The Boolean Trap

I got into my SUV and turned the ignition.

But before I threw it into reverse, I tapped a button on my smartphone.

The phone was sitting in the one of the cupholders beside me. But thanks to the magic of Bluetooth technology, it could stream music or podcasts straight through the car speakers.

I could be my own DJ. And I often was.

But not today.

The Bluetooth, you see, was not connecting properly. Sure, the little screen on the center console of my vehicle said it was connected, but no audio was streaming.

I set my sights on fixing the issue.

I toggled the Bluetooth switch on my phone’s settings off and on. I turned off the SUV and refired the ignition. I rebooted my phone.

By now, I’d wasted enough time troubleshooting that I was late for work. So, I put the vehicle in reverse and made the drive in silence.


That evening, I picked the thread up anew.

Sitting at my dining room table, I fired up my laptop, headed to the automaker’s support website and searched for help documentation.

It took a few minutes of dogged searching even to find my entertainment system on the site. The automaker had moved to a different system in newer vehicles, and most articles were for that system.

And the few support documents for my system were useless. They encouraged me to try what I’d already attempted. Plus, they site provided no way of reporting any issues that hadn’t been covered.

It felt as if the automaker was thumbing its nose at me. All the possible issues with this entertainment system are on this page. And if you find something else, you’re the issue.

I felt offended. I was enraged. I screamed into the void.


I had now wasted countless hours on this issue. I’d searched and toggled and stressed myself into oblivion — all to find a resolution to something that was working just a day earlier.

And yet, there was one thing I hadn’t attempted — resetting my car’s entertainment system.

It wasn’t for lack of trying. I’d gone through the settings menu on the console extensively. I’d combed those support documents until I had them memorized. No master reset option seemed to exist.

So, the next morning, I called the closest dealership and made a service appointment.

When I brought my SUV in, I explained the issue in full. The service tech listened intently. But he furrowed his brow when I mentioned the words console reset.

There’s not really a simple way to do that, he explained. I could unplug the battery for 10 to 15 seconds, and then reconnect it. That’s a hard reset. But I can’t guarantee it will fix the issue.

It was worth a shot. I gave the tech the go-ahead to try. He took my keys and drove the vehicle over to a service bay.

A short time later, I got the SUV back. Sitting in the dealership parking lot, I tried to connect my phone via Bluetooth. The connection went through.

My nightmare was over.


As children, we learn about prominent innovative thinkers. People whose innovations and discoveries have direct impacts on our lives.

Albert Einstein is synonymous with defining the mass-energy equivalence. Sir Isaac Newton is acclaimed for conveying the laws of gravity. Thomas Edison is renowned for inventing the light bulb. And Henry Ford is feted for revolutionizing the automobile.

George Boole doesn’t sit on this Mount Rushmore. But perhaps he should.

Boole was a 19th century English mathematician who didn’t even get to celebrate his 50th birthday. But in his short lifespan, he unfurled something that has come to underpin all corners of western society — Boolean logic.

Boolean logic is an algebraic system that contains two variables – true and false. It judges mathematical expressions by their attributes and classifies them accordingly.

If the expression contains a desired element, it gets coded as a 1. If it doesn’t, it gets coded as a 0.

That series of 1’s and 0’s can blaze a trail through complicated equations, getting to a final answer step-by-step.

If you think 1’s and 0’s sound like computer source code, you’re onto something. Computer systems have been built on Boolean logic since the 1930s, and the associated if-then logic is now synonymous with that technology.

Perhaps that’s why we don’t give George Boole his due. Or perhaps the century between his discovery and the computer age caused us to lose the thread.

Regardless, we are fully immersed in the Boolean world today. We’re accustomed to navigating true-false strings and if-then statements to troubleshoot just about anything, from our health to the strange noise coming from the refrigerator.

This works well. Until it doesn’t.


In the early 2000s, a technology journalist named Chris Anderson introduced a new theory to the world

Anderson saw how the computer age and the growth of the Internet had democratized the decisions consumers could make. In the Golden Era of network television, Americans had three options of what to watch on a given evening. But now, people around the globe could enter any search query they wanted into Google.

These searches tended to fall into a normal distribution, or a Bell Curve pattern. A small number of search terms got most of the volume.

But those low frequency searches at the ends of the curve, they mattered too. Search engines still returned results for them. And savvy businesses had ample opportunities to serve these audiences as well.

Anderson’s theory came to be known as The Long Tail. He wrote a WIRED article and a book about it. And many business professionals came to treat it with reverence.

Including me.

Early in my marketing career, I used long tail theories to create content for my clients’ websites. I was working at a startup agency at the time, supporting several small home remodeling firms.

A few years earlier, those businesses would have relied on the Yellow Pages and word of mouth referrals to stay viable. But thanks to The Long Tail and digital marketing, they now had a sustainable path to growth.

Long tail theory succeeded in filling the gaps of Boolean logic. It acknowledged that the world is messier than if-then statements can count for. And it resolved to clean up the mess.

But as technology has evolved and the economy has fluctuated, long tail theory has faded into the background. Innovators have favored tightening the Boolean engine over sweeping up the bits it misses.

This is what led to my odyssey to get my vehicle’s entertainment system fixed. There was no roadmap for me to follow because if-then logic didn’t account for the issue.

Out of sight, out of mind. Until it wasn’t.


You can’t fit a square peg into a round hole.

This proverbial wisdom has held for generations. And despite the attempts of innovators, streamliners, and futurists, it’s sure to endure for many more.

You see, ceding all infrastructure to Boolean theory is not a viable solution. It’s a trap.

Long tail concerns will not evaporate when swept under the rug. They will fester, agitate, and afflict. They will drive us to frustration, trust loss — or worse.

This corrosion has gone on far too long already. And it’s imperative that we keep the rot from settling in further.

It’s time that we give an audience to the edge cases once again. It’s time to inject independent judgement into the fringes of the logic machine. It’s time to account for all the outcomes we can imagine and consider solutions for the ones we can’t.

This process will be clunky and inefficient. It won’t provide the two true outcomes we’ve grown so accustomed to seeing in our systems.

But it will remove the daylight between our lived experience and the systems we rely on. It will allow us to optimize our outcomes at every turn.

And shouldn’t that be what matters?

Boolean logic is a great thing. But it needn’t be the only thing.

Let’s go for better.

The Heart of Morality

I just want to do the right thing.

Many of us have uttered these words after doing something unorthodox.

Staying on the straight and narrow sometimes involves deviating from routine procedures or making personal sacrifices. And this can envelop us with a sense of cognitive dissonance.

Whenever we veer off-script, a conflict emerges between the norm we’re breaking with and the result we’re seeking. Reminding ourselves that we’re doing the right thing helps reconcile that conflict.

The right thing can seem like a nebulous term. But the code it’s based upon is not.

We call that code morality.

Morality means everything to us. It’s the standard we judge others on. And it’s what we critique ourselves on as well.

But how do we derive morality? How do we distinguish between what’s appropriate and what’s unjust?

Many of us believe the answer is basic logic. We claim that tapping into widely accepted values helps us determine what to do next. And we argue that morality is simply the process of following those markers.

It’s a tidy argument. But the truth of the matter is far more complicated.


The final months of 2001 were nothing short of surreal.

America had endured the September 11th attacks. Our military had sent troops to Afghanistan to root out those responsible for the violence. Our economy was in a recession and a sense of tension was in the air.

I was in my early teens at the time, which made these events particularly jarring. In an instant, my youthful innocence was ripped away. A sobering reality took its place.

I went through all the emotions that come with trauma in those months. I oscillated between anger, fear, and sadness. But mostly, I was filled with confusion.

The terrorists who organized the September 11th attacks had committed unspeakable acts — killing 3,000 innocent Americans, toppling skyscrapers, and blasting a hole in the Pentagon. And yet, they claimed they were in the right. They blamed America for a culture of sin. And they touted the morality of their actions.

All of this made no sense to me.

How would sending operatives 5,000 miles to indiscriminately kill civilians be viewed as moral? It violated one of the Ten Commandments from the Bible. (Thou shalt not kill.) And it ran afoul of the guidance of the Quran. (You shall not take life, except by way of justice and law.)

To me, it was as if these terrorists had stacked a crime on a crime. They had done more than just violate the code of morality. They had ripped the code to shreds. This made them evil, in my mind, and thereby worthy of purging.

So, as I slogged through adolescence and early adulthood, I was filled with thoughts of vengeance. I openly cheered the killing of Osama Bin Laden. And I turned a blind eye to the torture of detainees accused of terrorism.

It all seemed so clear to me. Anyone who so blatantly disavowed the code of morality had to be eliminated. I stuck by this logic, even as it took me to darker and darker places.

But then, some new examples of misaligned morals enveloped our society. And this time, the situation was far murkier.

The killing of unarmed Black teens by law enforcement — a longstanding problem — gained widespread attention following the death of Michael Brown in 2014. Protestors took to the streets in Ferguson, Missouri in pursuit of racial justice.

Those protests grew violent, with looting and mayhem. This led to a militarized law enforcement response. Police sprayed tear gas, threw smoke bombs, and fired rubber bullets at the protesters.

In the wake of this confrontation, both sides claimed they were in the right. Supporters of law enforcement said it was their moral duty to prevent looting and assault. The protestors believed considered racial justice to be their moral quest. A calling that superseded the code of laws they might break along the way.

Neither claim to morality was fully upheld. But neither was refuted either. And in the years since then, the debate over morality has only grown fiercer. It’s become a defining marker of our societal divisions.

It’s uncomfortable living in conflict like this. So, we keep seeking to close the gap.

We search for that one bit of logic that will neutralize the other side, settling this debate once and for all. And, in the process, we keep finding nothing but futility.

Perhaps it’s time we try a new approach.


On October 6, 1965, the Los Angeles Dodgers dropped the first game of the World Series to the Minnesota Twins. Many players had a hand in the result. But one man who never saw the field seemed to grab the most attention.

Sandy Koufax — the Dodgers’ best pitcher — was supposed to take the mound in Minnesota that day. But October 6th also happened to be the date of Yom Kippur — the holiest day of the Jewish calendar — that year. Koufax, who is Jewish, refused to pitch on that day.

Many criticized Koufax for abandoning his job at such an important juncture. It seemed immoral to some.

But Koufax’s choice might actually have been the purest example of morality at work.

Baseball was Koufax’s profession. He was a steady, dominant force in a sport that meant a great deal to him. But his faith also mattered. It was as much a part of his values as baseball was.

So, when Koufax found the two halves of his identity in conflict, he listened to his heart and made his decision.

Yes, Koufax let emotion — not logic — define his morality. That gave him the clarity and conviction he needed to see his decision through.


The example Sandy Koufax set might seem extreme. But it’s far from extraordinary.

When we drop everything to be there for family or friends in need, we’re following our moral compass. And we’re often doing this at the expense of our logical one.

In a vacuum, such choices make little sense. They’re inconvenient and they pull us away from proven patterns of success.

Still, we can’t imagine not making these decisions. They clearly seem like the right thing to do.

It’s our emotions that are guiding us to go the extra mile. It’s our feelings that are helping us be there in the moments that matter. It’s our hearts that are defining our sense of morality.

Our emotions help us distinguish right from wrong. And through this process, we realize what it truly means to be human.

As such, our mandate is clear.

We must stop relying on logic alone to delineate right and wrong. We must listen to our hearts as well.

It’s our obligation to look beyond our self-interest. It’s our duty to care about each other, be good to each other and be there for each other.

So, the next time we’re faced with a tough choice, let’s resist the temptation to break out the spreadsheets. Let’s give our hearts the chance to guide the way.

The Fragility of Emotion

There have been thousands of sci-fi TV shows and movies throughout the years. But only a select few franchises have the level of popularity that Star Trek does.

Why that is remains an open-ended question.

It could be the aspirational mantra— To go where no man has gone before. It could be the fascination with all the technological flair. It could be the intrigue of the mysterious language of Klingon.

But I think the appeal of Star Trek comes from something far more fundamental — the allure of the protagonist.

The franchise primarily covers the adventures of the Starship Enterprise. The ship’s captain in the initial series — James T. Kirk — is a confident character who is not afraid to wear his emotions on his sleeve. Yet, his First Officer — Spock — is meticulously logical and comparatively emotionless.

Spock’s tendencies are biological. Spock is Vulcan on his father’s side, and Vulcans are defined by their adherence to logic. Kirk’s tendencies are also biological — as humans are often known for their bravado.

The dynamic between Kirk and Spock defines much of the narrative — both in the 1960s TV show and the 2000s reboot film series. Their interactions often demonstrate the conflict between emotion and logic.

This dramatic tension resonates. After all, logic and emotion are two core conditions of humanity. And they represent the two pillars of storytelling.

With this in mind, it’s no wonder Star Trek is so compelling. In a strange way, it’s the story of us.


Step away from the TV screen, and the view is much different.

In our everyday lives, we don’t want to explore the overlap of logic and emotion. We’d rather keep them separated.

So, we protect our emotions with vigor. We aspire to keep our mood steady. And we angrily rebuke anyone who pokes holes in our defenses.

This process takes no prisoners. Like an enraged dragon, our defenses engulf anyone who questions our decision making processes.

No one is spared when this inferno rages. Not our enemies. Not our acquaintances. And not even our loved ones.

And sometimes, entire industries feel our wrath for prodding a little too deeply. Two, in particular, get on our nerves most often — the news media and marketing.

These professions get all up in our business. They blast right through our varnished facades and expose the raw emotions within us.

We don’t like getting exposed like this. So, we brand the news media as Triggering. And we give marketers scarlet letter of Manipulative.

We sing the praises of other industries in their stead. Of professions that are more logical.

They seem like lines of work that Spock would excel in, if he wasn’t the First Officer on a famous Starship. And we aspire to be like Spock — or at least to appear to be like him.


Of course, in reality, we are not like Spock. Not even close.

Unlike half-Vulcans, we are driven by emotion. We feed off it. We rely on it.

We want to be loved, cared for and doted on. We want to experience joy, wonder and satisfaction. We want to our pulse to quicken, our heart to race, the blood to flow through our veins.

Most of all, we want to feel.

So, we lead with emotion. We let it pilot our decisions. Then we use logic to justify them.

None of this, on its face, is improper. After all, emotion is what makes us human.

Still, this approach comes with its own set of issues.

For emotion is fragile. Emotion is raw. And emotion leaves us vulnerable.

Our feelings can cloud our judgment. That means others can use them against us for nefarious purposes.

We avoid this outcome by spinning a narrative. By portraying ourselves as logic-based machines. And by rebuffing anyone who openly tries to stoke our emotions.

This is the objective we seek — this relentless homogeneity. It’s the safe play. Far safer than exposing the soft underbelly of our emotions.

But it’s also vanilla. Too vanilla for our tastes.

And that dissonance looms large.


When there’s a logjam, it’s best to cut through the clutter.

We want the stability of logic-based decision making. But we need information to feed our emotional side.

The legal and financial industries help give us what we want. They provide us the cornerstones of order and power — even as seem more detached from reality than someone hopped up on Valium.

But maligned industries like the media and marketing — they give us what we need. They call to our emotions, providing us the fodder to make choices in the manner we’re most accustomed to.

Yes, professions like these are the purest reflection of the human condition. They allow us to make profound connections. Connections that capitalize on the very fragility of emotion we so fear. Connections that build upon empathy to make the world a better place.

This is why I’ve chosen to work in both the media and marketing realms throughout my career. And it’s why it irks me to see them so callously smeared.

For there is a lot of good in these lines of work.

Indeed, unlike many “logic-based” professions, these industries are seldom zero-sum. It’s not about winners and losers, or lifting up one at the expense of another.

At their best, these industries think broader. They focus on connecting buyers and sellers, or providing knowledge to the uninformed.

These are the types of mutually-beneficial exchanges that can raise entire societies. When we have each other’s backs — when we’re focused on the same endpoint — we soar.

But we can’t get there by playing it safe. By putting distance between ourselves and those who are attempting to reach us. By deluding ourselves as to our true nature.

No, we must welcome vulnerability. We must accept the fragility of emotion. And we must recognize the potential that exists if we allow others to move us toward action.

To be sure, this is not a silver bullet. If we don’t do our due diligence, we can get badly hurt.

But it is a step in the right direction. A necessary step.

The fragility of emotion is not a bug in the human condition. It’s a feature.

Let’s get the most out of it.