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Jay Shetty says, "if you're scared to have a hard conversation with someone you love, that means you're not that close."
There you have it, the one sentence that describes why I have had distant relationships with everyone I have loved in my life. The sentence that has left me wondering if I have ever known anything about love at all, really. I have shared this before, but it comes to me with intensified commitment this morning - I've said if my boys ever come to me and tell me they are getting married or are entering into a deeply committed relationship, my first question to them will be, "what is the hardest conversation the two of you have ever had?" I have come to believe that the capacity to have hard conversations is one of the ultimate measures of love, if not THE measure. It is no small measure - no easy one at all - especially if you've grown up without a clue as to how to have hard conversations. I grew up with things I desperately needed to say while having not a soul that I could say them to. That is quite a tension to live with: getting good at holding things in that are begging to get out. It's a tension you carry out of childhood. Into adolescent friendships, into adult friendships, into family dynamics, into dating, into engagements, and into marriage. It seems too simple in looking back and wondering why none of them worked out for me to say the answer is found in the inability to have hard conversations. Really - the answer is in conversations? It is indeed the answer. Without question. When one of your greatest skillsets in life is protecting yourself from hard conversations, hard conversations become extinct. A relationship can come together behind the spark of a million different things, but if one of the MAIN sparks isn't the capacity to have hard conversations, coming together will never equal staying together. And if it does, it will be staying together at quite a distance. Nothing protects one from hard conversations quite as effectively as isolation. Avoidance. One of the greatest sources of joy in my life these days is leading trainings or cohorts of people who at the end of them say, one way or another, "I've never been able to say that out loud to anyone before." In other words, they had found a space where they could have the hard conversation that had been begging from within them to be had. In the end, that is what this capacity to have hard conversations really is - it is a place as much as a person. It is a SAFE place. I had a conversation with a friend just last night that left me wondering, is there a greater gift in life than to be in the midst of conversations where there are no voices reminding you to NOT say this or to NOT be that? Is there a greater gift than to be in conversations where there really is no distinction between easy and hard; safety makes them feel like one in the same. When Elliott exited his graduation Saturday, I handed him an envelope with printed copies of all the messages I wrote last week about his graduation, all the hard things his graduation was stirring in my heart and mind and soul. I imagine he was reading those articles many hours later when he sent me an out of the blue two word text message, the likes of which I don't ever recall receiving out of the blue from him. "Love you," it said. "If you love someone and they say they love you, a hard conversation should bring you closer together." ~Jay Shetty Hard conversations can indeed be hard to have, but nothing is harder in life than avoiding them. Nothing is more freeing in life than discovering you no longer have to. Hard conversations can indeed be hard to have, but no meaningful relationship will survive without them.
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Robert "Keith" CartwrightI am a friend of God, a dad, a runner who never wins, but is always searching for beauty in the race. Archives
March 2026
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