
“Empathy isn’t about agreeing—okay? It’s just about putting on someone else’s shoes and walking a mile in them, and then understanding why they’re mad at us for stealing their shoes.”
--Chuck Wendig, “Damn Fine Story”
One of the most impactful—and memorable—of the many ass-chewings I received during my 33-year Army career was brilliantly delivered by a man I greatly respected, and it featured this line: “Unless you’ve walked a mile in my boots, Milano, don’t you ever criticize what we’re doing on behalf of you and your team.” I was deployed at the time, and I immaturely and wrongly suggested to this leader that his organization was not doing all it could to support us in Iraq, and I rightfully got an earful for my error. I failed to consider the myriad challenges he and his team were facing during a very turbulent time during the war, circa 2004. I vividly recall the “conversation” because of how his words made me feel at the time—small, self-centered, uninformed. I was completely lacking in empathy, and it was a hard-hitting lesson about its importance as we engage with others. To his credit, it was a sobering teaching moment for me I’ve not forgotten.
Empathy and vulnerability are deeply interconnected, shaping how we understand and relate to others on a fundamental level. Empathy, the ability to share and understand the feelings of another person, requires a level of openness that is impossible without vulnerability. When we allow ourselves to be vulnerable, we lower our defenses and open up to the experiences, pain, and joys of others. This emotional openness enables us to connect with people on a deeper level, fostering more authentic relationships. Without vulnerability, empathy risks becoming a shallow gesture, lacking the sincerity and depth needed for true human connection.
Being vulnerable allows us to not only feel empathy but also communicate it more effectively. To show empathy, we must acknowledge our own emotions, which often makes us feel exposed or uncertain. Whether it's admitting our fears, sharing personal failures, or simply saying, "I understand your pain," vulnerability brings us closer to others. This shared experience of vulnerability strengthens relationships and creates trust. It is in these moments of openness that empathy can flourish, as both parties are participating in an honest exchange of feelings and understanding.
A great example of this connection can be found in the realm of mental health support. Imagine a situation where a friend is struggling with anxiety. If the person offering support keeps their emotions guarded and merely says, "I’m sorry you feel that way," the gesture, while well-intentioned, might feel impersonal. However, if the supporter opens up and shares a personal experience of feeling anxious or overwhelmed, saying something like, "I’ve struggled with anxiety too, and I understand how hard it can be," the empathy becomes genuine and impactful. In this scenario, the supporter’s vulnerability allows their empathy to resonate more powerfully with the person in need, creating a sense of mutual understanding and comfort.
"Empathy is a choice and it's a vulnerable choice…to connect with you, I have to connect with something in myself that knows that feeling.”
--Brené Brown
Empathy and vulnerability go hand in hand, each reinforcing the other. Empathy without vulnerability lacks depth, while vulnerability without empathy can feel isolating. Together, they foster stronger, more meaningful connections that allow people to more authentically share in each other’s experiences. By embracing vulnerability, we create space for empathy to thrive, ultimately leading to deeper emotional connections and more compassionate relationships.
For more about the connection between empathy and vulnerability, I invite you to read my book, Large and In Charge No More—A Journey to Vulnerable Leadership.


