I’ve probably interviewed and hired more designers than most people ever will.

When I ran my agency SuperFriendly, I was the only full-time employee for the first 9 years (of 10). But at our peak, we had about 70 contractors working across 20 accounts.

To run a network-based business like that, your network has to be much larger than what you actively use. We operated at around 10% capacity, which meant we had roughly 700 people in the network.

Until the last couple of years, I personally interviewed every single one of them. Not for projects. For the network. I’d talk to folks months or even years before a role opened up, so when the time came, I wasn’t scrambling; I already had the right person in mind.

When you interview that many people, you end up having to fire some too.

It sucks. I hate doing it. I’m sure the people I’ve fired hatedd being fired more than I hated firing them.

I’ve fired a little over a dozen people in my career. In every single case, I’ve noticed a pattern.

They always told me that it was my fault that they weren’t able to do their job.

That I was a bad manager. That I couldn’t make up my mind. That I was too closed-minded. Or too open-minded. That I had no business running a company. That I had no talent. That I couldn’t spot talent. That I “constantly move the goalposts.” That I’d never make it.

With hindsight, I get it. It’s a textbook defense mechanism called externalization, the brain’s way of protecting the ego. Getting fired induces shame, and blaming someone else is a way to deflect it. I try not to take it personally. It’s just people trying to hold on to their dignity in a difficult moment.

But dang if it doesn’t sit with me, sometimes even decades later. I remember the conversations vividly. Worse, I’ve started to believe some of it.

From a young age, I’ve known that I was different. I’m an INTJ, less than 2% of the population. A 5w4, also about 2% of the population. I’m also an Aquarius, which isn’t a rare astrological type, but Aquarians thrive on feeling rare. I’m Seventh-day Adventist, which only comprises less than 0.3% of the world’s population. I’m half Filipino, half Pakistani; I don’t have the stats, but I don’t meet a lot of people like me.

Whichever slice you pick, it’s a small group.

Which gets pretty lonely.

It also means most people generally don’t get me, and, work-wise, they don’t really know how to work with me. Early in my career, this wasn’t a problem. I just did what my bosses and managers told me. But I’m in charge at my companies, and, because of the power dynamic, the people I hire have an incentive to understand how to work with me when I’m not conforming. I try to balance out that dynamic. I encourage people to be themselves. I writing guides on how to work with me. But it’s not easy.

Over the years, I’ve let that morph into meaning that I’m not easy. That I’m too much. I’ve internalized that I’m difficult. I’ve resigned that no one can help me or contribute to whatever I’m doing because it’s too cryptic to understand for anyone other than me. If someone doesn’t follow my direction—whether that’s a direct report at work, my kids, or a teammate on the basketball court—I blame myself. I figure I’m not being clear. The running feedback I get is that I “expect everyone to read my mind.”

So, I over-communicate. I always have. It’s served me well as an individual contributor, a teammate, a subordinate, and a service provider. But it’s also a trauma skill. I’m the guy who will send you three blogs posts I wrote about the topic five years ago when you ask a simple question. (Like Say, Do, Say; Underpromise, Overdeliver; and The Crystal Email.)

When collaborations are smooth, I forget all this. But when there’s friction, my insecurities rush back. What am I not being clear enough about? What am I missing? What haven’t I tried? How can I say this differently to get them to get it?

Over the last year, ChatGPT has become one of my favorite tools to help me better articulate what I’m trying to say. It proofreads every article I write, and often improves them by saying what I mean with a fraction the words. (This article used to be 24% longer. You’re welcome.)

When I was recently struggling to align with someone, I asked it for help.

I expected edits. Instead, it surprised me by pushing back.

“You’re communicating just fine,” it said.

I blinked. That’s new.

I asked why there was a disconnect. ChatGPT replied: “The other person is being dense.”

Excuse me?

I was used to bending. Contorting. Trying harder. My fault, right?

I pushed back now.

“Am I asking them to read my mind?”

“Nope,” ChatGPT replied. “They need to do it correctly.”

“How do they know what ‘correctly’ is?” I challenged.

“You already established that in the original brief.”

Huh.

“But maybe they still don’t have enough context,” I admitted. “I’m worried that not helping them out more here leaves them on an island. This is touching a lot of nerves for me. I’ve received feedback in the past from people who work for me along the lines of, ‘You’re the most difficult stakeholder I’ve ever had.’”

As if cunningly waiting to strike, ChatGPT moved in for the final blow.