Crucial Skills®

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Crucial Conversations for Mastering Dialogue

When Is It Okay to Leave a Relationship?

Dear Crucial Skills,

Can walking away from a personal or professional relationship ever be the best solution?

One Foot Out the Door

Dear One Foot Out the Door,


Absolutely, unequivocally yes. No one should stay in a relationship—personal or professional—that is abusive or toxic. Don’t fool yourself. Walking away from a relationship is not the easiest solution, but in some cases it is absolutely the best solution. Nothing we teach in Crucial Conversations about repairing damaged relationships or taking responsibility for your own role in a situation should be construed as an endorsement of staying in a relationship no matter the cost.

That is the answer to your question in the clearest terms I can use. But, to avoid writing the shortest Q&A in the history of Crucial Skills, allow me to answer a question you didn’t ask: How do I know when to 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. One afternoon, I was on the phone with this facilitator, encouraging her to have a Crucial Conversation with our mutual colleague. I was sure they could work through the differences that were eating away at their relationship. To be fair, encouraging is probably much 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. Paraphrasing, 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 for him. She simply understood, because of many previous well-held 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.

What do you really want—for yourself, for them, and for the relationship? Take some time with this and try to move past 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?

Have you talked 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.

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 in frustration from this co-parenting relationship, I am drawn back by a deep purpose—to raise my children well.

As I think about your question, I wish I knew more about your situation. I wish I knew you. I suspect there is a wealth of pain and heartache that roils just below the surface of your very straightforward and rational question. I also wish I could know whether you’re a fan of the American singer Kenny Rogers, who offers up great wisdom for your question 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.

I wish you well, my friend, on this road you are walking.


You can learn more insights and skills like this in Crucial Conversations for Mastering Dialogue

16 thoughts on “When Is It Okay to Leave a Relationship?”

  1. julie hansen

    Thoughtful, thought provoking and compassionate, thank you —

  2. Jennifer

    Work related leaving-I have changed positions when my supervisor developed memory issues and lost every document I gave them for signature. When they left them at home on the kitchen counter and this person’s manager refused to take action. It was extremely frustrating to do my job and my supervisors job without any reprieve.
    Personal-I left my first marriage after my spouse installed a corn burning furnace and no way to replenish the fuel in it. With 2 small babies and no heat in the middle of winter it created an atmosphere of frustration and anger. He also never asked my opinion on input when purchasing large farm equipment. I am very much a flighter NOT a fighter and that is learned behavior from very early in my life. I had a very abusive brother.

  3. Chastity Daukas

    This hit home as I’ve just had a similar experience professionally and walked away from a role I thought I would be in for the remainder of my career. It was an unexpected experience and most definitely unhealthy. I appreciate the realness of this article. Thanks for sharing.

  4. John M. Wurz Sr.

    aAt a time I decided to walk away from a long time relationship; I found my self reading this! Thank you for your affirmation supporting my decision to walk away once and for all.

  5. Jan Bridges

    I have been in this situation and agonised for years about leaving a relationship, until on day, someone said to me, “have you considered that you two being together is preventing both of you from growing?” It realy resonated with me and I viewd the situation differently after that. Yes I did leave – know when to fold them!

  6. Heather Quinlan

    Upon realizing that a friend relationship was toxic, I walked away and never looked back. There were times when I missed this person, but then I would reflect on how manipulated I had felt during our relationship. I realized then that I had to validate and accept that it is okay to move on, sometimes and with some people, that is the best choice.

  7. Melissa Engelhard

    While working as a contractor for the government, there were multiple reasons for leaving my job. 1. They were having me charge to a project that I had never worked on. That is an ethical/legal violation. 2. I sat for almost six months without being able to work because my boss would not give me work. 3. When I reported these issues to my company, they said it was all okay and to keep charging to the wrong codes.

    I found another job and I have never looked back. I will not work for a company or in a job that goes against my ethics. So yes. It’s okay to leave.

  8. Rick Olsen

    I walked away from a long time mentor after this person got deeply engaged in conspiracy theories that made the relationship difficult because it would have narrowed to 1 or 2 very superficial topics and required me to dodge or seem to agree with many other topics. I said something to the effect of “You are going down a path I can’t walk with you. You’ve meant so much to me. I wish you the best. This will be my last correspondence.” There was vitriol in the response but then it was done. Sad. But far more helpful than managing what it had become.

  9. Sarah

    I walked away from 2 long-term friendships. One was because the relationship dynamic of her talking, me listening no longer worked for me. My attempts to shift the dynamic were met with stubbornness and even hostility. In the end, my friend acted especially selfish and even a bit mean-spirited. I felt bad about ending the friendship, but I also recognized that my friend is who she is, and absent any change or accountability on her part, the relationship no longer held value for me.

    The second friendship was with a person who got way into drugs; crystal methamphetamine to be precise. I saw her go from a sweet, gentle young woman to a user in every sense of the word, making excuses and offering false promises. At the time, my parents were becoming increasingly frail. I realized that I could either help my friend or help my parents, but I couldn’t help both. I chose my parents.

  10. Robin

    Dear Feet,

    You have two I assume 🙂 One outside and one inside.

    Another question to ponder… does this model your approach to intimate relationships when they get difficult? If so, forever walking away from people, rather than learning to have relationships, is a strategy but probably not the best one for you in the long run.

    Most people in today’s age just leave rather then learn how to love the other person for who they are and determine what level of intimacy is healthy with the other person. For example, if this is a friend, some friends are meant to be just movie/bowling/pool/painting/card night, etc. friends. No need to share much more in common than that because even though you may share a few interests you may not have much more in common (political views, religious views, whatnot) and deeper conversations may not be possible. Other friends you may connect with deeply on many levels and then some, you may trust completely.

    If this is a marriage partner, much more is at stake. In today’s world people often just leave, thinking that this will be easier. The divorce rate alone establishes this fact. When we treat marriage like it is disposable – and have no children – usually only the adults have to cope. However expecting children to cope with the changes divorce brings carries a greater impact.

    Regardless, focusing on our partner’s best qualities, and helping each other grow into better partners, parents, etc. is an art that seems lost to our society today. Instead, we often (me included) expect people to change to suit us, rather than changing ourselves to enhance the relationship, whether it be our expectations, our perspective, behavior, or thoughts.

    Co-parenting in marriage can be considerably challenging because we have to find common ground together. This (for me) is where the rubber meets the road. My spouse and I parent very differently. The majority of conflicts in our marriage can be attributed to this issue and our ability to negotiate solutions that work best for the children and then present a united front. This requires a great deal of discussion and compromise from both of us.

    From your brief question there is not enough information (for me) to know how to best respond. If you’re married (esp. with small children) and have a pattern of ending relationships when they get difficult, then as long as no physical abuse is involved (or verbal and I don’t mean the occasional tiff) then I’d consider staying and focusing on how to love someone else exactly as they are, and to bring out the best in them, yourself, and the marriage. You can leave, but there is the likely possibility that you will select a similar partner and repeat the same patterns.

    If it’s a friend relationship and is toxic (your friend abuses drugs, alcohol, and puts your safety at risk) this is an easy decision – leave.

    Whatever you choose, I hope this helped and I wish you peace.

  11. Trudy

    Leaving a toxic relationship with an adult that is not my child has been pretty easy for me to figure out and do, and not look back. With a child, it is just agony. I have an adult son who has an explosive disorder that never gets better, despite counseling that both my ex and I have paid for. Eventually, after years of relentless abuse of me, I cut off contact. It hurts forever. There is no bridge back, because now, he is too hurt by my rejection to even respond to emailed questions like, “might it be time for us to be in communication again?” or even, “some mail arrived for you here.”

    It seems whenever this topic of leaving a relationship comes up, we are not picturing parents and children; typically, we’re picturing partners or friends or colleagues. I’ve felt lost on how to make peace with myself when the heartbreak of estrangement from a child I love deeply was the best of awful options.

  12. Sharon H

    I spent 17 years in a position that I thought I would retire from – of course there were plenty of ups and downs over that time, but I generally loved what I did. I developed a process when things were difficult where I would make a list of what I liked about my job and what I disliked. I would take the dislike list and identify what on that list I could control or change and what I could not control or change. I would look at the things I could not control or change and decide what were things I could live with, and what were things I could not live with. Then I’d compare what I couldn’t live with to the things I liked about my job, and using many of the Crucial Conversations principles on myself, decide what was more important. Typically, I could overcome the unlivable things by mentally giving them less power and less importance; for instance just letting difficult people or situations be what they were and control my reaction to them. Regrettably, things evolved over time to a point where no matter how many things I liked about my job they no longer could compensate for the things I had no control over and could not change, and they were affecting my mental and physical health. Sometimes power dynamics are such that holding a Crucial Conversation isn’t an option, but you can still use the principles to resolve the issues by being the reasonable and rational part of the equation. I found another position, respectfully resigned and stayed on the high road. I am a much happier, healthier person now, even though it means putting off retirement for a few extra years.

    (PS – I love Emily’s reference to Kenny Rogers “The Gambler” – words to live by!)

  13. k w

    I’ve been married and divorced (now happily married for 30+ years!) and I’ve left a lot of jobs for different reasons. Although each departure was bittersweet at best, none were particularly tough, even when it wasn’t my choice.
    But in the past year, I severed a friendship with someone who I’ve known and was close to for 25 years! It was so difficult! Just deciding to do it was so tough and painful for me.
    My friend started changing several years before I ended our relationship. Her views, especially those associated with politics, ethics, violence in the world, began to shift and it was all she could talk about. If I had a different view, she was argumentative or demeaning to me. I found myself exhausted and frustrated after conversations. What used to be excellent flow of chatter back and forth became dominated by “her topics”. I didn’t know how to navigate these waters and I told her that I was uncomfortable, but she wouldn’t let up.
    I kept hoping things would change (back to how they used to be) but they didn’t. Finally, when I found myself feeling agitated and anxious before conversations, I decided I needed to take better care of myself and I shared that I needed a break. That ended the relationship. It was sad. I was deeply saddened as friendships don’t come easily for me, but I was also relieved.
    I’ve learned that we all change (I know I changed during all of these years) and sometimes people will come and go in my life. I learned I have to take care of myself and this includes my mental health. After a few months, I felt better, less burdened. And on rare occasions, I can sometimes think of the early years of this friendship and smile.

  14. Erika

    This is such an important topic to discuss. I’m a healthcare executive who has managed many people throughout my career. In the industry, we often talk about the “revolving door” that exists because people will not address conflict in healthy ways. However, we rarely address the silent group that perseveres in the face of adversity but often does not know when to leave.

    Last week I resigned from my position. I knew after three months that there would be serious relationship problems, but I tend to be one of those people that will stay loyal through anything, even when I should not. It took nearly two years for me to finally come to terms with the reality that the CEO and I have fundamental philosophical differences about leadership and management that cannot be resolved. We had an open conversation about this and we will part peacefully with goodwill for each other.

    As leaders, we need to communicate that endings are not always a bad thing.

  15. Denise

    I think we have all been in those situations, personally and professionally. Personally, I have walked away from a couple of friendships that seemed one-sided or toxic. And maybe I’m a bit callous in my old age but once I decided I was done, I had no regrets and I didn’t/don’t miss those people I’m also one that lets things go way past what other people will allow. I do have several very long-term friends whom I cherish and adore.

    I’ve also had the issue at work where I had to cut people off of the friendship zone or people in other departments were toxic. I just keep things professional and have readjusted some relationships from friend to colleague. It did cost me a career path the I loved but another one was presented. It all seems to work out and my mental health is worth every bit of the changes and decisions that have been made.

  16. Steven Carter

    Such an important question to explore! Looking forward to reading the insights shared in this post. Relationships can be complex, and understanding when it’s appropriate to leave is crucial for personal growth and well-being.

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