's of the world — I look at Greg and think about how he was able to turn his life (and the life of his family around). I think about how he was able to defy the odds of what everyone thought he would amount to a mere decade and a half ago.

I think about his street smarts. I think about his creativity and entrepreneurial spirit.

Even though the world will change — it'll never be able to take that away from him. The same goes for you and me.