Jeremiah Tolbert

Writer | Photographer | Web Designer

Freelance Tax Annoyances

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!

4 Responses »

  1. More often than not the 1099’s I receive are wrong in one way or another, so you’re right to keep your own detailed records. As far as hav­ing to file them with your return… hon­estly, I’ve been e-filing for so long I’m not sure. I never send any of the sup­port­ing doc­u­men­ta­tion (w-2’s, 1099’s, etc.), in other words. If and when the com­pa­nies you worked for do send the forms, they’re required to send one to the IRS as well, so I think as long as your records match theirs you should be OK. That being said, prob­a­bly best to make sure they do match before send­ing any­thing to the IRS. Note that employ­ers are not required to send a 1099 for any­thing less than $600.

  2. I always efile as well, and when my hus­band had 1099s before, the only time we needed to send any­thing in is when he was the one pay­ing some­one else. I would think if you’re efil­ing, you shouldn’t have to worry about whether they’re all in because you don’t actu­ally send them in.

  3. As one of the guilty par­ties and a 1099-MISC recip­i­ent myself: I don’t think you need to send the 1099s in — your clients do. You only need to know what they con­tain, so your records match up to the ones the IRS is get­ting from your clients.

    In the H&R Block e-file ser­vice I used today, infor­ma­tion from 1099s was used to pop­u­late my Schedule C, self-employment income. But the pro­gram didn’t spit out a 1099 form for me to send the gov­ern­ment (I’m mail­ing my stuff rather than e-filing) — just a Schedule C.

  4. You don’t sub­mit 1099s with your return. If you feel your records will match what the clients write on the 1099s then you can feel free to file before you get them. The 1099 comes up if you get audited.

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