Take Your Socks Off
Oct 17, 2025
This week I had an experience where I failed.
I was walking out of a choir rehearsal with a group of friends, and I casually struck up a conversation with one of them and asked how they were doing.
Normal conversation so far.
As we walked, instead of the casual niceties of , “I’m fine” or “Great!” they actually took the time to sincerely respond and shared some current challenges that were especially difficult for them.
Now whether I was tired, or in a hurry to get to my car, I admit in that moment I wasn’t a very good listener.
In fact, I was a very bad listener.
Instead of thoughtfully listening and validating this person, I entered into problem solving mode.
In retrospect, was the LAST thing this person needed in that moment.
And yet I blundered on trying to diagnose and fix the problem instead of listening.
Soon, I regained my senses and could tell they were a bit uncomfortable and even more distressed than before.
I felt terrible.
Realizing my mistake, I switched direction and tried to salvage the moment by intentionally focusing on them, instead of their needed solutions.
Though the conversation ended well enough, it certainly didn’t end as well as it could have.
And they probably didn’t feel much better either.
It just felt awkward.
What went wrong?
The real reason? I couldn’t take my own socks off.
We all have heard the phrase, “Don’t judge a person until you’ve walked a mile in their shoes.”
The only problem is... when we try to “walk in someone else’s shoes”, we never quite get it right.
That’s because most people can’t take their own socks off.
Sure we “think” we are stepping into another person’s perspective.
We say, “I can see your point of view.”
But no matter how hard we try, we tend to still bring many of our own biases along with us.
Just like wearing our own socks while walking in another person’s shoes.
How can we get better at this?
I find when I ask two questions in particular, that it helps me take my own socks off.
If a person is sharing about an obstacle they are facing, I ask, “What’s at risk to this person if this problem is not solved?”
Then I ask an even harder question, “What’s at risk to this person if this problem is NEVER solved?”
Take, for example someone trying to lose weight.
What’s at risk to this person if this problem is not solved? Well, their jeans might continue to be tight, and their self esteem might struggle. And of course there may be several other valid insecurities.
But what about the deeper question, “What’s at risk to this person if this problem is NEVER solved?”
If they NEVER can get to their healthy goal, they might be afraid that their family’s pre-disposition to heart disease might incapacitate them in some way in the future. They won’t get to be active in their children’s lives the way they want because they might be physically diminished. They might be afraid the burden of healthcare costs will be an extreme financial burden on those they love. And maybe worst of all, they are afraid will never make it to see their children grow up.
Can you see how asking this DEEPER question completely changes how you might see a person? Would you engage with more compassion if you knew the person was not just concerned with looking good for the family picture, but rather worried about being able to stand in the picture at all?
All of a sudden walking in their shoes feels more than just a mental exercise.
If I had asked myself these questions with my friend, the conversation would have gone very differently.
I would have shown up in a completely different way.
And the connection I could have built would have been more meaningful.
So this week when you have important conversations, how can you take your own socks off?
How can you better connect to people and relate to their problems...from their perspective?
You’d be amazed at how your conversations may change.
That’s because when you learn to take your own socks off, and walk in someone else’s shoes, you tend to go the “extra mile” a lot faster.
Together.
Christian
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