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 worms? It will just make things worse.

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

It took me many years to understand that 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 feelings of discomfort originated from my scars that bind my heart. Injuries 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?


Are you struggling in a relationship? Do you have a specific view of where your relationship should be, but don’t know how to get there?

You are stuck because your mind doesn’t see how you can improve the situation. That’s why you have a hard time taking action. You need someone to show you a new approach that will make transformation simple!

After the Relationship Audit, you will:

1. Understand how your actions are affecting the relationship.

2. Learn how simple skills will turn this relationship into a source of strength.

To book a free, 30-minute Relationship Audit, please click on the following link.

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