The Best Time for Roth IRA conversions: Before or After the Death of the Stretch IRA?

For many individuals, a series of well-timed Roth IRA conversions can be the best defense against the Death of the Stretch IRA.

The Best Time for Roth IRA conversions: Before or After the Death of the Stretch IRA?

A lot of clients ask me if I manage my own finances the way I recommend they manage theirs, and the answer is definitely “yes”.   I realized though, that I have not told you my own Roth IRA conversion story, and how my decision will affect my own family after the Death of the Stretch IRA.

Roth IRA Conversions – The Best Time is in Years of Low Income

Think back to 1998.  It was long before we ever had to worry about the Death of the Stretch IRA, and it was the first year you were permitted to make Roth IRA conversions.  Back then, if your Modified Adjusted Gross Income was more than $100,000 you were restricted from making Roth IRA conversions.  Our family’s income was over $100,000, so I thought my income restricted me and never imagined I’d be eligible to do Roth IRA conversions myself.  Then on February 16, 1998, our office was wiped out by a devastating fire that started in a pizza shop located directly below us.  Can you imagine this happening to a CPA firm in the middle of tax season?

I learned some valuable lessons from this experience.  First, never put your office above a pizza shop.  Second, I learned more about the insurance process than I ever cared to know.  We had extremely high expenses because everything needed fixed and, even though I was well insured, I didn’t get the check for the damage until 1999. That meant that 1998 was a very tough year for the business financially.   I couldn’t take a salary, and for the first time our family’s income was far less than $100,000.  Did I get upset?  No.  I said to my wonderful wife, “Cindy, I think we have an opportunity here”.

My wife and I had about $250,000 in Traditional IRAs between us.  I told her that our normal income level would restrict us from making Roth IRA conversions, but our income in 1998 was far below normal – making that year the best time for us to do Roth IRA conversions.  I told her that I thought we should convert the entire amount to Roth IRAs and voluntarily pay the tax due the $250,000 conversion amount.  After she got over her initial shock, she looked at the mathematical calculations I had done and, being an extremely intelligent woman, she immediately understood that our family would be better off by hundreds of thousands of dollars in the long run.  And so we did it – we converted every last dime of our IRAs to Roths.  And those Roth IRAs are now worth quite a lot more than they were in 1998.

The law has since changed, and there are no longer any income restrictions on Roth IRA conversions.  This means that you can do smaller Roth IRA conversions over a series of years rather than all at once like I did, and by doing so you can convert them at a lower tax rate than I was able to.  The best time for many retired individuals is the period after you’ve stopped working, but before you are required to take minimum distributions from your IRAs and retirement plans.  And with the Death of the Stretch IRA looming, there are probably even more reasons now for you to consider Roth IRA conversions than I had when my office caught fire in 1998.

Transferring my Roth IRA to My Child

Twenty years later, it is likely that Cindy and I will never spend those Roth IRAs.  Some people will argue that, if that’s the case, there was no benefit to us converting our IRAs to Roths.  Why pay tax when you didn’t have to, they ask?  Well, I guess it’s because, in the long run, I was thinking of what would happen when I die and my Roth IRA is transferred to my child.  My daughter Erica was only three years old when we did those Roth IRA conversions.  If I die tomorrow and my Roth IRA is transferred to her, she’ll be hundreds of thousands of dollars better off because I did that conversion.  And if I live for another twenty years, it’s not unreasonable to think that she’ll be more than a million dollars better off when I die.

When my Roth IRA is transferred to her after my death, Erica will still be required to take minimum distributions from the account every year.  If I die before the Death of the Stretch IRA legislation is passed, those minimum distributions can be stretched over her lifetime and the bulk of the IRA can continue to grow in a tax-free environment.  If I die after the Death of the Stretch IRA legislation is passed, she’ll be required to withdraw the entire IRA within five years.  Although the money will be forced from the tax shelter more quickly, at least the withdrawals will be tax-free to her.  And I can’t think of a better present for my little girl.

Stop back soon for more Roth IRA talk!

-Jim

For more information on this topic, please visit our Death of the Stretch IRA resource.

P.S. Did you miss a video blog post? Here are the past video blog posts in this video series.

Will New Rules for Inherited IRAs Mean the Death of the Stretch IRA?
Are There Any Exceptions to the Death of the Stretch IRA Legislation?
How will your Required Minimum Distributions Work After the Death of the Stretch IRA Legislation?
Can a Charitable Remainder Unitrust (CRUT) Protect your Heirs from the Death of the Stretch IRA?
What Should You Be Doing Now to Protect your Heirs from the Death of the Stretch IRA?
How Does The New DOL Fiduciary Rule Affect You?
Why is the Death of the Stretch IRA legislation likely to pass?
The Exclusions for the Death of the Stretch IRA
Using Gifting and Life Insurance as a Solution to the Death of the Stretch IRA
Using Roth Conversions as a Possible Solution for Death of the Stretch IRA
How Lange’s Cascading Beneficiary Plan can help protect your family against the Death of the Stretch IRA
How Flexible Estate Planning Can be a Solution for Death of the Stretch IRA
President Trump’s Tax Reform Proposal and How it Might Affect You
Getting Social Security Benefits Right with the Death of the Stretch IRA
The Best Age to Apply for Social Security Benefits after the Death of the Stretch IRA
Part II: The Best Age to Apply for Social Security Benefits after the Death of the Stretch IRA
Social Security Options After Divorce: Don’t Overlook the Possibilities Just Because You Hate Your Ex
Is Your Health the Best Reason to Wait to Apply for Social Security?
Roth IRA Conversions and the Death of the Stretch IRA
How Roth IRA Conversions can help Minimize the Effects of the Death of the Stretch IRA
How Roth IRA Conversions Can Benefit You Even if The Death of Stretch IRA Doesn’t Pass
The Death of the Stretch IRA: Will the Rich Get Richer?

The Death of the Stretch IRA: Will the Rich Get Richer?

Do Roth IRA Conversions Make the Rich even Richer? Will This Change After the Death of the Stretch IRA?

Do Roth IRA Conversions Make the Rich even Richer? Will This Change After the Death of the Stretch IRA?

My most recent blog posts have been about Roth IRA conversions, and how they might benefit you under both existing law and the proposed law that would spell the Death of the Stretch IRA.  This post continues this discussion, and outlines the benefits of transferring Roth IRAs to your children.

How Do the Rich Get Rich? 

There’s been a lot of media coverage about rich people lately, have you noticed?  The rich don’t pay taxes!  The rich are getting richer!  And so on.  Well, I’m going to go out on a limb here and suggest that there are many rich people who don’t deserve all of the abuse they get about their wealth.  Are there rich people who get their money from stealing and cheating?  Certainly, and I hope the long arm of the law finds every one of them and brings them to justice.  But I have many clients who are, by most people’s standards, rich – and not one of them ever failed to pay their taxes, or stole their money from someone else.  Most of them had decent but not high-paying jobs, and the vast majority of them didn’t inherit their wealth either.  So how do the rich get rich, and how do they continue to get richer?

In the late 1960’s, Stanford University conducted a study where the children who participated could receive a small reward (a marshmallow) immediately, or choose to receive a larger reward (two marshmallows) after waiting a short period of time.  Some of the kids, of course, ate the marshmallow immediately.  Others, though, waited for what probably felt like a lifetime, and were rewarded with the second marshmallow.

Most of my clients are two-marshmallow people.  This means that during their lifetimes, every financial decision they made considered both the short-term and long-term benefits.  Could they afford the monthly payment on a Cadillac?  Probably, but they opted for Fords instead and banked the difference between the monthly payments.  Could they use credit to buy new living room furniture?  Yes, but they waited until they had enough money saved up to pay cash because they wanted to avoid paying interest on their purchase.  Two-marshmallow people understand that sometimes it makes sense to do with less now, in exchange for a bigger payoff in the future.  That’s how many of the rich get rich in the first place, and could be why the rich continue to get richer.  And a similar mind set could be a lifesaver for you when the Death of the Stretch IRA legislation is passed, and you are scrambling to find ways to keep your hard-earned money out of the hands of the government.

Roth IRA Conversions: Not Just For Rich People Who Don’t Want to Pay Taxes

Many uninformed individuals think that strategies like Roth IRA conversions are simply tools designed to allow rich people to get richer, and to avoid paying taxes.   That’s not exactly true.  Roth IRA conversions can help anyone, not just rich people, get richer and avoid paying more taxes than necessary.    In fact, I would argue that Roth IRA conversions can be of more benefit to someone who isn’t rich, because an additional $50,000 over the course of their lifetime would probably be far more important than it would be to someone who has more money than they can ever spend.  But Roth IRA conversions can make a lot of sense if you are a two-marshmallow person, regardless of how much money you have.  And it’s especially true if your money lasts longer than you do, and you end up transferring your IRAs and retirement plans to your children.  Roth IRAs can make a significant difference for your heirs in light of the Death of the Stretch IRA.

Transferring Roth IRAs to Your Children

The video in this post compares two individuals – one makes a Roth IRA conversion of $100,000 and the other does not.  The conversion provides a small benefit during the Roth IRA owner’s lifetime – so even though he pays taxes on the conversion amount, he still ends up with two marshmallows.  But suppose he never spends the money and, at his death, the Roth IRA is transferred to his children?   Over the course of their lifetimes, the children get ten marshmallows.  And suppose his children don’t spend the Roth IRA, and instead transfer it to their own children (preferably by disclaiming it to a trust).  Over the course of their lifetimes, the grandchildren get an entire bag of marshmallows!

So did the rich get richer?  Yes.  Did they do anything illegal, or anything that you can’t do yourself?  No.  Roth IRA conversions were the brainchild of the government – they want you to pay taxes sooner than you have to so that they have more money to spend.  You may have change your way of thinking to that of a two-marshmallow person, and possibly do with less now in exchange for a greater payoff down the road.  But doing so can enable you to create your own family dynasty that will benefit your heirs for generations to come, and help them offset the devastating effects of the Death of the Stretch IRA.

Stop back soon for more Roth IRA conversion talk!

-Jim

For more information on this topic, please visit our Death of the Stretch IRA resource.

P.S. Did you miss a video blog post? Here are the past video blog posts in this video series.

Will New Rules for Inherited IRAs Mean the Death of the Stretch IRA?
Are There Any Exceptions to the Death of the Stretch IRA Legislation?
How will your Required Minimum Distributions Work After the Death of the Stretch IRA Legislation?
Can a Charitable Remainder Unitrust (CRUT) Protect your Heirs from the Death of the Stretch IRA?
What Should You Be Doing Now to Protect your Heirs from the Death of the Stretch IRA?
How Does The New DOL Fiduciary Rule Affect You?
Why is the Death of the Stretch IRA legislation likely to pass?
The Exclusions for the Death of the Stretch IRA
Using Gifting and Life Insurance as a Solution to the Death of the Stretch IRA
Using Roth Conversions as a Possible Solution for Death of the Stretch IRA
How Lange’s Cascading Beneficiary Plan can help protect your family against the Death of the Stretch IRA
How Flexible Estate Planning Can be a Solution for Death of the Stretch IRA
President Trump’s Tax Reform Proposal and How it Might Affect You
Getting Social Security Benefits Right with the Death of the Stretch IRA
The Best Age to Apply for Social Security Benefits after the Death of the Stretch IRA
Part II: The Best Age to Apply for Social Security Benefits after the Death of the Stretch IRA
Social Security Options After Divorce: Don’t Overlook the Possibilities Just Because You Hate Your Ex
Is Your Health the Best Reason to Wait to Apply for Social Security?
Roth IRA Conversions and the Death of the Stretch IRA
How Roth IRA Conversions can help Minimize the Effects of the Death of the Stretch IRA
How Roth IRA Conversions Can Benefit You Even if The Death of Stretch IRA Doesn’t Pass

How Roth IRA Conversions Can Benefit You Even if The Death of Stretch IRA Doesn’t Pass

How Roth IRA Conversions Can Benefit You Even If the Death of the Stretch IRA Doesn’t Pass

In my last post, I talked about a concept called purchasing power.  If you missed that post, I’d go back and read it because the information contained in it is the key to understanding the benefits of Roth IRA conversions.  In short, it explains why you need to consider more than just the dollar value of Roth and Traditional IRAs, in order to determine if a Roth conversion can benefit you.

Las week, we discussed that, if you measure your accounts in terms of their purchasing power rather than their dollar value, it is quite possible that you and your spouse can benefit from Roth IRA conversions.  The greater benefit, though, is likely to be recognized by your children and grandchildren.  This is true even if the Death of the Stretch IRA legislation does not pass, although I believe it will.

When Roth IRA conversions were first introduced, I believed that they could provide a huge benefit to my clients who had large IRAs.  It wasn’t just a feeling that I had, I did the math to support my position.  Unfortunately, many people were still afraid of this new-fangled idea, and they just didn’t want to hear about it no matter how much it might benefit their families. So I thought to myself, how can I get people to believe me?  In 1997, I published the very first peer-reviewed article on Roth IRA conversions.  Submitting a paper for peer-review is a daunting process.  Imagine a team of CPA’s who are just waiting to find fault with everything you say.  Well, guess what?  After they read it, they all said “He’s right!” – and my article on Roth IRA conversions was accepted for peer-reviewed publication. It was a ground-breaking idea, and I received a lot of attention by the mainstream media because I was a pioneer.  Even to this day I continue to advise several prestigious publications on this topic.  But for many individuals who have large IRAs, a series of Roth IRA conversions can provide an enormous benefit when used as part of a well thought out estate plan.

Roth IRA Conversions and Changing Tax Law

Some of you may think that a concept that was peer-reviewed twenty years ago has little relevance in today’s world.  Well, it’s true that back then, the tax rates were higher than they are now.  That means that, back then, Roth IRA conversions offered a greater benefit than they can under the current tax structure.  And now we are facing the possibility that the Death of the Stretch IRA legislation will pass, which would accelerate the income tax due on inherited IRAs.

The changing tax rules are the reason that you must measure your IRAs, whether they are Traditional or Roth, in terms of their purchasing power.   For many individuals, paying tax on the amount that you convert to a Roth IRA can provide a benefit to you, and an even greater benefit to your heirs.   It goes against my grain to pay income tax even a day sooner than I have to, but I put my own money where my mouth is.  Years ago, I paid the income tax due and converted a significant amount of both my own and wife’s Traditional IRAs to Roths.  I’m glad I did, because those IRAs have grown tax-free for decades.

Roth IRA Conversion Calculators

So let’s talk about those Roth IRA conversion calculators that are available online.  Are they accurate?  Well, if you want to try one out, please make sure that you find a calculator that uses the current tax rates.  Your results will not be accurate if you unknowingly choose a calculator that uses tax rates from ten years ago!  When personal computers first hit the scene, there was a popular saying about them:  “garbage in, garbage out”.  This was the developer’s way of saying that, while their programs were accurate, they couldn’t prevent you from making errors.  So if you were preparing your tax return using a well-known software and accidentally checked a box that said you were single when you were actually married, your tax return would still be right – if only you were single.

Ultimately, all an online calculator can do is estimate whether or not a Roth IRA conversion can benefit you.  In my opinion, an estimate is not good enough.  Before we make the recommendation to a client that they do Roth IRA conversions, our CPAs do actuarial calculations using several different scenarios.  They also calculate your tax return (and the tax returns of your beneficiaries) so that we know for certain whether Roth IRA conversions can benefit you.  If the Death of the Stretch IRA legislation passes as I believe it will, Roth IRA conversions will likely become a more important part of many estate plans.

Stop back soon for more Roth IRA talk!

-Jim

For more information on this topic, please visit our Death of the Stretch IRA resource.

P.S. Did you miss a video blog post? Here are the past video blog posts in this video series.

Will New Rules for Inherited IRAs Mean the Death of the Stretch IRA?
Are There Any Exceptions to the Death of the Stretch IRA Legislation?
How will your Required Minimum Distributions Work After the Death of the Stretch IRA Legislation?
Can a Charitable Remainder Unitrust (CRUT) Protect your Heirs from the Death of the Stretch IRA?
What Should You Be Doing Now to Protect your Heirs from the Death of the Stretch IRA?
How Does The New DOL Fiduciary Rule Affect You?
Why is the Death of the Stretch IRA legislation likely to pass?
The Exclusions for the Death of the Stretch IRA
Using Gifting and Life Insurance as a Solution to the Death of the Stretch IRA
Using Roth Conversions as a Possible Solution for Death of the Stretch IRA
How Lange’s Cascading Beneficiary Plan can help protect your family against the Death of the Stretch IRA
How Flexible Estate Planning Can be a Solution for Death of the Stretch IRA
President Trump’s Tax Reform Proposal and How it Might Affect You
Getting Social Security Benefits Right with the Death of the Stretch IRA
The Best Age to Apply for Social Security Benefits after the Death of the Stretch IRA
Part II: The Best Age to Apply for Social Security Benefits after the Death of the Stretch IRA
Social Security Options After Divorce: Don’t Overlook the Possibilities Just Because You Hate Your Ex
Is Your Health the Best Reason to Wait to Apply for Social Security?
Roth IRA Conversions and the Death of the Stretch IRA
How Roth IRA Conversions can help Minimize the Effects of the Death of the Stretch IRA