Ep 98 Initiating Difficult Conversations

August 16, 2023

Good morning from Montauk. What’s on my mind this morning is difficult conversations and here’s why. I was on the beach yesterday with my best friend, Marion, and I could tell that something was on her mind. She finally said to me, “there’s something I want to talk to you about.” It was very difficult for her to broach the subject. While I don’t need to go into the details of it, I will say that at the end of the conversation we both walked away with a Hmm, we really saw things differently on that one, and we were more committed than ever to keeping the line of communication open.

The whole experience got me thinking about risk-reward and how strange it is that the more you love someone – the more hurt you are, the more you care, the more fear you have about offending them – the more difficult it is to initiate the conversation. I think all of us tend to focus a little bit too much on the risk part of the risk-reward equation. The reward of being honest and putting on your big girl pants to initiate the conversation is the gift that keeps on giving. It’s what consolidates a relationship. It is oftentimes a time to cry, to connect. It’s an affirmation of love, yet we have a hard time initiating those conversations.

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