I finally stopped being nice about late payments after a $2,000 lesson

For years I'd send a friendly 'just checking in' email when an invoice was late. Last month, a regular who owed me two grand ghosted me for 6 weeks. The tip-off was when I saw his social media post from a fancy vacation. I realized my nice-guy approach was just letting people think my time wasn't valuable. Now I send a payment reminder the day it's due, no exceptions. Do you think being firm from the start hurts a good client relationship?

4 comments

4 Comments

the_elizabeth16d ago

Ugh, that's so frustrating. Seeing that vacation post would've made me snap too.

oliviabutler16d agoProlific Poster

Seriously, a late fee fixes that fast.

owens.laura16d ago

Okay but "a $2,000 lesson" sounds a bit dramatic lol. It's just business, people forget to pay sometimes. A friendly check-in after a week is normal, not you being a pushover. Jumping straight to a hard line the day something is due seems like a good way to annoy actually good clients over a simple mistake.

laura_wilson16d ago

Ugh, this is everywhere now. It's like people have forgotten that paying for things you agreed to is basic adulting (not just business stuff, but splitting dinner checks or paying back friends). Setting a clear line from the start just saves everyone the awkwardness later.