If you’ve ever dreaded following up on a late payment, you’re not alone. I saw someone post in a group recently asking how to get past the bad feelings of chasing money when a client hasn’t paid on time.

I get it—no one likes feeling like they’re bothering or annoying someone, especially when money is involved. But here’s the thing: those feelings shouldn’t even come into play. You’re not begging or pestering. You’re asking for what’s rightfully yours.

And if it does feel personal? That’s your sign to automate the entire process.

Why Do We Feel Awkward Asking for Money?

When someone misses a payment, the emotional spiral can start fast:

• “Am I being too pushy?”
• “What if they think I’m annoying?”
• “Is this going to ruin our relationship?”

The truth is, this shouldn’t be part of your mental load. You’re not asking for something extra—you’re asking for what was already agreed upon.

But when you’re manually sending payment follow-ups, those feelings creep in. It becomes a task you dread, and every email feels a little heavier.

That emotional energy is a waste of your valuable headspace. You’ve already done the work, provided the service, or delivered the product. You deserve to be paid.

The Fix: Automate Payment Reminders

The easiest way to remove those feelings? Don’t be the one doing the follow-ups.

Let a system like Dubsado send those payment reminders for you:

✅ Professional and Timely Emails: Automated reminders go out at regular intervals—7 days before, on the due date, and if necessary, after the due date. No more awkwardly wondering when to follow up.

✅ Consistent Follow-Through: Your system will handle reminders for every client, every time. No slipping through the cracks.

✅ A Softer Client Experience: When it’s the system sending reminders, it feels less personal to the client. It’s just business—and that’s how it should be.

How I Handle Payment Follow-Ups for My Clients

When I set up Dubsado for my clients, automated payment reminders are one of the first things we tackle. Here’s what I recommend:

1. Clear Payment Schedules: Build payment plans directly into your CRM so clients know exactly when payments are due.
2. Custom Reminder Templates: Use friendly, branded templates that don’t feel harsh or transactional.
3. Workflows That Trigger Automatically: Let your CRM take over once an invoice is sent. You don’t need to think about it again.

Why It’s Not “Bothering” Clients

Here’s a mindset shift: following up on a late payment isn’t pushy—it’s professional.

Your clients agreed to pay you. Reminders aren’t about pressuring them; they’re about keeping communication clear and ensuring expectations are met.

By automating your follow-ups, you take the awkwardness out of the equation entirely. It’s no longer a personal conversation—it’s a business process.

Final Thought: Let Automation Free Your Headspace

Getting paid is the foundation of running your business. If you’re spending emotional energy worrying about payment follow-ups, it’s time to let that go.

Use a CRM like Dubsado to automate the process, protect your time, and keep your business running smoothly—without the stress.

If this is something you struggle with, let’s chat. I’ll set up your Dubsado system to handle all the payment follow-ups for you. You focus on your clients; your CRM will handle the rest. 💸