An anonymous writer reflects on a relationship with money that has always felt complicated — elusive, charged with both possibility and fear. This episode sits with what it means to name that honestly, and the courage it takes to make a commitment before you know exactly how to keep it.
Letters may be lightly edited for privacy and clarity.
Dear Money—
I’ve been thinking about you a lot lately. Not just in passing moments or fleeting worries — but in a deeper, more reflective way.
Our relationship has always felt complicated. Like a dance I’m still learning the steps to. Sometimes I chase you, hoping to catch up. Other times you feel just out of reach, slipping through my fingers before I can fully understand what it means to have you. To trust you. To feel secure with you.
Growing up, I learned that you were both a necessity and a mystery. You could open doors — but just as easily close them. You could offer comfort, but also create tension. I’ve felt your presence as a symbol of both freedom and constraint. And honestly, there are days I wonder if I’ll ever truly figure out how to live alongside you. Peacefully. Without fear.
I know I haven’t always treated you with the respect you deserve. I’ve been reckless with you at times — unsure of how to hold onto you when you came into my life, and just as unsure of how to manage your absence when you were scarce. But I’ve also tried. Tried to understand your language. Tried to build a life that respects your power without letting it define my every choice.
In this new phase, I want to build something different with you. I want to see you as more than a resource or a means to an end. I want to stop running after you in fear and start walking alongside you in trust.
I’m ready to shift. To invite abundance rather than scarcity. I know it will take time, patience, and a lot of honesty between us. But I’m willing to do the work.
I see your value — not just in the practical sense, but in the way you can shape my sense of freedom, my ability to create, my capacity to give.
This letter is my promise to myself: that I will do better. Not because I want to chase you endlessly. But because I want to build something lasting.
I’m ready for this new chapter.
I want to say first, before anything else, that this letter is an act of courage.
It is hard to sit with something you haven’t figured out yet — and choose to write it down anyway. To send it. To let someone else witness it.
You describe your relationship with money as complicated. Like a dance you’re still learning the steps to. And I notice that you don’t rush past that. You don’t immediately pivot to solutions or plans or promises to do better.
Complicated. Elusive. Slipping through your fingers.
Those are your words.
And they’re worth sitting with.
Because before we can build something new, we have to be honest about what we’re actually working with. Not the version we wish we had. Not the version we think we should have by now. The real one.
And you’re doing that.
You also name the fact that money has been multiple things for you. A door that opens and a door that closes. A source of comfort and a source of tension. Freedom and constraint, sometimes at the same time.
That’s an accurate description of a complicated relationship.
You’re not misreading it. You’re seeing it clearly.
Another thing that stands out to me is that you don’t dismiss the fact that when it comes to your relationship with money - you have tried to strengthen it. A lot of us are really quick to blow past any positives. We catalogue our missteps and leave out our effort. But you hold both. The recklessness and the trying. The uncertainty and the intention.
That balance is not easy to hold.
And then you make a commitment.
Not a plan. Not a set of steps. A commitment. A promise to yourself to keep showing up to this relationship even when it’s hard, even when you don’t have all the answers, even when the path isn’t clear yet.
I want you to hear how significant that is.
Because the answers come later. The clarity comes later. The concrete steps come later.
But the willingness to take a stand — to say, I’m ready for something different — that has to come first.
And here’s what I’ve seen, again and again: when someone points themselves in a direction — genuinely, honestly, the way you have in this letter — the path has a way of revealing itself. Not all at once. But in small moments. A conversation you’re willing to have now that you weren’t before. A choice that feels different because you’re looking at it differently. A door you notice, because you’ve decided to start looking for doors.
That’s how it tends to work.
So keep showing up. In the big ways, yes. But also in the small ones. The small ones count. They accumulate. They become the thing you look back on and call a turning point.
You wrote this letter.
That’s where everything else begins.
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.
