The thing that makes empathy a tricky concept for driven leaders is that it seems entirely driven by someone else’s needs.

“Why should I bother empathizing here? It’s not me that’s struggling with the feeling. It’s them. And if I’m not struggling, then it’s possible for them not to struggle either. They just need to figure this out.”

You can’t really take on your own transformation “for other people”. It sounds noble and high-minded, but the moment you really come into conflict with the unknown, your fear, and your ego’s protective response, you’ll be right back to square one.

So here’s the simplest way to flip the script and get back on track:

Assertion #1: Your inability to empathize with someone over a particular emotional state is a reflection of your own inability to be with that state in yourself.

I never used to have time for people feeling sad, beyond a cursory “I’m really sorry”, and then moving us back towards the task at hand.

If I read what I’ve written above, I would shake my head condescendingly and say “Not me. I just don’t really get sad.”

This was a lovely fiction.

It didn’t occur to me like fiction, because I genuinely had no capacity to see or feel my underlying sadness.

So on some level, my fiction was true. I literally did not feel sad. And so, unsurprisingly, I also had no capacity to empathize with someone else who did.

Assertion #2: The places where your empathy is lacking represent places where you are not fully-expressed and not fully free.

Assertion #3: As a human, we feel all emotions — no baby comes out of the womb “just not feeling sad”.

Not feeling sad is simply an adaptive trait you learned. Like all adaptive traits, it served you to a point, but probably leaves you caught in its impact now.

It got you here, but now keeps you stuck here.

So, I could take on feeling sad, transformationally, so that I can better hold, empathize and lead other people to places that might lead to this emotion arising. That’s a step in the right direction.

The lack of our own freedom is the part I think is most important.

The extent to which you are unable and unwilling to feel sadness, is translated into places, people and circumstances where you must hold yourself in check, and/or outright avoid.

Back over here to me, those situations that might make people feel sad are places that I didn’t want to be. Over time, I’d avoid them more and more. I’d avoid the kind of people that express their sadness.

Slowly, like a muscle atrophying from a lack of use, my ability to be with sadness withers. I don’t cry at my parents’ funerals. I don’t work with people that express an emotional range that includes sadness. Over time, I start to do things like leave a party quietly and quickly, so that I don’t even have to be with saying goodbye.

We’re left certain that we just don’t feel sad, and yet our entire life becomes dictated by ensuring its absence.

You can take on all kinds of projects, take vacations, meet people, do neat things and so on. But what you can’t see is that, unconsciously, you are continually steering your life so as to avoid the feelings and experiences you cannot be with.

All of this is opened up by you beginning to study the art of empathy.

Let it be your guide, and learn to start setting yourself free.