The Twisted View of Risk

There’s still time to get Apple Care on that new iPhone.

Those were the associate’s words, as he handed the man across the table from me his new iPhone.

But the associate wasn’t finished.

We now have monthly or yearly plans. You can add it for as long as you own the phone, unlike those old two-year Apple Care plans. And if you break your phone, you’ll be covered.

The customer was unmoved.

If my phone gets messed up, he said. I’ll just buy a new one.

The associate looked perplexed.

You’d rather pay another $800 on a new device, than $30 on a screen repair? The math doesn’t add up.

It didn’t add up to me either. After the iPhone owner left the store, I told the associate that I would have gotten the new Apple Care plan.

And yet, as I left the store, I started to doubt my certainty.

After all, I’d made some travel arrangements the night before. Airline tickets, rental cars, hotel reservations — the whole deal.

Each of those purchases came with an option to buy insurance for cancellations, delays, and other mishaps. And in each case, I’d declined that coverage.

I was no better than the guy with the brand-new iPhone. Risk did not factor in.


There’s an infamous scene in the sitcom Family Guy that sticks with me.

The dim-witted protagonist — Peter Griffin — opens his front door and encounters a salesman hawking volcano insurance. Even though he lives far from any volcanic zones, Griffin uses his wife’s rainy-day fund to pay for the coverage.

Predictably, this ends up landing the Griffin family in financial ruin.

I think many of us look at insurance this way. We see it as a scam — one that leeches our hard-earned money in pursuit of bad outcomes.

We don’t want to think that we’ll get in a car wreck, or break our smartphone, or get food poisoning and miss our flight. And we definitely don’t want to throw money at those possibilities ahead of time.

We’d rather delude ourselves into a false sense of security, floating down a river of cost efficiency and good vibes.

I, more than anyone, know how ridiculous this is.

I’ve worked in the insurance technology space for more than a decade. I’ve seen the data. I’ve learned the nuances of coverage. And I know that the overall system — while imperfect — is far from a scam.

Plus, I’ve seen the benefits of insurance in my own life. Car insurance helped make me whole after a Dodge Ram smashed into one of the doors of my SUV. And event insurance reimbursed my entry fees when I had to drop out of the New York City Marathon due to injury.

Yet, I still find myself declining event insurance these days. And I still tend to favor cost efficiency over broad coverage when it comes to my car insurance policy.

The risk is there. The logic is not.


I don’t know much about the man who walked out of that store with a new iPhone.

But I would imagine he holds a few stocks and bonds. And if he were to find himself in Las Vegas, he’d likely take a turn at the slot machines.

This is not typecasting. It’s oddsmaking.

You see, there’s been a surge in recreational investors this decade – particularly in the wake of the pandemic. And Vegas casinos have always been popular with young adults.

I’d be hard pressed to imagine Mr. I Don’t Need Apple Care bucking those trends. Despite his insurance frugality, he seems to be in the peak audience for them.

Investing and gambling share common traits. Particularly the dopamine high of making a windfall, and the delusion that such happy outcomes will befall us frequently.

That’s what draws people in. That’s what keeps people at the table. And that’s what leads people to believe that risk is negligible.

This couldn’t be further from the truth.

Risk is multiplied in the each of these forums, in great part because control is out of our hands.

We don’t get to run the companies we invest in. And gambling is nothing more than a game of chance.

It’s likely that we’ll lose at least some of what we put in. And it’s unlikely we’ll be compensated for that loss.

Insurance might not be popular. But it turns out to be much more practical than the cool activities.

If only we’d come to our senses.


A great many historical figures are known for only one thing.

Sigmund Freud is not one of them.

The father of modern psychoanalysis helped people around the world discover their unconscious, unveiled the Oedipus complex, and redefined sexuality. And along the way, he introduced us to The Pleasure Principle.

The Pleasure Principle is an instinctive drive to seek pleasure and avoid pain. It guides us as we work to satisfy our biological and psychological needs. And it might explain our twisted view of risk.

You see, The Pleasure Principle aims to insulate us fully from bad outcomes. But in a world that’s often random and cruel, that mandate is in impossibility. Risk is always lurking, like a shadow. And pain is never far behind.

Our brains can’t square with this reality. After all, we can only keep our guard up so long before we wear ourselves out.

So, we let the The Pleasure Principle cast a spell of delusion. We get addicted to the prospect of winning while turning our backs on the mere mention of losing.

This dynamic is what draws us to invest, to place bets, and to chase dreams with vigor. And it’s also what leads us to get repulsed by mentions of warranties and insurance policies.

Simply put, we’d rather wish away the bad outcomes than have a plan for mitigating them.

Such thinking is foolhardy. But it’s a Freudian principle. It’s darn near inevitable.

That is, unless we lean into the skid.

Yes, it we play Jedi Mind Tricks on ourselves, we just might cajole ourselves back to our senses.

That means treating insurance like an investment, rather than a nuisance. It means expecting the worst, rather than the best. And it means treating positive outcomes as a happy surprise.

Such a shift requires some emotional jiu jitsu, and a fair dose of pessimism. But hedging our bets in this way, can help keep us from losing it all. It can keep us from losing it all.

That seems like a winning strategy to me. Let’s make it a reality.

The Paradox of Trust

A friendly face.

It’s a lifeline.

When we’re faced with novelty, a friendly face can make all the difference.

Friendly is familiar. And familiarity can cut through the jitters of uncertainty.

So, we seek out a friendly face at any opportunity. We seek to build a stable of people we can trust.

We believe that we’re setting ourselves up for success by doing this. But we could be booking a one-way ticket to trouble instead.


I’ve often been described as trustworthy.

Many times, I get this feedback directly. Sometimes I see it through the actions of others.

I take this accolade as an honor and a responsibility.

While it’s great to have others believe in me, I know I can’t rest on my laurels. I must work continually to validate that trust.

For trust is not a rubber stamp. It’s a contract.

If I fail to deliver on my end of that contract, it evaporates. I lose the goodwill of family, friends, and associates. And I end up hurt, perhaps irreparably.

And if I abuse the contract entirely — blatantly violating its terms for my own gain — it ignites. I lose the goodwill of family, friends, and associates when the truth comes to light. And they end up hurt, perhaps irreparably.

Yes, what builds us up can also tear us down.

And so, I am deliberate when it comes to trust. I strive to model trustworthy behavior, but I don’t overtly seek out the trust of others.

I simply put myself in a position to earn that label. And once I receive it from someone, I work extra hard to maintain it.

The stakes are too high to act otherwise.


Confidence artists.

We have a complicated relationship with them.

We love it when our favorite characters on the silver screen are putting on a ruse. But we loathe seeing such sequences play out in real life.

The gap between these two examples might seem stark. But they’re closer together than we might want to admit.

Whether it’s James Bond or Bernie Madoff, confidence artists draw from the same well — our sense of trustworthiness, and our unwillingness to question it.

And while it’s easy to trivialize those victimized by confidence schemes — labeling them as the naïve, the uber-rich, or the movie villains who had it coming — such dissonance misses the point.

All too often, we play fast and loose with the concept of trustworthiness. We hand over the keys to the Rolls Royce that is our life. And we just expect the valet in its charge not to go joyriding with it.

We hope that everyone’s better angels will shine through. But what if they don’t?

We have no contingency plan for the devil in our midst. We head out into the chaos of the world without an inch of armor. And the results are predictably tragic.

Perhaps it’s time to change the calculus.


My parents are both educators.

Ever since I was a child, they’ve been entrusted with the well-being of schoolchildren. During the busiest part of the day, they share a classroom – with no parents in sight.

This alone isn’t noteworthy. Or it shouldn’t be.

After all, the school system has been set up this way in America for two centuries. We entrust educators with our kids, no questions asked.

But recently, things have changed.

Revelations of physical abuse in the classroom by teachers have shattered any sense of trust. Schools have had to face tough questions about how they operate.

This has impacted my parents. They’re consummate professionals who have proven worthy of the trust bestowed upon them. But they now face a bevy of regulations and restrictions that impact how they teach.

There’s no question that these changes were needed. The old method of blind trust allowed predators to lie in plain sight, and plenty of lives were ruined in the balance.

Still, the current climate in classrooms isn’t exactly sustainable either. Education can’t happen in a trust vacuum, with all its mechanisms eroded away.

The solution lies somewhere in the middle, in the gray area between carte blanche and a surveillance state.

And it’s there, in the fog and the mist, where the path forward is so difficult to navigate.


Trust but verify.

Back when I worked in television news, I internalized these three words.

Speed was the name of the game. Getting the scoop, being the first to report — that meant everything.

But accuracy was the name of the game too. Putting the wrong information out there could get you in a boatload of trouble.

Choosing between these two edicts wasn’t an option. So, I went with the trust but verify approach.

Essentially, our news operation would implicitly trust the information we came across. But we’d still check with a second source to verify that intel, ensuring it was accurate.

This trust but verify approach speaks to the paradox of trust. We need it, but we can only rely on it so much.

There’s no true guidebook for this paradox. There’s no silver bullet that leverages the upside of trust without exposing us to those nasty downsides.

The best we can do is to approach the situation with eyes wide open. To lean into our vulnerability and to prepare ourselves for the worst outcomes.

We can do this by honoring the trust placed in us. Instead of taking this goodwill for granted, we can act to validate it day in and day out.

And when it comes to the trust we place in others, we can take our time. Instead of diving right in, we can verify that our faith is indeed justified.

On their own, these actions won’t mean much. Trust can still be broken. People can still get burned.

But as more and more of us follow these principles, those risks will diminish. We will bolster our faith in each other while working together to deliver the goods.

That’s a future we can all get behind. But it starts with our actions today.

So, let’s get started.

Shifting Barriers

Barriers can divide us. But they should never define us.

In the summer of 1997, my family took a trip to Washington with my godparents and their son. While we walked the National Mall one late afternoon, my godfather noticed a lost backpack on a park bench.

Since it was the age before cell phones, we took the backpack to our hotel and called the number we found on its ID tag. This allowed us to return the backpack to its rightful owner — a very embarrassed congressional aide.

As a sign of gratitude, the aide arranged a private tour of the U.S. Capitol for us. We took the Congressional Subway from the senate office building to the Capitol itself and got a behind the scenes look at the both chambers of Congress.

Looking back now, 20 years later, this story seems even less real than it did in real time. It would be inconceivable today to pick up a lost backpack from a park bench, let alone bring it back to a hotel in order to locate its rightful owner. And of course, just about no one’s getting a behind-the-scene tour of the Capital these days.

The landscape of this story is frozen in the past, in the same way the old Western tales are eternally tied to a frontier that no longer exists. And while the advancement of technology has certainly played a part in altering our perspective, so have changes in the barriers around us.

***

I have a unique perspective on shifting barriers.

I was born in the fading shadow of the Iron Curtain. The Berlin Wall fell about a month before my second birthday, and the Cold War mentality everyone had lived with for a generation fell with it.

It was a new era. One filled with seemingly endless optimism.

That optimism flowed all the way down to elementary school classrooms. I remember learning about Martin Luther King and the Civil Rights Movement in Kindergarten. Although the March on Washington was already 30 years in the past by then, my teachers kept talking about how the future was brighter than ever. They kept mentioning that there would be more opportunities and fewer barriers in our way.

And this was largely true. There was plenty of prosperity and innovation in America during the 1990s. We had a budget surplus for a while, and we quickly integrated the Internet into our lifestyles. An era barricaded by conflict, fear and distrust crumbled, with friendship and reconciliation filling its void.

It seemed that divisiveness would permanently become a relic of the past. Then the Twin Towers fell.

As I struggled to pick up the pieces after 9/11 — my innocence shattered and my heart broken — I noticed something different going on around me. The barriers our society had spent a decade tearing down started to appear all over the place once again.

These new barriers were evident at airports, border checkpoints and sports arenas, of course. But you could also see them in more subtle areas — such as attitudes toward minorities or reactions to abandoned backpack on a park bench. As an era of suspicion took hold, the cultural connections we’d worked so hard to build faded to grayscale.

Although the initial shock and horror of America’s darkest day soon subsided, it quickly became clear that these new barriers were here for the long haul. I remember checking in for a flight in Rome in 2004, only to notice a military sharpshooter perched overhead. It was a terrifyingly normal sight — one that reflected how an initial fear of terrorism had evolved into a societal norm.

This is not to say there haven’t been some barrier-smashing changes over the past 15 years. The invention of the smartphone and the election of a black president are testament to that. But still, it’s clear that the openness of the 1990s is as much a relic of the past as the toy in the Cracker Jack box.

The tide is most certainly rolling in.

***

This all begs one big question:

Are barriers a bad thing?

Some would say the answer is a unilateral yes. But I’d beg them to reconsider.

You see, barriers do have their benefits. They can give us privacy in our bedrooms and bathrooms. Or keep convicts away from their potential victims. Or help us define which plot of land is ours.

These are all worthy causes for boundaries. Necessary ones for our well-being and survival. After all, there is a saying that goes, “Those who wish to abolish all barriers have never spent a night in the rain.”

Still, the act of building barriers can quickly become dangerous. And our actions over the past decade or so have certainly crossed that threshold.

For in our quest to block out the danger of our world, we’ve been building a wall around our heart. And spreading seeds of deceit and distrust throughout our society.

Those seeds have grown into weeds now. They’re causing the divisiveness, anger and angst running wild through our society. They’re slowly tearing our society apart.

It’s high time that we cut these weeds down.

Let’s take some responsibility for what we’re doing to ourselves.  Let’s unchain our hearts and learn to trust each other again. Let’s accept hope and shun fear.

In short, let’s start building a more open future.

That’s a shift in barriers we can all get behind.

 

Order Matters

We live in a turbulent era — a time where order has been challenged. And for good reason. Our most fundamental right — the one that allows us to live — has been challenged by some of those sworn to protect it. And all too often, skin color is at the center of these tragic incidents.

As this grave issue has gained notoriety, related ones have come to light as well. We’ve collectively shown outrage at the blatant inequalities of our justice system, reopened discussions as to how we actually view black and white, and mourned disturbing acts of retributive violence that have rocked our communities.

We’re certainly a polarized nation. If you don’t believe that, look at the varying responses to NFL player Colin Kaepernick’s decision not to stand for the national anthem — a protest coined to shed light on race relations. Most of the support for the move has come from the black community; the white community has been much less forgiving.

Situations like these show our nation’s current predicament. We must fix these societal problems — but we need to do this in a unified, orderly fashion. This is a difficult feat, since there’s a crisis in confidence with our system of order at the moment. But it’s something we must pull off— as a world without order is fraught with danger.

***

I understand this as much as anyone. A short time ago, I went to a college football game in Oklahoma with a friend. Our seats were right next to the Oklahoma student section, and we decided to move over five feet and watch the game with the student body. While I was at first apprehensive about standing on the narrow metal bleachers with the student — especially considering it had just rained — I soon found out I had other concerns to contend with.

Shortly after kickoff, I felt something pushing against my back. It turns out the drunk guy behind me had dropped the cap to his pint of Jack Daniels, and he had knocked into me as he clumsily tried to pick it up. Moderately amused, I turned my attention back to the game. But a few minutes later, I found myself in the line of fire again — as the same guy started jawing with someone a row in front of me. As the argument got more and more heated, my focus for the evening drastically changed. I was no longer worried about watching the football game. I was instead worried about leaving the stadium in one piece.

Unfortunately, my fears soon became reality — although not courtesy of Mr. Jack Daniels. A man two rows above me had been trying to start fights all night. Someone finally obliged, shoving him and sending him flying; the man knocked me down a row as he fell, leaving me with a twisted ankle. When I looked up, he was charging through the crowd throwing haymakers.

It was only at this point that police and security showed up. They ultimately decided not to throw anyone out, but most of the troublemakers left on their own accord, as the game had become a blowout.

***

This experience was eye opening for me. A trip to a football game had become Jungle Law, simply because there was no one around to restore order. The situation was incredibly dangerous — although my minor ankle injury appeared to be the extent of the damage.

Take this scenario outside the walls of a football stadium, and the consequences are even more dire. While I certainly believe that Black Lives Matter and absolute power can corrupt absolutely, it’s clear that a complete lack of order is just as lethal as a corrupted system of order — maybe more. For when ill-meaning characters are allowed to run amok, we are all in the crossfire.

So we must not shun order completely. Instead we must work together to improve our system for everyone. We must ensure not only that innocent people are not victimized, but also that actual troublemakers are held accountable.

Restoring our confidence in order is not a black issue, or a white issue. It’s a gray issue.

It’s a challenge that affects all of us, but it’s one we’re compelled to take on directly.

Let us begin.

The Wreckage Of Radical Thinking

These are trying times.

Our way of life is under attack by those we cannot understand, and who refuse to understand us. Undocumented people within our borders cause uncomfortable situations, while a booming international drug business is causing problems on multiple fronts. The color of our skin can be a de facto death sentence in certain encounters with law enforcement. Our rights to self-defense, privacy, speech and religion are threatened by — of all things —our own actions.

These are turbulent times indeed, compounded by our collective difficulty grasping one key concept.

Complex problems can’t be solved by simple solutions.

A concise rational statement. But we seem to have lost all rationality these days, as many are  convinced that by simply removing a set of people from our midst, we’ll make everything better.

It doesn’t work that way. Why? Because no matter how you classify us — black, white, Asian, Hispanic, Muslim, Jewish, Christian, cops, businesspeople, journalists — we have rights in this country. We have rights to live and defend ourselves. We have rights to spiritual beliefs and to free expression. We have rights to moments of privacy. We have rights to public safety. And, provided we don’t unduly impinge upon the safety of others, we have a right to freedom.

Change is good. Progress is good. But when radical responses to injustice catch fire, an entire subset of our society is denied these inalienable rights — and everything that we should stand for goes up in flames.

It ain’t progress when we ostracize all law enforcement officers for the abhorrent actions of several bad ones. It ain’t progress when we propose disarming our entire society completely, even in the wake of senseless tragedies. It ain’t progress when we threaten to kick out all the Mexicans, or all the Muslims.

For when we do all this, we succumb to closed-mindedness. We regress into an ugly past where some human beings within our borders were considered three-fifths of a person based on the color of their skin. We open the doors for those with the lethal combination of ultimate power and evil intentions to order a mass exterminations of a subset of our population. We threaten to shun our societal values — the unique mixture of cultural diversity and universal rights that has allowed our culture to transform the world.

So, when it comes to pushing our culture forward in the wake of tragic setbacks, we should not let our emotions goad us into radical decisions. Instead, we should show restraint and take a more moderate, central path toward improvement.

By staying true to who we are, we can ensure that who we will be is so much better.