Welcome back to Grace Over Guilt. I am Dan Kaufman.

Last episode I talked about my first client after the collapse. About rebuilding trust through action. About finding the courage to show up even when every part of you wants to stay hidden.

Today I want to talk about something harder. Something that happened alongside the rebuilding but that I have not really named until now.

Grief.

Not grief for what I lost. I have talked about that. Grief for who I was. For the person who no longer exists. For the identity I had to bury so something new could grow.

This might be the most uncomfortable thing I have tried to put into words.

The Person I Used to Be

Before everything fell apart, I knew exactly who I was.

I was the guy who had his life together. Successful business. Beautiful family. Nice house. The appearance of someone who had figured it out. Maybe I had not figured it out completely, but close enough. Close enough to feel secure in my identity.

I was the guy people came to for advice. The one who seemed to know how to navigate complexity. The one who stayed calm when things got hard.

That was the story I told myself. And for a long time, the world seemed to confirm it.

Then the floor gave way.

And I discovered something brutal: the person I thought I was could not survive what happened. He was not built for it. He was built for success and optimization and steady upward progress. He had no framework for catastrophic failure.

So he had to die.

Not metaphorically. Not in some soft, poetic sense. Actually die. That version of me ceased to exist.

And I had to mourn him.

Why Nobody Talks About This

We have frameworks for grieving people. For grieving relationships. For grieving places and phases of life.

We do not have frameworks for grieving ourselves.

It sounds strange when you say it out loud. I am mourning who I used to be. People do not know what to do with that. It feels self-indulgent. Overly dramatic. Like you are making something out of nothing.

But it is real. And the lack of language for it makes it harder, not easier.

Here is what happens when you go through something that fundamentally rewrites who you are: there is a before and an after. The person in the before cannot exist in the after. They do not have the tools. They do not have the perspective. They were built for a world that no longer exists.

The new world requires a new you. And the new you cannot fully emerge until the old you is laid to rest.

That is grief. Real grief. For a version of yourself that is gone and is not coming back.

And it is lonely because most people do not understand what you are grieving.

What I Missed About Him

The old me was not perfect. Far from it. He had blind spots and arrogance and patterns that contributed to the collapse.

But he had things worth missing.

He had certainty. Not about everything, but about enough things to move through the world without constant questioning. He knew what he believed. He knew what he wanted. He knew, or thought he knew, how to get from here to there.

He had ease. Things that are hard for me now used to be automatic for him. Networking. Selling. Showing up in public spaces with confidence. None of that was work. It was just who he was.

He had innocence about certain kinds of pain. He knew struggle existed, but he knew it intellectually. He had not lived it. Had not felt it the way I feel it now. That innocence let him take risks I would hesitate to take now.

I miss those things. I am not pretending I do not.

But I also recognize that those things were not free. They came at a cost. They required a version of reality that was simpler than reality actually is. They depended on things not falling apart.

When things fell apart, the certainty revealed itself as fragile. The ease revealed itself as conditional. The innocence revealed itself as ignorance dressed in comfortable clothes.

Missing something does not mean it was sustainable. I can grieve the loss while also acknowledging that what was lost was never as solid as it seemed.

The Temptation to Go Back

For a long time, I tried to resurrect him.

I thought if I just worked hard enough, I could get back to before. Rebuild the business, rebuild the reputation, rebuild the confidence. Return to the person I was and pretend the middle part did not happen.

It does not work like that.

You cannot unsee what you have seen. You cannot unfeel what you have felt. You cannot revert to an earlier version of yourself like rolling back software. The experiences are written into you now. They have changed the architecture.

Trying to go back is like trying to fit into clothes you wore as a child. They do not fit anymore. Not because the clothes changed. Because you did.

The temptation to resurrect the old self is really a temptation to avoid grief. If I can just get back there, I do not have to mourn. I do not have to acknowledge that something died. I can pretend it is all still intact, just temporarily displaced.

But avoidance is not healing. And eventually, you have to face what is gone.

What Grief Actually Looked Like

I did not recognize it as grief at first.

I thought it was depression. And maybe it was partly that too. But underneath the depression was something more specific. A sadness about loss. A longing for something that could not be recovered.

It looked like scrolling through old photos and feeling a strange distance from the person in them. Like looking at a stranger who happened to share my face.

It looked like struggling to recognize myself in the mirror. Not physically. But in some deeper way. Who is that? Is that me? It does not feel like me.

It looked like moments of sharp, unexpected sadness when something reminded me of before. A song. A place. A phrase someone used to say. Little triggers that opened unexpected doors to rooms I could no longer enter.

It looked like confusion about what I wanted. The old me knew. He had clear goals, clear direction, a path he was walking. The new me did not have that. The new me was starting from scratch, and that was disorienting in a way that felt like grief.

Grief does not always announce itself. Sometimes it just shows up disguised as other things. Emptiness. Confusion. A vague sense that something is missing you cannot quite name.

That something is you. The old you. And naming it as grief is the first step toward moving through it.

What Helped

I cannot give you a neat resolution to this. The grief is not fully gone. I am not sure it ever fully goes. But some things helped.

First: acknowledging it as grief. Just naming it. Saying out loud, to myself and to people I trusted, that I was mourning who I used to be. That gave the feeling a container. It stopped being this vague, unnameable weight and became something I could approach directly.

Second: allowing the sadness instead of fighting it. Grief does not go away faster when you resist it. It goes away faster when you let it move through you. When I stopped trying to be positive or push past it or pretend it was not happening, the intensity started to ease.

Third: recognizing that the old me was not as good as memory suggested. Memory tends to idealize. Looking back, I saw the confidence but forgot the arrogance. I saw the ease but forgot the avoidance. I saw the certainty but forgot how much of it was based on things I had not examined.

Fourth: noticing what the new me had that the old me did not. Humility, which is not the same as weakness. Depth of experience. Empathy born from suffering. The ability to sit with people in their hardest moments because I had been in mine.

Fifth: time. Just time. There is no shortcut. Grief takes as long as it takes. The pressure to be over it faster does not speed anything up. It just adds shame to the grief.

The Person Who Emerged

I am not the person I was before. I will never be that person again.

For a long time, that felt like failure. Like I had broken something that could not be fixed.

Now I am not so sure.

The person who emerged from the wreckage is not better in every way. He is more uncertain. More cautious. More prone to doubt. He moves slower than the old me. He hesitates where the old me charged ahead.

But he is also more honest. More real. More capable of sitting with complexity instead of needing everything to be simple. He knows what it feels like to hit bottom, and that knowledge has made him less afraid of falling.

He has compassion the old me lacked. For others, yes. But also for himself. The old me was hard on himself in ways that created the conditions for collapse. The new me is learning to be gentle in ways that create conditions for sustainability.

He is not perfect. Far from it. He is still figuring things out. But he is real. And real is better than polished.

Maybe that is the point. Not to get back to who you were. But to become who you are. And who you are includes what happened. Includes the falling and the getting back up. Includes the grief and what grows in its wake.

What I Would Tell You

If you are going through your own version of this, here is what I would say:

You are allowed to grieve who you were. It is not self-indulgent. It is not dramatic. It is real. And suppressing it will not make it go away. It will just make it heavier.

You are not going to be the same. That is not defeat. That is transformation. And transformation, real transformation, requires something to die so something else can live.

The sadness you feel is not weakness. It is evidence that what you lost mattered. It is proof that you are not numb to your own life. That is worth something.

Give it time. Give it space. Do not rush it. And when people do not understand, remember that you do not need them to. This is your process. Their understanding is not required for your healing.

And one more thing: what emerges might surprise you. The new you might have gifts the old you did not. Might see things the old you could not. Might be capable of things the old you never imagined.

You will not know until you stop trying to resurrect the past and start paying attention to the present.

The Takeaway

Rebuilding after collapse is not just about external things. It is about internal things too. About identity. About who you are now that who you were is gone.

That transition involves grief. Real grief. For a version of yourself that no longer exists.

Denying the grief does not make it go away. Acknowledging it does not make you weak. Moving through it does not mean you are over it. It just means you are walking with it instead of running from it.

The old you served you for a season. And that season is over.

The new you is still taking shape. Give them room to become whoever they are becoming. Be patient with the process. Be gentle with the grief.

And know that on the other side of this is something real. Not a return to before. But something new. Something that could only exist because of what happened. Something that, in its own strange way, might be exactly what you need.

Thank you for listening. This series will continue. But for now, I think we have covered the hardest parts of the story. Next time, I want to shift from looking backward to looking forward. What does building actually look like from here?

Until then.

One step, one day. Grace over guilt.