What Regret Is Really Trying to Tell Us

I recently came across Daniel Pink’s research on regret, and it offered such a compassionate and useful reframe.

Most of us think of regret as something heavy. Something we carry. Something that points to where we failed, missed out, stayed too long, left too soon, said the wrong thing, or didn’t say the thing we needed to say.

But Pink’s work invites us to see regret differently.

• Not as punishment.

• Not as proof that we are broken.

• Not as something we need to stay stuck inside.

But as information.

• A signal.

• A doorway into what matters most to us.

In this episode, Mel sits down with Daniel to talk about the one emotion everybody has: regret.

Drawing on his World Regret Survey of 26,000+ regrets from 134 countries, Daniel breaks regret into four categories and shows you how to stop spiraling, stop avoiding, and use what you’re feeling to make better decisions.

You’ll learn the most common regret people share, why “later” turns into years, and a simple 3-step reset to move on and take action.

1. Foundation Regrets: “I wish I had done the work.”

Foundation regrets are about the structures we wish we had built earlier.

These often involve health, finances, education, career, habits, or taking better care of ourselves over time.

They can sound like:

• “I wish I had saved more money.”

• “I wish I had taken better care of my body.”

• “I wish I had created more stability for myself.”

• “I wish I had done the hard thing when it was still small.”

These regrets can be painful because they often show us where we ignored our own needs, avoided responsibility, or didn’t yet have the support, skills, or self-trust to care for our future self.

But underneath foundation regret is usually a longing for...

• Safety.

• Stability.

• Groundedness.

• Self-respect.

A foundation regret may be asking:

1. What structure in my life needs more care now?

2. What small habit would support my future self?

3. Where am I being invited to stop abandoning myself in practical ways?

4. This is not about shaming ourselves into discipline. It is about gently asking: What part of me needs more support to follow through?

2. Boldness Regrets: “I wish I had taken the chance.”

Boldness regrets are about the risks we did not take.

• The relationship we didn’t pursue.

• The business we didn’t start.

• The move we didn’t make.

• The truth we didn’t speak.

• The version of ourselves we kept hidden because we were afraid of being judged, rejected, misunderstood, or unsuccessful.

These regrets often sound like:

• “I wish I had been braver.”

• “I wish I had tried.”

• “I wish I had started sooner.”

• “I wish I had not cared so much what people thought.”

Boldness regret can be especially tender because it often points to places where our protective parts were working very hard.

• The part that said, “Don’t risk it.”

• The part that said, “Stay safe.”

• The part that said, “What if you fail?”

• The part that said, “Who do you think you are?”

From an Internal Family Systems lens, we do not need to shame these parts. They were likely trying to protect us from pain, embarrassment, rejection, disappointment, or loss.

But boldness regret may be asking:

1. Where is my life asking me to expand?

2. What desire keeps returning, even when I try to dismiss it?

3. What would my future self thank me for trying?

Sometimes the brave step is not dramatic. Sometimes it is sending the email, signing up for the class, asking for the conversation, setting the boundary, writing the first paragraph, or letting yourself want what you want without immediately talking yourself out of it.

3. Moral Regrets: “I wish I had done the right thing.”

Moral regrets are connected to integrity.

These are the regrets that arise when we feel we acted out of alignment with our values.

• Maybe we were dishonest.

• Maybe we hurt someone.

• Maybe we stayed silent when we wish we had spoken.

• Maybe we betrayed ourselves or someone else.

• Maybe we were not as kind, courageous, loyal, or honest as we now wish we had been.

These regrets can be some of the hardest to sit with because they ask us to be honest with ourselves without collapsing into shame.

And that distinction matters.

Shame says, “I am bad.”

Accountability says, “I did something that does not align with who I want to be.”

*There is a difference.

A moral regret may be asking:

1. What value did I violate?

2. Is there repair that needs to happen?

3. What would integrity look like now?

4. Can I hold myself accountable without abandoning myself?

Sometimes repair means apologizing.

Sometimes it means changing a pattern.

Sometimes it means telling the truth.

Sometimes it means choosing differently the next time.

And sometimes, when direct repair is not possible or appropriate, it means allowing the regret to shape us into someone more honest, more humble, more compassionate, and more awake.

4. Connection Regrets: “I wish I had reached out.”

Connection regrets are the most common kind of regret Pink found.

These are the regrets connected to relationships.

• The friendship that drifted.

• The family member we stopped calling.

• The person we loved but never told.

• The unresolved conversation.

• The distance that grew slowly until it felt too awkward to bridge.

These regrets often sound like:

• “I wish I had called.”

• “I wish I had said I loved them.”

• “I wish I had reached out sooner.”

• “I wish I had not let that relationship fade.”

Connection regrets are so human.

Often, we do not reach out because we feel awkward, embarrassed, uncertain, or afraid the other person will not care.

We tell ourselves, “It has been too long.”

Or, “They probably do not want to hear from me.”

Or, “I will do it later.”

But later is not always guaranteed.

A connection regret may be asking:

1. Who keeps coming to mind?

2. Is there someone I miss?

3. Is there a relationship that could still be repaired, softened, or acknowledged?

4. What simple message could I send today?

   It does not have to be dramatic.

Sometimes connection begins again with:

• “I was thinking of you today and just wanted to say hello.”

• “I know it has been a long time, but you crossed my mind.”

• “I just wanted you to know I appreciate you.”

• “I miss you.”

• “I am sorry.”

• “Thank you.”

• Small words can open doors that silence keeps closed.

Why the Things We Did Not Do Often Haunt Us More

One of the most interesting pieces of Pink’s work is the idea that regrets of inaction often stay with us longer than regrets of action.

In other words, the things we did not do often haunt us more than the things we did.

That makes sense to me.

When we take action and something goes wrong, we can often find some meaning in it. We can say, “At least I learned something.” Or, “At least I tried.” Or, “At least that experience shaped me.”

But with inaction, there is often no story. No attempt. No answer. No lived experience.

Just the question:

1. What if?

2. What if I had tried?

3. What if I had told the truth?

4. What if I had reached out?

5. What if I had trusted myself?

This does not mean we need to say yes to everything or force ourselves into constant risk-taking.

But it does invite us to pay attention to the desires, conversations, changes, and connections that keep asking for our attention.

A Gentle Reset for Regret

Pink offers a helpful three-part process for working with regret:

Inward - Outward - Forward

Inward: Meet yourself with compassion.

Before trying to fix anything, pause and soften toward yourself.

Regret already hurts. Shame does not help us heal. It usually keeps us frozen.

You might ask:

1. Can I speak to myself the way I would speak to someone I love?

2. Can I acknowledge that I am human?

3. Can I notice the part of me that is hurting without letting it take over the whole story?

Outward: Get it out of your head.

Regret becomes heavier when it stays vague and hidden.

1. Write it down.

2. Talk it through with someone safe.

3. Name what happened.

4. Name what you wish had been different.

5. Name what you were afraid of, protecting, avoiding, or unable to see at the time.

   This is where self-understanding begins.

Forward: Ask what it is teaching you.

The final step is not to stay in the regret, but to learn from it.

Ask:

1. What is this regret showing me that I value?

2. What is the next right step?

3. What pattern do I not want to repeat?

4. What would my future self want me to do now?

5. Regret becomes useful when it becomes a teacher instead of a life sentence.

A Practice for This Month

As we move into June, you may want to take a few quiet minutes with a journal and ask yourself:

1. What is one regret that still pulls at me?

2. Which category does it fall into: foundation, boldness, moral, or connection?

3. What value is underneath it?

4. What is one small action I can take now?

   Maybe the action is practical.

Book the appointment.

Create the budget.

Go for the walk.

Start the project.

Maybe the action is relational.

Send the message.

Make the call.

Offer the apology.

Say the loving thing.

Maybe the action is internal.

• Forgive yourself.

• Listen to the part of you that was scared.

• Stop using the regret as evidence that you are failing.

Regret does not have to keep us trapped in the past.

Sometimes it is the soul’s way of saying:

• This mattered.

• You mattered.

Your life is still asking something of you.

And there is still time to choose what happens next.