My heart still hurts a little when I think about it. It’s easier to break up when someone or something is all bad. In this case, I saw so much potential in both the person and the organization. There was an opportunity to create deep and lasting change, in a way that would have been a huge win-win. Yet, as time bent and unfolded, I noticed that our agendas were different. I didn’t have the gut-level trust and alignment that marks my professional engagements.

While I navigated the work on the outside and the turmoil on the inside, I paid attention to my reactions. I’m one of those people with a happiness default, yet I was stressed. My energy was down, my focus was fuzzy, and I was surviving instead of thriving. My rock-solid sleep went out the window.

As I tossed and turned in my bed, trying to solve the dilemmas at the forefront, this question kept popping up in my mind. Who would pay the price in the long term? My existing clients and their organizations? What about my business? Would my personal relationships suffer? What about the employees who would learn to trust me and then feel abandoned if I exited later? Who would pay the price for me hanging on too tightly to an opportunity that felt full of possibility yet drained the best parts of me?

Here’s the thing. The hardest relationships to let go of are those in which we know a person or opportunity has many good qualities. It may be a highly skilled employee who can’t interact effectively with other people. Maybe it’s a large customer who financially feeds your business while starving your staff of their oxygen. And then, of course, there’s the really nice employee who just doesn’t have the skillset to help the organization get to the next level.

Yet, even as I type, I realize that the above examples are clean. The harder examples are the ones that we can’t fully explain even to ourselves, where we feel confused, uncertain of our perceptions, wondering “is it me or is it them?” “Do I hang in there or do I walk?” “Do I give them another chance or do I fire them?” “Part of this is my problem, but even if I fix my half, it still doesn’t work.” The conceptualization is muddy and there are no clear metrics to guide our decisions.

These muddier examples leave us unsure of ourselves, even after we’ve made the call. However, we must make the call because negative situations never spontaneously heal. They generally get worse and the blast radius widens.

Here are some questions to help you make the call.

1. What would need to be different for you to get your sleep back?

2. Who else is paying the price for your indecision?

3. Are you diverting intellectual and emotional resources to this relationship instead of key goals or initiatives?

4. If you explain the situation to three wise people around you, what is their response?

5. Does the customer/employee/opportunity bring out the best in you?

6. Why do you need customers/employees/opportunities to be “all bad” before you let go of them?

I’m going to speak to your heart for a second, and to mine as well. We may not always know if we’ve made the right decision or the wrong one. Sometimes we may need to let go of understanding what has happened or ever getting the closure we want. It’s possible that we may need to accept that some relationships are matters of fit instead of conclusions about who is right and who is wrong.  If we live with our whole heart–pursuing the best in others, taking audacious risks, and stretching our capacity; we will inevitably land in situations that are not tidy and clean. Gather your people, gather your courage. Make the call. You’ve got this.