Jeremiah Tolbert

I’m para­noid about taxes.  I’m con­stantly afraid that I’m going to end up mag­i­cally owing twice what I think I owe to the point where I save nearly every penny in antic­i­pa­tion of the tax bill.  Freelancer taxes are really screwed up, you see.  Sure, we get to deduct a lot of things like home office space, but we end up pay­ing dou­ble the social security/​medicare taxes that the employed pay, because the employer pays half of that usu­ally.    And then there’s the state income taxes, and the fed­eral income taxes, which are nor­mal, except we don’t have the lux­ury of hav­ing them with­held for us.

I was not set up this year to pay esti­mated taxes because I had not intended when I started out to be free­lanc­ing for the entire year.  I spent half the year look­ing for a job before finally giv­ing up on that and set­tling into being a full time free­lance designer.  I’ve done alright for myself in those last 6 months.  But I’m look­ing at my sav­ings and know­ing that a con­sid­er­able chunk of it is owed in taxes.  How much exactly is what I would like to know.  I don’t even begin to under­stand how the tax sys­tem truly works.

That’s all a long way of get­ting around to say­ing, I file early every year.  As soon as I have the paper­work.  I almost never fail to have my taxes done by the sec­ond week of February.  This year, I’m not sure what to do, because of a bunch of 1099 forms from my clients are slow to arrive.  Several have not even been sent yet, despite the fact that the gov­ern­ment requires that 1099s be mailed no later than January 31st.  Now, I have very detailed records of my income thanks to using fan­tas­tic invoic­ing soft­ware.   I  don’t need the 1099s to know what I made.  But I think the gov­ern­ment expects me to send them in.

Any tax experts out there know what the require­ments are regard­ing 1099s that are so damned slow in arriv­ing?  If I report the income myself, does it mat­ter if I don’t send a 1099 that didn’t come in time?

Ugh.  It’s enough to give me an ulcer.  You know, it’s not like free­lancers don’t have enough to worry about.  The com­plete lack of income secu­rity is plenty!