Looking forward to an uncomfortable conversation

Last week, I went to a Connect and Learn where one of the VEL ambassadors talked about her inspiring journey from working for her dad, through becoming a teacher, to taking a big step of faith into entrepreneurship. Along the way, Elizabeth shared a lot of stories that centered on walking through discomfort and could be best summarized by the following quote

“A person’s success in life can usually be measured by the number of uncomfortable conversations he or she is willing to have.” – Tim Ferriss

This quote made me reflect on why it’s been so difficult for me to have uncomfortable conversations. 

It came down to logic. If I understood something, I’d talk about it. If I didn’t understand something, because it was driven by feelings I was afraid that the conversation would expose my weakness. We as men don’t want to be perceived as weak. It’s much easier for us to go to our cave and wait it out until the feeling passes … then we can go back to what we understand. 

The most basic example for me was my unhappiness in relationships. I was afraid to talk about what made me unhappy, because I didn’t think there would be a solution. Why open up a can of warms? It will just make the things worse.

It’s funny how I always understood that in order to become a better runner, I knew that I had to do a lot of uncomfortable runs. 

Yet it took me many years to understand that in order to be a better man, I must challenge myself to have more uncomfortable conversations. That’s how I learned that feelings are information and if I don’t clarify what they tell me, I’m missing out on a ton of valuable insights. 

As I have these uncomfortable conversations, I realize that the the feelings of discomfort originated from my scars. Scars that bind my heart. Scars that lose their grip the more I open up and realize how healing it is to get things off my chest.

What uncomfortable conversations are you avoiding? How would you benefit from having that uncomfortable conversation?


Don’t know how to get started? Please e-mail marek@cs1mindset.com for a complementary 30 minute coaching call that will help you experience the transformative power of an uncomfortable conversation.

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