I’m a bitch.
I’m annoying.
I’m getting on your nerves.
I’m bossy.
I don’t care what you call me. In the unminced words of Issa Rae, “Run me my money.”
You owe me $30,000.
You owe me $80.
You owe me $2,500.
Enough with the excuses. Run me my money.
I recently overheard two women talking about money. And honestly, I loved hearing it. They were discussing investments, real estate deals and the multiple homes they owned. One woman had recently closed a deal as a private investor and was trying to recover $30,000 she was owed. The borrower was three months behind and full of excuses.
But what struck me most wasn’t the overdue money—it was the way she described herself while trying to collect it.
“I feel like I’m annoying him,” she said. “I feel like I’m pestering him every time I call.”
Her friend immediately responded: “He owes you $30,000. You can call him 10 times a day if you need to.”
That exchange stayed with me because it perfectly captured how many women—even successful, intelligent, accomplished women—still struggle being direct about money.
We will negotiate million-dollar contracts, manage households, raise families, lead teams and run businesses. Yet somehow, asking for what we are rightfully owed can make us feel rude, aggressive or just too much.
A few days later, I found myself doing the exact same thing.
I had loaned a family member $80. Per my own lending rules (yes, I literally wrote a blog about this), I let them choose the repayment date: two days later, they promised. But when the repayment date came, instead of directly asking, “Hey, is the money still coming today?” I danced around it.
I called to “clarify” who would actually be sending the payment (the money was loaned to one family member for use by another, her adult son). That was my soft, polite, indirect way of asking, “run me my money.” And the irony is—I knew better.
A few years ago, I completed a ghostwriting assignment for a client who never paid me. Not one cent. I still have the manuscript. He has partial drafts, but I never delivered the final version. Here’s a sampling of the emails I sent him—each one softer than the last:
Me:
“Hello:
Can you do Cash App? If so, I’m at $XXXXXXX.
Chat soon.”
Client:
“Ok, I apologize and you will see a payment next week. Sorry for the delay.”
Weeks later, after multiple ignored messages, I wrote:
Me:
“Hello:
I wanted to know if you wanted me to keep going with the project or pause for a bit. Let me know either way. I can spend the next few weeks wrapping it up and get it over to you. Let me know how you want to handle the payment.”
Translation?
This man owed me thousands of dollars and I was still talking like he was doing me a favor. I buried the real reason for contacting him beneath soft language, over-explaining and politeness. Instead of saying, “Your payment is overdue and work is paused until payment is received,” I practically whispered around the issue.
Unfortunately, many women struggle with being assertive is these types of scenarios. How often do we apologize when no apology is necessary? How often do we shrink our language to make ourselves sound less demanding, less intimidating, less difficult?
We say:
- “Sorry to bother you …”
- “Sorry, I just had a quick question …”
- “This might be a silly question, but …”
- “I’m no expert, but …”
- “Just following up …”
- “Kind of …”
- “Maybe …”
- “Sort of …”
- “That’s just my two cents …”
We soften.
We cushion.
We dilute.
Especially when money enters the conversation.
And yet these are smart women. Strong women. Women who negotiate contracts, manage budgets, build businesses and hold entire households together. Women who are exceptional communicators. Women who can command a room.
So why do so many of us suddenly become tentative when it’s time to advocate for ourselves financially? Because somewhere along the way, many women were taught being direct about money makes us greedy. Harsh. Aggressive. Unlikable.
But there is nothing rude about expecting to be paid.
There is nothing inappropriate about enforcing boundaries.
There is nothing “bossy” about protecting your money.
Sometimes financial literacy isn’t just about budgets, investing or credit scores. Sometimes it’s about language. Confidence. Boundaries. Clarity. Sometimes it’s about learning to say:
“You agreed to pay me two weeks ago. I need the payment today.”
No over-explaining.
No apology.
No shrinking.
Just clarity.
Because when it comes to money, words matter.
So, the next time someone owes you money, remember: asking to be paid is not being “difficult.” It’s business. And women deserve to speak about their money with the same confidence they use to earn it.
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