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.

I was speaking with a friend of mine recently who really wants to have a heart-to-heart conversation with her sister. It’s about something that is talked about in the family, yet she hasn’t found a way to let her sister know just how concerned she is. I think the narrative in her head is that her sister is giving her cues that she doesn’t want to have the conversation. She also has this fear of really offending her or hurting her feelings, yet she’s coming from a place of love and concern.

I’m not quite sure where I’m going with this conversation except for to say I do think it’s really important that we’re brave enough to initiate a hard conversation, and I think it’s important to be aware that the stakes feel really high the more you love someone. So, we need to shift the focus from the risk to the reward. The reward comes in many different forms. It can be just a physical relief. Yesterday, I noticed that when Marion and I were coming back from the beach, we were both simply lighter. We both felt this sense of relief in the connection and in the intimacy that we shared, and though she didn’t say it to me I’m guessing that she wishes we’d have this conversation some time ago.

So I’d like to end today simply by urging those of you who may have something weighing on your heart, who may have that conversation playing through their head that they’re afraid to initiate. It’s so important to be brave and so worthwhile when you’re able to find a way to initiate the conversation. No one wants to have difficult conversations, but very often it’s the most loving thing to do.

I’m not sure who needs to hear that today I thought I’d share my experience because Marion and I have been friends for 50 years yet here we are having some difficulty with those difficult conversations.

That’s all for now. Until next time, from my heart to yours.