How To Know When To Leave a Relationship

Kim Kimball
4 min readNov 23, 2021


A friend reached out and asked me a question the other day: “Do you think when you’re in a partnership, you should do anything for them and stand by them ‘no matter what’? Or do you believe that everyone needs personal boundaries and if crossed the relationship needs to end?”

The deeper question here is really, “Should I stay or should I go”?

This question of “unconditional acceptance” as I like to call it crops up in so many places, not just our romantic partnerships: in friendships, jobs/careers, and in our families.

How much do I tolerate? When should I stick it out? When is enough enough and I should leave? Am I leaving too soon and things would have turned around if I had stayed? Am I wasting my time and need to let go of something that has run its course?

These are just a few of the questions we may find ourselves asking.

My answer to these very valid questions may surprise you:

I don’t know what you should do.

Someone else never has the correct answers for your life.

I’m not on a pedestal above you, but rather, walking beside you holding up a mirror so you can see yourself clearly and find your own answers within.

It’s so tempting to turn to a source outside of ourselves and look for someone to make a decision for us, to take away the heavy lifting of discerning our truth.

Finding out what is your deep truth of whether you should stay or go in a relationship is a skill set that can be sharpened and learned. It is also something that can be facilitated incredibly well in a coaching relationship, because we often have difficulty sorting through and processing our internal experiences, emotions, and thoughts. Having someone who is trained to do just that can help you to see yourself and your truth more clearly.

I don’t believe in “unconditional acceptance”, that no matter what someone does or how they behave, that I will stay and continue relationship with that person (married or not). I do, however, believe in unconditional love.

Sometimes, unconditionally loving means leaving, and sometimes it means staying.

Maintaining relationship with me is a privilege, not a right. In order to maintain relationship with me, there must be mutual respect, love, and trust.

These conversations are incredibly nuanced and hold many paradoxes.

There are many occasions where I believe that people can give up too soon, and that things would have resolved if they had both done their own internal work.

And there are many situations where the hurt runs too deep and despite one person wanting to make amends, the other person simply doesn’t have the capacity to do so.

There is an entire spectrum at play with loads of nuance that is entirely case specific and dependent on not only each individual person’s wants, needs, and desires, but also the dynamic of the couple. (I think it’s important to state here that I’m not speaking about emotionally or physically abusive relationships here)

Although I cannot give you the answers, I can ask you powerful questions that will help you start peeling back the layers to get to your sacred truth of whether you should stay or go in your relationship.

Questions To Ask Yourself When You’re Contemplating Leaving A Relationship:

  1. If I stay, what would be my reasons for staying?
  2. If I go, what would be my reasons for going?
  3. What is my role in our relationship, and how am I contributing to the current relationship dynamic? Have I taken radical responsibility for it?
  4. If there was harm done by myself or by another, has repair been made? Have I accepted that repair (from myself or the other?) Do I feel that the repair attempt was genuine and there have been noticeable changes since?
  5. What would I need to feel good in this relationship? Do I think the other person is capable of giving that to me? What evidence do I have that they are or aren’t?
  6. What do I need to do to have peace that I’ve done all that I can and taken personal responsibility for what I’m bringing into our relationship?
  7. What Stories/meaning do I have about leaving? What Stories/meaning do I have about staying? How are those Stories influencing my current actions and thoughts?
  8. Is there active participation from both parties in working on themselves and the relationship in a way that feels good to you?
  9. What would be most consistent with my values right now?
  10. How do I know when I know something? *hat tip to Madison Morrigan for this question
  11. What signals are my body sending me that I perhaps haven’t picked up on or have been trying to ignore? If my body could speak, what would it be saying?
  12. What do you really, really want?

Finding YOUR truth instead of outsourcing answers brings deep peace, self-trust, and equips you for more ease in making tough decisions in the future.

If you find yourself in a season of asking yourself if you should stay or go (in a partnership, job, career, or friendship) and would like someone to hold up a mirror so you can see yourself more clearly, book a complimentary, no obligation 60 minute coaching session with me here. I’d be honored to support you.



Kim Kimball

Women's Leadership Coach helping women leaders, coaches, + entrepreneurs stop people pleasing + perfectionism in their biz, life, + relationships.