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When Is It Okay to Leave a Relationship?

Friday, September 15, 2023

At Crucial Learning, we offer a course around Crucial Conversations—how to communicate when opinions vary, the stakes are high, and emotions run strong.

But how do you know when to disengage and walk away from a personal or professional relationship?

Years ago, I was working with a gifted facilitator and consultant. She was struggling with a professional relationship she had with one of my close colleagues. Then, as now, I love and respect both of these good people. I was sure they could work through the differences that were eating away at their relationship. One afternoon, I was on the phone with this facilitator, encouraging her to have a Crucial Conversation with our mutual colleague. To be fair, encouraging is probably too soft a word. I was bringing all my persuasive, manipulative, pressuring skills to bear and really trying hard to make her have a conversation. It wasn’t my best moment.

It was in that moment, though, that she taught me a valuable lesson. Paraphrased, she said, “Emily, I have asked myself what I really want here. What I want for me, and what I want for him, and what I want for our relationship. And the answer is, I don’t want a relationship with him.” She went on to explain the good things she wanted for herself and the good things she wanted for this colleague. She didn’t have malice or bad intent toward him. She simply understood, because of many previous well-conducted Crucial Conversations, that this relationship wasn’t serving either of their interests.

No one but you can decide when it is time to walk away from a relationship, but I will offer three questions to consider as you evaluate your path forward:


First, what do you really want—for yourself, for them, and for the relationship? Take some time considering this and try to move beyond your initial answer, whatever it is. If your initial answer is, “I want to be respected, I want them to die miserable and alone, and I want this relationship to be erased from history,” consider asking the question again. Move past the emotion. Can you, like my friend, come to a place where you can see the other person as a fallible, imperfect human being and create a space for good intent toward them?

Second, have you talked with them about it? I think all relationships deserve effort, grace, and persistence. If you have never talked about the issues or have only talked about them once or twice, consider whether you have really given it your best. If you are expecting the other person to be perfect and are disappointed that they have hurt you, consider whether you can extend grace.


And finally, is there a mutual purpose? Many years ago, I made the decision that I needed to walk away from a relationship—my marriage of eight years. For me, the relationship was unhealthy and unsustainable. So I ended my marriage with my husband and started my co-parenting relationship with the father of my children. Over the several years since, this has proven to be one of the hardest relationships of my life and the one that has taught me the most. Because every time I want to walk away from this co-parenting relationship in frustration, I am drawn back by a deep purpose—to raise my children well.

American singer Kenny Rogers offers up great wisdom in his classic song “The Gambler.” He tells us that when it comes to the cards we are dealt, we must know when to hold them and know when to fold them. But more than that, he reminds us that “every hand’s a winner, and every hand’s a loser.” I believe that is true with human relationships. Every relationship has the potential to be nourishing or toxic, safe, or destructive. All we can control is what we give to the relationship and what boundaries we draw.

About the Author

Emily Gregory is coauthor of Crucial Conversations and a Crucial Learning master trainer who has helped thousands of organizations such as Intel, Yahoo, and the Mayo Clinic achieve new levels of success. Emily holds a Medical Doctorate degree from the University of Utah and a Master of Business Administration from the Marriott School of Business at Brigham Young University.

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