Reflections

You Can Wish You Had Chosen Differently and Still Be Kind to Who You Were

There are choices I imagine most of us would change if we could.

Things we would say differently.

Things we wouldn’t say at all.

People we would hold onto longer.

People we would let go of sooner.

Times we would speak up.

Times we would listen instead.

Doors we would walk through.

Doors we would finally close.

It’s tempting to think that being kind to our younger selves means finding a way to make all of those choices okay.

It doesn’t.

Some things weren’t okay.

Some choices really did hurt us.

Some hurt other people.

Some cost us time, relationships, opportunities, or pieces of ourselves that took a long time to find again.

You can acknowledge all of that.

You can wish with everything in you that you had chosen differently.

And you can still be kind to the person who made the choice.

Those things can exist together.

Regret doesn’t have to become a life sentence.

Regret can be useful.

It can tell us that we’ve changed.

That we understand something now that we didn’t understand then.

That our values are different.

That if we were given the same choice today, we might make a different one.

There is something meaningful in that.

But sometimes regret stops being information and becomes punishment.

We replay the moment.

We build a case.

We collect evidence.

You knew better.

You should have tried harder.

You should have left.

You should have stayed.

You ruined it.

And somehow we convince ourselves that if we punish the person we were for long enough, it proves that the person we are now understands what happened.

But what if understanding doesn’t require punishment?

What if the fact that you would choose differently today already tells you something?

You are judging an old decision with a newer version of yourself.

That doesn’t mean the old decision was right.

It means the person evaluating it has changed.

You have lived more life since then.

You have seen consequences your younger self couldn’t see.

You may have learned how to set boundaries.

How to recognize patterns.

How to trust yourself.

How to apologize.

How to leave.

How to stay.

How to ask for help.

How to say no.

Maybe you learned some of those things because of the very choice you now regret.

That doesn’t make the choice good.

It makes the story more complicated than I should have known better.

Sometimes we only know better because we lived through what taught us.

There is a difference between explanation and excuse.

This one matters.

Understanding why you did something doesn’t mean pretending it didn’t matter.

You can say:

I understand why I stayed.

and also:

I wish I had left.

You can say:

I was afraid.

and also:

My fear hurt someone.

You can say:

I didn’t have the tools I have now.

and also:

I am responsible for what I did.

You can say:

I was doing the best I knew how to do.

and still recognize that your best at the time wasn’t enough for someone else.

Kindness doesn’t erase accountability.

It changes what we do with it.

Instead of using the truth as a weapon against the person we were, we can use it to decide who we want to be now.

Maybe the question isn’t “How do I forgive myself?”

Sometimes that question feels too big.

Maybe you’re not ready to forgive yourself.

Maybe you don’t even know what forgiveness would mean.

That’s okay.

Try a smaller question.

Can I understand myself?

Can I look at the person who made that choice and become curious about them instead of immediately condemning them?

What were they afraid of?

What did they believe?

What did they need?

What were they trying to protect?

What didn’t they know yet?

What did they think would happen?

What would they learn because of what happened next?

Understanding doesn’t change the past.

But it may change the relationship you have with the person who lived it.

If you owe an apology, kindness doesn’t erase that either.

Sometimes looking back means recognizing that someone else was hurt by something we did.

Being kind to yourself doesn’t mean skipping over their pain.

Maybe there is an apology you can still make.

Maybe there is something you can repair.

Maybe there isn’t.

Sometimes the person is gone.

Sometimes contact wouldn’t be appropriate.

Sometimes the repair is simply becoming someone who behaves differently now.

You may not be able to change what happened.

But you can allow what you learned from it to matter.

You can become more careful with someone else’s heart.

You can tell the truth sooner.

You can listen better.

You can stop repeating something that once felt inevitable.

Maybe one of the most meaningful things we can do with regret is let it change what happens next.

You don’t have to keep hurting yourself to prove that you understand.

Read that again.

You don’t have to keep hurting yourself to prove that you understand.

You are allowed to remember.

You are allowed to regret.

You are allowed to take responsibility.

You are allowed to wish you could go back.

And you are allowed to eventually put down the punishment.

Because there is a difference between carrying a lesson forward and dragging your younger self behind you.

One helps you become someone new.

The other keeps both of you stuck in the same moment.

A question to sit with

Think of something you wish you had done differently.

For just a moment, set aside the question:

“Why did I do that?”

Try asking:

“What do I understand now that I didn’t understand then?”

And then one more:

“How am I living differently because I understand it now?”

Maybe there is something to repair.

Maybe there is an apology to make.

Maybe there is simply a choice you make differently today.

Whatever the answer is, let that matter too.

Your regret is part of the story.

But it doesn’t have to be the last sentence.

Want to keep writing?

5 Letters to Your Younger Self gives you five gentle places to begin exploring the person you were, what they carried, and what you might want to tell them now.

Begin the 5 Free Letters