so i have this friend, brilliant developer, seriously one of the best i know - he does the design, the code, everything and clients love his work.
but asking for money? dude completely falls apart.
i don't think it's about confidence, it's more like he genuinely believes that if he does good work, people will just pay and that the invoice is enough and that he shouldn't have to follow up because that would imply he doesn't trust them.
he told me about this one client, delivered a full website sent the invoice got a "cool we'll sort it" message and then nothing for three months, three months and in that whole time he sent maybe one follow-up email, felt terrible about it, and then just went quiet.
he said he kept drafting messages and deleting them because they felt too pushy, too formal. like he was accusing them of something.
the client was posting on linkedin the whole time, clearly not struggling.
what finally worked - and this is the bit that got me - was whatsapp. not a formal reminder, just a message and something like "hey - can i check about the invoice from last month, is it sorted ?"
most of them replied within the hour. some of them apologised and said they hadn't even seen the email.
he's tried it across a few late clients now and it's worked almost every time the emails were going into an inbox nobody was actually checking and the whatsapp went to their personal phone.
he's still awkward about the whole thing, still waits longer than he should but at least now when he does chase, it actually lands.
anyone else deal with this? the psychological bit more than the practical - like actually getting yourself to send the message in the first place?