On Counterfactuals

My father shuffled the cards and dealt them out.

Face up on the table in front of me were a 6 of Diamonds and an 8 of Spades.

My sister and mother each also had two cards face up in front of them. I took a quick glance at the cards. But then, my father set me straight.

Don’t worry about them, he stated. The goal of this game is to beat the dealer. In this case, me.

I asked him how I might do that.

It’s simple, my father replied. Your cards just need be closer to 21 than mine, without going over 21.

My father went on to explain the rules of Blackjack.

Both my cards were face up, while one of his was face down. I’d have to add my cards together and determine if my hand was better than the dealer’s.

This was a guessing game as much as it was an exercise in arithmetic. But there still was some skill involved.

For each round, the dealer would ask each player if they’d like more cards to help their cause. If any of the players said Hit me, they’d get another card. If they said I’ll stick, they wouldn’t.

This meant that if I didn’t like my chances, I had ample opportunity to improve them. But I’d need to manage that opportunity artfully.

I looked at my cards again. They totaled 14, which was a far cry from 21. I’d surely need more to win.

So, when my father asked what I wanted to do next, I emphatically said Hit Me. He dealt me a 2 of Hearts, bringing my hand up to 16.

This still seemed too far from 21. So, during the next round, the words Hit Me again left my lips.

I got an 8 of Diamonds.

I had a higher card total than the dealer. But I’d also gotten my hand up to 24.

I’d busted. I’d lost.


I didn’t take my failure all that well.

But as I sat there sulking – as 8-year-olds do – my father took a moment to coach me up.

You don’t need to go ‘Hit Me’ on every turn, he said. Sometimes the math makes that too risky.

Sometimes the best way to win is to stick.

This stunned me.

I had never considered how not doing something could be more impactful than springing into action.

How could I have?

My entire life to that point was defined by motion. I bounced from activity to activity, at school, at home, and everywhere else.

Sure, there was plenty of downtime. Regimented bedtimes in the evening, regular naps in the mid-afternoon, and so on. But I had no recollection of the stillness, as I was unconscious throughout those quiet moments.

I’d never really gotten good at mastering the pause. At seizing the non-event. At embracing the absence of action.

All these years later, I still haven’t excelled in those areas. And I’m not alone.


You can’t prove a negative.

This is a common refrain. You hear it often during Monday Morning Quarterback sessions.

The point is straightforward. Time moves in one direction, and only on one track.

We can ponder what would have happened if we didn’t make a certain move, meet a certain person, or pursue a certain dream. We can muse about how much better or worse we’d be for choosing a different path or encountering a different fate.

But these are just pontifications. We can’t know for sure.

There’s plenty of logic behind this theory. After all, we humans have long been proficient in notating things. As we’ve evolved from stone etchings to silicon computing chips, we’ve kept the thread of recording events alive.

Those data points have proven essential to understanding our world. We recount history so that we might replicate successes and avoid repeating disasters. We keep scientific notations to prove hypotheses and spur innovation. And we look at numeric indicators to help prognosticate what’s to come.

Absent these readings, we have nothing. No data to ground our musings in. No substantive proof of how an alternative path would have played out.

And so, the prevailing wisdom has been to ignore the negatives. To avoid spending energy on what could have been. To proclaim Hit me when the dealer offers another round of cards, over and over.

Yes, away from the Blackjack table, the do-nothing option is too unproven to even be an option at all. No wonder we don’t pursue it.

But, at long last, that might finally be changing.


In recent years, a term has garnered some buzz.

Counterfactuals.

This term describes an alternative fact set. Not in the form of lies or half-truths, but more in the prevalence of empirical simulations.

Counterfactuals have existed for quite some time. But their use was traditionally limited to certain situations, such as courtroom testimony. (Think of the question from prosecutors in too many Law and Order episodes: And if that hadn’t happened, what would you have done?)

But now, things are changing. Thanks to advances in data science and artificial intelligence, we can take a fresh look at the past. We can change one input and see what the statistical outcomes were likely to have been.

This new age modeling has changed the game for decision making.

It’s broadened the scope of possibilities beyond the triumphs and failures of record. It’s helped us to preview occurrences without clouds of doubt. It’s allowed us to experiment free of the shadows of collateral damage.

Yet, this potential still comes with a cost. Namely, the cost of our innocence.

No longer can we be willfully blind to the road not taken. No longer can we shun the outcomes we – or our predecessors – had not experienced firsthand.

Those storylines now written in probabilities and code. The do-something- option, the do-something-else option, the do-nothing option – they’re all out in in the open.

It’s our obligation to look at them before choosing a path forward.

This might seem like a daunting task. An uphill climb. A joyless sojurn.

But it doesn’t have to be.


I am a huge fan of Malcolm Gladwell.

Longtime readers are familiar with my Gladwellian obsession. His bestselling books adorn my bookshelf. His acclaimed podcast fills my audio feed.

There’s a certain clarity in Gladwell’s work. A mix of eloquence and boldness in his statements.

But that’s not what draws me to him like a moth to a flame.

Malcolm Gladwell is somewhat of a contrarian. He’s embraced counterfactuals since long before it was cool. Before there was data science and advanced computing to back up his views.

Indeed, in those early days, Gladwell would often dive deep into obscure datasets and historical studies to support his claims. He would connect disparate dots in a manner that wouldn’t become clear until the story was nearly over.

Gladwell’s perspective was maddeningly uncomfortable to me when I first encountered it.

I yearned follow the prevailing winds. I desired to kowtow to custom. I wanted to go Hit Me on every round.

I had no appetite to upset the apple cart. I wasn’t buying what Malcolm Gladwell was selling.

Gradually, though, his well-informed perspectives won me over. I became less consumed by perspectives, and more enamored with getting closer to the truth – as unsightly as it might be.

The prospect of encountering counterfactuals became exciting, not exhausting. And my decision-making chops flourished.

I no longer play Blackjack. But if I did, I’m certain I’d be far more proficient at it these days. For I understand the subtle pull of the do-nothing option in an environment yearning for another card. And I’m willing to give it an audience.

Such power lies within all of us. I am sure of it. We just need to harness it.

And that starts with the right mindset. With embracing counterfactuals, rather than running from them.

Are you ready to take that quest?

Analyst or Innovator?

When I was growing up, I loved baseball. I loved playing it. I loved watching it. But most of all, I loved checking out baseball statistics.

Even though I was no math whiz, my young mind recognized that those numbers I saw in the newspaper box scores were actually a barometer. A player who batted to a .330 average with 30 Home Runs and 100 Runs Batted In would be someone I’d want to see starting for my favorite team. One who batted .210 with 5 homers and 25 RBI would not.

Whenever I saw those guys with poor statistics in a box score, I responded with bemusement. Why would a team run a player out there who hadn’t proven he could hit?

Of course, I failed to consider the ancillary reasons for those low numbers. Maybe the player was known for his outstanding defense. Maybe he was anxious because his wife was due any day with their first child. Maybe he was suffering from colitis but trying to tough it out anyway.

These scenarios wouldn’t erase goose eggs in a box score. But they would put them into context.

In particular, they had the power to integrate the human element into an industry based on numerical benchmarks. And given baseball’s legacy of pageantry and tradition, this element was sorely needed.

***

Sadly, that human element is harder to find these days.

It’s long gone from baseball. Statisticians are now an integral part of the sport’s brain trust, and players are judged on obscure metrics like WAR, Exit Velocity, Launch Angle and Spin Rate. (Sometimes, when I tune in to a baseball broadcast, I feel like I’m watching cyborgs.)

But it’s disappeared from many other industries as well. Big data is in vogue and seemingly every decision out there comes from cold, hard numbers. A whole new class of employees spend their days looking at analytics and reporting to their bosses solely on those very same numbers. They might not know it, but these analysts are now the key cogs that define their employers’ strategies.

This all seems well and good on the surface. More young adults can now have access to corporate jobs that actually impact their employers’ strategies. And companies don’t have to gamble with profitability each time they change things up; the cold, hard data is within arm’s reach.

But dig a little deeper, and you’ll find the quandary.

***

We were never meant to take the human element out of the equation. Anyone who’s watched Star Trek knows that instinct and emotion are just as critical as logic in completing our mission.

On a high level, our love affair with data-based decision making excludes us from any growth opportunities that require breaking from the norm, or bending the rules. It sacrifices our independence of thought in favor of hard numbers, thereby compromising our integrity.

But on a more basic level, our all-in data approach has created a new class of professionals. A class that is as stuck in the mud as Joe Pesci was in My Cousin Vinny.

You see, it’s relatively easy to analyze data that’s already there. Assuming one has a certain level of specialization, it’s even a secure area to work in.

But this type of occupation doesn’t provide a great opportunity for growth. There’s no need to go beyond the numbers. After all, no one’s looking for us to do that.

***

We were meant for something greater. We weren’t meant to be analysts. We were meant to be innovators.

And while the world at large seems to be pulling in the other direction, we don’t have to follow suit.

We have more to contribute than the digits on our spreadsheets and the colored arrows on our charts. There are untold stories behind those trends and totals. Stories that tie the often-unpredictable course of human psychology to the concrete data we cultivate like corn on a Nebraska field.

We must tell those stories to tie everything together. We must tell these stories to forge a new way forward for a society that has doubled down on a solitary variable. We must tell these stories to lead.

This process might seem uncomfortable. Unsafe even.

That’s OK. Innovators never take the well-worn path.

But regardless of our apprehension, we owe it to ourselves to explore our true potential. We owe it to humanity to take that leap. We owe it to our future to make the right choice.

Analyst or innovator?

The answer should be clear.