How do you know when to leave?

A Note From Now

I wrote this in 2023, when leaving was still one of the central ways I understood change.

At the time, I had recently mad

e several enormous decisions about my own life, and I was trying to understand how we know when something has truly run its course. I still believe much of what I wrote here. But I understand the question a little differently now.

Not every feeling of discomfort means we should leave. And leaving isn't always the brave choice any more than staying is. Sometimes the work is changing the circumstances. Sometimes it's changing ourselves. Sometimes it's waiting long enough to understand what we're actually being asked to do.

What I still believe is that there are moments when we begin to recognize that something no longer fits. And before we know what to do with that realization, we have to be willing to hear it.

This is what I was learning about that in 2023.

When I think about untying my lines, I don’t see it as a journey of selfishness. I think about it as an awakening to oneself.

As we transition into adulthood, our identities become heavily burdened by other people, social norms, and cultural obligations. We believe the stories we are told, and we willingly jump on the adulting treadmill, only to thoroughly exhaust ourselves and realize one day that we’ve actually not gone anywhere.

And then something happens to wake us up from the grind.

I call these events a driving force.

A driving force can be as simple as a comment from a friend that holds a mirror up in front of us. It could be an argument with a partner that you’ve had 100 times before, and this time is one time too many. It could be a book you read that exposes you to yourself.

As we wake up and begin to imagine a life beyond all the layers that have been applied to us, we may realize that something has to change. Maybe it means ending a relationship, leaving a job, moving away, or letting go of an identity we’ve outgrown.

But knowing something needs to change and knowing what to do about it are two very different things.

I recently watched the film Women Talking and then went back to my journals from the years when I was trying to decide whether or not to leave my marriage.

The film follows women in a Mennonite colony faced with an unimaginable decision after learning that women and girls in their community have been repeatedly drugged and sexually assaulted. They debate three possible responses: stay and forgive, stay and fight, or leave.

Reading my old journals, I could see myself wrestling with my own version of those choices.

While the options may sound straightforward from the outside, deciding whether to stay or leave can be agonizing. Every option can carry both compelling reasons and enormous sacrifices.

The severity and urgency of each situation are different. My decision to leave my marriage was a process that took more than four years. Shortly afterward, I left a long-term career for a completely different job. That decision happened much more quickly.

But looking back, I think there were a few things that helped me recognize when change had become necessary.

Listen to what you're feeling

Sometimes we know something isn't right before we can explain why.

Reading my journals, I found this line:

“All of my insides have been disrupted. They are strewn about and I’m frantically trying to put them all back inside.”

I knew I needed something to change because I couldn't settle. I felt a profound lack of ease in my own life.

I've learned to pay attention to those feelings. Restlessness, exhaustion, constriction, or the persistent sense that something isn't right aren't necessarily instructions to leave. But they may be invitations to listen more closely.

Sometimes our knowing arrives before our explanation does.

Visualize your future

One of the most powerful driving forces for me came during a workshop when the facilitator asked us to imagine where we saw ourselves in ten years if we could create any life we wanted.

I wrote that I saw myself traveling, running a thriving business where I was helping people, and spending time outdoors every day.

Then I looked at the life I was actually living.

Staying exactly where I was wasn't going to lead me toward the future I had just described.

That exercise gave shape to something I had already been feeling. I could suddenly see not only what wasn't working, but what I wanted to move toward.

That vision became a kind of life force for me.

If the future you imagine for yourself feels impossibly far from the path you're currently on, it may be worth asking why.

Name your fears

Sometimes the biggest thing keeping us stuck is fear of change.

My fears were big, and for a long time they held me in chains. I didn't even completely understand what I was afraid of. I just knew that doing something different felt terrifying.

Eventually, I sat down and wrote all of my fears out.

Some were very legitimate. Others became less frightening once I could actually see them on paper.

For each one, I asked myself: What would I do if this actually happened? What would I need? Who could help me?

Once I stepped back and looked at all of it, change seemed a little more achievable. The fears seemed more overcomeable — yes, I'm still making that word up.

Sometimes the idea of fear is greater than the actual things that scare us.

Consider your personal agency

This one was big for me, and I think it is for many of us.

As we think about our lives, we can sometimes discover that we've slowly lost our sense of personal agency.

How much do you feel like you are participating in the direction of your own life?

Our ability to maneuver, change, grow, choose, and transition is part of being human. When we lose touch with that ability — when life begins to feel like something that is simply happening to us — it can create a profound sense of misalignment.

For me, rediscovering my own agency became one of the most important parts of untying my lines.

Maybe the question isn't only whether to leave.

Looking back, I think that's the piece I understand differently now.

The signals I wrote about here don't necessarily mean leave.

They mean pay attention.

Something may need to end. Something may need to change. Something may need to be repaired. Or maybe there's a truth you've known quietly for a long time that you're finally ready to acknowledge.

You don't have to know the answer immediately.

But there is something powerful about becoming willing to ask the question.