The Empathy Conundrum

February 12, 2024

Hello, I'm JAIME
advisor, coach, and connection cultivator. Associate certified coach (ACC) and member of the international coaching federation (iCF) and the canadian positive psychology association (cppa).
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Empathy comes up A LOT when I work with leadership teams. Some people roll their eyes. Many dislike the concept.

Generally, I hear things like:

UGH. People are so needy these days…I don’t want to hear about their problems all the time!


Being empathetic just means that you have to listen to peoples’ excuses.


Empathy is exhausting. I have enough of my own garbage to deal with, I don’t want to carry other peoples’ stuff.

I like to get curious, and I ask, “how do you define empathy?”

They’ll say,

“it’s when you’ve walked a mile in somebody else’s shoes”


“when you know how somebody feels because you’ve been there”


“when you feel bad for somebody when they’re struggling”

Many of us have empathy all wrong, and we’re missing out.

The whole shoes, thing? Come on – how can I truly know what it’s like to be in somebody else’s situation?

I can’t possibly know.

I might have an idea, based on my intuition, lived experiences, and what I know about the other person. Let’s not be presumptuous, darlings! The good news is that we can let ourselves off the hook here– we don’t have to have “walked a mile in their shoes”. We can empathize with people that we know nothing about, who have lived lives completely different than our own. That’s why empathy is such a powerful skill for connecting with others.

And, for-the-love-of-all-things-kitten-related, I don’t need to feel bad for somebody. I don’t actually want to carry other peoples’ pain and suffering around with me. That’s an energy drain. AND, I don’t want to pity another person, I want to connect with them and act on my sincere urge to help. But I don’t want to take away their agency and power, and make them a victim of their circumstances.

I’ll offer a few thoughts that might make empathy less murky, bewildering or downright terrifying.

  • Empathy has nothing to do with agreement. I can offer connection to somebody, and validate what they’re experiencing without condoning or agreeing with their actions. I can offer an empathetic ear to a friend, even if I believe that they made a wretched decision. I can be empathetic with a team member when they drop the ball, AND still communicate expectations for their part of the project. We can offer another person this gift, even when we don’t like what they’ve been up to.
  • Empathy doesn’t have to be all or nothing. You don’t have to choose to be a non-empathetic robot, OR a blubbering mess, crying alongside your colleague. Feeling all the feels shouldn’t be your standard. In fact, I DO think that when we approach empathy this way, we CAN burn out. Let’s face it – it’s exhausting feeling our own sadness, anxiety or frustration. The trick is – how can we be empathetic AND have emotional boundaries? How can we be empathetic in a way that doesn’t take on the heavy emotion, but is rooted in concern and shared understanding?
  • Empathy doesn’t only connect you to distress or pain. Why can’t we utilize empathy and hone in on others’ joy? Think about a time when a dear friend got that fantastic promotion, or had her baby, or, got a mind-blowing deal on those vintage Chanel slingbacks? Get in on some joy, and let it energize you.
  • Empathy is a skill. You can become more empathetic if you choose to be.


  • Notice your judgements, and replace them with curiosity. If you regularly make quick assessments of people and situations, curiosity will help you better understand different perspectives.
  • Challenge your assumptions. Ask yourself, “how true is that, really?”
  • Listen deeply. Stop your brain from scrolling when somebody is speaking with you. (I know you’re smart and helpful and have something AWESOME to say next, but stop yourself.) Also, listen with all of your senses. Watch for their body language, which can clue you in on what’s happening.
  • Invite connection through sharing. Empathetic connection goes both ways. If you experience empathy, this can help you hone your skills and strengthen your commitment to being more empathetic yourself.
  • Meet people and talk to them. It’s pretty special when you gather an amazing insight from somebody who thinks differently than you do.
  • I am definitely not going to suggest that you spend more time on social media, but, if social media is your thing – try following some people who have different lived experiences than you do. This advice extends to the events you attend – get yourself into some more diverse audiences, babe!
  • You know how there’s that one person you just can’t stand at work? Or that person at the grocery store who leaves their cart in the middle of every. friggin. aisle. And who is on the same shopping circuit, so you somehow seem to meet when you go to grab YOUR shampoo. Or YOUR avocado. Or YOUR blue-ribbon baloney?? (Yeah. I love baloney. So sue me.) I challenge you to come up with one complement for that person AND ACTUALLY TELL THEM. Force yourself to give an authentic complement to somebody who gets under your skin. This strengthens our ability to see the positive, or the good. It also builds our perspective-taking ability. And seriously – when you give a thoughtful complement to another person, it just FEELS GOOD.

The other trick here, is that we must be empathetic with ourselves, before we can get good with others. If you’re a high achiever, like me, this might feel difficult to do.

Stay tuned for an upcoming post and we will dive into that!

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