An anonymous writer shares what it feels like to navigate money without a clear sense of what’s “right.” This episode explores the weight of guilt, confusion, and shame—and what it means to begin learning without turning every decision into a measure of your worth.

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—

I think you and I need a change.

My whole life, I was taught to be afraid of you — and that my wants weren’t worthwhile. So now I don’t know what a valid financial decision even looks like.

Somewhere along the way, you became embarrassing. Even degrading.

The thought of asking for help is terrifying. And when I hear people say I need to spend you to make you, my whole body goes into fight-or-flight.

I feel guilty when I have you, and like a failure when I don’t.

I know you can be fun. You’ve given me things to look forward to in my life.

But you also come with so many secrets. I constantly feel like I’m trying to catch up to you.

It’s frustrating watching other people seem to move through you so easily — like they get to enjoy you without a care in the world.

Meanwhile, I’m in the dark, asking:

How much is enough?When do I get to enjoy what I’ve made?Will I ever feel safe with you?

And don’t even get me started on taxes.

It feels like they wipe out everything I’ve managed to save over the year. I know they matter. I know they serve a purpose. But I still haven’t figured out how to survive April on my own.

I’m working really hard on giving myself permission to enjoy my life.

And part of that is believing that the money I earn can be used without guilt.

I’m not there yet.

Every dollar I have after rent still feels tight — like it’s wrapped around my neck.

I know I haven’t been fair to you.

I’ve avoided learning about you, afraid it will only make me feel worse… even though I know that learning is probably the only way this relationship gets better.

Because I do want something different.

I want to understand you.I want to use you in ways that actually matter.I want you on my side.

I want to create more connection, more understanding… maybe even a little bit of magic.

But I need to figure out how to do that without biting my nails every time I get a receipt… or don’t have a job lined up… or make another overwhelming tax payment.

So please… be patient with me while I learn.

In the meantime—

I’m banking on you.

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

The first thing I really want to acknowledge about your letter is your honesty.

It’s the kind of honesty that’s willing to name embarrassment.Willing to admit confusion.Willing to say, I don’t actually know what I’m doing here.

None of that is small.

Because embarrassment has a way of keeping things hidden.It tells us to stay quiet.Not ask questions.Pretend we understand more than we do.

And I hear how strong that pull has been for you.

Money hasn’t just felt complicated.

You use a really striking word…You say it’s felt degrading.

And as I sit with that, I think about how exposed that can feel.

Like everyone else somehow understands the rules…

You talk about watching other people move through money with ease—spending, earning, deciding—while you’re left questioning every choice.

That kind of distance can feel incredibly lonely.

Because at that point, it’s not just about money.

It’s about belonging.About wondering if there’s something you missed…or something you were never given access to in the first place.

And at the same time, there’s this expectation—that you should already know how to do this.That you shouldn’t get it wrong.

Even though no one showed you how to get it right.

And yeah—that’s a painful place to stand.

So when you say that even the idea of learning about money feels like it might make things worse…That totally makes sense to me.

Because if money has been tied to shame,then learning doesn’t feel like empowerment.

It feels like you might finally confirm the thing you’ve been afraid of—that you’re behind…or that you’ve been doing it wrong.

But there’s something else in your letter that I want to highlight.

There’s a lightness.

A part of you that knows money can be fun.That remembers looking forward to things.That even uses the word magic.

I think that part of you has been living alongside the fear.

And so there’s this tension.

The part of you that wants to enjoy what you’ve created—and the part that tightens every time you spend.

The part that wants to feel free—and the part that’s bracing for something to go wrong.

That sounds like someone who, just like you said, was taught that wanting is dangerous…but is now trying to learn how to want anyway.

You ask some questions that don’t have quick answers.

How much is enough?When do I get to enjoy what I’ve made?Will I ever feel safe with you?

Those aren’t technical “number” questions… They’re relationship questions.

And even as you name how hard this relationship with money has been…

You’re not pretending.You’re not pushing it away.

You’re turning towards it.And maybe that’s where this begins.

Allowing yourself to be a beginner…without making that mean something is wrong.

You said you want more connection.More understanding.Maybe even a little bit of magic.

And while it’s hard to know exactly how magic happens…

I don’t think it comes from having everything under control.

So maybe the next step is just softening the idea that you’re already behind.

Letting yourself learn…without turning every moment into self judgement.

And noticing—

that even in the middle of fear,confusion,and a lot of unanswered questions—

You’re still curious.And willing.

And that might be more of a beginning than it seems.

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.

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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