This was my first year filing as an Independent Cont. where I made enough to get myself into trouble. I made some mistakes, but need some advice on prioritizing my way out of it. I didn't do quarterlies as I went through some hardships this past year and used that money with plans to catch up of course. (mistake I know) I had LOTS of legit, IRS acceptable write offs, thousands of dollars worth, and my CPA still shocked me with a tax bill of a bit over $9000.00. I honestly thought it would be a quarter of this. I sent in a small amount with the extension that had to be done anyway due to a form that had not yet come in.
Due to making it my priority this year to pay off some debt I have been holding and saving much more, I can already see my income will be increasing by at least $20,000+ this year. But after doing a VERY thorough budget recently, I am really getting frustrated at how I will accomplish all of this. Never the less I will somehow, but I am just trying to figure out how best to accomplish this.
1. Even with busting my ass, I do not see myself raising the entire amount owed for my 2013 taxes by October 15th while taking care of other financial obligations. I have this years taxes included in my monthly budget plus the additional for my increase in income. Is my thinking correct that the best move for me is to keep up with sending current quarterly taxes in, and biting the bullet and doing a financing for my 2013? I HATE putting myself on their radar like this. Should I instead focus on throwing every tax dollar I make at 2013 instead making smaller quarterly payments? Is the fact that I am having to have them finance anything as bad as I think it is?
2. So I am upping my advertising and a few other areas this year to cut the next tax bill down. How much is too much? Is there a point that will cause me to be flagged even if it is all legitimate small business expenses? I would rather invest in my "company" then throw it at the gov. like I clumsily did last year.
3. And last, from my understanding contributions to a Roth IRA are not dollar for dollar write offs but more that that amount will not be taxed. Is there anything for retirement that can be written off dollar for dollar? At this point, until I get myself out of this mess I don't know how I can fund a retirement plan well unless I can subtract from estimated taxes as I am really squeezed already.
I am just super frustrated right now, as I am generally very frugal, the debt I have is mostly for my vanilla career investment which is slowly coming together, and it seems the more I make it doesn't help much at all. Snowballing my debt has been slowed down, and savings has too...and yet I am f*cking working more than ever!!! Grrrr....just ranting now, but I do hope to get some sage advice about the main questions.



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