Getting Your Financial Ducks In A Row Rotating Header Image

Roth conversion

A Terrible, Terrible Idea

christopher robin and the terrible horrible no good very bad day by CarbonNYCMy thanks for Natalie Choate for analyzing and pointing out the following information.  Ms. Choate is truly a rock star in the world of IRA law, and much gratitude is owed to her by those of us in the financial community for her thorough analysis and commentary that she provides on such matters as this.

If you live long enough, you’re liable to see just about anything… the following is an example of the most extreme example I’ve ever heard of for using the tax law to your own advantage, deliberately flaunting the law for purposes of evading tax.

The Facts

If you intentionally over-fund your Roth IRA, above the amount that you’re allowed to contribute for the tax year.  The tax law allows you to remove the excess contribution by October 15 of the year following the year of contribution.  If you do not remove the excess contribution (and the gains associated with it) by that point, you will be subject to a 6% excise tax on the excess contribution until the situation is rectified.

The situation can be rectified by either crediting the excess contribution to a future years’ contribution, or by withdrawing the excess amount prior to the deadline for the following year.  Each year that you do not rectify the over-contribution you will be subject to the excise tax.

The Anomaly

If you do not remove the excess contribution and the growth associated with it by October 15 of the year following the year of contribution, once you’ve been assessed the excise tax, your rectification is only required to the extent of the excess contribution – not the growth associated with it.  The growth is no longer considered (under present tax law).  In other words, you can rectify the excess contribution at that point by simply removing the excess, but the growth doesn’t have to be removed.

If you’re following the way this is working, you’ve probably figured out the gist of the “idea” we’re talking about here.

The Terrible, Terrible Idea

Here’s an example of the bad idea in play:

Let’s say you have no Roth IRA at all, but you have $20,000 that you’d like to invest.  Furthermore, you don’t have compensation that would make you eligible to contribute anything to a Roth in the first place.  Ignoring all convention, you open an IRA and contribute the $20,000, investing it in the latest hot stock.  October 15 the following year rolls around, and your hot stock has doubled in value.  (It should be noted that if your hot stock didn’t do so well, such as losing money, you could pull it out now and walk away with no consequence.)

Under the normal conventions, you could withdraw the entire $40,000 (your contribution plus your gain), but you’d have to pay ordinary income tax on the gain of $20,000.  Doing this, you’d avoid the excess contribution 6% excise tax, $1,200.

However, in this terrible, terrible idea, you decide to wait until after October 15, and pay the excise tax on the over-contribution.  Now you have three choices:

  • If you’re otherwise eligible for contributions to the Roth in the current year, part of the excess contribution can be used (credited) as a regular contribution.  You would then be subject to the excess contribution tax on the remainder of the over-contribution until it’s been used up by future credits (this is one of the right things you could do).
  • If you’re not eligible for the contributions, you could withdraw the excess contribution at this point, along with the growth in the account, paying ordinary income tax on the growth.  This is the other right thing you could do.
  • If you’re up for a challenge (and possibly jail time), you could withdraw only the excess contribution and leave the growth in the account to grow tax free for the rest of your life.  It probably won’t do you a lot of good in Alcatraz, though.

The Reason This is a Terrible Idea

The IRS is never in favor of kooky tricks like this that don’t work as the law intended.  So what might happen?  Well, the IRS could review your IRA account and disqualify it completely, on the basis that the custodian should never have allowed the excess contributions in the first place.  In this manner, you’d be subject to tax on the growth in the account and the whole account would be null and void.  Your IRA custodian is likely to be in hot water as well, as this would be a violation of the basic rules of IRAs.

Since the entire concept of the ability to withdraw the excess contribution is designed to help taxpayers resolve an honest mistake, abusing this provision is likely to be soundly disallowed.  If the facts were known, (which they would be discovered eventually), the IRA is likely to be disallowed completely, and the abuse is likely to carry with it severe penalties.

The IRS doesn’t presently have remedy for the situation – and in the case where you honestly make a mistake and elect to leave the funds in the account (crediting against the current year, as in the first bullet point above) – it wouldn’t be too much of a leap for the IRS to disqualify distributions from the gains.  This would become especially so if the activity I’ve described becomes a rampant abuse.

It’s best to follow the rules as intended and leave well enough alone.

Photo by CarbonNYC

Using Capital Gains and Losses to Help With a Roth Conversion

libr0500Many analyses done with respect to Roth IRA conversions only come out to a positive outcome when the attendant tax on the conversion is paid from non-IRA sources.  For many folks this shoots down the entire prospect, as there is no available cash outside of IRAs and other investments to use to pay the tax on the conversion.  Taking the cash from the IRA in the form of a distribution can result in a 10% penalty, which can kill the whole plan.

One source of funds that you may not have considered is within your non-IRA investment accounts – especially if you have inherent capital gains and losses (even moreso if you have carried-over capital losses that wouldn’t otherwise be utilized readily).

Offsetting Gains With Losses To Produce Cash

Here’s how it works: You sell your “loss” positions, establishing a capital loss for tax purposes.  Then you can sell your “gain” positions in like amounts, giving yourself a tax-free source of cash, since the loss will offset the gain for taxation purposes.

For example – imagine that you have a $100,000 IRA that you’d like to convert.  Running the numbers, you’ve come to realize that the conversion will cost $25,000 to complete.  In addition to the IRA, you also hold some non-IRA money, in the form of two investments.  One of these investments has an inherent loss of $20,000, and the other has an inherent gain of $30,000.

By selling out of the “loss” position completely and selling just enough of the “gain” position to offset the tax loss you’ve realized, you have effectively created a tax-free source of income in the amount of $20,000.  This still leaves $5,000 if you’re planning to convert the entire amount.

After you’ve finished with your conversion activities (and after 30 days has passed so that you don’t run afoul of the wash sale rules), you can re-invest the leftover money in those same investments, keeping your allocation at least similar to what it was before.

At this stage you have three choices, assuming you don’t have an extra $5,000 laying around:

  1. You can choose to only convert a portion of your IRA – the amount that you can generate tax-free money to pay tax upon.  In our example, this would be $80,000.
  2. You can use more of the cash that you freed up from the sales of your non-IRA gain and loss holdings.
  3. You can convert the entire amount and take distribution of the additional $5,000 to pay the extra tax.  Actually you’d need to pull out $5,500 in order to pay the penalty on that amount that you’re distributing.

Of these three, I’d recommend option 2, which is the outcome where you complete the conversion of the entire amount without having to pay additional tax or penalty on the money that you’re using to pay the tax on the conversion.  Yeah, that last sentence belongs in a museum.  Happy converting!

Photo by NOAA Photo Library

Roth Conversion While Receiving 72t Payments

convertible sedan by aldenjewellWith all of the conversation going on with regard to Roth IRA Conversions, I thought it would be useful to address a special set of circumstances with regard to Conversions.  As the title implies – we’re talking about the eligibility of an IRA for conversion if it is also subject to 72t, or a Series of Substantially Equal Periodic Payments (SOSEPP).  For background on SOSEPP, you can see the article Early Withdrawal of an IRA – Series of Substantially Equal Periodic Payments.

As you know (if you’re read the article about Penalties for Changing SOSEPP) it can be costly to you if you make a change to your SOSEPP once you’ve set it up.  The good news is that a Roth Conversion is NOT considered a “distribution for purposes of determining whether a modification”, and therefore in itself will not trigger a loss of the penalty-exempt status of the SOSEPP.

What does happen then, in such a circumstance?  Well, that’s when things go into the “it depends” category, followed closely by a whole lotta “no guidance from the IRS”.

If you have converted the entire balance of your IRA that is subject to the SOSEPP to a Roth IRA, you will be required to continue taking your series of payments from the new Roth IRA just the same as if they were still coming from the traditional IRA.  If you don’t, you will most likely be subjected to recapture of the penalties on the earlier SOSEPP distributions, unless you’ve reached the end of the distribution requirement period – five years or age 59½, whichever is later.

On the other hand, if you’ve only converted a portion of the traditional IRA to a Roth IRA, this is where it gets murky.  The IRS has not provided definitive guidelines on exactly how you handle the SOSEPP from here… it is abundantly clear that you must continue your series of periodic payments until the end of the distribution period.  What’s not clear is if you must continue taking the payments from the remainder of the traditional IRA, or from the Roth IRA, or proportionately from both accounts, or in any amounts you choose from either account, as long as the amount is proper to fit the bounds of your SOSEPP.

The best way to deal with this situation would be to convert the entire account if that’s feasible.  If it’s just not feasible, then you should ask for a Private Letter Ruling from the IRS – especially if we’re talking about sizeable amounts (you be the judge).  If the possible tax and penalty is relatively minor, I’d suggest taking proportionate amounts from the trad and Roth IRAs until the SOSEPP distribution requirement period ends.  Make sure that you keep documentation on all of these transactions – you’ll need it if the IRS comes a-callin’.

Photo by aldenjewell

Tax Diversification for Investments

tax by definition by alancleaver_2000In past articles I have advocated the concept of spreading your tax-treatment out – so that you have money allocated in three major types of accounts:  deferred tax (such as IRAs and 401(k) plans), tax-free (Roth IRAs), and capital gains taxable accounts.  The reason behind this is that our fine government has this tendency to change the rules, often, and by spreading your tax treatment out you can help to ensure that funky new rules don’t throw off your entire retirement investing plan.

The trick to all of this is to know how much to have in each kind of account… of course there are no hard and fast rules to determine what’s the best percentage to have in each kind of plan, but below is a discussion of some of the factors that you should consider as you balance out your tax treatment.

Early in life…

Early in your investing career it probably makes the most sense to load as much of your savings into your 401(k) or other tax-deferred savings vehicle as possible, in order to maximize the benefit from tax savings up front.  The biggest reason for this (beyond the tax savings) is so that you take advantage of your employer’s matching benefit, along with deferring taxes on your income as it increases over time.

Later in your career when your income is higher, maximizing contributions to tax-deferred accounts will have a greater benefit to you from a tax savings standpoint – and this is assuming that you expect for the taxes you’ll pay later (during retirement) will be lower due to your diversification of tax treatment.

Also early in your investing career, as your income supports it you should begin making contributions to your Roth IRA as soon as possible.  This is partly due to the restrictions on income around investing in Roth IRAs – but mostly because you are paying tax at lower rates (in your lower-earning days) than you might later on in your career when your income increases.

And then on top of it all, when your income has grown to a point that you can maximize the other options (401(k) and Roth), you should begin investing in an account that is treated by capital gains tax (primarily).  This will give you the third leg of the tax-diversification stool.  Since capital gains are (presently) taxed at a much lower rate than ordinary income – which is what your IRA or 401(k) distributions are taxed at – it makes a great deal of sense to have some of your money invested in these accounts as well.

Later in life…

Later on in your life, as you reach that point where you will have to begin taking Required Minimum Distributions (RMDs) from your IRA and 401(k) accounts, it might make sense to take significant portions of those accounts and either convert them to Roth accounts or capital gains taxed accounts.  The preference would be to place the funds distributed into a Roth IRA, especially if you are in a position where you will not need access to the funds for some time and therefore can benefit from the tax-free growth of the account.  But you may also want to balance those conversions to Roth with some non-tax-deferred investments as well – because you never know what may happen with the tax code.

It’s (very!) possible, given the government’s need to increase tax revenues to pay for things like the health care initiative, that there could be changes in the works for how tax-deferred plans are taxed.  Just a few options that have been put forth in recent memory include:

  • extra taxes on IRA assets (this was in place back in the mid-80’s)
  • changes to the minimum distribution rules to require faster distribution or to eliminate “stretch” capabilities
  • adding investment restrictions, such as requiring a portion of IRAs to be invested in “socially responsible” investments
  • nationalization of retirement accounts – e.g., governmental takeover of all IRA and 401(k) plans in exchange for a superannuization plan like some socialized countries use

Yet another option, especially if you have very few assets outside your IRAs and 401(k) plans, you can reduce your taxable estate (when we have an estate tax again, that is) by taking extra distributions from your IRA or 401(k) and making gifts to your children and grandchildren.  You could place the assets in a trust that represents a completed gift, or give the money directly to your future heirs – this way you are able to see your children and grandchildren enjoying the fruits of your labors while you’re still living.

Photo by alancleaver_2000

How to Resolve an Over-Contribution to Your IRA

green walls of BART by Darwin BellEven with our “best laid plans”, sometimes we make mistakes.  Perhaps you underestimated your income for the year and contributed more to your IRA than could be deductible; maybe you rolled over an amount that was not eligible for rollover; or maybe you made a contribution to an IRA that you were not eligible to contribute to, such as an inherited IRA.  Whatever the case, you’ve over-contributed money into an IRA and need to take action, otherwise you can be setting yourself up for some penalties and other un-wanted taxation.

Actions for Dealing With an Over-Contribution

You have three options for dealing with the over-contribution situation:  you can pull the over-contribution out; you could also re-characterize the contribution; or you could do nothing.

Pull the over-contribution out. This is known as a corrective distribution.  Essentially this is exactly as it sounds:  you pull out the money that represents the over-contribution, plus (here’s the wrinkle) any growth or income attributed to the over-contribution.  You need to do this by the due date (including extensions) of the tax return for the year of the contribution… In this case “due date” has a special meaning:  if you filed your return on time (including extensions) this means October 15 of the year following the year of the contribution, even if you did not use an extension; however, if you did not file your return on time, the deadline is (was) April 15 of the year following the contribution year.

So if you contributed a total of $1,000 more than you were eligible for to your IRA, and there was growth and income of $200 attributable to the over-contribution, you need to withdraw $1,200 before October 15 of the year after your contribution year.  And, you’ll need to pay ordinary income tax on the $200 of earnings – plus 10% in early distributions penalty.  Of course if you didn’t file your tax return on time, (actually if you plan to not file your tax return on time) you need to pull out your over-contribution by April 15.

Recharacterize. This method resolves an over-contribution to a Roth IRA, by changing the character of the contribution to a traditional IRA instead of a Roth IRA.  This can only be done if you’re eligible to make a contribution (either deductible or non-deductible) to a traditional IRA (you meet the income, other plan coverage, and age limits).  To do this you submit Form 8606 to the IRS indicating a change to the over-contribution amount, plus or minus any earnings or losses that have occurred attributed to the over-contribution, from Roth to traditional.  This has the same deadlines mentioned above for the corrective distribution.

Do nothing. In essence you’re not exactly doing nothing – you’re accepting the fact that the over-contribution occurred, and you’ve chosen to accept the consequences.  The consequences are that for any amount you’ve over-contributed, you are subject to a 6% penalty for excess contribution.  This may be the best course of action if the over-contribution can be absorbed as a contribution in the following year.

As an example, maybe you made a contribution to your Roth IRA of $5,000 for the year, and it turns out that your income level only allows a contribution of $4,800 – something you didn’t discover until it was too late.  The consequence is that you’ll owe a penalty of 6% – $12 total – on the over-contribution of $200.  As long as you are eligible to contribute at least $200 to your Roth IRA in the following year (and you don’t over-contribute again), you can pay the penalty and leave the money where it is.

Unfortunately, if the over-contribution amount in question is large, this method doesn’t really help much.  This can be the case if you’ve mistakenly rolled over an inherited IRA into your own IRA instead of an inherited IRA – and you’re a nonspouse beneficiary.  If you don’t catch it in time, you will be subject to the 6% penalty for the year of the rollover and every subsequent year thereafter until you distribute the IRA.  When you finally catch the mistake (or rather, the IRS catches your mistake, more than likely), you’ll be subject to ordinary income tax (and retroactive penalties and interest) on the entire distribution as well, since you effectively treated the IRA as your own money from the very start.

Photo by Darwin Bell

Roth Conversion Analysis – Make Sure You Get the Tax Right

Chevrolet-conversion-vanThere are almost as many ways to perform the analysis on Roth IRA conversions as there are reality TV shows about celebrity brat children these days… The point of this article is to make certain that any calculation you’re doing with regard to a Roth Conversion treats the tax appropriately.

In reviewing whether or not a Roth IRA conversion in 2010 makes sense and furthermore whether you should spread the tax over the next two years, you need to consider what the tax cost is for a conversion in 2010, weighed against the costs you’ll experience if you spread the tax over 2011 and 2012.

Unfortunately we often shortcut the analysis by only taking the marginal rate on the income including the conversion and calculate the tax – this would give you an erroneous result, since our tax system includes graduated tables.  I’ll illustrate this below.

How to Properly Calculate the Tax

The only way to ensure that you are working the tax numbers out correctly is to work through the operation as if it were on your tax return.  The table below shows a simple example of an individual with a fixed income contemplating a Roth Conversion of $75,000 paying the tax in 2010, and the second and third columns analyzing paying the tax in 2011 and 2012.

2010 2011 2012
“Normal” Adjusted Gross Income (AGI) $80,000 $80,000 $80,000
Roth Conversion $75,000 $37,500 $37,500
Total AGI with conversion $155,000 $117,500 $117,500
Standard Deduction -11,400 -11,500 -11,600
Personal Exemptions -7,300 -7,400 -7,500
“Normal” Taxable Income $61,300 $61,100 $60,900
“Normal” Tax $8,358 $8,325 $8,292
Taxable Income w/conversion $136,300 $98,600 $98,400
Marginal tax rate 25% 25% 25%
Actual Tax (with conversion) $26,437 $17,000 $16,938
Difference in tax $18,080 $8,675 $8,645
Actual rate on conversion 24.11% 23.13% 23.05%
Total tax on conversion $18,080 $17,320
Effective rate on conversion 24.11% 23.09%

Since the marginal rate for the example is 25% for all three years, you might mistakenly believe that 25% is the rate that you should apply to the entire conversion, which would give you an erroneous result.  Since the Actual Rate on the conversion is just a bit lower for the spread years versus 2010, there is an advantage to spreading the tax instead of paying it in 2010.  It’s not a huge difference, $760 in this example, but it’s a difference nonetheless.

Keep in mind that this is only an example, and that the 2011 and 2012 tax tables and other provisions are guesses at best.  But the point is that you shouldn’t make assumptions about tax costs for conversions and the spread option – it’s best to make sure that you work your way through the returns to see the results in the “real world”.

In addition, this particular analysis is only reviewing the tax cost to help decide whether spreading the tax over 2011 and 2012 is beneficial – there are a great many other factors to consider when doing analysis of a Roth Conversion beyond this.  Make sure your analysis is thoroughly considering all of the factors before proceeding.  And get professional help if you need it.

Photo by wikimedia

Roth IRA Conversion Tax Payment Wrinkle

anti botox brigadeSome very clever folks have looked at the 2010 Roth IRA conversion facts, including the ability to spread the tax over tax years 2011 and 2012, and have discovered a unique situation… What would happen if I did the Roth conversion in 2010, elected to be taxed half in 2011 and half in 2012, but during 2011 I withdrew all of the funds from the account?  This way, you’d effectively have access to 100% of the funds while only paying tax on half of them.  (This assumes that your Roth IRA is otherwise qualified – e.g., you’re over age 59½ and the account has been in place for five years.)

Hold on there, cowboy!  There’s a problem with your kooky little scheme – the IRS has planned for just such an eventuality.  Effectively, any amount that you withdraw from your Roth IRA that is not previous contributions or conversions, will be subject to tax in the year that you withdraw it, until you’ve paid the tax on the conversion.  This is in addition to the amounts that you owe tax on during that year due to your election to spread the tax.  Gobbledygook, right?  Right – howza bout an example?

An Example

You have an IRA worth $100,000, and in 2010 you decide you’d like to convert it to a Roth IRA.  You have an existing, five-year-old Roth IRA, with $20,000 in it.  In 2011, you withdraw $30,000 from the Roth IRA.  At the end of the year, instead of owing tax on $50,000 (half of the conversion amount of $100,000), you actually owe tax on $60,000.

This is calculated as:  your withdrawal was $20,000 from earlier contributions, and $10,000 from the conversion.  That $10,000 must be added to the previously-agreed-upon $50,000 amount that you knew you’d owe tax on for 2011.  And then in 2012, you will owe tax on the remaining $40,000 from the conversion.

So, in other words, the IRS has determined that this two-year tax deferral is not going to be used as a tax-free method for achieving tax-free withdrawals from your IRA – once the amounts have remained in the account until 2012, any amount can be withdrawn without tax.  But of course, you’ve already paid the tax on the conversion by that point (or rather, you will by tax day in 2013).

So what happens if you withdraw the funds in 2010 after converting earlier in the year?  Effectively this is treated as a distribution from your original IRA (actually recharacterized from the Roth conversion), so you’d owe tax on that amount in 2010, and the remaining amount would be split between 2011 and 2012.

The “Hole”

I suppose that technically there is a time period where you could have access to 100% of the funds having paid zero tax:  between January 1, 2012 and April 15, 2012, when the tax bill is due for the first half of your conversion amount.  So you have three and a half months to unleash your devilish scheme on the world… not sure what you’ll do with this information, but perhaps there is some advantage that you might receive by leveraging the amount.  I doubt there’s much advantage to be had, especially given the loss of deferral if you withdraw the funds, but maybe you have a plan.  Go to town!

Photo by marya

What Hath Congress Roth?

… or better yet, what will they Roth in the future? You’re right, terrible attempt at a pun.

wrought iron steps by Rennett StoweIn case you aren’t a retirement and financial planning geek like myself, there has been a proposal put forth by the current administration to require all employers to automatically enroll employees in a retirement plan.  I find it interesting that the choice for a “default” retirement plan for the proposed system is a Roth IRA.

The reason this is so interesting is because a Roth IRA doesn’t provide the participant with an immediate benefit – there is no tax deductibility, no employer match, etc..  Granted, any sort of retirement savings is a good idea, but this type of plan will be a hard sell for those folks who haven’t already bought into the concept of saving strictly for the benefit of saving on their own.

In addition, there’s the current push (in 2010) for lots and lots of Roth conversions.  This one is even better – there’s not only no adverse tax revenue consequence, there’s a great tax revenue advantage if lots of IRA money is converted and taxed. This push has been referred to as a “mortgaging of the future” – since we’ll get lots of tax revenues from the conversions today at the expense of future revenues on the growth in the accounts. It wouldn’t be hard to imagine a future administration pointing to 2010 as the first domino that caused the soon-to-be current circumstances.

Is there more to it?

Perhaps there is more to it – obviously, a dramatic increase in participation in deductible IRAs could have a significant negative impact on tax revenues, hence the Roth being recommended as the default.  But what if Congress decides at some point down the line that this Roth deal looks too good for the taxpayer??  What if the idea of completely tax-free distributions starts to cause extreme anxiety among our legislators (as un-taxed benefits often do)?

It’s quite possible that the reason the Roth IRA account has been deemed the plan of choice is primarily because of the non-existent tax impact in the short run.  And the longer-run consequence (the mortgage of the future) of potentially locked up funds that will bring no tax revenues can be dealt with by future administrations – when such tough decisions can be confronted far distant from the decision-makers who helped us to get into the position in the first place.

Another thing that’s pretty interesting is the fact that many of the online Roth Conversion calculators are reportedly over-stating the benefits of Roth Conversion – putting far more emphasis on the potential for future higher tax rates and the benefits of no RMDs than is warranted.  It’s not hard to guess why asset-gathering companies might suggest that it would be in your best interest to convert assets to Roth IRAs; conveniently under the management of the company who recommends conversion.

Imagine the case in 20+ years when a great amount of the wealth in this country is locked up in Roth IRA accounts – with no tax ever to be paid on it (under current law), and no Required Minimum Distributions (RMDs) of the funds.  I can imagine that there might be an “emergency needs-based” change to the law – perhaps something simple like a requiring RMDs, with maybe a value-added tax, along with possibly inclusion of Roth IRAs as taxable assets in your estate.  That would pretty much knock all these conversion schemes on their collective ears, don’t you think?

Your Defense

It is for these reasons that I believe most folks are best served by not putting too many eggs in one tax treatment basket – you should not only have traditional IRA or 401(k) assets along with Roth IRA or 401(k) assets – you should also have taxable savings, such as a standard brokerage account and/or savings account.  By diversifying your savings across multiple tax treatments you can hedge your bets against whatever adverse changes there may be for the future.

In addition, cast a wary eye toward any recommendation for conversion to a Roth IRA – make sure that this makes complete sense to you, both from a tax payout standpoint today, and from the point of view of what you know and expect about future tax rates and laws.  Most importantly, don’t take advice strictly from someone who stands to benefit from the very advice he’s giving.  Don’t take this to mean that Roth IRA conversion isn’t ever beneficial: for many people there are compelling reasons to convert at least some assets to Roth.  It just makes good sense to proceed with caution and make no swift, dramatic changes.

And pay attention, because these things have a tendency to happen so subtly that you might even think it’s a good idea…

Photo by Rennett Stowe

Roth Conversion – What Could Possibly Go Wrong?

warning by jurvetsonIt is expected that in 2010 there will be more Roth IRA conversions than in any year in the past – maybe all years added together.  With all this converting and cavorting going on around IRAs and Roth IRAs, there are bound to be some problems arise.

One particular type of problem that could arise would specifically impact 2010 conversions – those conversions that qualify to be eligible for the special tax spreadout over the following two years.  That problem is the impact you’ll have when a significant sum is converted in 2010, the option for tax payment over 2011 and 2012 is chosen, but alas, the investments chosen go awry, terribly so, eroding your ability to pay the tax.

Specifically, this situation can cause a huge problem if the downturn on the investments occurs long after the conversion – long enough to be beyond the scope of the recharacterization possibility.  Below is an illustration of the situation I’m talking about.

Illustration

Here’s an example of the problem:  You have a significant sum in your IRA – let’s say $500,000, just for grins.  You have run the numbers and determined that it makes sense for you to convert this entire IRA to a Roth IRA in 2010, electing to spread the tax over 2011 and 2012, as you’re eligible to do.  You’ve chosen to do this because you expect that by retiring in late 2010, you will have a much lower taxable income in 2011 and 2012, thereby reducing the tax bite.

You estimate that your taxes will be $200,000 on the conversion, and since you don’t have that kind of scratch just sitting around in a savings account, you expect to pay that tax from the proceeds in your Roth account, $100,000 in 2011 and $100,000 in 2012.  Furthermore, you consider yourself a sharp cookie – you’ve decided to invest the entire amount of your Roth IRA in the hottest new mineral exploration company; you heard about it from a buddy at the club, and he’s always making money, or so he says.

By the October 15, 2011 (the last day that you could choose to recharactrize the conversion), your mineral exploration stock investment has grown 50% – now your Roth IRA is worth $750,000.  Things are going great!  Since the account has grown, you decide not to recharacterize the conversion, and you’ll just sit back and watch your stock grow.

Problems on the Horizon

Until… along about mid-March in 2012, the company you’ve bought into becomes a party of an environmental lawsuit, placing a restraining order against further exploration activities.  The lawsuit is not expected to have merit, it will just be a bump in the road – but the stock falls out of favor, dropping in value by 50%.  Your Roth IRA is now worth $375,000… and you have to pull out $100,000 to pay taxes in 30 days.  After doing so, the account is now worth $275,000.

Now you’ve decided that your hot tip wasn’t such a hot tip, but since you have faith in the company and truly believe that the lawsuit is just a bump in the road, you hang on.  And, in fact, in mid-June, the stock does come back, but nowhere near the 172% you’d have to gain to get back to the all-time high, and not even the 45% that you’d have to gain just to get back to your original $500,000.  More like about 20%, which brings your account balance up to $330,000.

these boots were made for throwing by Coyote2024More Footwear Decends

Just in time for the other shoe to drop:  in late October of 2012, the CEO of your mineral company is arrested for insider trading – and the stock takes another dive, losing 30%.  Your Roth IRA account is reduced to $231,000 – you decide the rollercoaster ride is over for you and you sell out, putting all your money in the money market at a 1.5% return.  When it comes time to pay the other half of the tax in April of 2013, you’ve achieved a bit of a return on the money market holdings, so that your account is now worth approximately $233,000 – but you’ve got to pull out the tax payment.  After you pay your taxes, your nest egg is now worth $133,000.  You’d planned on having at least $300,000 at this point. and now what you have left will be tough to get by on.

What Can We Learn?

What could have been done to avoid this?  Presumably you had weighed the risks and the plan met your needs, as long as the aforementioned problems hadn’t occurred.  This comes down to the long-time planning adage of not putting all your eggs in one basket… you should never try for the “home run” sorts of returns with your entire nest egg.  I’d say you should give up on taking your buddy’s stock tips as well – especially with regard to investing more than you can afford to lose in any one issue as was illustrated.

Of course, something similar could have happened in a diversified account; we have only to look at late 2008 and early 2009 for an example of an across-the-board downturn.  But the likelihood of a repeat of such a downturn is very low, and diversification across many asset classes can provide a buffer against that possibility.

In addition to diversification across asset classes, it makes great sense to diversify across tax treatment as well.  In your savings plan you should have some money invested in all three types of tax treatment: capital gains taxable, tax-deferred (as in an IRA), and tax-free (as in a Roth IRA).  Of course if you have the ability to have all of your money in a tax-free account (as the example did) that would be great, but as you can see, getting the money to the account could be problematic.

Photo #1 by jurvetson
Photo #2 by Coyote2024

Roth Conversion Timing Where After-Tax Contributions Are Involved

time reloaded by lrargerichYet another point that you need to keep in mind as you plan your Roth IRA conversion strategy is the timing of the activities.  This is especially true when you have after-tax contributions to your IRAs in addition to the growth on those contributions and the typical deductible contributions.  As you’ll see below, in some circumstances it can make a big difference in how much tax you’ll have to pay…

Timing Examples

Example 1. You have an IRA worth $100,000, of which $50,000 is after-tax contributions, $20,000 is deductible contributions, and $30,000 is growth on your contributions.  This is the only IRA that you own (which is a key fact, since the IRS considers all IRAs in a lump when determining the taxability of distributions).

Have decided that you’d like to convert $40,000 to a Roth IRA.  When you do so, half of the amount converted ($20,000) will be taxable and the other half non-taxed, since you have after-tax contributions amounting to $50,000 of the total account value of $100,000.

Simple enough, right?  Okay, let’s complicate it…

Example 2. Same circumstances as in Example 1, except that you also have a 401(k) plan worth $100,000, all deductible contributions – and you’ve just retired.  You decide at your retirement that you’d like to rollover the 401(k) to an IRA – you never liked the restrictive investment options available in that old 401(k) plan anyhow.

As in the first example, you want to convert $40,000 to a Roth IRA this year.  (Here comes the timing part)

IF you convert the $40,000 to your IRA BEFORE you rollover the 401(k), you will only be taxed on $20,000 of the conversion, just like example 1.

HOWEVER (and there’s always a however in life, don’t ya know) – if you rollover the 401(k) first and then convert the $40,000 to Roth, you will be taxed on $30,000 of the conversion.  This is because, now that you’ve rolled over the 401(k) plan, you have IRAs worth $200,000, of which only 25%, or $50,000 is after-tax contributions… therefore, only 25% of the conversion distribution is tax-free, and the remaining 75%, or $30,000, is taxable.

So – there you have it.  Timing is very important indeed…

Photo by lrargerich