That's not silly at all - I think the root of that fear is that we don't want to be perceived as 'nagging' individuals anג perhaps harm any potential future pro

That's not silly at all - I think the root of that fear is that we don't want to be perceived as 'nagging' individuals anג perhaps harm any potential future projects. However think about it - would you like to work repeatedly for a person who doesn't pay you in time? Would you stay at a job where your salary would be delayed by 10-20 days every time? The answer is most likely no, then why do we settle when we are freelancers?