An anonymous writer reflects on receiving a large inheritance too young—and the complicated relationship with money that followed. This episode explores responsibility, regret, and what it means to return to a relationship once taken for granted.

Transcript

Hi. I’m Miata. This is Dear Money.

Here, we tell the truth about our relationship with money—the parts we usually keep private.

Each episode, I read and respond to a real letter to money that has been shared anonymously.

The goal (for all of us) is never to judge. It also isn’t to fix or to advise. Just to listen, reflect, and try to open some things that’ve been tight or hidden.

Let’s begin.

Letters may be lightly edited for privacy and clarity.

Dear Money—

What happened to us?

That’s usually how a breakup starts, but this isn’t that. It’s not even an intervention. But we have to admit something has been off for a while.

Sometimes I feel like I understood you better when I was a teenager. Back then we were saving for small things — a new TV, a video game console. Simple.

Now I’m thirty-five, and it feels like we’re strangers.

Why?

Was receiving you in the form of a six-figure trust when I turned eighteen a mistake?

I know we used some of you to help pay for my undergraduate degree alongside my parents. But maybe I had too much access to you too young. When I look back, I see how recklessly I treated you — almost running you dry. I just assumed you’d always be there without me having to work for you.

And I hated what that made me feel like.

I felt like a hypocrite — turning into one of those trust-fund kids I claim to despise. That tore me apart. And because of that, I wasn’t showing up in this relationship the way I should have.

The truth is… I shouldn’t be angry with you.

Yes, I was irresponsible. But my parents probably should have created more distance between us. It might have been healthier long-term. No one really equipped me with the emotional tools that would have helped us become a better team.

And as supportive as you’ve been of my hopes and dreams, sometimes I wonder if the decisions we made about school were short-sighted. I took more from you than I should have, and now I’m afraid I can’t give back what you’re owed.

Maybe there were warning signs. But no one we trusted ever sat us down to talk honestly about the risks of taking that leap.

I took the leap.

But you… you moved ahead without me.

Now you’re focused on things like debt, loans, index funds, global markets, interest rates, retirement savings — all these grown-up conversations that feel far beyond me.

And I feel left behind.

You’re still there for essentials and emergencies, and I’m grateful for that. Truly.

But it doesn’t feel like we’re on equal footing anymore. Sometimes it even feels like you’re looking down at me with pity.

Maybe that’s not how you see it. But I want you to understand how it feels from here.

Because despite the distance between us, I want you to know something.

I’m doing okay.

And the leap we took together wasn’t for nothing.

There’s no way to prove this, but I believe I might have become the worst version of myself if I hadn’t taken that risk. Bitter. Fearful. Living a life that never fully happened.

Instead, I’ve seen incredible things. The leap we took gave me the courage to live in fascinating places. And because of that… I met the love of my life.

Maybe you’ve met her.

So yes — I’m doing okay.

But I want to be more than okay.

And I’m ashamed to say this, but I need your help again.

It’s not just me anymore.

Someone else is counting on me to become the best version of myself. I wish we lived in a world where your involvement wasn’t necessary for that.

But we don’t.

That doesn’t mean I want nothing to do with you.

In fact, writing this letter has made me realize how much I miss you. How much I took you for granted.

If we can come together again, I promise things will be different this time.

More devotion.More attention.More respect.

Less taking.

I want to get to know you again — the version of you that exists now.

I want to understand how you see the world.

But only if you want that too.

Only if you’ll have me.

So… what do you say?

Let’s pause and just sit with that for a moment. Just breathe and let yourself notice anything this letter brings up for you.

As I read this letter, the first thing that strikes me is how much honesty lives inside it.

I don’t see any defensiveness… I see someone who is willing to look back at themselves clearly.

You open your letter like the beginning of a breakup conversation: What happened to us?

But as the letter unfolds, it becomes something else. It’s not a breakup… it’s just an acknowledgement.

You remember a time when money felt simple.Saving for a television.Saving for a game console.

Back then the relationship was clear.You worked.You waited.And eventually you arrived at the thing you wanted together.

But then the relationship changed.

Money stopped being something that came slowly through effort and instead it became something that arrived all at once.

A six-figure trust at eighteen.

And when something that powerful enters a relationship that early, and without guidance, it can change the dynamic overnight.

Money doesn’t just become larger.

It actually becomes more complicated.

So you describe looking back and seeing recklessness.Seeing how easily you assumed that money would always be there.

And I hear something important in the way you speak about it.

You’re not hiding from your responsibility.

You’re willing to say: I ran you close to dry. I took more than I should have.

That kind of honesty takes courage.

But you also recognize another truth...

You recognize that responsibility doesn’t belong entirely to the eighteen-year-old version of you.

Being given access to that kind of money without conversation… or preparation… without someone sitting down and saying,

Here’s what this means.Here’s how to think about it.Here’s how this relationship changes now.

Without that, that leaves a really young person navigating something pretty enormous totally without a map.

We would never hand a teenager the keys to the car and simply hope that they drive well.

We teach them.We sit beside them.We help them understand the responsibility they’re carrying.

Money deserves that same kind of guidance.

And what I hear in this letter is someone realizing that the younger version of himself was never really given that support.

You were given the responsibility… and then you were left to figure out the meaning later.

That creates a complicated mix of emotions:

Gratitude.

Regret.

Some shame.

And a fear that the relationship has been damaged beyond repair.

There’s a moment in the letter that really stays with me.

It’s when you say it feels like money has moved on…into conversations about markets, loans, retirement, interest rates—the grown-up conversations that feel like they’re happening without you.

I’m wondering if part of what you’re experiencing isn’t so much distance from money…

but distance from the version of yourself that feels ready… that feels equipped to actually sit at that table.

Because the truth is, money didn’t actually move ahead without you.

Life just became more complex.

And complexity requires new skills.

The beautiful thing is that you’re not hiding from that.

You’re naming it.

You’re willing to say: I want to understand you now. I want to learn the version of this relationship that exists today.

That kind of humility is rare.

And there’s another piece of honesty in your letter that I also want to point out.

You talk about the leap you took… or the leaps you took: the education, the travel, the life experiences that came from the choices you made.

And even as you acknowledge the cost, you also acknowledge something else.

The leap changed you.

It gave you courage.It gave you perspective and a life that might not have happened otherwise.

Sure that doesn’t erase any mistakes. But it does mean the relationship with money wasn’t meaningless.

It was actually formative.

And now something new is happening.

You’re no longer that eighteen-year-old who received that trust.

You’re a thirty-five-year-old who is willing to sit down and ask a very different question:

How do we rebuild this relationship with more honesty… more devotion… more respect?

Those are your words and that question alone, it tells me that the relationship isn’t over.

It’s really just beginning again.

Yes the relationship became more complicated. But so did you.

And your willingness to return to the conversation with humility is probably the most important step in building something stronger this time.

Thank you to the writer for trusting me with this letter.And thank you for listening.

Dear Money is a space for honesty, not answers.You don’t need to do anything with what came up today.

But if you find yourself holding a truth you haven’t named yet, you’re welcome to write your own letter to money. I’ll be here.

New episodes are published every Thursday.

Until next time.

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