Managing unexpected challenges in daily business operations, from invoicing to debt collection

Been running solo for a few years now and honestly, some weeks everything that can go wrong does go wrong.

Last month had three clients suddenly change payment terms mid-project, one invoice got “lost” for six weeks, and ended up having to chase down a $2,800 payment that was three months overdue.

Starting to think I need better systems in place but curious how others handle these curveballs when you’re wearing all the hats.

Same thing happened to me twice with lost invoices. Now I email them with read receipts and follow up in writing if no confirmation within a week.

For payment changes, I charge a project change fee now - even $100 makes clients think twice before switching things randomly.

Three months overdue is brutal. I add late fees to all contracts after getting burned on a $1,500 job. People pay way faster when there’s a penalty.

Clients push you around when they think they can negotiate. I made payment terms non-negotiable from the start. Contract says net 15 - no exceptions.

For “lost” invoices, I switched to certified mail. Costs a few bucks but magically invoices don’t get lost anymore.

This video shows how to set payment terms that actually stick:

Get stricter about money and clients will respect your time. The ones who don’t? Drop them.

I always ask for 50% upfront on jobs over $1000. Saves me from chasing down big payments later.

I put all payment terms in writing before I start. Client wants changes? We stop and renegotiate everything first.

Invoice tracking saves my butt constantly. I’ve got a basic spreadsheet with invoice number, date sent, amount, days overdue, and last contact attempt.

I update it every week. Once something hits 30 days, I pick up the phone instead of sending another email.

When clients want to change payment terms mid-project, I tell them “let’s talk about that when we finish this one.” Keeps things moving and pushes changes to where they make sense.

I also make new clients fill out a credit app if they want net 30. Most would rather just pay upfront than mess with forms.

Cash jobs only now. No invoicing headaches when they pay before I leave.

Same here. Just keep calling until they pay.