Playing Chess with Someone Who Doesn’t Play by the Same Rulebook

("Playing Chess With A Sociopath" was originally written 2019 - updated for clarity in 2026)

It’s nice to know the rules when playing any game. It’s even nicer to know when someone else isn’t using the same rulebook.

Today we’re talking about a pattern of behavior often labeled “sociopathy.” Clinically, the diagnosis is Antisocial Personality Disorder (ASPD). The terms sociopath and psychopath aren’t formal DSM diagnoses, but they’re commonly used to describe people who show a consistent pattern of disregard for others, limited empathy, chronic manipulation, and violation of social norms.

Before we go further: Not everyone who lies, manipulates, or avoids accountability has a personality disorder. Human behavior exists on a spectrum. This article is about recognizing harmful patterns - not diagnosing your ex after one argument. That said…

A small percentage of the population meets criteria for ASPD. Most people operate with an internal brake system - guilt, shame, empathy, remorse. Some people simply don’t experience those brakes in the same way.

That difference changes the game.

The Chess Problem

Imagine you’ve spent your whole life mastering chess. You know how the pieces move. You respect the rules. You assume everyone else does too. Then someone reaches across the board and moves a pawn like a queen. “You can’t do that,” you say.

But they can - because in their mind, the goal isn’t to play by the rules. The goal is to win.

When you’re playing by empathy, and someone else isn’t, confusion sets in fast. And confusion is a powerful manipulation tool.

What This Pattern Can Look Like

Again — this is about patterns over time, not one bad day.

1. Rarely flustered when caught. Some people become calm, calculated, and verbally agile when confronted. Excuses appear instantly. Justifications flow. The speed itself can make you doubt your instincts.

2. Superficial charm. Warm handshake. Easy smile. Clever humor. They often know exactly what to say — because they’ve practiced what works.

3. Low empathy. When conversations turn emotional, something feels… off. The words may be correct, but the depth isn’t there.

4. Strategic secrecy. Information is currency. They share what enhances their image and withhold what doesn’t. Triangulation — positioning people against each other — may show up.

5. Manipulation through victimhood. “Poor me” becomes a recurring theme. Accountability rarely sticks. There’s always an explanation that removes personal responsibility.

6. Sensitivity to their image. Reputation matters. Admiration matters. Being exposed in a negative light? That matters a lot.

7. Long-game patience. Some individuals will play the slow, strategic route to get what they want — whether that’s status, money, control, or admiration.

8. Chronic boredom and risk-seeking. Impulsivity and stimulation-seeking can show up in different ways — conflict, risk, drama, boundary violations.

9. Relationship burn patterns. Connections may be intense at first and then abruptly discarded once utility fades.

And 10: Entitlement: You OWE them. And they’ll carry on and on about the debt, or title, or praise, etc. until they get it with complete belief that they are entitled to it (whatever it may be).

Again — no single trait equals a diagnosis. Patterns over time are what matter.

The Stare

Some people report what feels like a “predator stare.” It’s not mystical - it’s often dominance testing. Extended eye contact can be a subtle way to assert control or gauge reaction. If your nervous system feels unsettled around someone repeatedly, don’t dismiss that data. Awareness isn’t paranoia — it’s information.

(And yes, cats will always win staring contests.)

The Real Danger: Confusion

The most destabilizing part of interacting with someone who lacks internal brakes isn’t their aggression. It’s the confusion.

If you’re operating from:

• fairness

• mutual respect

• shared moral assumptions

… and they’re operating from:

• outcome

• advantage

• image

… you’ll spend years trying to understand something that doesn’t operate from your framework. That’s the trap.

The Part That Matters Most

Years ago, I found myself in what felt like a long chess match. Problem was, I didn’t know I was in a game. For me - it was my life. In my ignorance, I assumed shared values. Shared conscience. Shared emotional reality. I was wrong.

It took years to recognize that what I thought was mutual connection was, in fact, strategic positioning. They were playing a game with all of the things in life that I held close to my heart and emotions like guilt or shame weren't a factor in the moves they made.

That realization was destabilizing. It shook my sense of identity. My security. My foundation. My reality.

Story-time

I was alive physically but emotionally hollow. At one point, I was so - meaningless - that when a white Ford Truck swerved towards me in the street outside my house, I didn't move. I just stood there. I wasn't afraid because I had nothing of value to lose, anymore.

The side mirror missed me by less than an inch. And I didn’t flinch. I just stood there and watched the truck drive away. That moment became the doorway to one of the most important lessons I’ve ever learned.

And here it is: Even if someone destabilizes the external parts of your life - your reputation, your confidence, your relationships - you are still you. Amazingly, I hadn't just disappeared into nothing. I was still there and more importantly, I was still me.

I discovered something I didn’t know I was missing: Independence from external validation.

When the illusion of external value was nearly stolen and collapsed, I survived.

Stronger. Less afraid of loss. More aware. And far less likely to assume everyone is playing by the same internal rulebook.

Final Thoughts

Most people are not sociopaths. Most people are flawed, wounded, defensive, reactive - but are still capable of empathy. However, a small number of individuals consistently operate without the emotional guardrails most of us rely on.

Which is good to know.

Hear me, awareness isn’t about becoming cynical. It’s about understanding that not every chess game on the board is the same game.

If you’ve ever felt like the rules kept changing mid-match, you’re not crazy.

You may have just been playing someone who wasn’t using your rulebook.

Awareness up.— Jed Thorpe, CMHC