u/Lanky_Pineapple9516

A friend of mine used to delay reminder emails for DAYS because he hated sounding pushy, and honestly I realized most people are weirdly uncomfortable asking to be paid 😭

Especially the fake: “hope you’re doing well 🙂”

before mentioning the overdue invoice.

I ended up building him a tiny automation tool for reminders just to avoid the whole awkward follow-up process.

Now I’m curious how other freelancers / small business owners handle this stuff.

Do you automate reminders or still do them manually?

Why is asking clients to pay invoices so painfully awkward?