Self Sabotage

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"The World is all that is the case"
-Ludwig Wittgenstein

It’s a simple idea. We are the authors of our own dilemma. We are who we want to be. We control our own destiny. We get what we deserve. Our choices create the world that is the case. And what is the case?

Generally, the case is that what we say we want, individually and collectively, is wildly at odds with our behavior. For example, we say as a society that we want peace, freedom, prosperity, brotherhood of man, etc. We say as individuals we want to live a good, virtuous, healthy life.

But one could only conclude from our collective behavior that as a species we want to devastate the environment, we need war, famine, poverty, general human misery and an ever widening gap between rich and poor. As individuals, it would seem from our behavior – except for a statistically insignificant few – that we want to be overweight, overworked, underachieving, dysfunctional, and generally we want to spend too much time watching television.

It strikes me as singularly curious, given the easily observable facts, that so little comment is made on the obvious discrepancy between what we say we want and our behavior which in general, obviously and by any empirical analysis, undermines those stated goals. This phenomenon I observe with some irony as a pathology I call Self-Sabotage. Irony because if we adjust our framework – admit your true goal in life is to be overweight and fiscally irresponsible – then all your behavior makes sense, you have achieved your goal, you are “successful”. You are your true self, the one you want to be, the one you wish for.

It seems to me that all the empirical evidence can lead to no other conclusion. If we didn’t at some fundamental level want, or need the state we find ourselves in, actually the state we achieve, we would make different choices, individually and collectively. And it wouldn’t really be that difficult to do. At least after we reach puberty. Yet it is impossible.

Very seldom is it the case that we acknowledge – take responsibility for – the fact that we are who we want to be, what we want to be, where we want to be. When was the last time you said, “I really do want to be overweight.” Yet, there you are, painfully overweight, eating that extra cannolli.

When was the last time you said, “I have enough money.” Yet there you are, behind on the rent, while spending too much on a car, home, boat, vacation, wife and girlfriend.

Which brings us to denial, an essential ingredient of Self Sabotage. Being in total denial with respect to the extent to which deliberate choices have created your sorry situation allows one to continue the behavior unabated and unexamined. Raising the phenomenon of your own self sabotage to a conscious level is a difficult exercise. And although awareness of self sabotage is the necessary first step in dealing with it, awareness solves nothing. Your behavior will remain a formidable a problem. Consciousness of self-sabotage is in fact a very deep subject, full of complications and for a later discussion.


What has come to my attention, through years of empirical observation, in a career that has covered corporate, criminal and entertainment law is that the phenomenon of Self Sabotage is ubiquitous in  all walks of life. I could write a book about how it manifests itself in each of these areas.  What follows will be specifically focused on how the phenomenon of self sabotage controls the fate of a huge percentage of commercial endeavors. This phenomenon invariably includes an individual I call a Self Sabotage Master who, along with complicity and emulation from partners and subordinates controls the fate of the venture. And in the business world, the phenomenon of Self Sabotage follows an almost unwavering and strict pattern of empirically observable behavior. This behavior invariably turns up in all but a small percentage of ventures – those that are successful.

So this essay is first of all an observation of behavior which seems to repeat itself in almost every entrepreneurial venture. These observations will be useful to the investor attempting to determine the wisdom of funding a venture.  For the investor, I am noting the flags that all but guarantee he is going to lose all of his money in an entrepreneurial train wreck.  This would certainly be contrary to investor’s goal – unless of course the investor’s own self sabotage compels him to be involved in a funding disaster.

Ironically, these observations will also be useful to someone who is deeply into self-sabotage but hasn’t yet mastered all of the tricks.

Is there a possibility that by recording all of the facts, there might by a way to “cure” the dysfunctional self-saboteur and change the behavior so that it is consistent with achieving the stated goals?  Is it possible some solutions might suggest themselves?  Unlikely.   Being brutally honest with entrepreneurs about the incontrovertible evidence of their self sabotage will most likely get one fired, or at the least eased out of the line of site which, on some levels raises the question of your own self sabotage.

Nevertheless, once the flags start turning up, the behavior of the SS master and the fate of the venture become predictable with about a 95% degree of accuracy.  Unless you hate money, it is time to grab your wallet and run.