Hi there! I am currently kicking myself…I’ve REALLY made a mess of my finances and record-keeping. See, I’m over 18, and yet this is the first time I’ve ever tried doing my taxes myself. in the past it’s been 95% my father doing the work, 5% me running around, confused, trying to find forms he says I need and that I don’t remember getting but must have put…somewhere. Now, I highly doubt I’ll ever meet any of you in person, so your opinions really shouldn’t matter, but before I go into this next part I feel compelled to just add here that i am NOT an idiot…well…not usually. When it comes to finances, though, I’m finding that general rule of thumb just doesn’t apply.

So here’s the story. I’ve always been pretty entrepreneurial, doing some freelance writing, ebay selling, babysitting, event planning, stuff like that. For 2009, though, my primary income, in addition to waitressing, was 1) babysitting and 2) advertising/marketing writing–to be specific, working on commission to sell stuff for folks. I kept TERRIBLE records (i.e. none), not because I was trying to be dishonest or piss of the IRS, but because I just didn’t think about it. So you can imagine what a disaster my trying to file this year has been! The only good records were from the waitressing job–about k–which has been the majority of my income. Other tax form areas I saw and for which I REALLY wished I had better info: medical expenses and charity. If I’d kept better records for both, I think taxes could have been SIGNIFICANTLY less than they turned out to be (about k total (federal and state), but even more–about 00–before I fix the error i made when sending in the first return. I think this is called an amendment…will this increase my chances of an audit?)

I also found out I’m supposed to pay quarterly estimated taxes, which I will start doing as soon as i get the error straightened out.

So here’s my basic question. Starting now through the end of the year (and beyond, of course:)), I plan on keeping very good records. I’ll be keeping track of:

1) medical expenses
2) charity work/donations

For these I’m confused about several things. First, the standard deduction? I heard I should usually take this for medical and charity, and that medical has to be at least 7.5% of income to qualify (which mine always is).

Then there’s the ever-intimidating:
3) Business finances.

As I understand it, I am considered to "own" two different businesses. One is babysitting (which I do in the family’s home), the other, "advertising/marketing services."

For babysitting, the kids live a quarter mile from me, so I’m not planning on trying to figure out deductions related to driving. what I’m planning to do in for this is just record each time I get paid (day and amount), and my expenses (almost all of which are me buying stuff for the kids during the day–the parents reimburse me for those when I get paid, so I’ll just make a note of them.)

For the writing/advertising, though, it gets a bit more complicated. Sometimes I take on big projects for folks who are losing their homes and need everything out by a specific date. For instance, last month I did a 3 1/2-week job for a guy who owned a four-bedroom house, everything still inside. I coordinated estate sales, private sales, listed stuff on craigslist and in different forums, etc. The guy lived almost 30 miles away, and I was constantly driving back and forth to meet potential buyers. On several occasions I also had to hire folks to help with the sales when I couldn’t be there at a specific time. There were lots of miscellanious expenses, etc. and some people we even paid in "stuff."

What I’m planning to do for this second biz from now on is to record each time a sale is made, what my commission is (if it’s not something I bought to re-sell), and what my expenses are. I’ll also try to log mileage as it occurs.

As for other deductions, I think it might be a good idea to just leave those alone, because almost everything I use for my business (computer, car, etc.) is also for personal use. So that whole "home office" deduction would definitely not apply, because my "office" is the computer in my bedroom (and I don’t pay rent), and my "inventory," when I’m buying and re-selling rather than just working on commission, is just piles of whatever stuff it is I’m marketing.

When it comes time to file those 2010 taxes, is this going to be pretty much the majority of what I’ll need? Other than the w-2 from my waitressing job and the (miniscule) statement from my stock shares, have I covered everything I’ll need? and if not, what else should I be aware of? I want to make sure NOTHING like this EVER happens again!!!

Thank you so much for any input you can provide!