A woman named Rachel sat across from me at a coffee shop on Amsterdam Avenue last winter, stirring her oat milk latte with a wooden stick she’d already splintered at both ends. She’d come to one of my coaching sessions because her partner had told her, plainly and without cruelty, that she wasn’t as empathetic as she thought she was. Rachel had been devastated. She considered empathy her defining quality. She’d built an identity around it. She told me she always knew what people were feeling, that friends came to her with their problems, that she cried during documentaries about strangers. And then she said the thing that stopped me mid-sip: “So how do I learn to be more empathetic? Because apparently I’m failing at the one thing I thought I was good at.”
That question, spoken through genuine confusion and a cracked sense of self, contained more empathic potential than all of Rachel’s years of believing she already had it mastered.
The paradox of asking
There’s a quiet paradox embedded in the question “how can I become more empathetic?” The act of asking requires you to acknowledge a gap between where you are and where you want to be. It requires you to sit with the discomfort of not knowing, of being incomplete in a way that matters. That willingness to see yourself clearly, even when the view is unflattering, is the psychological bedrock of self-awareness. And self-awareness, as it turns out, is the prerequisite that makes genuine empathy possible in the first place.
Research in educational psychology suggests that people who actively reflect on their own skills and gaps tend to show more growth over time than those who assume competence without examination. The same principle applies to emotional skills. When someone pauses long enough to ask whether they’re truly understanding another person’s experience, that pause itself is a form of emotional intelligence in action.
I’ve spent years in therapy untangling my own patterns of people-pleasing, a behavior I once confused with empathy. Growing up in a turbulent household in Connecticut, I became exceptionally skilled at reading the room. I could sense my mother’s volatility before she said a word. I could feel my father’s emotional withdrawal like a temperature drop. I thought this made me empathetic. What it actually made me was hypervigilant. There’s a difference, and it took me most of my twenties to understand it.
Why self-declared empaths often miss the mark
People who confidently announce “I’m a very empathetic person” tend to do something psychologically interesting: they confuse emotional reactivity with emotional understanding. They feel things intensely in response to other people’s pain, which is real and valid, but they often process those feelings through their own lens rather than the other person’s. A 2025 piece in Psychology Today explored how empathy and projection can become entangled, where what feels like deep understanding is actually the externalization of one’s own emotional experience onto someone else.
I know this pattern intimately because I lived it. During my first marriage, I was convinced I understood what my ex-husband was feeling at all times. I’d interpret his silence as sadness, his distraction as disinterest, his need for space as rejection. I wasn’t reading him. I was reading myself and projecting the results onto him. When he tried to tell me what he actually felt, I’d override it with my version, because my version felt so vivid and certain.
That’s the trap of unexamined empathy. When you believe you already possess it fully, you stop doing the work that real empathy demands: asking, listening, checking your assumptions, and being willing to discover that your instinctive read was wrong.
The self-awareness gap
The concept of self-empathy offers a useful framework here. To truly empathize with others, you first need the capacity to recognize and understand your own emotional states with honesty. You need to be able to say, “I’m feeling defensive right now, and that defensiveness is coloring how I’m hearing what this person is telling me.” Without that internal clarity, empathy becomes a performance, a well-intentioned one, but a performance nonetheless.
People who ask how to become more empathetic have already crossed the threshold into self-awareness. They’ve acknowledged their limitations. They’ve done the hardest part, which is admitting they might not be as good at something as they assumed. This admission creates space for actual growth.
People who claim they’re already empathetic, by contrast, have often built a wall (made of certainty) around the very trait that requires constant humility. They’re not bad people. They’re just stuck. Their confidence in their own empathy prevents them from examining it, and what goes unexamined doesn’t evolve.
I’ve written before about how people who are unhappier than they realize often don’t notice because they keep going through the motions of a life that looks fine from the outside. Something similar happens with empathy. You can go through the motions of caring, of nodding, of saying “that must be so hard,” without ever truly stepping outside your own emotional framework to inhabit someone else’s.
What genuine empathy actually requires
Real empathy is effortful. It’s a skill, not just a feeling. It requires you to temporarily set aside your own narrative and genuinely wonder what someone else’s experience feels like from the inside. That wondering is uncomfortable because it means tolerating uncertainty. You don’t get to feel sure. You don’t get to be the person who “just knows.”
My husband David models this better than anyone I know. When I come home overwhelmed after too much sensory stimulation (a packed subway, a loud café, the particular chaos of running errands in Manhattan), he doesn’t immediately try to fix it or relate it to his own experience. He asks a question. Usually something simple, like “What’s the hardest part right now?” And then he waits. He doesn’t assume he knows. He asks because he understands that my inner world, even after three years of marriage, contains rooms he hasn’t entered.
That willingness to not know, to approach someone you love as if they might still surprise you, is what separates genuine empathy from the performed version.
The cognitive bias of emotional intelligence
There’s a well-documented cognitive bias where people with limited competence in a domain tend to overestimate their ability, while people with genuine competence tend to underestimate theirs. Psychologists David Dunning and Justin Kruger identified this pattern in their research on logical reasoning and grammar, and the principle seems to apply to emotional skills as well.
The people who most loudly proclaim their empathy often have the least refined version of it. They feel strongly, yes. They care about others, certainly. But they haven’t developed the reflective skill of examining their own empathic process, of asking whether their understanding of someone else’s pain is truly about that person or filtered heavily through their own wounds and assumptions.
Meanwhile, the person sitting quietly with the question “how can I be better at this?” has already demonstrated the reflective awareness that the self-declared empath lacks. They can see themselves from the outside. They can hold two truths at once: “I care about people” and “my caring might not always translate into genuine understanding.”
This is where self-awareness becomes both a gift and a burden. When you can see your own patterns clearly, you lose the comfort of certainty. You can’t hide behind “I’m just an empathetic person” anymore. You have to reckon with the gap between intention and impact, between feeling like you understand and actually doing the work to understand.
What I’ve learned from getting it wrong
My younger sister calls me regularly from Connecticut, usually when she’s struggling with something she can’t articulate to anyone else. For years, I treated these calls as opportunities to prove my sensitivity. I’d listen for thirty seconds, then launch into analysis. I’d connect her situation to a psychology concept I’d read about. I’d offer solutions. I’d do everything except the one thing she actually needed: to feel heard without being interpreted.
This idea connects to a video I watched recently from Justin Brown called “You’re NOT Special”—it explores how believing you’re uniquely exceptional actually deepens isolation, which feels like the exact parallel to people who insist they’re already empathetic without ever examining that assumption.
She finally told me, gently, that talking to me sometimes felt like being a case study. That stung. It stung because she was right. I’d been so focused on demonstrating good listening that I’d forgotten to actually do it.
That conversation changed how I show up. Now, when she calls, I try to ask more than I explain. I try to let silence exist without filling it with insight. I try to remember that empathy isn’t about being the smartest person in an emotional room. It’s about making the other person feel like the room belongs to them.
Research on self-compassion and social attitudes suggests that how we treat ourselves during difficult moments is linked to how we show up for others. When I stopped judging myself for getting empathy wrong and instead got curious about why I defaulted to analysis over presence, everything shifted. Self-compassion created the internal safety I needed to actually examine my behavior without collapsing into shame.
The question is the answer
If you’re reading this and wondering whether you’re truly empathetic, that wondering is the point. The question itself reveals a mind that can observe its own processes, a mind willing to sit with the possibility of falling short. That’s self-awareness. And self-awareness is the soil in which empathy grows.
The people who never ask the question aren’t necessarily unkind. Many of them care deeply. But their empathy has calcified into an identity rather than remaining a practice. And anything that becomes an identity stops being interrogated. It becomes something to defend rather than something to refine.
I still catch myself projecting, still notice moments where I’m responding to my version of someone’s pain rather than theirs. The difference is that now I notice. Now I ask. Now I treat empathy as something I practice daily, like meditation or yoga, rather than something I achieved once and can stop working at.
Rachel, the woman from the coffee shop, eventually stopped mourning the loss of her empathetic identity and started building a more honest version of it. The last time we spoke, she told me she’d started asking her partner a simple question at the end of each day: “Did I understand you today?” Some days the answer was yes. Some days it wasn’t. But she kept asking.
That’s what empathy looks like when it’s real. Humble. Ongoing. Full of questions. And always, always willing to be told it missed the mark.
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