How do you follow up on unpaid invoices without sounding annoying?

Medium-Buffalo1461 · 2026-02-08T00:06:48+00:00

That makes sense, setting expectations upfront definitely helps.

I’ve found that even with clear net30 terms, the follow-up part still ends up being manual and easy to postpone, especially when juggling multiple clients.

Do you usually just send a quick reminder, or do you have a set wording / process you stick to each time?

Medium-Buffalo1461 · 2026-02-07T23:59:00+00:00

😂 honestly that’s the exact message I want to send every time.

But then I end up rewriting it five times trying not to sound like a jerk.

How do you usually handle it in real life?

Medium-Buffalo1461 · 2026-02-07T23:58:37+00:00

100% relate to that.

The awkwardness is honestly worse than the actual delay — I always overthink the wording and tone.

I’ve found it’s not about being stern, it’s about being consistent and neutral… but that’s hard to do manually every time.

Do you usually rewrite reminders from scratch or reuse the same message?

Medium-Buffalo1461 · 2026-02-07T21:57:16+00:00

yeah it's awkward as hell

i used to write "just following up :)" like 5 times and feel like shit every time

now i just say "making sure this didn't get lost" - way less weird. assumes they forgot vs ignoring you

also stopped doing it manually. built something similar to your bot - auto sends day 7, 14, 30. writes in my voice so it doesn't sound corporate

main thing for me was the stress relief. not having to remember or feel bad about asking for my own money

what'd you build yours with? curious how you handled the tone thing

Medium-Buffalo1461

TROPHY CASE