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An anonymous writer reflects on growing up in a home where money was rarely spoken about except when it was missing. This episode sits with the fear that can be quietly passed down through generations—and the courage it takes to question the financial stories we inherit.
Letters may be lightly edited for privacy and clarity.
Dear Money—
I’ve been afraid of you for as long as I can remember.
Growing up in a Latino household, we didn’t really talk about you — except when you were missing.
You were always this distant thing. Something to chase, but never quite catch.
I watched my parents struggle with you, constantly worried about where you would come from next. And whenever you disappeared, anxiety filled our home.
I learned early that your presence — or your absence — seemed to control everything.
That fear stuck with me.
Even now, you still feel elusive. Unpredictable. Out of my control.
When I have you, I hold on too tightly, anxious that you’ll disappear as quickly as you arrived.
And when I don’t have you, I feel powerless — like I’m sinking, unable to provide for myself or the people I love.
For most of my life, I’ve been terrified of you.
Sometimes it felt like you were always just out of reach. Other times it felt like I didn’t deserve you at all.
But I’m tired of living like this.
I want to break free from the anxiety that has defined our relationship for so long.
I’ve seen what this fear has done to my family — how it shaped our decisions, our sense of security, even our vision for the future.
It’s a weight we’ve carried for generations.
And I want to be the one who breaks that cycle.
I don’t want to pass this fear down.
I want to change how I see you.
I want to stop feeling like you control me and start realizing that I have a say in this relationship too.
I want you to be something I can welcome into my life with balance and gratitude — something I can use to support myself, my family, and my community.
I want to build a new relationship with you — one where I trust my ability to manage you, use you wisely, and share you in ways that lift others up too.
I want to break the scarcity and fear that were passed down to me and build something different.
A new legacy.
This is my commitment to you, Money.
I know the road won’t be easy.
But I’m ready for a new beginning.
One built on trust, balance, and a better future — for me, and for those around me.
What stands out to me first in your letter is how early the relationship with money begins.
Your relationship with money didn’t start with your first bank account or job. It started in the emotional atmosphere of your home.
I think a lot of us can relate to that.
You describe growing up in a household where money wasn’t really discussed except when it was missing.
And it doesn’t happen on purpose, but that kind of environment teaches children that money carries weight.
Anxiety.Uncertainty.Urgency.
When a kid grows up watching adults worry about money, they learn something long before they ever earn their first dollar.
They learn that money can determine how a room FEELS.
Whether it feels calm… or tense.
Whether the people in the room feel secure… or afraid.
So it makes sense that the fear you describe started early because you were paying attention.
You were watching the way money moved through your family and you were noticing the emotional impact it had on the people you loved.
I think that when we’re young we’re pretty good at absorbing those patterns, and they become stories we carry long after the circumstances themselves have changed.
Stories like:
Money disappears.Money can’t be trusted.Money controls everything.
These stories often travel through generations—not because parents want to pass down fear, but just because they’re doing their best to survive their circumstances.
There’s a moment in your letter though where you start to recognize that you don’t have to hang on to this fear you inherited.
And I want to point that out because questioning the beliefs we grew up with can actually feel disloyal.
Especially if they belong to people who protected and raised and loved us.
But breaking a cycle isn’t about rejecting them…It’s about honoring what they carried… while asking whether you still need to carry that burden forward.
You describe wanting to build a new relationship with money.
Rooted in balance.
In gratitude.
In the ability to support your family and your community.
That vision says that the fear you inherited hasn’t turned into resentment or rejection.
It’s turned into a question:
What kind of financial legacy do I want to leave behind?
That question is awesome.
Because we don’t have to have certainty to create generational change. We just have to recognize that the stories we inherited came from real circumstances AND they don’t necessarily have to define the future.
When you share that you wanna have a say in this relationship too? That’s another super important shift.
You’re not pretending that money is always predictable or that your fear is gonna disappear overnight.
But you’re seeing that the relationship with money isn’t something that just happens.
It’s something you participate in.
It will evolve as your understanding grows.
And that is absolutely how you start a new legacy.
Thank you to the writer for trusting me with this letter.
Dear Money is a space for honesty, not answers.
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.
An anonymous writer shares the exhaustion of working relentlessly and still feeling like financial stability is always just out of reach. This episode sits with the cycles of progress and setbacks that many non-traditional earners experience—and the dangerous belief that when money is hard, it must mean we’re failing.
Letters may be lightly edited for privacy and clarity.
Dear Money—
Where do I start?
We have a complicated relationship. And I wish it were better. I want to do better — for me, for you, for us.
When I was younger, I didn’t know how to treat you. No one ever taught me what to do with you. And even now, as an adult, I’m still not sure.
I feel ashamed of that.
No matter how hard I work, I can’t seem to get enough of you. No matter how many things I learn or how many jobs I’ve had, I’ve never earned enough to comfortably cover my bills.
And when I do have you, I don’t know how to keep you around.
It’s an endless cycle that keeps me stuck — never moving forward the way I want to.
I admit it. I need your help.
Back in 2020, I had a great year. I thought I was finally on the right path with you. I paid off all my credit card debt.
But now, a few years later, I’m in debt again.
When I’m lucky enough to have you, I pay for the things I need. But there’s never enough left to save or invest. Never enough to prepare for the slow months.
I’m constantly in the red.
It’s embarrassing. And I’m so over it.
I need your help paying back my parents and finally taking control of my life. Independence has always meant everything to me, yet I haven’t been able to reach it consistently.
Putting strain on the people around me hurts. I carry so much guilt about that.
I love what I do for work. Making music is everything to me. But without you, everything becomes harder.
I need you to help me feel a sense of freedom.
Freedom to take care of myself and the people I love.To build an emergency fund for health issues or whatever life throws my way.To go out to dinner occasionally with my partner.To take vacations with friends.To invest in my career and my well-being.
I’m tired of always feeling like I’m without.
I want to enjoy my life the way I imagined I would when I was younger.
To maybe afford to have a child someday. Or even a pet.
That would be something.
Sometimes I feel sad thinking I may never get to experience those things because I couldn’t figure you out.
But I have made some strides this year.
My student loans are gone. Financial grants helped me pay down medical bills after serious health issues last year. My parents helped me open a Roth IRA, even though I won’t be able to contribute yet unless things change.
I’ve paid off my auto loan. And my credit card debt is going down.
I am working really, really hard.
But it still isn’t enough to live comfortably. My bank account is overdrawn almost every month.
It feels so hard.
I do wonder if something in me is broken because we’ve never had a stable relationship.
But I don’t want to keep living this way.
I want to build stability with you — something strong enough that I never have to struggle like this again.
I want to give back to the people who’ve supported me. To my community.
I want to feel peaceful. To sleep well at night.
To reach my fullest potential as a human being.
So please… Can we move forward in a positive way?
Thank you for hearing me out.
I look forward to what we might accomplish together.
As I read this letter, the word that stays with me is effort.
You write about working really, really hard. And I believe you.
There’s a kind of exhaustion that comes from trying to build stability while the ground keeps shifting. Especially when the work you love—music in your case—doesn’t provide the predictable rhythm that money seems to prefer.
Many of us living with irregular income know this feeling well.
Some years are good.Some months are great.
And then suddenly you’re back in the red again, wondering how it happened.
It makes the relationship with money feel like a puzzle you just can’t solve.
I hear the shame that has started to creep in around that.
You ask whether something in you might be broken and if the reason this relationship has been unstable is because you somehow failed to figure money out.
But as I listen to your letter, I don’t hear someone who isn’t trying.
I hear someone who has been navigating a relationship that was never explained to them in the first place.
You say something important:
No one ever taught me what to do with you.
That sentence shows up in so many letters like this one.
When we grow up without guidance around money, we end up believing that our struggle is a personal flaw.
But learning how to work with money is not something most of us absorb naturally.
It’s a skill.A relationship.
A set of practices that usually require time, support, and many imperfect attempts.
I also hear something else in your letter.
The belief that once things start going well financially, they’re supposed to stay that way.
So when a good year is followed by a difficult one, it feels like failure.
But relationships with money—especially for people with creative or non-traditional careers—rarely move in a straight line.
They move in seasons.
Some seasons are expansive.Some are restrictive.
That doesn’t mean the relationship is broken.It means the relationship is alive.
It really stands out to me how much responsibility you’re carrying.
You want to pay back your parents.You want to support your community.You want to care for a future family.
You’re not asking money for luxury.
But you are asking for stability and independence and the ability to breathe.
That’s all incredibly human.
And I just want to point out that even though you describe exhaustion, you also share real evidence of movement.
You paid off your student and auto loans, reduced medical debt, opened a Roth IRA…
These are not small things.
These are signs that even with the difficulty, the relationship has been changing.
Maybe not as quickly as you hoped… But it is changing.
And sometimes when progress happens slowly, it is harder to recognize.
The thing I hear the most clearly in your letter is persistence.
You’re still asking questions.Still working.Still imagining a future where the relationship with money feels calmer and more supportive.
That kind of persistence doesn’t guarantee an easy outcome but it does keep the relationship open.
Your exhaustion is real. But so is the effort you’ve continued to bring to this relationship.
And that may be one of the strongest foundations for building something steadier over time.
Thank you to the writer for trusting me with this letter.
Dear Money is a space for honesty, not answers.
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.
An anonymous writer reflects on the uneasy feeling that caring about money somehow makes us worse people. This episode sits with the tension between creative fulfillment, financial stability, and the cultural stories that make it difficult to hold both at once.
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—
It’s been a while, hasn’t it?
I would love to never have to worry about you. But that’s difficult when you’ve been so scarce lately. Honestly, I’m at a loss for how to keep you around.
I hate to sound desperate, but I do miss you. And I’ll admit it — you’re an important part of my life. You matter a great deal.
But the truth is, I hate having to think about you at all.
Even when there’s enough of you, I prefer putting you on the back burner. I have other things I’d rather spend my time on.
I know that sounds wrong.
I just don’t like the thought of appearing materialistic. That’s not a good look for a woman. I guess that belief is sexist… and probably something I need to get over.
My middle-class upbringing also taught me not to value you too much. That you’re not everything. That you can’t buy happiness.
I’ve since learned that you can at least buy peace of mind.
Working for a bank helped me see that more clearly. It also helped me question some of the assumptions I was raised with.
And having that job was my way of trying to make sure you’d be in good company for a while. But eventually I got too tired to keep up the charade — a career I increasingly hated, even though it kept you nearby.
I need something that makes me happy too.
I’m still working on that.
But it would ease my mind to have you back for a little while. Just while I figure things out.
I promise I’m ready to work on learning more about you — and better understanding how to help you stay.
Does that sound good to 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.
As I read this letter, what stands out to me is the tension you’re holding.
On the one hand, you miss money.You say it pretty clearly: you matter a great deal.
But on the other hand, there’s a part of you that wishes you didn’t have to think about money at all.
And that tension is normal.
So many of us were raised with a story that caring about money somehow makes us smaller, makes us materialistic, greedy, selfish.
Especially for women, there can be an added layer — the message that talking about money too openly makes us look bad...
So we keep our distance.
We say things like:Money isn’t everything.Money can’t buy happiness.
Money isn’t what matters to me.
And there’s truth in those statements.
But sometimes those ideas become a way of keeping money at arm’s length — a way of staying morally safe by pretending the relationship doesn’t matter very much.
The problem is that our relationship with money doesn’t disappear when we stop paying attention to it.
In fact, the less attention we give it, the more uncertain the relationship becomes.
And the uncertainty tends to create fear.
I hear that cycle very clearly in your letter.
You don’t want to seem materialistic, so you keep money in the background.Because it stays in the background, it remains uncertain.And because it’s uncertain, it becomes frightening.
And that brings money right back to the center — but now with anxiety attached.
That’s a difficult loop to live in.
What I appreciate about this letter is how willing you are to question the assumptions you have… the ones you grew up with.
You name the sexism.You name the messages from your upbringing.
You also describe how working at a bank was a different kind of influence. It helped you to see money differently.
All of this reflection you’re doing matters.
It’s demonstrating in real time how our relationship with money doesn’t stay the same.It is something that evolves as we do.
And there’s something else in your letter that I find so honest.
It’s when you describe working in a career that kept money nearby — even though the work itself made you increasingly unhappy.
That’s another story so many of us live in.
The idea that the only responsible way to keep money around is to choose the steady path… even if that path slowly drains the life out of you.
So we end up faced with an impossible choice:
Ignore money and risk instability.Or pursue money in ways that make us miserable.
Is it surprising that so many of us avoid the conversation entirely?
What I hear in your letter, though, is someone who is beginning to step out of that bind.
You’re not pretending money doesn’t matter anymore.You’re not pretending happiness doesn’t matter either.
You’re allowing both of those truths to exist at the same time.
And that’s where a more honest relationship with money can start.
You say you’re ready to learn more about money now.Ready to understand how to help it stick around.
That’s a powerful shift. Because curiosity is a very different place to begin than avoidance.
The tension is still here.But so is your capacity to face the relationship directly — without pretending money doesn’t matter, and without pretending that it’s everything.
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.
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.
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?
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.
Dear Money is a space for honesty, not answers..
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.
An anonymous writer reflects on growing up around money that was never spoken about—and the shame that followed. This episode sits with secrecy, criticism, and the anger that can form when we’re left to navigate money without guidance.
Letters may be lightly edited for privacy and clarity.
Dear Money—
Oof. We have a complicated relationship, huh?
I grew up in a house of privilege, but you were never talked about. My family went through hard times but never stopped living like we had you. I heard whispers about debt and struggle, but so much was hidden. To this day, I still don’t know how much my family makes or where we truly stood financially.
I got into credit card debt for the first time in college. Instead of teaching me how to be better with money, my parents asked my grandmother to advise me. She wrote a $5,000 check, paid off the card, and told me to close the account—no coaching, no conversation. I was grateful, but I was also confused. I wanted to learn.
I’ve always been a spender. If I have money, I feel like I should use it before someone else needs it. I don’t know where that belief came from, but it means I’ve rarely kept much in savings.
When I was married, I found myself in a strange dynamic. I was ambitious, and my partner wasn’t. He worked minimum-wage jobs and didn’t return to school, which made me the primary breadwinner. I worked three jobs and went to rehearsals at night. He criticized how I handled our finances but never helped me learn to do better. Instead, he reinforced my shame.
I got into grad school on a full ride, but I still took out loans to cover our rent and groceries so we could live. After we divorced, I was left with $72,000 in debt—debt he couldn’t help with, but had been happy to benefit from.
I took what money I had left and moved to New York City. I landed a great job and eventually found a partner who’s been gently coaching me around finances. I’m growing more confident, but it’s still a struggle.
I’m looking forward to building a better relationship with you— even though part of me hates you right now.
For me what stands out immediately in this letter is the silence.
You grew up around money—but not with it.There were whispers.There were appearances.There were hard times hidden behind maintained lifestyles.
But there wasn’t conversation.
And when there’s no conversation, children fill in the blanks.
You learned that money is something we don’t name.Something we don’t ask about.Something that somehow exists—and yet can’t be spoken aloud.
That kind of silence creates confusion.And it also creates shame.
When you got into credit card debt in college, what you actually wanted wasn’t rescue.You wanted to learn.
Instead, the problem disappeared—but the questions didn’t.
The card was paid off.The account was closed.But you didn’t come away with any understanding.
That matters.
Because when money mistakes (and we all make them) are erased without conversation, what lingers is the sense that you did something wrong… and you’re still not sure what it was.
And then, in your marriage… it’s interesting because on the surface what you describe seems completely different - but I think there’s an important similarity.
Here you worked and carried responsibility and stretched yourself thin.
And in this case what did you get?
Criticism.
Just like with your debt, there was no partnership, no collaboration.
So this also created a reinforcement of shame.
There’s something deeply disorienting about being the one who holds things together—and still being told you’re mishandling them.
It makes sense that you have anger.
In the final line of your letter you name that anger as hate.
But underneath that I hear something else:
I hear a longing to have been taught… to have been supported… to have not carried so much alone.
Money just became the surface where all of that played out.
The silence.The criticism.The unequal burden.The debt left in your name.
Sometimes when we say we “hate” money, we are really grieving the ways we were left alone with it.
The ways we weren’t guided.The ways we weren’t protected.The ways responsibility came before understanding.
Hate can be a shield for that grief.
And it can also be the first honest emotion in a relationship that’s finally being brought into the light.
But you also share something very different in the final part of your letter. You share that
You moved.You started over.You found work.You found a partner who speaks about money gently.
Gently.
That word shifts everything.
Because what you may be discovering now isn’t just better budgeting or financial strategy.
You’re discovering what it feels like when money is discussed without secrecy or criticism or punishment.
That’s not a small shift.
It sounds like you are someone who is finally being given space to learn without shame.
And that changes everything.
Your anger doesn’t need to magically disappear. It can exist along with your willingness to stay in the conversation.
And that willingness is what creates the possibility (I would even say the likelihood) of developing your own relationship with money into something different than you were ever shown.
Thank you to the writer for trusting me with this letter.
Dear Money is a space for honesty, not answers.
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.
An anonymous writer realizes that fear—not irresponsibility—has shaped their relationship with money. This episode sits with control, scarcity, and what it means to loosen our grip without abandoning ourselves.
Letters may be lightly edited for privacy and clarity.
Dear Money,
Isn’t it funny how, in all the years we’ve been together, I never once addressed you?
If I had to guess why, I’d say I was afraid—and that might be the easiest guess I’ve ever made. I’ve always thought of you like one of those toxic men who can’t commit. I spent so much time worrying about when you’d come, whether you’d stay, that I never really enjoyed being with you.
They say having you should set me free—open possibilities. That’s what everyone wants: money always around. But the moment I see you, I lock you in a closet. I’m too afraid you’ll leave.
What’s the point of making nice memories if you’re gone the next day? I ask myself. Are a few hours of sunshine worth your absence in the morning?
As I write this, I hear a small voice in my head shouting, Yes. It’s worth it. Life can end tomorrow. What’s the point of keeping possibility locked away?But still, I can’t bring myself to let you out. Is it trauma? I don’t know.
As long as I can remember, you were something I knew about but couldn’t mention. My parents shared you carefully, making plans about who would get to use you and when. There was never enough. Someone was always giving something up. And when they offered me your company, I couldn’t accept it—I worried they’d be left alone. So I pretended I didn’t care about you. I walked beside you, but never acknowledged you. I thought that way, you’d stay.
Then I went to an elite school where people weren’t so careful. They had you with them all the time—building beautiful rooms, wearing beautiful clothes, going beautiful places. And I watched, holding your hand tightly, telling myself, At least I know you’re staying.
Writing this now, I wonder: if I were you, would I enjoy being with me? Probably not. I was an overprotective parent. I kept you in a closet. I held you too tightly. I never allowed you to become anything else.
It reminds me of a play I once saw—a girl rescues a bird and keeps it in a cage to heal it. She falls in love with the bird, and when it’s ready to fly, she can’t let it go. But if she truly loves it, she should. It’s heartbreaking. And it’s true.
I see now that you are my bird. I was so afraid to lose you that I may have suffocated you—keeping you locked away, calling it “safe.” The truth is, I’m afraid. I live in a foreign country without my family. I don’t have a 9–5. I don’t know how I’ll take care of myself next month. If you leave, what happens to me? Who am I then—other than alone?
I know I need better plans. I need guidance so I can look beyond fear and finally free you—so I can free myself, too. I don’t want to keep living the way I always have. I’ve grown up. I’ve changed. Maybe you have too.
Would you be open to really getting to know each other? If I unlock the cage, will you promise not to run away? Will you teach me how to play? Will you be safe?
Because I don’t think I’ll ever be okay without knowing if you are.
As I read this beautiful letter, what stays with me most is how much tenderness there is in the fear.
Your words really tell the story that’s a direct opposite to one of carelessness with money.
You’re telling a story about devotion. Not just devotion to money… but devotion to your parents… you share the ways you were with money to take care of your parents… to make sure they were okay.
From the very beginning, money wasn’t something you were allowed to relax with. It was something to be managed, shared carefully, protected. Someone was always giving something up. Someone was always at risk of being left without enough.
So, as we do, you took away an early lesson from all of this:if you didn’t ask too much,if you didn’t want too openly,if you didn’t acknowledge money at all—maybe it would stay.
Your lack of acknowledgement - it’s easy to just call it avoidance. But I see it as your strategy for loving something that feels fragile.
When you describe locking money away—holding it tightly, keeping it close—it sounds like fear shaped into responsibility. Like someone trying to prevent loss by controlling proximity.
And then there’s this moment in the letter that feels especially alive to me. It’s when you ask if allowing yourself to enjoy money is worth the risk…
And you share that small voice that is shouting at you:Yes. It’s worth it. Life can end tomorrow.
That voice isn’t reckless.It isn’t naïve.
It’s the part of you that remembers that safety without living isn’t really safety at all.
And sure—hearing that voice isn’t overriding the fear.You’re not pretending it’s gone.
To the contrary. You name it.
You don’t look away from what it’s like to live far from family.To not have a fixed employment structure.To not know what next month will bring.
And you have the courage to name the real question.
“Who am I if money leaves?”
I feel like writing this letter was such an exercise in discovery for you. Your willingness to explore says a lot about where you are now.
When you ask whether money would enjoy being with you, something important happens. You stop seeing yourself as the problem to fix—and start seeing the relationship itself. The relationship you have with money.
The image of the bird illustrates the challenges of this relationship beautifully.
Sometimes what we call safety is actually a cage built out of love.
And sometimes what we call control is just fear trying to prevent heartbreak.
I hear someone who has grown enough to question the rules they learned early—and whether those rules still fit the life they’re living now.
You ask if money would be willing to really get to know you.If it would promise not to run away.If it would teach you how to play.
Those are human, really grown up questions.
You’ve already named so much in your letter. And I want to gently add this:
Money has already been with you through uncertainty.Through change.Through moving countries.Through not knowing.
It didn’t disappear the moment things felt unstable.And you didn’t disappear either.
So maybe the next step here isn’t unlocking the cage all at once.And it isn’t finding certainty or “freedom” from fear before you make a move.
Maybe it’s simply noticing that fear and care have been living side by side this whole time.
The fear is still here.But so is your capacity to stay in relationship—with money, and with yourself.
Thank you to the writer for trusting me with this letter.
Dear Money is a space for honesty, not answers.
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.
An anonymous writer shares what happens after the debt is gone—when saving becomes another way fear tries to keep us safe. This episode sits with how scarcity can linger long after financial “success,” shaping choices even when nothing is technically wrong.
Letters may be lightly edited for privacy and clarity.
Dear Money,
When I was a kid, I was scared I would never have enough of you as an adult. My mom was a teacher, so she never had much. My dad could never hold down one job for long, so he definitely never had enough. I figured that if I kept my head down and worked hard, maybe my future could be different.
I took out student loans—lots of them. I took out a car loan to afford my first car when I moved to Los Angeles. And… there it was. Suddenly, you were nowhere in sight.
Still, I told myself I would never regret going into debt for my education. I worked hard, cut coupons constantly, and budgeted the best I could for years. And now, my student loans are paid in full, I own my car, and I have no long-standing credit card debt.
Weirdly, my problem now is that I find myself hoarding you.
It’s as if what I have is never enough—as if something terrible is bound to happen, and at least I’ll be prepared for the worst.
Some people might say, “You have plenty of money in savings—how is that a problem?”
Well…
I worry that I should be investing you more, but my lack of knowledge and confidence leaves me continuing to just save you instead.
I worry this obsession with endlessly saving you is keeping me from pursuing more in my life: starting my own business, living in a slightly nicer apartment, or even buying a house.
I worry that making sure you’re always coming in keeps me in jobs I don’t love instead of finding possibly lower-paying work that might actually feed me creatively.
Now that I’m an adult I can see that I’ve built solid money habits - that I probably don’t actually need to be worried about you at all. But the fear that you might suddenly leave—that you’ll just disappear one day—well now that’s the thing holding me back.
I look forward to the day I can see you as an ally and truly trust you. I hope that trust will allow me to move forward in all the other areas of my life.
As I read this letter, I’m struck by how careful this relationship with money has been.
You learned early that money could be unreliable. That it might not stay. That it might never quite be enough. And so you did what we’re told is the right thing to do.
You worked hard.You took calculated risks.You invested in yourself.You paid your debts.
And it worked.
THAT really matters.
You took out student loans and weren’t dragged under.You borrowed money to buy a car and survived it.You built habits.You did the long, unglamorous work of responsible day in, day out sacrifice.
You did that.
And yet—here you are, still afraid.
What stands out to me is that this fear didn’t disappear once you “proved” yourself. It didn’t go away once the debt was gone or once the savings account grew.
And let’s be honest - I think that’s what we believe is going to happen.
As soon as I get “here” I won’t be afraid anymore.
Instead, the fear just changed shape.
It went from you “better do these things or else” to you “better hold on really tight to these things or else”
There’s something here that’s helpful to recognize.
We’re often told—pretty explicitly, everywhere—that confidence comes after success. That once we do enough, earn enough, save enough, trust will naturally follow.
But your letter tells a different truth.
You did the things.And trust didn’t arrive.
Instead, safety became something to protect at all costs.
As I read this, I don’t see someone who doesn’t trust money because they’ve misused it. I see someone who doesn’t trust money because they’ve learned (watching others) how easily it can vanish—and they’ve learned first hand how much effort it takes to rebuild.
Saving became the place where certainty lives. The proof that nothing bad has happened yet.
And so the question has shifted from
“Do I have enough?”to“How do I make sure this never disappears?”
That’s a very understandable shift.
But it also creates a strange bind.
The very habits that kept you safe… are now the ones making your life feel smaller.
You’re not stuck because you lack discipline. You’re stuck because the finish line keeps moving.
I’ll trust you when I invest more.I’ll trust you when I feel smarter.I’ll trust you when nothing bad happens for long enough.
But “long enough” has no end date.
What I notice is that trust here isn’t waiting on more evidence. You already have evidence.
It’s waiting on permission.
Permission to believe that the skills you’ve used to reach this place… might also be the skills that will catch you whenever you leap.
You say at the very end of your letter that you look forward to the day when money feels like an ally.
I wonder—what it would be like to look at your relationship with money and notice that money already has been an ally.
Not perfectly.Not without fear.But consistently.
You’ve faced challenges. You’ve made tough choices.
You adapted.You learned.You stayed standing.
Maybe trust doesn’t arrive all at once, like a finish line you cross.
Maybe it begins the moment you stop asking money to guarantee the future—and start noticing how often you’ve already found your way through uncertainty.
Not to decide anything today. Not to change a single behavior.
Just to notice.
That the fear didn’t stop you before.
And it doesn’t have to be a verdict now.
Thank you to the writer for trusting me with this letter.
Dear Money is a space for honesty, not answers.
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.
An anonymous creative admits a truth many of us avoid: money doesn’t just create stress—it creates fear. This episode sits with what happens when overworking becomes the only source of safety, and what it means to name that fear without rushing to fix it.
Letters may be lightly edited for privacy and clarity.
Dear Money,
I am simply terrified of you. I’m scared to look at you, to use you, to touch you—to do anything involving you. I’m so scared that I can’t even tell whether my situation with you is good or bad.
The only thing that feels stable is when I’m working like crazy. When I’m working nonstop, I feel like I spend you less and earn you more… but I also feel miserable. Still, at least that’s when I feel secure.
Even then, I can’t relax. I still worry about whether you’re really there—whether you’ll still be here next month, or two months from now, or whether you’ll disappear in a matter of days. Maybe it’s anxiety. Maybe it’s that I don’t trust myself. I don’t even have strong urges to spend you, but I’m terrified of something horrible happening and not having enough of you to protect me.
The worst part is that I have to spend you in order to keep pursuing my art. And when I spend you, I have to work more. But when I work more, I have less time to actually make the art. Sometimes I take jobs I hate just to keep you close enough to survive—and so I can still call myself an artist. I would rather work harder to have more of you than work less, do more art, and risk losing you.
Everyone in my life has a tendency to throw you away. I’ve watched family members find success and spend everything on hobbies and interests until you’re gone. I’m so scared that will happen to me that it feels like we can’t trust each other. You can’t trust me, and I can’t trust you. But all I want is for you to be on my side.
I want you to have my back—so I can explore my creative impulses and support my artistry in a real, tangible way. I could be an actor, probably. My dreams might actually happen. I could live in New York without the fear that I’ll have to run home crying, needing help.
I would do anything to have you in my life forever… but I don’t even know where to start.
I believe that when someone says, “I’m terrified of money,” we often rush to explain it away. Anxiety. Lack of information. But I think your fear is actually a very intelligent attempt to stay safe.
Your fear makes sense.
You’ve learned that the only time you feel even a little bit secure is when you’re working relentlessly. When you’re exhausted. When you’re overriding your own needs. That’s not a personal failing — that’s a nervous system doing its best to protect you.
For all of us… money can stand in for lots of things. And it’s often things we want… abundance, freedom, power, success.
But in this case I notice how much money seems to be standing in for something you NEED: Safety.
And when money is holding that much—when it’s responsible for whether you can rest, or breathe, or trust the future—of course there’s terror.
Of course there’s overworking. Of course letting go feels impossible.
What also stands out to me is that this fear isn’t coming from recklessness.It’s coming from memory.
You’ve watched money disappear in the lives around you.You’ve seen what happens when it’s spent too freely, trusted too easily, assumed to be endless.So you learned to become the one who never lets it slip.
That’s not a flaw. That’s a strategy.
And it’s been working—just not without cost.
I’m struck by the bind you’re living in: You have to work more to feel safe — but working more pulls you away from the very creative life you’re trying to protect.
I don’t hear a budgeting problem here. I hear the weight of something that’s been lost—or maybe never fully felt possible.
Underneath all of this, I hear a mourning for a life that feels just out of reach. A life where you could make art without fear. Where you could live in New York without a constant escape plan. Where money had your back instead of holding you hostage.
Right now, money isn’t the thing you trust. Work is.
Work has become the coping strategy. Work is the place where control lives for you.
And until that’s acknowledged — until it’s spoken out loud — nothing “practical” will ever land.
So if you were sitting with me, I wouldn’t start with how to fix this.
I’d ask: When did working yourself to the edge become the only way you felt allowed to feel safe?
Not to answer today. Not to solve. Just to notice.
Because the first step here isn’t changing your behavior. It’s honoring the intelligence of the strategy you’ve been using — and gently questioning whether it still has to cost you everything.
You said you don’t know where to start.
I want you to know this: You already have.
Telling the truth about fear — without trying to dress it up or outgrow it — is the beginning.
Thank you to the writer for trusting me with this letter.
Dear Money is a space for honesty, not answers.
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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