Sip Sessions are a powerful experience for all of those fortunate enough to attend them. I’ve been to many Sips and it was an incredible honor to speak at one.

The beauty of a Sip Session is that everything is held in an experimental context. There is no right or wrong way to approach it—they simply exist to provoke and inspire those in the room to think about concepts in a multi-dimensional way.


My Sip covered the broad and encompassing topic of empathy—and how we do (or don’t) show it in our daily lives. How do we lead with empathy is a question I’ve often asked myself. As a publisher of non-fiction books and memoir, I must dig deep on a daily basis to show empathy toward the person and the story I am being entrusted with. To decide you want to write a book and tell your story, requires you to be raw and vulnerable in an oftentimes exposing way. In those settings you must be met with a kind and empathic person on the other side to truly feel comfortable in sharing your story.

I am not an expert on empathy. I’ve never taken a class on it and admittedly so, while I’ve watched all of Brene Brown’s videos, if I’ve never actually read her books (I know!).


But what I do know is that Empathy is a fundamental backbone of good leadership and even general interpersonal skills and interactions with people.

As I begun writing my memoir, House on Fire (coming Fall 2020), after having coached dozens of others through the process, I saw a theme. The theme I wanted to explore is the relationship between Judgement and Empathy.


That is what I brought to the table for discussion at September’s Sip.

How do we lead with empathy?
How is it different than sympathy?
And how do these two things impact our daily communications and interactions with those around us?

We began the evening discussing the nuanced differences between empathy and sympathy. We went around the room as brave individuals shared their beliefs on the differences between these two powerful, yet unequal emotions.


Unanimously we could see using statements such as, “At least you…” in reaction to someone’s strife or pain are often unhelpful and are not rooted in empathy. For example, “I had a miscarraige.” The sympathetic response is “Well, at least you have a healthy and happy four year old.” The empathetic response would be to just sit and listen and be “in it” with that person in the moment. You don’t need to have the right answers.


I witnessed “ah hah” moments among the participants.

Multiple times over the night we broke up into small groups to answer tough questions like—

  • What is ONE situation where you could have benefited from someone showing you empathy? Or when you felt someone was judging you. Dig deep.
  • What is ONE situation where you were required to bring empathy to a conversation? How did it make you feel?

I watched in awe as people took the exercise to heart and they did dig deep. I watched as people began to open up about areas of their life where they hadn’t experienced empathy before and how different things could have been, had they been show the simple act of an empathetic listening ear not wrapped in judgement.


There were amazing deep conversations and takeaways for how we can bring even the littlest bit of empathy into our daily lives and slowly work toward leading in this way.


Photography and video by Mike Marques of Arbor Light Studio

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