The Money You Already Made
Be firm rather than soft when asking for money you already earned, so cash sitting in someone else's account moves into yours this week.
By James Schramko · Updated September 2026
You already did the work. The invoice is out. The client used what you delivered. The money is still sitting in their account instead of yours. Either you never followed up at all, or every reminder you sent was polite enough to ignore.
This is a collections conversation. The decision is already made. They agreed to the price and the terms when they bought. A friendly nudge treats it like a sale they still have to decide on. What is missing is the ask that makes settling today easier than settling next month.
Where I Learned This
I used to be a debt collector. In 1991, I was a trainee assistant manager debt collector for a collections company based in the city of Sydney. Each day I'd be on the phones collecting overdue bills on behalf of clients. In that office we sent out a lot of legal letters and would follow through to the court if they were not paid.
A short time later, I took a telephone collections role at General Motors Acceptance Corporation. That was the finance company behind a lot of the cars sold in Australia at the time. My core focus was collecting overdue car payments over the phone.
In 1992 I was promoted to field agent. That meant I got to drive around repossessing cars.
People who were very late were good at making excuses for not paying. But when the tow truck got hooked up to the car, suddenly the money would appear.
The lesson is that you need some kind of mechanism for the payment to be made.
From the time I was 20 years old to now, I've always felt strongly about one thing. The fair thing to do is for people to pay what they owe.
Everything below comes from that position.
Why Politeness Stops Working
A friendly reminder gives the other side an easy way to file it as low priority. No date, no consequence, no cost to ignoring it again. Every unpaid invoice competes with everything else on someone's desk. A soft nudge loses that contest every time.
One video production agency owner I worked with had $132,949 sitting in unpaid invoices, more than $67,000 of it overdue. She read the numbers as a revenue problem. She started looking at new offers and new traffic to fix it. The real twelve month picture told a different story: the business was $162,000 net profitable. The money was there. It was owed, not missing. Once the diagnosis moved from revenue to collections, she collected $30,000 of it in two days. She made payroll without touching a credit card.
The fix included one direct ask for money she had already earned.
The Direct Demand
A direct demand names three things a friendly reminder never does: the amount, the deadline, and what happens if the deadline passes. No anger. No apology either. State the position and hold it.
Before you write it, check three things. The invoice is due. The amount is correct and not in dispute. Your terms allow what you are about to say.
Compare the two.
A friendly reminder: "Just following up on the invoice from last month, whenever you get a chance."
A direct demand: "Invoice #4521 for $8,200 was due on 14 August. Please settle it by Friday 12 September. If it is not settled by then, the late fee in our terms applies and no new work starts until the account is clear. On 19 September the account goes to a collections agency."
The first invites another week of silence. The second gives the other side one decision to make, and a date to make it by. It works because it removes the wiggle room a friendly reminder leaves. Wiggle room is what lets an invoice slide to the bottom of someone else's list.
The same structure holds whether the amount is two hundred dollars or two hundred thousand. Name the figure, the date, and what happens on the other side of the date. Put nothing else in the message. The consequence has to be one you are entitled to carry out and prepared to carry out. Three qualify. A late fee your terms provide for. No new work until the account is settled. Referral to a collections agency on a named date. Pausing work you have already delivered is no consequence at all. Pausing work you are contracted to finish can put you in breach.
Detach Before You Ask
Founders soften the ask because it feels personal. You built a relationship with this client. Naming an unpaid debt feels like putting the relationship at risk.
One founder I coach separated the two cleanly. Asked whether a payment was settled, he handed the question straight to the people whose job it was to chase it. No charge in his voice either way. His own description of the shift: he did not need to attach his personality to it. The invoice is a business fact. Whether you like the client is a separate fact. Mixing the two into one conversation is what keeps founders sending friendly reminders long after friendly has stopped working.
Detachment means you do not let the discomfort of the ask decide whether the ask gets made. It does not require coldness. It does not require an apology tour once the money lands. State the terms, hold the terms, and let the relationship carry on as it always has once the invoice is settled.
Self-Diagnostic
Run this on every invoice sitting unpaid past its terms right now.
Has more than one reminder gone out with no date and no consequence attached? If so, you have a reminder habit and no collections process.
Are you avoiding the direct version because you are worried about the relationship? Or because you have not decided the number and the date yet? Name the real reason to yourself before you write anything. An unpaid invoice sitting for months puts the relationship at more risk than a plain message asking for it.
Could you hand the follow-up to someone else? A bookkeeper, a specialist, a formal notice. Let the business fact travel without your personality on it. If yes, that is often the fastest fix there is. The message lands with none of your hesitation built in.
Is the total sitting in unpaid invoices bigger than the gap you have been trying to close with new sales? If so, stop looking for new revenue. Collect the revenue you already earned first.
What To Send Today
Pick the oldest unpaid invoice on your books right now. Write the amount, the deadline, and what happens if it passes. Send it today. The plain words above beat anything you will find by waiting.
Then do the same for every invoice on the list, oldest first. Founders who run this once usually keep running it. The first result arrives faster than they expected, and a working process is easier to trust the second time.
Quick Reference
- A friendly reminder has no date and no consequence. A direct demand has both, plus the exact amount.
- Outstanding invoices are a collections problem. Do not go looking for new sales to cover money already earned and unpaid.
- Detach the ask from the relationship. The unpaid invoice puts the relationship at more risk than a plain message asking for it.
- Hand collections to someone else where you can, so the ask travels without your personality attached to it.
- Start with the oldest invoice on your books today.
I pay invoices immediately, and I recommend business owners do the same. And I recommend we avoid becoming a free bank. When people owe us money, we should collect it. It's the right thing to do by your business, your team, and yourself.
Getting paid for work you have already done is one of the fastest cash moves inside Mentor. For an invoice nobody disputes, it often needs one thing. A precise ask with a consequence attached.