The Instability Of Ambiguity

I enjoyed how psychologist Esther Perel defines today’s popular dating game as “stable ambiguity.” This definition applies to many more situations than the dating game, but I’ll start by hanging my hook on Esther’s relationship wagon.

Aloof Irreverence

Esther uses stable ambiguity to describe people who, in relationships, do not truly commit to one person and instead hop around from one to the other, sometimes in parallel. Guided by the fear of missing out, those people attempt to find “the one” by sampling, bragging about their popularity, and appearing in complete control of their destiny. On the surface, at least.

Completely suppressing any empathy and respect, those people feign their independence and, in self-adulation, celebrate their escapism combined with hide-and-seek as the ultimate free-will power you are supposed to admire. The game is; you use people until you use them up, in the words of the late and forever great Bill Withers, and move on to the next.

As I described ten years ago in the multigeneration debacle depicted by the Millionaire Matchmaker television dating show, the plethora of online dating sites, such as, promote ambiguity even more by allowing you to swipe people in and out of your life with remarkable irreverence.

Having experienced ghosting, icing, and simmering myself, many people have attempted to push me into that fray to recover. No thanks, is my response. I refuse to surf the waves of flatlining ambiguity whizzing at internet speeds. When I am ready, I will go for a connection that shall not be captured by a facial swipe in what Esther astutely calls a race to the bottom.

I have experienced too many pretty faces with shitty personalities.


Of course, the pursuit of ambiguity comes back to haunt all people involved in this popular scheme.

Except for those pretending to live in a fantasy world, the quality of a relationship is based on overcoming various struggles to calibrate and perfect the relationship. The depth, openness, and sincerity of how two unique individuals connect and relate define their relationship’s quality, renewal, and endurance.

Hordes of aloof people skimming the surface of life induced by ambiguity will not divulge who they truly are or who they could be to each other. And worse, it will turn the unpicked selection of available candidates quickly subprime.

That scenario has long been cleverly depicted in the HBO hit show “Sex in the City,” where the main characters became even more clueless about life than when they started.

Stable ambiguity is a dangerous societal predicament.

In Finance

The big downside of stable ambiguity is that it dramatically diversifies interests based on pancake economics. Wide in circumference, shallow in depth.

In finance, we know those investment strategies yield the sub-priming of investment returns and a rat race for the cascading value of an index-of-self, diametrically opposite of what the expanding fractal of humanity requires. The best of the worst soon becomes the most plausible definition of financial excellence.

As I explain in a narrated presentation, ten levels of bottom-heavy embedded diversification in asset management before spending a single dollar earns it the grandfather of ambiguity title.

In Venture Capital

Ambiguity is also practiced by venture capital investors excessively diversifying, fragmenting, and syndicating investments—a thesis of innovation arbitrage as capable of producing consistent returns as winning consistently in Las Vegas. A sector now relying on a chain of ambiguous greater-fool investors hoping not to be the last in the pump-and-dump schemes of valuations without tangible socio-economic value.

Over the last twenty years, ambiguity in venture capital has failed to produce limited partner confidence to make this private equity subclass grow in proportion to the opportunity to innovate.

The Ambiguity Plague

I see ambiguity everywhere, promulgated by social media and practiced by people incapable of challenging themselves. Without learning much, they quickly end an endeavor and jump into another, spreading their aloof inaptitude and self-inflicted insecurity like wildfire. Are you surprised suicide is at a 30-year high in the United States?

As NYU professor Jonathan Haidt explained, the behavior protected by a coddling culture of not rocking the boat of life too much sets our generation and the shallow relationships we engage in up for personal and grand-scale societal failure.

We can and must build better systems of humanity to spawn grit and determination, not a lifeless game of ambiguity, to challenge the foregone conclusions that allow us to reinvent ourselves.

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The sign of a vibrant, innovative nation is its willingness to pursue the ever-unfolding discovery of nature's truth and reinvent itself continually against those proven new normalizations upstream. Let’s inspire the world with new rigors of excellence we first and successfully apply to ourselves.

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