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Earl R Smith II, PhD

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The initial focus of my mentoring engagements centers around the words that an individual use to describe themselves. I generally start with a detailed self-assessment. The process tells me a great deal about how a person sees themselves and the labels that they choose.

Labels Can Be Dangerous Things

One of the most frequently used labels is entrepreneur. It is used so frequently that I got to wondering if it had any stable meaning or if it had become one of those overused tags that was now almost completely meaningless. So I set about asking each person what they meant by the term.

I found that, when I drilled down to what a person actually meant by that label, the word itself had virtually no stable meaning. I’ll show you what I mean by describing several recent interactions with individuals who used the tag to describe themselves.

      Joseph Campbell

The Sole Proprietor: I was recently approached by a person who had spent almost two decades as an independent contractor. She provided advice on marketing and branding. When I asked her to describe herself, the first word she used was ‘entrepreneur’. When I asked her what that tag meant, she replied, “an entrepreneur is someone who is their own boss.” Drilling down a bit she had a few defining characteristics:

  • Heads an company
  • Is their own boss
  • Does not work for a large company
  • Is in control of their decisions

The Consultant: Another person who recently asked me for help had spent more than a decade working for a large, local company. He was laid off and had started a consulting practice and also called himself an entrepreneur. In a similar exercise, here was his list:

  • Works outside hierarchical structures
  • Provides knowledge and expertise
  • Sells his time on an hourly or retainer basis
  • Chooses who he works for and with
  • Chooses what he works on

The Perennial Founder: Several years back I worked with an individual who bragged that he had started a dozen companies. Although none of his companies grew beyond the start-up stage and only two of them ever generated significant revenue, he also saw himself as an entrepreneur.

  • An idea man
  • The one who thinks things up
  • The spark that gets things going
  • The person who sets it in motion

The Student: I am asked, on occasion, to give lectures to classes – mostly in business schools around Washington, DC and mostly before classes that are focused on one or another part of the process of founding and growing companies. During the meet-and-greet after one recent lecture, a student introduced himself, stated that he was a budding entrepreneur and could I give him some advice on the best way to arrange an exit that would maximize his wealth. When I asked him about his company, the replied, “I haven’t started it yet but you can’t start planning too early.”

  • A way to become wealthy
  • It doesn’t matter what the company does, it’s the exit that counts
  • Being an entrepreneur is the way to wealth
  • There is not particular skill required, you just have to be determined to succeed


So now, let’s turn to two definitions of the word entrepreneur. First from the dictionary:

“… a person who organizes and operates a business or businesses, taking on greater than normal financial risks in order to do so.”

The two key words in this definition are organizes and operates. In all four cases described above both were absent. There was a mostly random walk in search of sources of income int eh first three and none at all with the student. But the vision, planning and implementation that makes for effective entrepreneurial activity was missing. Operations were limited to managing each person’s time and resources. Absent was any concept of operations beyond the individual’s focus.

There was a relatively simplistic view of the world of business and entrepreneurial undertakings. There was no detail behind the initial descriptions. Even the understanding of what it meant to be an entrepreneur was lacking organization and operation.

I would add some details to the dictionary definition. Here is mine:

An entrepreneur is a person who has participated in the founding and building of a business to the point it has generated at least a hundred million dollars in annual revenue for a minimum of three years in a row.

In my view, the title entrepreneur can only be claimed based on such results. It must be earned. Calling yourself an entrepreneur when you haven’t built a business is like calling yourself tall because you habitually hang out with people shorter than four feet tall. The world ‘tall’ must mean something other than ‘by comparison as a result of selective contextualizing’.

A friend used to but it this way, “you can call yourself anything you want. Hell, we could cut off your legs, paint you blue, widen your mouth and call you a mailbox. But that won’t make you one.


My point is that a self-image – poorly constructed – can cause real damage to a person’s life experience. Think of it this way. Every person carries around a manufactured self-image – I call it an Avatar. If the Avatar is substantially different from the true self, a destructive tension develops. People can spend their entire lives trying to be the person that they unrealistically imagine themselves to be.

Word should have a core meaning. Turning them into a kind of silly putty has dangers. And that is no truer than when they are used to describe ourselves. Saying that you are this or that is not only insufficient if you are neither this or that; it does you real harm. Developing an accurate self-knowledge is the way avoid these damages.

You need that rite of passage before you can continue on
That brave self-understanding that you can lean your dreams upon.

Mentoring – good mentoring – is a journey to that ‘brave self-understanding’. It’s not a matter of ruefully accepting. It’s a journey of joyful discovery. 


And what of the four people that I described above? Every one of them made that journey. The ‘sole proprietor’ took to referring to herself as a ‘shop keeper’ and glorying in it. The consultant now introduces himself with that tag and is focused on the knowledge and experience he can bring to his clients. The ‘perennial founder’ came to the realization that it was better to find his passion and focus his energies there. As for the student, he decided to be a student until he had enough life experience to make the more mature decisions.

Life should not be about living a virtual life. That path is such a waste of precious time and energy. Life should be a journey to your true self and then a joyful exploration of the possibilities of the unique life you can lead. Life should be about discovering your true name and glorying in the discovery. Life should not be about a name you give yourself but about a name that describes who you truly are.

© Earl R. Smith II, PhD

I look back on the first three months of my work with Dr. Smith with wonder. My journal reflects a journey of self-discovery so vast that I hardly recognize the person who wrote the first entries. It's been a year now and I am happier now than I have ever been.

PJ, Mentoring Client

"It's the most amazing experience I have ever had. I needed to find a new path. A friend recommended Dr. Smith. What was most amazing was the wisdom and perception that he brought. New vistas have opened up and, as a result, a new chapter in my life. There's no way that I could put a value on what he has contributed to my life."

Mentoring Client, CEO and Serial Entrepreneur

"Chief - that's how Dr.Smith was introduced to me and, based on our work together, I have come to understand why - helped me focus on the possibilities that I had been missing in my life. He guided through developing a new vision for my life. My life is richer because of working with him."

Mentoring Client

"Earl is a wise mentor with lots of experience. He has a great way of explaining things and getting you to look at them from another perspective. Dr. Smith is a tough mentor, but, if you can learn just some of what he knows, your life will change forever."

Mentoring Client, Deloitte

“Dr. Smith is a very different kind of mentor. If you’re looking for a warm and fuzzy adviser, this is the wrong guy for you. But if you are dedicated to change and want to be challenged by a very experienced mentor Earl may be just what you are looking for.”

CEO of Croix Connect and Host of ABC Radio’s ‘Taking Care of Business’

“Dr. Smith's mentorship has been of great value and inspiration to my personal and professional development. I felt the need to take a new direction. He helped me sort out the possibilities and showed me ones that I never considered. Working with him has been a truly life-changing experience.”

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