Karen: A cautionary tale

Karen was a fine woman. No, she wasn’t.

Karen was a fine woman. No, she wasn’t.

She was the finest woman I’ve ever met.

For 35 years, she has spent every day in a windowless office doing one thing and one thing only: making children feel better.

So no, she was not a “Karen.” She was an INFJ – my magnetic match (or so I thought at the time) : finding that rare opposite who feels like home.

And her look. My God. She was dressed impeccably, but understated. Like a Kennedy. I told her, “You look like you just stepped off a Hinckley at Hyannisport.”

She smiled and said “you aren’t the first person to say that.” She was often told she looked like Jackie O.

I had looked forward to our date like you look forward to a movie that you believe you will love. You settle in, you’re excited when it starts, but the beginning is underwhelming.

You tell yourself, just wait, it’s going to get better. With this cast? With this director that you love? It’s gotta get better. But after fifteen minutes, the truth sets in: they got nuthin’

I felt rejected in the first moment we met. She made me feel as if she had taken one look at me and said “no.”

We met at an outdoor cafe. She wore sunglasses, but I believe the eyes are the window to soul, so I removed my sunglasses as soon as I sat down. She kept hers on.

She sat with her back half-turned away. Her emotions ran the gamut from A to B. She complained about politics but offered no insight. She asked me no questions of substance. She wasn’t just vanilla. She was store-brand vanilla.

By the time she sent her final text at 8:43 that evening, I already knew what it would say:

“It was nice to meet you, but I think we bring a very different energy to the table that doesn’t match up. Thanks again for the beer and take care.”

We were not in alignment.

INFJs are different from every other type

Here’s the thing about INFJs: they can come across as emotionally flat when you first meet them. Guarded. They don’t perform for strangers, and they conserve energy until they decide you’re safe. Sometimes, what looks like absence is simply their intuition saying not yet.

That’s the way Tammy was on our first date. We only became inseparable after I showed her an extraordinary act of kindness — a wonderful story, but not for now–it was only after I performed that act of kindness that she opened up to me.

So maybe Karen really was an INFJ in “guarded mode.” Or maybe she wasn’t an INFJ at all — maybe AI or wishful thinking wrote her profile. Either way, what I experienced felt like a door closing before I even knocked.

The INFJ/INTJ Dynamic

For an INTJ like me, INFJs are the magnetic opposite — the rarest of the rare. Only one or two people out of a hundred are INFJs. Same odds for my type, INTJ. I’m looking at you, Mark Zuckerberg:

When an INTJ finds an INFJ, and both are open, it’s fireworks. Daily companionship, shared depth, wordless understanding — like I had with Corrine, Tammy and Vanessa.

But when that same dynamic misfires, it burns hotter than anything else. The pain isn’t just disappointment. It’s devastation. Because you know what it could have been — and how rarely it comes along.

Most of you will never feel this exact intensity, nor the pain of watching it collapse in real time. So, if you become a user of MagneticMatch™ don’t worry — it’s statistically extremely unlikely that you will suffer this pain. That’s why I’m telling this story. To show both sides of the dynamic: the fire…and the ashes.

My drive home

I drove away angry. I wrote bitter lines about her: “store-brand vanilla,” etc.

But they weren’t true.

Those words weren’t about Karen. They were about me. My anger. My disappointment. My failure to connect.

At the root of anger lies hurt. And I felt deeply hurt. For 90 minutes, I had done everything I could to engage her, to connect with her, to persuade her to trust me. But I failed.

The truth is, Karen has spent her life doing more good than I ever will. She has helped children every day for 35 years. She was wise enough to see misalignment in a moment, and kind enough to sit with me for 90 minutes. That’s not nothing. That’s grace. And I am grateful to her.

She wasn’t being mean. She was just being Karen. She was her authentic self.

Alignment and Misalignment

“To paraphrase Churchill: Myers-Briggs is the worst form of matchmaking — except for all the others.”

But the MagneticMatch™ strategy is more than Myers-Briggs. It merely uses Myers-Briggs as a tool. Myers-Briggs is a framework for understanding personality; MagneticMatch™ is a framework for finding connection.

For me, INFJ is my magnetic match. But alignment has many dimensions, and Myers-Briggs doesn’t capture them all.

Energy was the fault line that night. Karen saw it instantly. I didn’t.

And that’s the hard truth: even when you get the match “right,” misalignment can still undo you.

The takeaway

I went home that night feeling devastated. But in the morning, I realized something larger: this isn’t just my story. It’s a cautionary tale for anyone who thinks Myers-Briggs guarantees success. It doesn’t.

MagneticMatch™ is still the best starting point I know. But misalignment in other dimensions — energy, history, interests, pace — can still leave you crushed.

Karen’s text at 8:43 p.m. was short, kind, and wise:
“We bring a very different energy to the table that doesn’t match up.”

She was right.

Eight words, sent at 8:43 p.m., told me more about misalignment than eight years of reading about Myers-Briggs ever could.

So I tell this story not to diminish her, but to honor the truth she named — and to remind you that even the rarest and most magnetic match can misfire. When it does, the pain is sharp, but the lesson is deeper: alignment matters, but it is never guaranteed.

My name is Alan Jacobson. I'm a web developer, UI designer and AI systems architect.

I have 13 patent applications pending before the United States Patent and Trademark Office. They are designed to prevent the kinds of tragedies you can read about here.

I want to license my AI systems architecture to the major LLM platforms—ChatGPT, Gemini, Claude, Llama, Co‑Pilot, Apple Intelligence—at companies like Apple, Microsoft, Google, Amazon and Facebook.

Collectively, those companies are worth $15.3 trillion. That’s trillion, with a “T” — twice the annual budget of the government of the United States. What I’m talking about is a rounding error to them.

With those funds, I intend to stand up 1,414 local news operations across the United States to restore public safety and trust.

AI will be the most powerful force the world has ever seen.

A free, robust press is the only force that can hold it accountable.

You can reach me here.

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