Emptying a Roth IRA account
If you have multiple accounts, you have to empty them all before you can deduct any losses. Your loss is not a capital loss, its a deduction. It is calculated based on the total amount you have withdrawn from all your Roth IRA's, minus the total basis. It will be subject to the 2% AGI treshhold (i.e.: if your AGI is > 100K, none of it is deductible, and you have to itemize to get it). Bottom line - think twice. Summarizing the discussion in comments: If you have a very low AGI, I would guess that your tax liability is pretty low as well. Even if you deduct the whole $2K, and all of it is above the other deductions you have (which in turn is above the standard deduction of almost $6K), you save say $300 if you're in 15% tax bracket. That's the most savings you have. However I'm assuming something here: I'm assuming that you're itemizing your deductions already and they're above the standard deduction. This is very unlikely, with such a low income. You don't have state taxes to deduct, you probably don't spend a lot to deduct sales taxes, and I would argue that with the low AGI you probably don't own property, and if you do - you don't have a mortgage with a significant interest on it. You can be in 15% bracket with AGI between (roughly) $8K and $35K, i.e.: you cannot deduct between $160 and $750 of the $2K, so it's already less than the maximum $300. If your AGI is $8K, the deduction doesn't matter, EIC might cover all of your taxes anyway. If your AGI is $30K, you can deduct only $1400, so if you're in the 15% bracket - you saved $210. That, again, assuming it's above your other deductions, which in turn are already above the standard deduction. Highly unlikely. As I said in the comments - I do not think you can realistically save on taxes because of this loss in such a manner.
Indeed, there's no short term/long term issue trading inside the IRA, and in fact, no reporting. If you have a large IRA balance and trade 100 (for example) times per year, there's no reporting at all.  As you note, long term gains outside the IRA are treated favorably in the tax code (as of now, 2012) but that's subject to change. Also to consider, The worst thing I did was to buy Apple in my IRA. A huge gain that will be taxed as ordinary income when I withdraw it. Had this been in my regular account, I could sell and pay the long term cap gain rate this year.  Last, there's no concept of Wash sale in one's IRA, as there's no taking a loss for shares sold below cost. (To clarify, trading solely within an IRA won't trigger wash sale rules. A realized loss in a taxable account, combined with a purchase inside an IRA can trigger the wash sale rule if the stock is purchased inside the IRA 30 days before or after the sale at a loss. Thank you, Dilip, for the comment.) Aside from the warnings of trading too much or running afoul of frequency restrictions, your observation is correct. "One ""con"" I have not yet seen mentioned: retirement accounts are generally protected from creditors in a bankruptcy.  There are limits and exceptions, Roth has a 1.2 million dollar limit and can be split by a divorce QDRO for instance.  Link Since it seems you have no income this year, you may may be raiding your IRA for living expenses.   If there is a chance you may declare bankruptcy in the next year or so, consider doing that first and raid the IRA for seed money after." "To answer your question point by point - I'd focus on the last point. The back of my business card -  Let's focus on Single. The standard deduction and exemption add to over $10K. I look at this as ""I can have $250K in my IRA, and my $10K (4%) annual withdrawal will be tax free. It takes another $36,900 to fill the 10 and 15% brackets. $922K saved pretax to have that withdrawn each year, or $1.17M total.  That said, I think that depositing to Roth in any year that one is in the 15% bracket or lower can make sense. I also like the Roth Roulette concept, if only for the fact that I am Google's first search result for that phrase.  Roth Roulette is systematically converting and recharacterizing each year the portion of the converted assets that have fallen or not risen as far in relative terms. A quick example. You own 3 volatile stocks, and convert them to 3 Roth accounts. A year later, they are (a) down 20%, (b) up 10%, (c) up 50%. You recharacterize the first two, but keep the 3rd in the Roth. You have a tax bill on say $10K, but have $15K in that Roth." Generally, you have 60 days to return funds.   If you've been stowing away money in to a Roth IRA and an emergency strikes you pull out contributions sufficient to tackle the emergency while leaving at least the earnings in there.  You've never paid taxes on these earnings and the earnings will continue to grow tax free.   If you've been stowing away money in a vanilla taxable account and an emergency strikes you pull out whatever amount to tackle the emergency.  You've been paying taxes on the earnings all along but there's no paperwork. You can't replace the money in the Roth IRA (outside the 60 day limit except for some specific same year rules that you should iron out with your custodian) but you also haven't lost anything.  Either way in the event of an emergency the funds are removed from an account, but in one case you haven't been paying taxes on gains. IF you want to go the route of a Roth IRA wrapper for your emergency fund you shouldn't be touching the funds for small events, tires for your car and the like.  If your goal is to juice the tax free nature of the Roth IRA wrapper for as long as you can then repurpose the money for retirement if you never experienced an emergency with the understanding that you may have to gut the account in an emergency, that's fine.  If you expect money to routinely come in and out of the account a Roth IRA is a horrible vehicle. "One thing people are missing is that you may not be eligible to contribute to a Roth IRA based on your MAGI. There are income ""phaseout"" ranges which determine how much, if it all you can contribute." "In the case of Fidelity, the answer is ""no."" Although when you leave your employer and roll over the account to an IRA, leaving it with Fidelity allowed me to keep money in those closed funds. My Roth IRA was not able/allowed to buy those funds." You are permitted to withdraw the deposits from the Roth with no tax or penalty any time.  To Dilip's point, the Roth is a good place to keep the investment, and what you might consider is a 'self-directed' account. This type of IRA or Roth IRA permits a choice of investments that are not typically handled by banks or brokers, including Real Estate and the type of Angel investing you seem to be considering.  Note - the rules are tough, you need to be very careful to not be self-dealing, or dealing with certain related parties. "no, good questions my friend.  when did you do this rollover? if it was this year, your firm should have forms that you can fill out to ""undo"" the roth conversion - only earnings on your investments will be taxed, and everything gets rolled over to a traditional IRA. not fun for tax filing but...  you can also leave them as is and pay the taxes (usually only a good option if it's a low income year for the filer).  i would consult your tax advisor regardless in this situation." I wrote an article about this a while ago with detailed instructions, so I'll link to it here. Here's a snippet about how to use the Roth IRA loophole and report it properly: You don’t have any Traditional/Rollover IRA at all. You deposit up to the yearly maximum (currently $5500) into a traditional IRA. In your case, you re-characterized, which means you essentially deposited. The fact that it lost money may help you later if you have extra amounts in Traditional IRA. You convert your traditional IRA to become Roth IRA ($5500 change designation from Traditional IRA to Roth IRA).  You fill IRS form 8606 and attach it to your yearly tax return, no tax due. You have  a fully funded Roth IRA account. If you have amounts in the Traditional IRA in excess to what you contributed last year - it becomes a bit more complicated and you need to prorate. See my article for a detailed example. On the form 8606 you fill the numbers as they are. You deposited to IRA 5500, you converted 5100, your $400 loss is lost (unless you have more money in IRA from elsewhere). If you completely distribute your IRA, you can deduct the $400 on your Schedule A, if you itemize. "That's Imbalance-USD (or whatever your default currency is). This is the default ""uncategorized"" account. My question is, is it possible to get the ""unbalanced"" account to zero and eliminate it? Yes, it's possible to get this down to zero, and in fact desirable. Any transactions in there should be reviewed and fixed. You can delete it once you've emptied it, but it will be recreated the next time an unbalanced transaction is entered. Ideally, I figure it should autohide unless there's something in it, but it's a minor annoyance. Presumably you've imported a lot of data into what's known as a transaction account like checking, and it's all going to Imbalance, because it's double entry and it has to go somewhere. Open up the checking account and you'll see they're all going to Imbalance. You'll need to start creating expense, liability and income accounts to direct these into.  Once you've got your history all classified, data entry will be easier. Autocomplete will suggest transactions, and online transaction pull will try to guess which account a given transaction should match with based on that data." "I wrote the whimsically titled ""The Density of Your IRA"" to discuss this exact issue.  In the 25% bracket, your pretax 401(k) would have $18,000, with a future tax due. But the Roth effectively took $24,000 in pretax dollars, and put the $18K in post tax money in the account. Since the limits are the same, the Roth is a denser account." "I think what those articles are saying is: ""If you want to leave some money to charity and some to relatives, don't bequeath a Roth to charity while bequeathing taxable accounts to relatives.""  In other words, it's not ""bad"" to leave a Roth IRA to charity, it's just not as good as giving it to humans, if there are humans you want to give money to. In your situation, the total amount you want to leave to relatives is less than the value of your Roth.  So it sounds like the advice as it applies to you is: ""Don't leave your relatives $30K from your taxable funds while leaving the whole Roth to charity.  Instead, leave $30K of your Roth to your relatives, while leaving all the taxable funds to charity (along with the leftover $20K of the Roth).""  In other words, the Roth is a ""last resort"" for charitable giving --- only give away Roth money to charity if you already gave humans all the money you want to give them.  (I'm unsure of the details of how you would actually designate portions of the Roth for different beneficiaries, but some googling suggests it is possible.)" "This is the infographic from the Fidelity. It exemplifies what's wrong with the financial industry, and the sad state of innumeracy that we are in.   To be clear, Fidelity treats the 401(k) correctly, although the assumption that the withdrawals are all at a marginal 28% is a poor one. The Roth side, they assume the $5000 goes in at a zero tax rate. This is nonsense, as Elaine can't deposit $5000, she has to pay tax first, no? She'd deposit $3600, and would have the identical $27,404 at withdrawal time.  And this is pure nonsense -  ""Let’s look at the numbers another way. Tom takes the $1,400 he saved   in taxes from his $5,000 pretax contributions, and invests that money   in a taxable brokerage account. That could boost his total at age 75   to $35,445."" The $1400 saved is in his 401(k) already, there's no extra $1400. $5000 went in pretax.  Let me go one more step, and explain what I think Joe meant in his comment below - tax table first -   At retirement, say a couple has exactly $168,850 of income. With the $20K in standard deduction and exemptions, they are right at the top of the 25% bracket.  And have a federal tax bill of $28,925. Overall, an effective rate of 17%.  Of course this is a blend from 0%-25%, and I maintain that if some money could have gone in post tax while in the 10%/15% brackets, that would be great, but in the end, if it all skims off at 25%, and comes out at an effective 17%, that's not too bad.  The article is incorrect. Misleading. And offends any of us that have any respect for numbers. And the fact that the article claim that ""87% found this helpful"" just makes me... sad.  I've said it elsewhere, and will repeat, there are not just two points in time. The ability to convert Traditional 401(k) to Roth 401(k), and if in IRAs, not just convert, but also recharacterize, opens up other possibilities. It's worth a bit of attention and ongoing paperwork to minimize your lifetime tax bill. Time makes no difference. There is no ""crossover point"" as with other financial decisions. For this illustration, the results are identical regardless of time.  By the way, in today's dollars, it would take $4M pretax to produce an annual withdrawal of $160K. This number is about top 2-3%. The 90%ers need not worry about saving their way to a higher tax bracket." "The IRA contribution limit is a limit on the total amount you can contribute to all of your Roth and traditional IRAs.  It's not a per-account limit.  (See here and here.)  Once you've hit the contribution limit on one account, you've hit it on all of them. Even so, supposing you had a reason with try to take money out of one of the accounts, the answer to your question is ""sort of"".  The limit is a limit on your gross contributions, not your net contributions.  It is possible to withdraw Roth contributions if you do so before the tax filing deadline for that year, but you must also withdraw (and pay taxes on) any earnings accured during the time the money was in the Roth (see here).  In addition, doing this may not be as simple as just taking the money out of your account; you should probably ask your bank about it and let them know you're ""undoing"" the contribution, since they may otherwise still record the amount as a real contribution and the withdrawal as unqualified early withdrawal (subject to penalties, etc.)." If you keep the account in your name only and your girlfriend is depositing money into it, then she is in effect making gifts of money to you. If the total amount of such gifts exceeds $14K in 2014, she will need to file a gift tax return (IRS Form 709, due April 15 of the following year, but not included with her Federal tax return; it has to be sent to a specific IRS office as detailed in the Instructions for Form 709). She would need to pay gift tax (as computed on Form 709) unless she opts to have the excess over $14K count towards her Federal lifetime combined gift and estate tax exclusion  of $5M+ and so no gift tax is due.  Most estates in the US are far smaller than $5 million and pay no Federal estate tax at all and for most people, the reduction of the lifetime combined... is of no consequence.  Another point (for your girlfriend to think about): if you two should break up and go your separate ways at a later time, you are under no obligation to return  her money to her, and if you do choose to do so, you will need to file a gift tax return at that time. If you will be returning her contributions together with  all the earnings attributable to her contributions, then keep  in mind that you will have paid income taxes on those earnings all along since the account is in your name only.  Finally, keep in mind that the I in IRA stands for Individual and your girlfriend is not entitled to put her contributions into your IRA account. Summary: don't do this (or open a joint account as tenants in common) no matter how much you love each other. She should open accounts in her name only and make contributions to those accounts.