Freelancer Woes: Taxes, Taxes, and More Taxes

While I've gone through periods of working part-time gigs and freelancing for a little extra cash on the side, 2008-2009 will be the first year when I'm likely going to be a contractor all year long. I love the freelance lifestyle, as I can finish my work hours when everyone else is asleep, or get all my hours done straight through and leave myself time to relax for an extra weekend day, if possible. There are so many things I love about being a freelancer (albeit one with a stable freelance gig) that I'd be hard pressed to give it up.

One thing that might, just might be able to get me to give this wonderful lifestyle up is taxes.

Just trying to figure out how to sort out my taxes owed as a freelancer seems like a giant nightmare. On top of that I now have Prosper taxes (which sounds like it will be worse than a nightmare to file) and my various stocks, ETF and mutual fund accounts to tax...

Originally I thought sorting out my taxes would be simple as taking 25 percent of all my income each month and putting it into a highish-interest ING savings account. Come tax time, my tax money will have made a little money (although that will be taxed to) and if all worked out as I originally thought, the money in that account would certainly cover all my state and federal taxes... plus I would have saved some money by holding off on paying it throughout the year.

Given that I finally stopped to smell the dead roses, I did a little research and found out about the "Self Employment Tax" which seems to be another 15.3 % on top of the 25%. So does that mean I should be putting 35% of my income each month into my ING "for tax season" account?

And then... apparently freelancers are supposed to pay an estimated tax each month. What I don't understand is if this is for the convenience of the freelancer (don't have to worry about spending all your tax money and being in serious trouble come April 15) or if it's actually required by law to pay taxes on a monthly basis instead of in one lump sum at the end of the year. If it's not illegal, I really don't understand why more people wouldn't just do what I think I'm doing with this savings account and getting a few extra dollars on the money that will ultimately go to the IRS at the end of the year. But maybe I'm thinking about this all wrong.

I'm, quite frankly, terrified of tax season next year. This year is complicated enough with my two full-time jobs and freelance earnings. But next year? Well, I know I'll have to hire an accountant. But what is it I should do now, as it starting 1.5 months ago, to make my life bearable next year... and more importantly, so I don't accidentally end up in jail for tax fraud out of ignorance and confusion?

ps: I think I just found my answer... (I guess I do have to pay in advance!!!)
http://www.irs.gov/publications/p505/ch02.html#d0e5923

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(Thanks to the IRS for explaining, in fairly clear language, how I can give them my money)

When To Pay Estimated Tax

For estimated tax purposes, the year is divided into four payment periods. Each period has a specific payment due date. If you do not pay enough tax by the due date of each of the payment periods, you may be charged a penalty even if you are due a refund when you file your income tax return. The payment periods and due dates for estimated tax payments are shown below.

For the period:		Due date:
Jan. 1 1 - March 31		April 15
April 1 - May 31		June 15
June 1 - August 31		September 15
Sept. 1 - Dec. 31		January 15 next year 2

1If your tax year does not begin on January 1, see Fiscal year taxpayers, below.

2See January payment, below.

Saturday, Sunday, holiday rule. If the due date for an estimated tax payment falls on a Saturday, Sunday, or legal holiday, the payment will be on time if you make it on the next business day. For example, a payment due on Saturday, September 15, 2007, will be on time if you make it by Monday, September 17, 2007.

January payment. If you file your 2007 Form 1040 or Form 1040A by January 31, 2008, and pay the rest of the tax you owe, you do not need to make the payment due on January 15, 2008.

Example.

Janet Adams does not pay any estimated tax for 2007. She files her 2007 income tax return and pays the balance due shown on her return on January 24, 2008.

Janet's estimated tax for the fourth payment period is considered to have been paid on time. However, she may owe a penalty for not making the first three estimated tax payments. Any penalty for not making those payments will be figured up to January 24, 2008.

Fiscal year taxpayers. If your tax year does not start on January 1, your payment due dates are:

1. The 15th day of the 4th month of your fiscal year,

2. The 15th day of the 6th month of your fiscal year,

3. The 15th day of the 9th month of your fiscal year, and

4. The 15th day of the 1st month after the end of your fiscal year.

You do not have to make the last payment listed above if you file your income tax return by the last day of the first month after the end of your fiscal year and pay all the tax you owe with your return.

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Ok, now I just have to figure out exactly how much I have to pay them. Hmm.

Here are some helpful links I'll be reviewing to help me figure out just that, and I'll report back here when I actually understand what I'm talking about:

1. Write From Home: Taxes for Writers: Paying your Estimated Tax
2. Huge Taxes for Freelancers?
3. California Tax Service Center

Once I do understand all this, I can work as a freelance freelance accountant. :)

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Crap. I got pulled over.

I can't blame anyone else for this mishap. My registration expired... a while ago. However, I paid the $120 registration fee at the DMV (which, I think included a late fee) and was to get my smog checked by Jan. I had until Jan 1 to get my smog checked and get my stickers for my plates.

Of course, being the procrastinating idiot that I am, I waited a little too long to get this done. I received one ticket (for $35) for my expired registration while my car was parked in a public lot. So I finally got around to getting my smog checked THIS MORNING. I paid $90 for my smog check & an oil change that was overdue.

Ten minutes later, I was driving on the freeway and I got pulled over.

I showed the cop my smog receipt and the little registration card (that may or may not have been expired... I'm a bit confused about whether it expired on the 1st of the month, or at the end of the month.)

The worst thing was that somehow my insurance card had gone missing. I kept it in my glove compartment, but the robbers threw everything out of my glove compartment when they went through my car last month. I thought I had put everything back, but apparently my insurance information was missing.

So now I have this "notice to appear" paper that says that I have an infraction for an expired registration and it also notes that I did not have insurance on me, though neither the infraction or misnomer boxes are checked for that. I'm not sure what that means.

The cop said that I should get my sticker and then go to any police department with the paper. He didn't really explain whether I'm going to owe a zillion dollars or if I just need to prove that I'm actually registered to avoid paying.

This really sucks because today I decided I'm going to start being really tight on my budget and living with a minimal amount in my checking account. I figure I'll spend less if I pretend I have less to spend. Simple psychology ought to do the trick.

Except now I'm worried I'm going to get an overdraft fee because of all of these unexpected expenses. That'll teach me to stop procrastinating, eh?

I owe quite a bit of money for different things... $200 for health insurance... $150 for my cyst removal bill... $35 for my ticket... and now who knows how much more for this other ticket-type-thing.

Right now I have $600 in my checking account. I'm supposed to get paid Monday for my work... so that would bring me up to $3900. BUT I plan on putting $1000 of that in a special ING savings account for taxes. That leaves me with $2900, and I have to pay rent in a few days. So I'm at $1850. Not so bad, but after I pay all those bills, plus my phone bill, plus the cable/internet bill, plus the gym bill, plus buy a new phone in two days (my old one is lost and I am eligible for the discount on a new phone on Monday)... well, I won't have much money left for food.

At least this setup will keep me from spending money on clothes I don't need!
At least that will keep me from

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Attempting to learn how to Budget with Beehive

Thanks to an anonymous poster for reminding me how I really need to start budgeting. After my little shopping trip to the local mall the other day, I realized just how little control I have over my spending. One of my biggest problems (and I know I'm fortunate to even have this problem) is that I have $20k+ in savings, so often I feel like even though I shouldn't be spending that money (I should be SAVING it for grad school or a house) - but it just feels like those bigger ticket items are so unreachable that I might as well just spend my money now. And I get such a rush buying clothes. Especially ones that I feel good about buying... when I feel like I've bought items that I'll wear again and again. It makes the endorphins kick in. Shopping is my drug. But it's an expensive habit. And I need to quit it.

In any case, I've decided to try to make a budget and to... hopefully... stick to it. There's no reason I can't get through a month on a monthly salary of about $3000. It's pathetic that I'm still losing money. Ok, so I haven't actually gotten through my first "full" month of work, so last month was just a mess financially anyway, with my time off between jobs and everything. In any case, I looked online to find some budgeting tools, and of course, I found a zillion. I picked one out at random...

Beehive basically helps you make your budget. I'm going through right now and filling in all of my income and expense information. This should help me see exactly how much money I have to use to budget per month.


I'm trying to estimate low for non-fixed income, since I'd rather end up with more money at the end of the year than less. When they asked how much I make per year in investments, I put down $200. I think my CDs probably take in about $300 per year, but the way my other investments... Roth IRA and Mutual Fund are doing, I'll be lucky if I break even this year.

Meanwhile, I'm estimating high on most expenses. I'm really confused on how to budget, but I guess ultimately if I put in $100 a month for clothing I NEED to stick to that.

Here's what I'm budgeting for non-fixed expenses...

(per month)

Clothing: $100 (um, can I really just spend $100 a month on clothing?) $200: I don't have to spend all $200, but I'd rather save some money for clothing each month and then go on a massive shopping spree, as opposed to only having $100 to spend.
Gasoline: $250 (it's been that high in the past few months because of all of my commuting for various reasons. In september, my gas costs should come down quite drastically, but it can't hurt to estimate high, right?
Entertainment: $200. Should include alcohol costs. Because that's what adds up.
Beauty: $100. I figure between eyebrow/face waxing, and my occasional hair cut, beauty costs average out to about a hundred a month. Maybe I should estimate higher. Hmm.
Alcohol: $50. Here, I'll through in an extra $50 for those rare months when I actually have a social life.
Travel: $100. That'd get me to Hawaii in a year.

Anyway...

Now I'm entering in "Assets"

I'm confused as to how I should record my assets for my investments. Should I note how much I put into the funds, or how much currently exists in the funds? It doesn't look like there is a spot to track the funds, or to note how much its average earnings (or losses) are per year. Hmm.

I guess I'll put in what they're currently worth. It will make me less sad to start off with a smaller amount in my budget anyway. And I can kind of (try to) forget that thus far my investments have lost $400.

...

15 minutes later.

...

Ok, so I've decided "Beehive" sucks as a budget tool. I really wish there were an easy way to make a budget and track my finances.

One thing I don't like about Beehive is that when you're inputing your expenses for the month, it lumps all your "personal expenses" together. That includes everything from clothing to gasoline. What I really need is a breakdown of my "personal expenses" spending. I guess it's not a terrible idea to start thinking of it as a lump sum, because then I might be motivated to spend less on eating out in order to support my shopping addiction. But, still, I think it's important for me to break down my spending via category, and see where the money goes each month.

Meanwhile, I find it's really difficult to keep track of expenses that I am supposed to get reimbursed for at work. I feel like they should be counted separately, but I need to make sure to note that any future income that's actually reimbursement needs to cancel out.

Does anyone out there know of a good way to make (and keep) a budget? Help!

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Diversification?

This isn't my first blog, nor will it be my last likely, but after randomly falling into the online investment blogging community, I decided it's a good idea to start tracking my finances and the like via the Internet... anonymously, of course.

So here's a little bit of info about me to get started: I'm a young professional in her early 20's. I've been out of undergrad for two years now. My income is $35k a year, benefits included, except sans a 401k. Chance of raise/promotion within next year: 15%. Chance of company going out of business: 55%.

I'm fortunate in the sense that I have a decent amount of savings and no college loans. Savings from both my dad putting aside some funds for me for the awkward post-college year, and then extra cash from a lawsuit over a broken arm when I was little. My networth right now is around $27k. So I realize I'm better off than many other people my age, despite the fact that they might be making $50k a year and I'm only at $35k. Or at least our actual income after bills and other expenses is usually about the same.

Since this is an anonymous blog, I feel ok talking about the details of my finances. I haven't talked about it much on my main blog since it feels weird letting people know about how much I'm worth, or not worth. But finances are one of the things that I really need to talk somewhat publicly about, since I'm unsure of how to handle my money, with the exception of spending it. I'm very good at spending it.

So I recently opened a few random mutual fund/IRA/CD accounts, as I'm attempting to "diversify" my portfolio. I know I'm supposed to be living under my means, but I often fail to do that and spend more per month than I take in. Obviously that's a bad idea. But i'm hoping that at the least, putting some of my funds in high-interest accounts will balance out my poor spending habits.

Ok, so here's the breakdown of my accounts right now... (I'm going to try to keep tabs of this, as well as my budget, on here)

$2,143.54 - Checking
$7,421.99 - CD - 3.1 % Interest, matures 8/28/08
$5,510.58 - Maximizer Checking
$1000.63 - Savings
$5,000 - 8-month 5.01% Interest CD
$3,000 - Vanguard Mid-Cap Growth Index Mutual Fund
$3,000 - Roth IRA, in 2050 Retirement Plan fund

Well, the last three of these items haven't officially been started yet. I signed up for them yesterday. I'm waiting for all of the electronic transfers to go through. I realize investing in a Mid-Cap Growth Index Mutual Fund. Afterall, the smart thing to do is to invest in large caps, right? But I figure if I put $3000 into a mid cap fund, I can also invest in a large cap fund if/when I ever get a raise. I'm $1000 to maxing out my Roth IRA fund.

I don't understand the Roth versus regular IRA option, being as I know the Roth is all after-tax income and the regular IRA is pre-tax income then invested. But what should I be investing in now? I'm only making $35k a year, so it seems like I'll most likely be in a higher tax bracket when I want to retire. Afterall, I plan on making more than $35k per year when I'm 55 or 65 or whatever age it is I can retire.

And if I sign up for a Roth IRA now, can I move to a regular IRA at any time? Or am I stuck in the Roth?

Finally, how about my mutual funds - how much will it cost to change them from mid-cap to large-cap if suddenly I realize I ought to be a bit less risky in my investing? Gosh, I'm so confused.

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