Stop Chasing Invoices: How to Ditch Awkward Money Conversations and Get Paid Automatically
Tired of chasing invoices and tiptoeing around money talks? Here’s how to automate your payment process so you get paid faster, more confidently, and without awkward follow-ups.
You didn’t start your business to chase down unpaid invoices. But if you’re like most online service providers I work with, you’ve found yourself spending way too much time writing awkward follow-up emails, double-checking Stripe, or second-guessing whether it’s “too soon” to remind someone to pay you.
Let me say this clearly. You are not a bill collector. You’re a business owner. And your business should pay you first.
Let’s talk about why this keeps happening—and how you can fix it with systems that do the money talk for you.
The Real Reason You're Always Chasing Payments
Most service providers are amazing at their craft. You're generous, you overdeliver, and you genuinely want your clients to feel supported. But when that generosity bleeds into letting payments slide or waiting weeks to follow up, it's not noble. It's draining your time, your energy, and your confidence.
This usually isn’t a discipline problem—it’s a systems problem.
You don't have a structured payment process, so you're winging it every time. And that inconsistency leads to late payments, uncomfortable conversations, and cash flow chaos.
Payment Conversations Shouldn’t Be Personal
And they don’t have to be.
Automated systems can take over the “awkward” parts of getting paid, so you can stay focused on serving your clients—not stressing over whether they’ve opened your invoice.
Here’s what I recommend for most online service businesses:
Use a CRM like Dubsado, HoneyBook, or 17hats to send branded proposals and invoices that include your payment terms upfront.
Connect Stripe or PayPal for seamless payment processing.
Set up automated payment reminders so your system follows up for you.
Trigger thank-you emails when a payment comes through—automatically.
When you set this up correctly, no one’s guessing. Not you, not your client.
Build a “Get Paid” System That Runs Without You
One of the best things I’ve ever helped a client do? Stop thinking about payments at all.
We set up a system where:
New clients automatically receive a contract and invoice when they book.
Their payment is required before a single second is booked on her calendar.
If they don’t pay? The system cancels the session.
She gets notified instantly when the payment hits.
This is how we scale sustainably. Not with more hustle, but with better backend systems.
Getting Paid Is a Part of Client Experience
Here’s what most people don’t realize - your payment process is a direct reflection of your brand. When it’s seamless, clients feel held. When it’s messy, they feel unsure.
A clear payment process builds trust. It signals to your client that this isn’t your side hustle. You run a legit operation. And that’s the kind of provider people want to keep hiring and referring to others.
Pay Yourself First—Like the CEO You Are
Here’s your new mantra: I pay myself first. Not when the invoice gets paid. Not if the client remembers. Not after chasing three reminders.
You set the terms. Your systems enforce them. And your energy stays focused where it belongs: on the work you love, not the money you’re owed.
Want My Help Setting Up a Payment System?
If this hits a nerve in the best way, and you’re ready to stop chasing payments and start leading like a CEO—I can help.
I work with online service providers to set up smooth, scalable systems in Dubsado, Zapier, and other automation tools that make getting paid feel effortless.
👉 Let’s talk about building your “get paid” system.
Because you deserve to be the first one your business takes care of.
