Welcome back to Grace Over Guilt. I’m Dan Kaufman.

It’s Christmas Eve as I write this, and that matters because this time of year has a way of turning the volume up on relationships.

You feel it in the songs. You feel it in the traditions. You feel it in the empty seat at the table, or the text message you wish would come, or the phone call you are not sure you are allowed to make. You feel it in the pressure to be cheerful when you are carrying something heavy.

Most people, when they talk about rebuilding after a crisis, aim outward first.

How do I fix my marriage? How do I reconnect with my kids? How do I repair my professional reputation? How do I rebuild friendships? How do I prove to everyone that I am not who my worst moment says I am?

Those questions matter. I am not minimizing them. If you have ever lost a relationship that was central to your identity, you know how real that pain is.

But there is one relationship that does not get talked about enough, and it sits underneath every other relationship you will ever try to repair:

The relationship you have with yourself.

If that relationship is broken, everything else becomes unstable.

If you do not trust you, it is hard to build anything that lasts.

And when you have lived through consequences that were partly caused by your own choices, one of the hardest things to face is not what other people think of you.

It is what you think of you.

It is whether you believe your own word.

It is whether you trust yourself to make good decisions again.

It is whether you can look in the mirror and see someone worth rebuilding.

That is what this episode is about.

Not self help in the shallow sense. Not a motivational quote.

This is about rebuilding the hardest relationship you will ever rebuild: the relationship with yourself.

When the outside collapses, the inside starts talking

When I came out of jail the first time, there were obvious external losses.

I did not have my old life waiting for me.

I did not have my home.

I did not have my marriage.

I did not have the same access to my daughters.

I did not have the business identity I had built.

And the social world I thought I belonged to felt unfamiliar. Sometimes it felt like it was gone. Sometimes it felt like it did not want me anymore.

That is all real, and it hurt.

But one of the hardest things to deal with was quieter.

It was internal.

I had lost trust in myself.

And if you have never lost trust in yourself, you might not understand how destabilizing that is.

Because when you stop trusting yourself, everything becomes uncertain.

Every decision becomes loaded.

Every choice feels like it might blow up your life again.

Even small things. Even normal things.

You start to second guess the simplest judgment calls.

You start to wonder if your instincts are broken.

You start to fear that the part of you that makes decisions is unreliable, and that fear makes you hesitant, and that hesitation makes you passive, and passivity turns your life into something other people decide for you.

Loss of self trust is not just emotional.

It is functional.

It is the collapse of your internal leadership.

It is the feeling that you cannot safely be in charge of your own life.

The messy truth: circumstances mattered, and so did my choices

I want to be careful here, because this is where shame loves to sneak in.

My situation had layers.

Yes, I was a victim of circumstances beyond my control.

Yes, my client betrayed me.

Yes, my attorney gave me terrible advice.

Yes, there were dynamics happening that I did not fully understand at the time.

Those things are true.

But it is also true that I made choices along the way that contributed to the outcome.

And part of rebuilding self trust is being honest about that without using it as a weapon against yourself.

Here are some of the choices I had to face:

I am not listing these to punish myself. I am listing them because self trust does not rebuild on denial.

If you want to rebuild the relationship with yourself, you have to tell yourself the truth.

Not the shame story. Not the self hate version.

The truth.

The truth is usually more complex than the extremes.

It is not “I did nothing wrong” and it is not “I am a monster.”

It is “I made some choices I regret, and I can learn from them.”

That kind of honesty is uncomfortable, but it is also the beginning of freedom.

Because when you can accurately name what happened, you can start to change what happens next.

What it feels like when you cannot trust yourself

Let me describe this in real terms, because it is easy to keep it abstract.

When you lose trust in yourself, you wake up and you do not feel grounded.

You feel like you are standing on a floor that might collapse.

You feel like your mind is arguing with itself.

You are not sure which voice is wisdom and which voice is fear.

You are not sure if your gut is a compass or a broken alarm system.

You might be carrying questions like:

Then, because those questions are painful, you do what many people do.

You avoid decisions.

Or you hand decisions to someone else.

Or you make decisions impulsively because certainty feels better than anxiety, even if it is the wrong certainty.

This is why broken self trust is dangerous. It is not just emotional damage. It changes behavior.

It changes how you show up.

And it often creates a new cycle of regret.

The hidden foundation: you cannot rebuild outward without rebuilding inward

A lot of us try to repair the external first because it feels more measurable.

You can track the external.

A text message was sent. A therapy session happened. A job application went out. A conversation occurred. A boundary was set.

The internal is harder to measure, so we neglect it.

But here is the reality I learned the hard way:

The relationship you have with yourself becomes the foundation for every other relationship you try to rebuild.

If you do not trust yourself, you will struggle to trust others.

If you do not forgive yourself, you will struggle to forgive others.

If you do not believe you are worthy of love, you will struggle to receive love, even when it is offered.

If you do not believe you can keep your word, your promises to your kids will feel like risk, and your presence will feel unstable, even if you want to show up.

I could not fully show up for my daughters, and I could not do the long work of rebuilding connection, until I started rebuilding the relationship with myself.

Because how can you be a stable, trustworthy presence for someone else when you do not trust your own stability?

How can you model healthy self worth when you are drowning in shame?

This is why the internal work is not separate from the external work.

It is the foundation.

Rebuilding self trust is like rebuilding trust with another person

This was one of the most helpful reframes for me:

Rebuilding self trust works a lot like rebuilding trust with someone else.

It happens slowly.

It happens through consistent action over time.

It requires accountability and grace.

Not one or the other. Both.

If you try to rebuild with only accountability, you will crush yourself.

If you try to rebuild with only grace, you will avoid the lessons and repeat the patterns.

Accountability and grace are not enemies. They are partners.

You need both.

Let me break that down.

Step one: accountability without self attack

Accountability means being honest about where you went wrong.

Not to beat yourself up. That is shame, and shame is not productive.

Accountability is not the same as self punishment.

Accountability is curiosity with integrity.

It is asking:

For me, one of the biggest patterns was trusting authority figures without questioning them.

My attorney said everything would be fine, so I believed him.

I did not get a second opinion.

I did not push back.

I deferred to his expertise even when something felt off.

Now, let me say this clearly: experts have value.

But I learned something I will never forget:

Ultimately, I am the one who lives with the consequences of my choices.

So if I am uncomfortable, if I sense a red flag, if something feels unclear, it is my responsibility to ask more questions.

It is my responsibility to seek another perspective.

Not because I am smarter than professionals, but because I am the one carrying the outcome.

That lesson alone has changed how I do business, how I do relationships, and how I do life.

Accountability also meant owning my choices around honesty.

It is hard to admit that half truths create real damage.

Half truths are not neutral.

They are often fear in disguise.

They are an attempt to manage outcomes and avoid discomfort.

But avoidance always charges interest.

It charges it in trust.

So accountability for me meant learning to tell the full truth earlier, even when the full truth is uncomfortable.

Especially when it is uncomfortable.

Step two: grace without excuses

Grace is where many people get confused.

Some people think grace means pretending nothing happened.

Some people think grace means calling it all “a mistake” and moving on without making repairs.

That is not grace.

Grace is not denial.

Grace is not minimizing.

Grace is not letting yourself off the hook.

Grace is the refusal to define your identity by your worst chapter.

Grace is the decision to believe that you can learn.

Grace is the belief that you are allowed to grow.

Grace is forgiveness that makes transformation possible.

I had to forgive myself for the mistakes I made.

That is not easy.

Sometimes it is easier to hold onto guilt, to punish yourself indefinitely, to believe you deserve to suffer for your failures.

Because in a twisted way, self punishment feels like control.

It feels like “at least I am paying for it.”

But that mindset does not help anyone.

It does not bring your family back.

It does not rebuild trust.

It does not make you wiser.

It keeps you stuck.

And on a deeper level, it is pride masquerading as humility.

Because it says: “My failure is so powerful that it has the right to define me forever.”

Grace says: “No. My failure is real, but it is not my whole identity.”

The practical method: small promises, kept

Here is where I get really practical, because this is not just philosophy.

How do you rebuild trust with yourself?

The same way you rebuild trust with anyone else.

Small promises, kept.

If you have let yourself down, you cannot immediately make huge commitments and expect to follow through.

You have proven to yourself that you are capable of failure.

So you start small.

You rebuild credibility with yourself the same way you rebuild credibility in business: consistent delivery.

Not big speeches.

Not dramatic intentions.

Delivery.

It can look like:

Each time you make a small promise and keep it, you deposit into the trust account.

You prove to yourself that your word means something.

You prove to yourself that you can follow through.

Over time, those small deposits add up.

You start to believe yourself again.

And that belief becomes the foundation for bigger commitments, bigger goals, and bigger changes.

This is not glamorous.

It is not fast.

But it is real.

A warning: do not make promises that are really punishments

There is a trap here.

Sometimes we make “promises” that are not designed to build trust.

They are designed to punish us.

Things like:

Those are not promises. Those are fantasy punishments.

They guarantee failure, and failure reinforces the belief that you cannot be trusted.

So when I say small promises, kept, I mean promises that are realistic.

Promises that respect where you are.

Promises you can keep.

Your goal is not to impress yourself.

Your goal is to rebuild credibility.

The emotional shift: from “I am bad” to “I am learning”

One of the biggest internal shifts I had to make was separating guilt from shame.

Guilt says: “I did something wrong.”

Shame says: “I am wrong.”

Guilt can be useful. It can signal values. It can prompt repair.

Shame is corrosive. It makes you hide. It makes you lie. It makes you isolate.

It makes you believe you are unworthy of connection.

Rebuilding your relationship with yourself requires this shift:

From “I am bad” to “I am learning.”

That does not erase consequences. It does not erase responsibility.

It simply changes the posture you face your life with.

And that posture changes everything.

What rebuilding self trust gave me that I did not expect

I used to think self trust was about confidence.

Now I think it is about stability.

When you trust yourself, you can tolerate uncertainty.

You can make decisions without spiraling.

You can hold discomfort without needing to escape.

You can be honest earlier because you are not terrified of what honesty might cost.

You can apologize without collapsing.

You can show up consistently, not perfectly, but consistently.

And consistency is what relationships are built on.

Especially relationships with your kids.

If you are trying to rebuild trust with someone you hurt, your words will matter less than your pattern.

Your pattern is what they will watch.

But you cannot build a new pattern outwardly until you build the internal capacity to keep it.

That capacity is self trust.

The relationship underneath: why this changes how you relate to everyone else

Let me connect the dots clearly.

When you rebuild trust with yourself:

And those changes show up in every relationship.

Especially in the relationships where you are trying to repair something.

Your kids do not need perfect. They need stable.

Your friends do not need speeches. They need reliability.

Your future does not need your shame. It needs your integrity.

This is why the relationship with yourself matters so much.

It is the relationship underneath.

If you are in the “I cannot trust myself” season, start here

If you are reading this and thinking, “That is me. I do not trust myself right now,” I want to give you a simple starting point.

Not a complicated program. Not a ten step plan.

A starting point.

1) Name what broke trust

Do not generalize. Be specific.

Was it dishonesty? Avoidance? Addiction? Anger? Infidelity? Financial recklessness? Legal trouble? Chronic overpromising? Emotional absence?

You cannot repair what you refuse to name.

2) Identify the pattern behind it

What were you trying to avoid?

What were you trying to protect?

What did you believe would happen if you told the truth?

What feeling were you unwilling to feel?

Patterns are usually coping mechanisms. Understanding them does not excuse them, but it helps you change them.

3) Choose one micro promise for the next 24 hours

Not seven promises.

One.

A promise you can keep.

Make it measurable.

Write it down.

Then keep it.

4) Track evidence, not emotion

You will not feel trustworthy before you become trustworthy.

Your feelings will lag behind your behavior.

So track evidence.

I kept my promise today. I did what I said I would do. I showed up. I stayed honest. I did not hide.

Evidence rebuilds identity.

5) Practice repair instead of self attack

If you break a promise, do not spiral into shame.

Repair.

Ask: what made it hard? What do I change? How do I make it smaller? Who do I need to involve? Do I need professional help? Do I need accountability?

Self attack is not repair. It is avoidance disguised as morality.

Repair is how trust is rebuilt.

Christmas Eve, and the kind of grace that makes the future possible

It is Christmas Eve.

A time when a lot of us are thinking about relationships.

Family we are seeing.

Family we are missing.

Connections we wish were stronger.

And sometimes, the relationship that hurts the most is the one we carry inside our own skin.

If you are carrying broken trust with yourself, I want to encourage you:

That can be healed.

It takes time.

It takes accountability and grace in equal measure.

It takes small promises, kept.

But it is possible.

I am living proof.

I still have work to do. I am not pretending I have arrived.

But I trust myself more today than I did when I walked out of jail.

And that trust is making everything else possible.

Merry Christmas.

And to everyone: may you find grace for yourself this season.

The kind of grace that allows you to take responsibility without drowning in shame.

The kind of grace that allows you to forgive your past, show up in your present, and build a future that is still worth hoping for.

Grace over guilt.

A simple self trust reset: 7 days, one page at a time

If you need something concrete, here is a one week reset. This is not a magic fix. It is a way to build momentum with integrity.

Day 1: The truth audit (15 minutes) Write down the three situations where you most feel you lost yourself. Not every detail. Just the facts. Then write: “What did I do? What did I avoid? What did it cost?”

Day 2: The pattern audit (15 minutes) For each situation, answer: “What was I afraid of?” Fear is often the engine behind self betrayal.

Day 3: The boundary audit (15 minutes) Where do you need boundaries to protect your future self? People, places, substances, spending, screens, secrecy, isolation. Write one boundary you will practice for the next 24 hours.

Day 4: The micro promise (10 minutes) Choose one promise you can keep today. Keep it. Then write one sentence: “I kept my word today.”

Day 5: The repair practice (10 minutes) If you owe an apology that is appropriate and safe to give, draft it. Focus on ownership, not explanation. Ownership rebuilds trust.

Day 6: The support step (10 minutes) Identify one person or professional who can support your growth. Text them. Call them. Schedule it. Shame isolates. Healing connects.

Day 7: The next right thing (10 minutes) Ask: “What is the next right thing for me?” Not the next big thing. The next right thing. Then do it.

Over time, these small actions become a pattern. A pattern becomes a reputation. And a reputation becomes identity. That is how self trust comes back.

Grace over guilt.