the nightmare that is figuring out taxes and health insurance as a freelancer

the absolutely marvelous news is that i just landed a steady, well-paid, 30 hrs/week contract gig for the next three months.

the bad news it that now i have to figure out how on earth to get myself decent health insurance... and how to sort out my income and expenses for tax season.

contract work is great because of the flexibility, but all the additional "work" I have to do to be self-employed is rather terrifying.

first off -- health insurance: i already know i will be denied if i tell the truth on my health insurance applications, because i took lexapro ONE MONTH for "major depression." On the Tonik health insurance application, you get to click off your pre-existing medical conditions. Guess what category major depression falls into? "Bipolar disorder/Major Depression/Schizophrenia"

Um. I went to a psychiatrist for about two months, took meds for one month, and i kind of feel better now.

My psychiatrist kind of warned me about the potential health insurance issues, but she wasn't very clear about it. She just said that she doesn't like working with health insurance -- because it takes her forever to get paid. And then when she was considering diagnosing me with bipolar, she asked me if it would be ok to note that on my diagnosis form, since most clients don't want that on there, as it could hurt their chances of getting health insurance later on.

First off, I was rather ignorant at the time, thinking that health insurance existed to help you get better (wrong) and that it would be cheaper for me to use my $15 co-pay visits with a 'major depression' diagnosis as opposed to 50% pay for ADD or anxiety or anything else that I probably actually have (I doubt I have major depression. It's probably recurring, but I go through phases in my life. Life is hard and sometimes i'm sad and sometimes I need someone to talk to, but I don't think this is a life-long condition). Anyway...

So I got my $15 visits, which was nice for the two months I say my psychiatrist and my therapist. And now? Well, chances are I won't be able to get health insurance. Because apparently whatever it is I have is just as bad as SCHIZOPHRENIA in the eyes of my potential insurers.

I spoke with a health insurance agent who, off the record, basically suggested that i take the risk and lie on my application, because that would be the only way i could get decent insurance. but, of course, then i could basically screw myself over by doing that, since health insurance companies could find out that i lied and make me pay for EVERYTHING since when i signed up for their insurance. that's a scary thought.

Or - do I just be honest and watch as my applications get denied? I haven't got my forms for Cobra yet, but I'm sure that will be ridiculously expensive. I had really good health insurance (Blue Shield PPO) through my employer with a $250 deductible, and now I'm looking at whatever I can get with a $1500-$5000 deductible and poor benefits. And to get that I might still have to lie.

But I should have health insurance. I realize it's stupid to be living without health insurance. I just am not sure what kind to get. Basically I need the doctor to prescribe me Yasmin birth control pills each month (and hopefully for them not to cost me a fortune) -- I need "Yasmin" specifically for hormonal imbalances and such, but unfortunately getting cheaper pills through something like planned parenthood will not let me get that brand.

Besides health insurance, there's the issue of taxes. Gosh, I'm so behind of keeping tabs on what I've made in contract work this year. I know, bad me. I just set up a google docs spreadsheet to start taking detailed notes from hereonout, but I'm not 100% sure what I've made thus far this year. In any case, I know that taxes are going to take a HUGE CHUNK out of my income, which is fine, they did that before, but it's just really hard to determine how much taxes will be when I don't even know how much work I will have each month.

At least now I have a stable three month gig where I will be making $3300 a month, assuming they like me and want to keep me for the entirety of the contracted position. After that, either I get to stay on board, or it's back to the drawing board. We'll see. Meanwhile, my goal is to pick up one or two freelance web design projects per month, where I'd make anywhere from $500-$1000 per project (although I'm starting out with really cheap rates of like $200 per project.)

Anyway... for the next three months, my 'income' before taxes, minus any additional web design projects, should be $3700, which includes the contract gig and another ongoing contract project where I make $400 a month writing a few articles for my uncle's marketing firm. $3700 a month is definitely not a bad wage, but after taxes, and health insurance, I'm not sure how much that actually is. It'd be something like $2700 a month or something? So after rent, that's $1650 a month. Phone bill, gym membership and cable tv/internet are like, $200, so then I have $1450 left. Ok, not bad. Health insurance, assuming I go for a decent kind, will be like $300 a month. So that's maybe $1150 left for food, entertainment and such.

Ok, I guess that's not awful. But I just am scared about not understanding taxes and all the complicated stuff that goes into expensing things and such. Meanwhile, I just read that self-employed individuals pay a lot more in taxes because usually the company pays for like half of the taxes, but when you work for yourself you are your own company.

So. I guess I have a lot of figuring out to do. In the meantime, I have to wrap up three projects I'm working on. I'm writing some company for a startup (basically, I'm writing all the copy that will go on their site), then I have to finish this one website for a client, and then I've got to wrap up the basic design for a project I'm doing in a 'trade' deal with a personal trainer. 5 hours of web design for 4 hours of personal training. It's not a bad deal, considering she charges $78 an hour and I charge $50. Anyway, I can tell she's getting antsy to see the page (I already had three training sessions this week, but I told her I'd show her something this weekend.) Well, I've got to finish that. I'm trying my darndest to figure out Flash because A) she seems to really like pages with Flash in them and B) I need at least one site for my portfolio that incorporates Flash, so I can show clients that I can atleast put some basic animation on their pages.

Anyway.

Life is going pretty good, minus all of this confusion. My birthday is coming up next week. I'm turning 24. Happy, uh, confused birthday to me.