What were you Thinking?


If I were to ask a room full of people to think of a single word to describe entrepreneurs such as Richard Branson, Henry Ford, Estee Lauder and Walt Disney I would expect to hear (from experience) the word courageous. How else can we describe someone who has betted against all odds and not just succeeded, but achieved success and financial returns way beyond most of our immediate comprehension?

Consider for a minute that if ‘courageous’ was at the good end of a continuum, in other words at the finish line, what would describe the other end, i.e. the starting line? Suggestions often include the word ‘cautious’, but for the EnQ continuum, which is an important viewpoint for placing the entrepreneurial journey into context, the opposite end of the courageous continuum can best be described as careless.
Before dismissing this suggestion, consider how easy it is to think about someone who has “dug a big financial hole” as having not taken care of something obvious. When, having lost a business, these entrepreneurs will hear a lot of questions like “What were you thinking?” and “it was surely obvious that you were losing money a long time ago, why didn’t you stop then?” There are many reasons why the “obvious” after the fact wasn’t quite so obvious before it. But the primary difference between operating as a courageous entrepreneur rather than a careless one is not their mind-set but their skill-set, which is made up of the knowledge and experience that comes with perseverance along their journey. It wasn’t what they were thinking that was the issue; it was more likely their know-how and application thereof that needed input and growth.

Take a closer look at the entrepreneurs who have succeeded and it is highly likely that you will find many situations in which they conducted themselves “carelessly” until they learned to be more conscious. Many a successful entrepreneur has started all over again because they recognized that their experiences had left them with something far more valuable than immediate and easy returns. Their experiences had left them with concrete knowledge that could be applied repeatedly to regain - and eventually outweigh - all initial losses on a consistent and quantified basis, instead of a random “lottery” basis.
There are very few, if any, formal qualifications that offer relevant and all-inclusive guidance to an entrepreneur as a vocation. We learn mostly by experience and our mindset is the same when we are at the careless end of the continuum as when we are at the courageous end. We are pioneering and we are brave and we must not change this approach or we will never set off. What changes as we progress along the continuum is our skill-set (knowledge, learning, experience and wisdom) and this we learn from the “school fees” we pay by getting things wrong. What is important to recognize is that whilst we do need to take some precautions, it is our courageous mindset that will ultimately lever us beyond what the majority consider to be safe and even possible, and are thereby limited to.
As entrepreneurs we must recognize that we have to get good at what we do very quickly but we cannot be too scared to try because others might label us as careless if we don’t succeed the first or second time around. Those same “others” will certainly label us as “courageous” when we get it right, and just for the record, because we didn’t stay down, don’t be surprised to also be labeled “lucky”.

"The paradox of courage is that a man must be a little careless of his life even in order to keep it".

Gilbert K Chesterton 

Sandy Guyer



Educational Publisher, Author, Specialist sales trainer and business coach

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