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.

Learning Experiences

It was a simple dish.

Eggs, sliced potatoes, and onions – all bonded together and cooked in a skillet. Kind of like a quiche without the cheese.

The delicacy was known as Tortilla Española. I’d sampled it at restaurants across Madrid as a teenager. Now, as an adult, I wanted to prepare it in my own kitchen.

I recalled my father making the dish from scratch a few times after my return from Spain. So, I asked him for the recipe. Then I gathered the requisite and ingredients.

I peeled the potatoes and cut them proportionally. I diced the onions. I scrambled some eggs in a bowl.

I added olive oil to a cast iron skillet and fired up the stove. I poured the ingredients into the skillet and let them settle.

I took another glance at my father’s recipe. The next task was to flip the tortilla over, so that it could cook evenly.

But how?

I had a glass lid on the skillet, but it wasn’t stable enough to stand on its own while inverted. And I didn’t have a similar-sized pan to flip the tortilla.

The sizzling sound from the skillet reminded me that there was no time to run to the store for supplies. I was going to have to do this the old-fashioned way.

I took the silicone spatula and dug into the bottom of the tortilla. I lifted it up, rotated my wrist…and caused a mess all over the stovetop.

Perhaps the tortilla wasn’t quite set enough. Perhaps my wrist flick wasn’t all that precise.

Regardless, the solid disk had disintegrated into an incongruous pile of egg and potato bits, with some onions mixed in. Most of it was still in the skillet, but some had landed around it.

My dish was ruined.

I did my best to salvage what was left – letting the eggs cook through and then consuming some of it. The rest went into Pyrex containers stashed in the refrigerator.

I’d be having my failure for dinner for nights to come.


Not long after, I told my father what happened.

Did you consider flipping the tortilla onto a plate? he asked.

I hadn’t.

I’d made a multi-meal mess and wasted hours of prep work. All because I didn’t pull a plate out from the cabinet during the moment of truth.

I was filled with regret at first. But then I remembered another of my father’s axioms.

You can make a mistake. Just don’t make the same one twice.

This was not a failure. It was a learning experience.

It was on me to grow from the experience. To do better next time around.

As it turns out, next time looked a bit different. I never did make Tortilla Española in my kitchen again. But my cooking habits for similarly complex dishes were vastly improved

No longer was I blinded by the mouth-watering outcomes of my craft. I instead devoted extra effort to preparation.

That way, I wouldn’t panic when the burners were on. And I’d be better able to adapt.

I don’t believe I would have been able to lean into that approach if everything hadn’t happened the way it did.

The botched flip. The meals upon meals of messed up results. My father’s introduction of a ready alternative. All helped me to internalize the lesson and rise from the ashes of disaster.

The story still has its scars. I cringed a bit while writing it just now.

But I have no regrets.


What is school for?

Marketing guru asked this question at the onset of a TEDx talk some years back.

Godin went on to explain how the modern iteration of American education came about.

Public school districts and standardized tests were not the natural evolutions of one-room classrooms and reclusive boarding academies. They were the vehicles of industrialist ambition, meant to confer obedience and consistency across the youth population.

The modern system of schooling seemed sensible in the early 20th century, when scores of pupils parlayed their diplomas into factory jobs. It also served its purpose in the middle of that century, when vigilance in the face of nuclear war was paramount.

But obedience and consistency seem antiquated these days, in an era where college dropouts can create trillion-dollar companies and financial strategists tend to think outside the box.

Yet, the top-down, cookie-cutter educational experience continues to proliferate. Children are expected to maintain excellence from as early as Kindergarten. There is no other option.

It’s all a bit difficult for me to comprehend.

You see, my own youth is merely decades in the rearview. But it might as well have been in the Stone Age compared to the present reality.

My teachers gave me a fair amount of free reign in the classroom and the recess yard through elementary school. I was supervised, sure – even graded on homework I turned in. But I wasn’t restrained.

The goal was to let me stumble upon knowledge organically, and therefore absorb it fully. This meant literal stumbles were accepted, not shunned.

So, I made mistakes. Lots of mistakes. Both in the classroom and out of it.

But by feeling the consequences of these missteps, I was able to move beyond them. I was able to learn, grow, and adapt. And I was able to keep the sting of regret holding me back.

It’s a throughline that carried directly to adulthood. It drove my response to the Great Tortilla Española Disaster in my kitchen, and countless other setbacks.

And it’s becoming a novelty.


What happens when the leash is too short?

We don’t need to imagine the answer. Examples are all around us.

Many of my peers now have children of their own. And in talking with them, I get a distinct sense that they’re under a microscope.

They’re expected to provide the best experience for their kids at all times – or else risk the branding of bad parent. And they’re expected to short circuit any signs of failure in their offspring.

Failure, you see, represents divergence. It puts daylight between a child and their peers. It forges a gap between expected marks and mandated ones when it comes to reading, arithmetic, and reasoning. It’s the first skid down a slippery slope.

Modern parents don’t intuitively believe this, of course. None of them hold their infants and muse They better not screw anything up in 65 months from now, or they’re toast.

No, this edict is foisted upon parents by their children’s schools, which are chock full of militant rigor and ongoing assessment.

Add in the societal pressure to bring these values home, and parents find themselves in an impossible position. It’s as if they’re meant to choreograph their children’s lives, rather than provide sturdy guardrails for growth.

This might all seem mundane. But the long-term effects could be catastrophic.

Indeed, what happens if an entire generation is shielded from the consequences of failure? How will they develop resilience?

I shudder to think about how the next generation might handle a kitchen mishap down the road – let alone anything more substantial.

Adversity is a great teacher. It’s the only real instructor for moments like these. Moments that we will inevitably encounter in our lifetimes.

And yet, adversity is being kept out of reach. Left on the top shelf of the cabinet until it’s too late for us to locate it.

Let’s change that.

Let’s stop being so allergic to failure and shackled by regret. Let’s start reframing our missteps as learning experiences instead. And let’s teach future generations to do the same.

Sometimes wrong is the first step to right. Commit to the journey.

Consolidated Options

It was darn near Pavlovian.

As the players jogged off the field and into the dugout, the fans in the stands focused their eyes on the scoreboard high above the right field wall.

It was cap shuffle time.

An image of a baseball appeared on the scoreboard. Then suddenly, a stylized baseball cap appeared, covering it up. Two identical-looking caps emerged on the big screen to flank it.

Music blared from the stadium speakers as the baseball caps shuffled around the screen. All the while, the fans tried to keep track of the cap with the ball underneath it.

Finally, the music stopped. The baseball caps froze in place across the scoreboard, the numbers 1, 2, and 3 displayed underneath them.

At the top of the screen, a question now appeared. Which cap has the ball?

There was a momentary pause. Then a murmur rose to a dim roar.

Two! Two! Two!

A few seconds later, the cap over the number 2 on the scoreboard lifted. The baseball re-appeared.

The crowd went wild.


The cap shuffle has long been a staple at ballparks.

It’s long proven to be a cost-effective way to keep fans engaged, even when the ballplayers are off the field. And it’s an easy contest to win.

Now, that’s not to say the shuffle is easy to follow. The scoreboard maneuvers can even flummox the fans with the keenest eyes and sharpest attention spans.

But those who lose the ball get a second chance. With only three options to choose from, guessing is simple. And the roar of the crowd can nudge those guesses into the educated column.

Indeed, I’ve rarely kept track of the winning cap when I’ve gone to the ballpark. I’ve guessed nearly every time. But I’ve rarely guessed wrong.

The wisdom of the crowd carried me through.


The cap shuffle is just a bit of amusement. No more. No less.

But it illustrates an entrenched element our society – The Rule of Three.

The Rule of Three is a principle that was first articulated by the Boston Consulting Group (BCG) in the 1970s. It states that most corners of commerce, there are only three significant competitors. Think Chrysler, Ford, and General Motors in the automotive space. Or Burger King, McDonald’s and Wendy’s in the fast-food sector.

The market might have started out with more competitors in these industries. But over time, those three frontrunners rose from the fray.

Such market domination has as much to do with human nature as business strategy. You see, our brains can only consider three to four options at a time. We simply cannot process a Big Six of automakers, fast-food proprietors, or nearly anything else.

But the Rule of Three only partially explains the world we live in. For while there might technically be three dominant options in just about any industry, only two of them tend to get the lion’s share of attention.

Consider soft drinks. In Texas, Dr Pepper is an immensely popular option. But once you leave the state, it’s barely relevant. Coca-Cola and Pepsi carry the mail.

The same is true in the world of computer operating systems. Linux is one of the top three options in that realm, but it doesn’t hold a candle to Apple and Microsoft.

Binary choice reigns supreme. For better or for worse.

The better refers to reliability for consumers, and a predictable revenue flow for providers. When there are only two dominant choices, each party knows what to expect.

But the worse feeds directly from those advantages. With so few dominant options, consumers must contend with the trappings of monopoly power – including higher prices and lower levels of innovation. And the main providers must contend with each other – leading to polarization and its associated ugliness.

Sound familiar?

Yes, American politics also follows the Rule of Three. Two parties have reigned supreme for generations, while a smattering of independent politicians have sat on the periphery. This dynamic has made rhetoric more extreme and consensus harder to come by with each passing year.

Representative democracy only seems to embody the most sinister corners of American existence. Elections feel like a choice for the least bad option.

And when those perceived least bad selections make it to the seat of power, precious little gets done. Accomplishments requires compromise. And compromise is a bridge too far.

This quagmire has proved demoralizing to many Americans. And the murmurs of their discontent have now risen to a dull roar.

Give us more choices, they say. Get rid of the two-party system.

It’s a seemingly sensible plea. But appearances can be deceiving.


What would a multi-party political scene look like?

We don’t have to dive into fantasyland to imagine this. Real world examples exist an ocean away.

Countries such as Germany, France, Israel, and Australia have relied on a parliamentary system for governance. That means citizens vote for parties, rather than individual politicians.

There are plenty of parties for voters to choose from, and diverse parliamentary bodies. To govern effectively in this environment, parties have traditionally formed coalitions with relatively like-minded legislators – offering a smidge of compromise in order to pool votes.

But recently, that strategy has become less of a sure thing. Voters in some of those nations have given fringe parties with extreme views a seat at the table. And traditional parties have focused on differentiating themselves in response.

Consensus has been harder to find. Coalitions have been fewer and further between. And government productivity has gone down.

The byproducts of this shift are far from pretty. Economies have stagnated. Protests have proliferated. And snap elections have become commonplace.

This is what politics would look like in America without the two-party system. But since voters select individual politicians in our nation, the dysfunction would be on another level.

Without compromise, coalitions, or consensus, bureaucracy could grind to a halt. With gridlock overwhelming funding deliberations, government shutdowns would be inevitable. Without a shared sense of accountability, dereliction of duty would weaken the nation.

Expansive choice is no panacea. Far from it.

It’s time we get used to that fact.


When I was young, my parents would ask me a question each evening.

Do you want one bedtime story, or two?

Bedtime was non-negotiable. But I still had some say over the proceedings.

I often went with the second choice. I’d listen intently to a rendition of one children’s book, then another. And by the end, I’d be down for the count.

I didn’t give this ritual much thought at the time. But I sure do now.

You see, I don’t have children of my own. But I know that kids can be a handful after the sun sets.

Crankiness, mania, hyperactivity – all are possible as youthful energy wanes. Children need their rest, but good luck getting them to acquiesce to it.

This is why my parents’ bedtime system was so brilliant. By consolidating options, they made the wind-down manageable for everyone. And they set me up for success.

I think the same is true for consolidated options in general. We might want more than Coca-Cola and Pepsi, or Republicans and Democrats. We may yearn to see 7 caps shuffling on the scoreboard.

But what we’ve got is manageable. What we’ve got is reliable. What we’ve got is familiar.

It might not work to our specifications. It might barely work at all. But it works.

And that’s no small thing.

Tragic Misconceptions

It was a jarring sight.

A Toyota sedan missing all four wheels. The disk-like rotors were fully exposed to the elements, as a small rock kept the rest of the chassis off the ground.

Some bad actors had stolen away with the tires and hubs in the dead of the night. An inner-city occurrence that was all too frequent.

Only this car wasn’t in the inner city. It was parallel parked along a tree lined street in a suburban neighborhood. My neighborhood.

Oh God, I mused as I passed the disabled vehicle. Am I safe here?

I thought back to a few nights earlier, when I’d taken an evening stroll on that same street. I don’t remember seeing the Toyota sedan parked there yet. But I don’t remember seeing much of anything at all.

You see, the streetlights were out in that area. The sidewalk was pitch black.

I wasn’t worried about criminals attacking at that moment. I was more concerned about tripping over a rogue tree branch or colliding with an aloof squirrel.

But now, I recognized the error of my ways.

I should have been more vigilant. I should have reported the extinguished streetlights – on that street and every other across the neighborhood. I should have been prepared to face down thugs on every corner.

Or maybe not.


The disabled car sat on that rock for a couple of weeks before it was towed away.

All the while, I scanned the neighborhood for other signs of mischief.

I started walking the neighborhood with a flashlight, protecting myself against a potential ambush. I perused postings on Ring and Nextdoor, looking for the patterns of local perpetrators. I pondered enrolling in a Concealed Carry course.

But trouble never came to my doorstep. Just like lightning, it only struck once.

This left me in a strange purgatory.

My neighborhood had proven to be about as safe after the wheel theft as it was before it. But that incident was too brazen to ignore. It had skewed my judgment.

No matter what the numbers stated, I could never truly feel safe there again.


Wrong place, wrong time.

It’s the predominant explanation for tragedy.

We do not tend to court misfortune. Yet, it sometimes finds us anyway — in the most random fashion possible.

There’s no way to truly rationalize these brutal occurrences. Wrong place, wrong time is all we have for an explanation.

But there’s a hidden implication in this statement. Namely, an acknowledgement that a right place and a right time exist somewhere else.

The quest for that somewhere else has served as our societal North Star for generations.

It has led us from colonial encampments to the wild frontier. It has led us back to the cities and then out to the suburbs. It has spurred innovation and infrastructure, but also White Flight and gentrification.

Yes, the legacy of the quest for somewhere else is a complicated one. For the world is not as straightforward as we’d like it to be. And the green grass on the other side of the fence is sure to turn brown once we trample all over it.

Our quest for utopia is a recipe for disaster. And yet, we commit ourselves to baking the cake.

We condemn the Southside, the South Bronx, and South Central. We exalt the fancy enclaves with the elite public schools and the well-heeled police forces.

We wrap ourselves in the illusion of safety. And when the veneer is stripped away, we feel the full weight of the betrayal. Just as I did when I saw the wheel-less Toyota sedan a mere 500 feet from where I lay my head at night.

It’s an insidious pattern. And we’re to blame for it.


Our society is obsessed with rankings.

We’re always eager to see how the football team we root for, the college we attended, or the price we paid for gasoline compares to the other options out there.

Fortunately, there are several organizations out there to satiate our list-mania. One of them is WalletHub.

The personal finance company is best known for its credit card recommendation tools. But it also publishes rankings of the safest cities in America.

WalletHub’s most recent annual edition released a few weeks before I sat down to write this article. So, naturally, I gave it a thorough read.

The first few cities didn’t lead to any raised eyebrow. They were in predominantly rural states that featured low populations.

But when I saw the city ranked #6 on the list, I gasped.

That city was Yonkers, New York.

While I’ve been a Texan for my entire adult life, I spent my childhood in Yonkers. I grew up in a decently-sized house with a front yard and a backyard — luxuries most residents of nearby New York City did not have.

The surrounding neighborhood was hilly, shaded by tall trees that dumped bushels of leaves every fall. The streets were quiet. The neighbors were too.

It had all the appearances of a nice place. But appearances can be deceiving.

When I was just 6 years old, someone stole my father’s car from right in front of our house. A few years later, a nearby home was burglarized. Shortly after that, someone drove across the front lawn of our across-the-street neighbor before plowing into a retaining wall.

It was all more than a bit unsetting.

I wanted to believe that my home was safe. That I didn’t have to worry when I closed my eyes at night.

But each time the blue police lights lit up our street, I doubted that premise. And each time my father installed an alarm system or trimmed the hedges a little lower, uncertainty proliferated.

I moved away from Yonkers many years ago. And my parents eventually sold my childhood home.

Several months after they left the city, a man in a parked car shot a Yonkers police officer approaching his vehicle. The officer’s partner returned fire, leading to an extended shootout. Terrified onlookers told news reporters that it felt like the wild west.

The whole incident took place on the same block where I grew up. If I were still there, I could have watched it unfold from my childhood bedroom.

Yet, despite that shooting and all the criminal activity I witnessed before it, Yonkers found its validation. Despite its star-crossed legacy as the site of the fire that killed Malcolm X’s widow, the arrest of the Son of Sam killer, and the early misdeeds of the rapper DMX, Yonkers was ultimately lauded as a beacon of safety.

What gives?


Signal and noise.

It’s the central paradox of statistics.

As we accumulate data, we yearn to find meaning in its patterns. But some of those associations ultimately don’t hold water. They’re the noise that the proven conclusions — the signal — must compete with.

The officer-involved shooting near my childhood home is a prime example of this. It spooked the neighborhood, no doubt. But it also was the first time in 30 years that a Yonkers Police Officer was shot in the line of duty.

In the grand scheme of things, it was not signal. It was noise.

The prior criminal incidents I witnessed on that block also fell into the noise column. While each was unnerving, they took place far too infrequently to cause real concern.

My childhood neighborhood, it seems, has long been a predominantly safe place. It just wasn’t perfectly safe.

The same can be said about my current neighborhood. And many others across our nation.

It’s that variance that gets me — that gets many of us.

Safety is such an existential need that we seize upon any sign of imperfection. One lapse is too many, and two is catastrophic.

But this trend is not feasible or productive. It leads us to overestimate bad outcomes and succumb to paranoia. It fosters tragic misconceptions of the places we frequent, and the people we share those places with.

We need to let go of those delusions, and to choose a more sustainable path instead. We need to recognize the risk of a wheel theft or a crash into a nearby retaining wall for what it is – low, not zero – and calibrate our responses accordingly. We need to stop casting out the good with the bad.

This will be an uncomfortable shift for many of us. Myself included.

But it’s a necessary one.

We will never find a true sense of security without making peace with our surroundings.

It’s starts with us. Let’s get to it.