Feb 102016

Earl R. Smith II, PhD

My work as a mentor always starts with the life that a person is living. That’s one of the things that sets me apart from most mentors and coaches. I don’t have a packaged process. There is no twelve step path to follow. In the beginning there is a feeling of dissatisfaction on the part of the person who comes to me – a feeling that they are not living the life they were meant to. Many times the cause centers around decisions that were made in high school of undergraduate college. One of the most common is a decision to become an entrepreneur.

I earned a Master degree from the Sloan School at MIT. Much of my work put me in contact with engineers. It was an exhilarating experience. There was a saying among the students, particularly the ones who came to MIT for engineering but discovered that it wasn’t for them. “A week ago I couldn’t spell engineer, now I R one.”

Experience is as helpful in discovering what you should not be doing as much as it is for discovering what you should be doing. But sometimes experience is ignored and the person makes the same mistake over and over. A life’s journey is one of discovery that should result in self-understanding. . The great Scottish song writer and singer, Dougie MacLean in a song titled “Rite of Passage” makes the point.

“Oh you need that rite of passage
Before you can continue on
That brave self understanding
You can lean your dreams upon
You may want for children
You may crave for man and wife
But you need that rite of passage
To the summer of your life”

In mentoring terms, the gateway to the “summer of your life” is the first step on the path you were meant to travel. Whether it is termed your calling, becoming what you were meant to become or simply finding your way, that first step shears away the chaos and uncertainty that is the burden you have been carrying.

Finding the “right path” means that a person has been traveling the wrong one. But how did this come about? Why the wrong one? Traditional societies knew the answer to these questions. That is why they had initiation rites – rites of passage. The meaning of being born again was exactly that – a second birth, this time as an adult member of a society – one who casts aside the visions that parents and peers gave them and finds and follows their own path.

Working with entrepreneurs is particularly challenging as the vision for their life is often centered on a general model – that of the entrepreneur. Most people who so aspire make the decision to follow that path long before they understand what it means to be an entrepreneur. Some have been pursuing the dream since high school. Maybe their father gave them the idea. Maybe a teacher contributed. But the net result is that they are on a path that increasingly feels wrong. Here is a brief description of a mentoring engagement that might help you understand what I am getting at.


Nothing is truly new under the sun and that applies to entrepreneurs as well as any others. They make the same mistakes as their predecessors. That doesn’t make them wrong or inept – just human.


I was asked to work with a young CEO by one of the angel investors in a particular company. The company was growing but revenues had started to flatten. My friend asked me to get involved because he was coming to suspect that the CEO was not meant to be an entrepreneur. My first session with Fred was a get-acquainted one. It was the second session that began to show the nature of the challenge that he was facing. We focused on governance and the increasing pressure the board was putting on him.

“I know what they are looking to me for but I just don’t seem to be able to deliver on it. Life was so much simpler when we were just five friends pursuing a dream.” That statement told me a lot about what and where the problem was. It was between the CEO’s ears and in his heart. It was an indication that the path he was following was increasingly alien to who he was and was meant to be.

As we worked together, it became obvious that Fred was experiencing the real implications of decisions he had made years back. “I always wanted to be an entrepreneur.” But it was also clear that his vision of the range of options before him was provincially narrow. First an entrepreneur and then decide what kind of company to build was his formulation. I decided to focus our work on an area more fundamental – prior to – his decision to become an entrepreneur.

Unintended ConsequencesIn any logical structure, there are key assumptions that, if overturned, will result in the total disintegration of that logical structure. In philosophical terminology, these are ‘synthetic judgments a priori’. The point is that these assumptions are taken as given without question. Examples might be ‘god exists’. ‘I am alive’ or ‘today is the day after yesterday’. However, if these assumptions are proven false, the entire structure that has been built upon them crumbles and falls.

Synthetic judgments a priori are an essential part of philosophy but they are an insidious component of any life vision. Unwarranted assumptions cause more distress than any other causes. It does not have to be that way and only is because individuals avoid the hard questioning of the founding assumptions that have lead them to start down a path.

So, let’s take a short diversion and visit a friend of mine who is an entrepreneur and on the right path for him. He carries a card in his wallet with the following guidance on it:

1. Question everything
2. Particularly the most important assumptions
3. Accept nothing as true
4. Unless you have drilled down to bedrock
5. Blind faith is religion
6. Intelligence is validating and debunking
7. Debunking is as important as validating
8. Fools accept – authenticity validates

I have watched him take it out during strategic planning sessions that I was facilitating for his company – and I smiled because I knew what he was reading and why. Mostly this took place when I was unmercifully attacking one of the ‘sacred cows’ that his team had enshrined as a ‘given’ in their thinking about the company, its value proposition and importance in the general scheme.

These conversations are usually difficult. Most team members – and certainly the CEO/Founder do not like to have the founding assumptions of their dream of success and wealth creation questioned. If they engage in validation at all it usually focuses on the less important assumptions like financing, customer satisfaction or the appropriate distribution model. I do not mean to imply that these are unimportant issues. However, if the core assumptions are not aggressively tested and adjusted, the result will be a highly inefficient structure that will have a sharply diminished chance of success.

Picture 039Now back to Fred. One of the best ways to avoid the proverbial ‘kamikaze raid on a vacant lot’ is to work with a very experienced mentor. I regularly engage with people like Fred and often the results have been stunning. It is amazing how easily someone with two or three decades of experience can see through to the core of problem and identify the ‘of course’ – the ‘synthetic judgment a priori’ that lies at its center. This is the center of our initial work together. “You are on the wrong path. You need to go back to the foundations of your self image and question every one of them.”

The first meetings were an explosive occasions. I handed Fred a copy of the card my friend used. The initial response was predictable. Fred spent a lot of time and energy defending his assumptions against an experienced and focused onslaught. His self-image was at stake. If he admitted that I was right the implication was avoidably that he was wrong – at least in his mind. That was, of course, not the case. It took a lot of hard work to get past that wall.

Eventually the truth began to sink in. We were focusing on Fred’s life – a limited commodity with a roughly defined shelf life. The atmosphere in our sessions began to change when he began to accept that he was in danger of living his life without ever discovering what he should be doing with it or who he really was. He might die without knowing who he really was.

It took almost two years of hard work to sort it out but Fred stayed with it. He discovered that he had been diving into complex situations because he felt that the more challenging his life was the more authentically he was living it. Sans family, he was wandering from challenge to challenge and feeling more and more adrift as the years advanced.

And how does this story end? Well, Fred decided to stop self-sabotaging and find those things that he really loved to do – the things that warmed his soul and brought a smile to his face. He’s a CEO of sorts now. He and his island wife run a boat charter service in the Caribbean. Gone are the nightmarish fantasies of changing the world and building an empire. He world now centers around a dozen boats, regular clients who return year after year and a lifestyle that adds rather than subtracts years to his life. Oh yes, and my angel investor friend is one of his most regular clients! He and I had drinks a while back. He refers to Fred as “that luck bastard”!

© Earl R. Smith II, PhD


I provide mentoring to those who have both the courage and determination to make a truly transformational journey. My approach is heavily influenced by core principles of Zen Buddhism. I don’t offer quick fixes or follow the latest fads. If you are willing to make the long journey – if it’s time for you to come to know the person you really are and the path you should be following – if you want to start living life you were truly meant to live – then perhaps we should talk. Send me an e-mail and we can arrange a time to chat.

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