Unpopular opinion: quarterly estimates were easier before all these apps

I was talking to my old boss at the HVAC supply house last week and he said he still mails paper checks with actual stamps. Honestly I spent 3 hours last quarter messing with three different payment portals and still got a late fee anyway. Has anyone else just gone back to writing a check and dropping it in the mail?

4 comments

4 Comments

the_ben2h ago

Would it kill these companies to just let me mail a check like a normal person? I started paying my business insurance by mail last year and haven't had a single late fee since.

finleym376m ago

Wait, you're telling me you haven't had a single late fee since switching to mailing checks? That's wild, I can't even remember the last time I mailed a physical check for anything. Honestly, with how often online payment systems glitch or auto-pay fails, this almost sounds too good to be true.

ryan_hart386m ago

And THIS is why I keep a stack of actual checks in my desk drawer. I found that the trick is to use the bill pay service through my bank instead of just writing them myself. They print and mail the check for free and I can set it up to go out five days early. If a vendor takes forever to cash it I don't even care because the bank shows the payment date as the day it was mailed. That alone saved me from like three late fees last year when vendors claimed they never got my payment.

kellyallen6m ago

That's where I'm at now with a couple of my vendors... the mail just works. Set it up like a monthly bill, stamp goes on, out the door. No waiting for a confirmation email that never comes, no wondering if the site processed it right. Plus my bank sends me a photo of the cleared check so I've got proof if anyone argues.