You Should Have Pushed Behavior Changes
- Shirley Enebrad

- Jun 14
- 3 min read
This is one of the heaviest “shoulds” we carry in grief.

The ones that don’t just whisper… they accuse.
I should have pushed harder.
I should have said more.
I should have done something—anything—to make them stop.
When the person you love struggled with something self-destructive—drugs, alcohol, smoking, or any behavior that slowly chips away at their health—this kind of guilt can wrap itself around your heart and refuse to let go.
I understand this one deeply.
My youngest brother was a musician. He was out in the world, doing what he loved, touring in Asia with his band. Somewhere along the way, he got hooked on heroin.
We knew.
We saw it.
And we tried to talk to him about it.
Those conversations—those attempts—live on in your memory, don’t they? You replay them. You wonder if you said the wrong thing… or not enough of the right thing.
The good news—the part we held onto—was that he did eventually stop.
But addiction doesn’t always leave quietly.
The damage done during those years left his body vulnerable. When cancer came, it came into a body that had already been through so much.
And when he died… it was a tragedy.
Not just because we lost him.
But because of everything that came with it.
The questions.
The regret.
The relentless what ifs.
As a family, we all felt it:
We should have tried harder.
That sentence can echo for years.
But here’s what I’ve learned—both from my own life and from sitting with so many others in their grief:
You did not cause their behavior.
And you could not control it.
We want to believe that love gives us that kind of power. That if we care enough, push enough, say it just right—we can change the course of someone else’s life.
But addiction, and deeply rooted behaviors, don’t bend to love alone.
People change when they are ready.
Not when we are afraid of losing them.
Not when we are begging them to stay.
You may have spoken up.
You may have tried gently.
You may have tried firmly.
You may have backed off to keep the relationship intact.
And grief will still come in later and say, “It wasn’t enough.”
But there is no clear line that says, “If you had just done this, everything would be different.”
That line doesn’t exist.
Even if you had pushed harder…
even if you had drawn boundaries…
even if you had shouted instead of whispered…
There is no guarantee it would have changed the outcome.
And that is one of the hardest truths to sit with.
Because it means you were standing in a place of love… and powerlessness at the same time.
That space is excruciating.
After my brother died, I had to come to terms with this myself. Not all at once. Not neatly. But slowly.
I had to stop letting my mind rewrite the past into a version where I had more control than I actually did.
Because that version only led to one place: blame.
And grief does not need blame added to it. It is already heavy enough.
So when those thoughts come—and they will—try gently answering them with truth.
When your heart says, “We should have tried harder,”
answer it with,
“We did try. We cared. We showed up.”
When guilt whispers, “You didn’t do enough,”
answer,
“His choices were his own.”
When regret tightens its grip,
remind yourself,
“We loved him through it.”
Because you did.
You loved them.
You worried about them.
You had the hard conversations.
And love is not measured by your ability to save someone.
It is measured by your willingness to stand beside them—even when you couldn’t change the outcome.
Please don’t turn your grief into a lifelong punishment.
You have already experienced the loss.
Give yourself the grace you would offer anyone else telling you this same story.
Because if someone sat across from you and said,
“I lost my brother.
He struggled.
We tried to help.
I wish we had done more…”
You wouldn’t look at them and say, “You failed.”
You would say,
“You loved him. I can hear it in every word.”
So, say that to yourself.
And keep saying it…until it softens the edges of the guilt and makes room for something else—
Compassion.
Understanding.
And eventually… peace.
Be well,
Shirley




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