I hired a shrink to 360-review my life

You are probably a jerk in some way. We all are.

But if you're anything like me, you aren't all that aware of it. You warp every situation to give yourself the most charitable interpretation. Our brains do our best to protect our egos. It's not fun to look at the darker sides of your personality.

This is a highly adaptive aspect of humanity. It enables us to get through life. But ignoring your flaws is no way to become the optimal version of yourself. At work, we all understand the value of 360 reviews. Deeply understanding how we are affecting those around us and how we can improve. Pain + reflection = progress.

A few years ago, my friend Mohnish Pabrai told me about a psychologist named Jack Skeen who had done a 360 review on his entire life. It sounded fascinating: he did a deep dive on every part of his day-to-day life. How he perceived himself. How his family and wife perceived him. His co-workers. His friends. As a result, he said that he changed his entire life.

It sounded kind of interesting, so I hired this guy, Dr. Jack Skeen.

He spoke with my closest friends, my wife, my co-workers, and we spent hours on the phone together.

He'd ask me weird uncomfortable questions like:

"Are you a good person?"

And

"What is your purpose?"

And

"Are you well liked?"

With long, awkward silences on the other end of the line to make me squirm, while he took notes.

I also did a series of multiple choice personality tests

All in all, it probably took 6-8 hours of my time, with another 10 hours of interviews across all my friends and colleagues.

What came out of it was brutal.

It was a complete picture of me...including all the horrible stuff. It was chock full of gut wrenching feedback and anonymized comments from the people who knew me best.

There were lots of positive things too, but it was a shit sandwich. Positives wrapped around the stuff nobody wants to read.

Here's a few:

"He is quite hard to work with. He is a terrible manager. He never gives positive feedback."

"He is oblivious of how he comes across to others."

"He needs to do the hard work of 'real' relationships. He can drop people when the work gets hard."

"Sometimes I feel like he's acting in social situations."

"I get the impression often that Andrew isn't happy."

As I read the report, I felt like I was going to hurl.

I immediately regretted it, and it put me into an existential tailspin. One of the key insights from the report was something I had felt but never quite put my finger on.

I scored high on the "histrionic" scale…

Something I had never heard of.

TLDR: Behaving in a histrionic manner = essentially being able to "perform" for others, craving attention, and wanting short term gratification.

Fortunately my score wasn't so high that it was a serious problem (for some people, it's a full on personality disorder and it ruins their lives), but it felt apt.

I'd noticed this in myself. That I could be dying inside, miserable, but when I needed to I could perform.

This was an incredibly valuable business skill. It helped me deeply connect with people and build positive relationships, but what I came to realize was that it was actually draining my life force. I'd arrive at a meeting I didn't want to go to and LIGHT UP, putting on my mask. Big smile. Firm handshake. Asking all the questions. Making the other person feel good. Tap dancing. Faking it.

But inside, I was secretly sad. I was being inauthentic. Something I had learned to do, for some reason, in my childhood.

I was an expert of wearing a mask, and it was making me profoundly sad.

There were a ton of other insights like this— some so personal I won't share to 20,000 people on the internet—but it all culminated in me making huge changes to my life…

I got divorced.

I completely changed my day-to-day life.

I started focusing on different things at work.

I changed the way I interacted with friends.

Stopped wearing the mask.

You name it, this psychological "Roadmap" I did with Jack Skeen rocked my world. It's been a few years now, but it's still one of the most impactful things I've ever done. It felt like 10 years of therapy in one month.

I know it sounds scary, but I highly recommend doing it yourself, if you can handle it: www.jackskeen.com

Originally published in the You are probably a jerk in some way. issue of Never Enough.