On Breaking Up

July 20, 2015

How do you know when it’s the right time to break up with someone?

The confusion around this question has caused me lots of frustration.

As a single guy, it stopped me from really loving someone deeply, because I was afraid of getting stuck.

In relationships, my uncertainty led to anxiety about how to deal with times when I felt disconnected. Was it a sign we should break up? How would I know when enough is enough?

After years of inner struggle, I started to gain clarity. The pieces started to fit and pretty soon, I felt I could make sense of this seemingly impossible question. Today, I feel at peace. I see my relationship struggles more for what they are and I don’t spend as much time questioning whether I should be in or out of my relationship. It’s such a relief.

These are my biggest insights on the subject of breaking up.

You May Not Be Following Your Truth

One of the hardest pills to swallow was seeing that when I felt like ending the relationship it was almost always because I wasn’t being true to myself. For me, following my truth means living my life in a way that feels aligned with who I am. It means making my interests a priority and not selling out for the sake of pleasing others.

When I don’t live this way, I feel trapped. I begin to panic and my relationship takes the blame. It’s as if I’m in an ocean, I can’t swim and I’m gasping for air. Nothing else matters but breathing, or in this case, feeling free.

For example, I have a need to be alone and write. Sometimes my weeks get so busy that I feel like I’ve neglected my writing, and it starts to take a toll on my mental health. I feel frustrated and blame the relationship for not “letting me” write.

If I was single, I’d have more time to myself.
I would take time off but Paula won’t like that.
Being married is too much work.

If I believe those stories, then my only option is to consider ending the relationship, since it’s clearly holding me back. What I discovered after going through this over and over again is my desire to end the relationship was a desperate gasp for air, not a sign that the relationship should end.

Now, I recognize my desire to end the relationship as a sign I’m neglecting myself. When these negative thoughts arise I return to the truth of who I am and what I want. Maybe I go to my calendar and plan a half day by myself, maybe I schedule a night out with friends, maybe I take a week off for a writing retreat.

Are there things I want and ways I want to live that my partner wouldn’t be comfortable with? Yes, and I’ve found that the majority of the time, I can meet my needs in a way that works for both of us, but only if I’m willing to share vulnerably and not blame her for the way I feel.

Breaking Up Happens Gradually

When I really understood this idea of following my truth and not blaming the relationship, it helped me in times of upset, but philosophically it led me back to the original question.

How do I know when it’s time to break up with someone?

Clearly, not every relationship should last, so if I’m following my truth and not blaming the relationship, will there ever come a time when the relationship should end? How will I know?

What I noticed when I pondered this was it didn’t matter. If my partner and I were both committed to living our truth and our values weren’t aligned, we would naturally grow apart. The break up would ultimately be something we acknowledge is already there.

That made sense, because healthy break ups seemed to already operate this way. Two people would naturally drift apart as they lived what was true for them. As I thought more about this, I realized that if we are really taking care of ourselves, the concept of breaking up is something that we notice has already happened, not something we force upon the future.

This was a huge realization for me, because I stopped having to worry about making a decision to break up or not. All I needed to do was live a life that felt good to me, encourage my partner to do the same, and if we weren’t meant to be together, we would notice.

This sounds simple of course, but it’s not easy. We get attached to being with people so it’s hard to be ok with a relationship ending. There is an important value here that makes this all possible.

Happiness > Longevity

For most of modern history, we’ve measured the success of a relationship in longevity. We hear about a 50-year marriage and think “that’s wonderful”, then hear about a divorce after three years and think “oh, that’s too bad”. It doesn’t take us long to see that the default setting for a long marriage isn’t happiness. That’s not to say that there aren’t wonderful marriages that last a lifetime, there are, but the connection between how long you stay married and how happy you are is simply an old story that we cling to.

The reason I bring this up is it was really important for me to not be afraid of divorce. In fact, being afraid to break up with my wife was one of the main factors that kept me from living my truth.

Instead of trying to keep our marriage together at all costs, we were better served by understanding that our happiness was more important than how many years we accumulated though a marriage punch clock. It turns out focusing on your own happiness is also a great way to be happy in your relationship, which lead me to the last point.

My Happiness Is Up To Me

So often we break up with someone because we aren’t happy, then we become single and the truth is we’re not really any happier, and now we have no one to blame. Then we get into another relationship and repeat the same pattern over and over and over again.

There is one phrase I love, and I say it to myself whenever I’m thinking that changing my situation will make me happier.

Wherever you go, there you are.

It doesn’t matter where I go, whom I’m with or what my circumstances are, at the end of the day, my happiness is up to me, and blaming my relationship for that will only make it worse.

So often we break up with someone as a deluded attempt to fix what’s really going on inside of us. It doesn’t have to be that way. Separating in love may not be something we hear about in country songs, but it’s something that happens every day among people who would rather not carry resentment and bitterness into their next relationship.

The Freedom of Not Knowing My Future

Do I know if Paula and I will be together in ten years? I don’t. In fact, I have no idea what my relationship will look like. We could grow apart or one of us might die. We never know what the future holds.

Resting in the truth of this allows me to do something wonderful. It allows me to experience my relationship here and now. If I have worries about the future, I can simply return to the reality of my present situation. Am I following my truth? Am I selling myself out for the sake of what I think Paula wants? Am I doing my best to be happy, independent of what’s going on for her? Can I really know that breaking up with her will give me the freedom I desire?

Being present and able to enjoy my relationship in this moment is the greatest gift these questions have given me, and I hope they do the same for you.


This is part 3 of a 4-part collection entitled The Roller Coaster Ride of Marriage

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