Empathy (not Sympathy) Grows in the Trenches
Apr 14, 2026
In Leading With A Clear Purpose, I shared about the only time in my professional career where I remember feeling completely exhausted. I was routinely working 50+ hours each week in what ended up being my last full time job and nearly as much in our new (at the time) business. I stressed that sharing that was in no way me looking for sympathy, but to emphasize the point that we can all feel at least some degree of burn out when the work we’re doing no longer seems to connect with a clear purpose.
For our purposes here, I believe it would serve us all well (me included) to differentiate sympathy and empathy. Here are the key differences I found in a quick Google search:
- Definition: Sympathy is feeling concern or compassion for someone's hardship. Empathy is the ability to truly understand and feel what another person is experiencing from their perspective.
- Perspective: Sympathy keeps the focus on your own feelings (e.g., "I feel sorry for you"). Empathy focuses on the other person's experience (e.g., "I understand your pain").
- Connection: Sympathy can feel detached or create distance, sometimes leading to superficial comfort. Empathy builds connection, intimacy, and trust.
- Action: Sympathy often results in offering pity or trying to "fix" the problem, which can feel dismissive. Empathy involves validation and active listening, sitting with the person in their emotion.
Make no mistake, Cindy and I came to terms with some of the issues Matthew was dealing with, I wasn’t very good at either. With my highly DRIVEN behavioral style, I’ve never been one to offer much pity but I most definitely look for any possible way I can jump in and fix whatever someone so much as hints may be broken. Unfortunately, I have indeed seen that be received as dismissive. When it came to Matt’s health, fixing just wasn’t within my control - and that sucked.
Before I go on, let’s address one thing so there’s no confusion later. I realize Hill’s eighth leadership attribute says “The successful leader must be in sympathy with their followers. Moreover, they must understand them and their problems.” Since I wasn’t around in 1937 when Think and Grow Rich was published, and since we can’t go back in time to ask him directly, I’m going to make the case that what he shared aligns with the idea of empathy that we’re looking at here.
Learning to understand the problems Matt would be working through as he approached adolescence required active listening over fixing. That called for a tremendous amount of patience in order to gain the deep understanding I’d need - and that was damn hard. This was a seed that required a type of relational soil that professional setbacks rarely demand. In the workplace, it’s often a matter of out-working the problem or identifying how we can move team members around to get the necessary results; family doesn’t work that way.
I won’t pretend that I learned to practice this kind of empathy overnight, I can say that this - coupled with the financial struggles we were working through at the same time - was a valuable seed that I’d find myself nurturing for years to come. We’ll dig into that in more detail later. For now, I’ll share that living those experiences allows me to show empathy in many situations today that I had no way of doing back then.
We’ll push forward by looking at how consistency can help us through whatever chaos we’re facing shortly. First, give some thought to how that eighth attribute could apply to a family challenge you’ve faced. Consider how you handled it then, what you could have done differently, and how what you’ve learned from it helps you be more empathetic today.
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