> Who do I look unprofessional to? The IRS? I can live with that. The problem is, the IRS could quickly become suspicious out of sheer bureaucracy and start au

> Who do I look unprofessional to? The IRS? I can live with that. The problem is, the IRS could quickly become suspicious out of sheer bureaucracy and start auditing you closely and then you could be in for another lesson on your obligation to preserve records, bills and book keeping etc... And at least in Europe, if you fail to pay taxes and especially insurances, they could notify your customers, no less, that whatever money those owe you has to go to them instead. At that point you are pretty much done for unless you are fortunate enough to have enough cash to quickly take care of any open debts to them. I really understand your best intentions but unfortunately the tax authorities aren't exactly in the service industry and they are extremely used to getting only exactly the right kind of input, any deviation from the standard usually ends in chaos, in the best case. And your story suggests you were STILL trying to remediate it on your own, despite them sending you bills including fees for being late... I hope this is not the case. > If you've missed something that's actually important, they'll let you know. Otherwise, everyone's better off leaving well enough alone. This is generally true, one of the nice things of being a freelancer - you only have to worry about things that actually matter. On the other hand missing certain deadlines could mean disadvantages or more bureaucracy for you, that's where the professional help comes in. Also, opening your own company/one-man-show comes with certain responsibilities and unfortunately knowing a bit about taxes or at least knowing enough to realize you typically can NOT do them yourself is one of them. So, while your approach is surely commendable trying to do the right thing, it is also somewhat naïve - that's where the tone came from, as a friendly reminder "this is serious business"! :)