Taxes: Reevaluating My ROTH Conversion Strategy (2024)

High Taxes Gobble Up Income

Taxes: Reevaluating My ROTH Conversion Strategy (1)

I am reevaluating my ROTH conversion strategy. For the most part I have tried to avoid going into a higher tax bracket, but I have done ROTH conversions each year for the past ten years. For example, in April 2019 I converted 500 shares of ABBV at a total taxable value of $38,785. In other words, I paid income taxes on that dollar amount.

Those shares are now worth 138.47 per share, or $69,235. In addition, I have received $12,058 in dividends that will never be taxed. But it doesn’t end there. I have also received $1,556 in covered call options premiums. So my initial tax liability on about $39K has given me tax-protected benefits of $82,849. That is a real deal. And the real deal keeps giving year after year.

Taxes: Reevaluating My ROTH Conversion Strategy (2)

Now, however, I will be required to take my first RMD next year. As a result, I am rethinking my strategy.

The Big Pieces of the RMD Puzzle Create a Moving Target

The problem with the puzzle is that there are many pieces, and they are not static. The first piece, of course, is the total balance of my traditional IRA. It is very likely that the year end balance will be at least $1.8M. Withdrawals must start in 2024. Therefore, I will have a large withdrawal and it will mean we must pay a significant amount of income taxes to the federal government and to Wisconsin. Each year the percentage of the withdrawal increases based on my increasing age. In addition, if history repeats, it is not unimaginable to think that the traditional IRA balance will grow at least by six percent per year. That is very conservative. Eight percent or more is highly likely.

If you were prudent during your working years, it is not that hard to accumulate a significant amount of assets in a traditional 401(k) or traditional IRA. When withdrawals start, you need to think about your total income and the income taxes that will be required each year. Those taxes are likely to increase because of the way the withdrawals increase mathematically by age.

Because I wanted to stay in a lower tax bracket, I have been more conservative in the IRA conversions to a ROTH IRA for the last ten years. The good news is that I did some conversions. This moved not only the investments from my traditional IRA to my ROTH, but it also moved the dividends from the IRA to the ROTH. As a result, my ROTH IRA now generates about $42K in annual tax-free income.

Aunt IRMAA is Like Uncle Sam

The other thing I was trying to avoid is Aunt IRMAA. She has her hand out and she must be paid. The 2024 IRMAA Medicare Brackets (Income-Related Monthly Adjusted Amount) are published. The Medicare IRMAA Brackets premium surcharge was, I thought, a significant factor. I now believe I have put too much emphasis on that piece of the puzzle.

ROTH Conversion Secrets

Craig Wear wrote two books, one of which I read because he sent me a free PDF version. The book is: Roth Conversion Secrets. I also listened to his high-level explanation to understand what he and his team look at for doing conversions when a person has at least $1M in a traditional IRA or 401(k). I think I may need to rethink my tax boundaries and my concerns about Medicare premiums. “Roth Conversion Secrets” is about 102 pages of “secrets” he really doesn’t share. He gives you enough to think you might want to do what he suggests, but he also makes it very clear that you probably can’t do it yourself. In other words, his book is thinly-disguised marketing materials. I suspect his other book, “Paying the Piper,” is the same thing. I don’t recommend reading “Roth Conversion Secrets” unless you want to pay for marketing materials.

Projected RMDs and IRMAA Tax Consequences

I also want to look at my total projected RMDs and the tax consequences of doing nothing. If our income (MAGI) is less than $206K then there is no added “adjustment” or penalty. However, if our income exceeds that amount, then Cindie and I will pay a combined additional amount of $1,677.60 in Medicare premiums. So it might seem wise to keep our income below the adjustment threshold. The problem with this logic is that it ignores the long-term total taxes from RMD withdrawals and the income that could flow from ROTH IRA investments. In other words, it might make sense to convert up to $250K of the traditional IRA assets, pay the taxes in 2023, and pay the increased Medicare premium for one year. NOTE: The income amount applies to future year IRMAA – not to the 2024 IRMAA!

Who started me thinking about this? Craig Wear did.

Who is Craig Wear?

Here is what I learned about the author of two books that suggest they deal with the subject: “After a thirty-two-year career as an independent financial adviser and Certified Financial Planner™, Craig sold his practice and focuses his business interest, experiences, and efforts toward alerting savers of the large tax obligations that are built into their retirement accounts. This has birthed two Amazon #1 Best Selling books, Paying the Piper, and Roth Conversion Secrets. The tax issues are very real and a very large concern for many savers.”

Taxes: Reevaluating My ROTH Conversion Strategy (4)
Taxes: Reevaluating My ROTH Conversion Strategy (5)

Gathering The Data

I rather doubt what Craig does is all that difficult. Perhaps what he charges for his services is reasonable. I don’t know. However, in the last couple of days I have been building a spreadsheet. The spreadsheet contains sheets that include: 1) My estimated 2024 RMD and all other sources of income so that I can see our total expected 2024 income. 2) Our total anticipated pre-Medicare premium Social Security income. 3) The Medicare IRMAA premiums by income level. 4) Cindie’s RMD from her traditional IRA. 5) The holdings in our traditional IRA accounts so that I can be strategic in determining which assets I might convert to the ROTH in 2023 and again in 2024.

Conclusion and Suggestion

The problem in 2024 is that I have to take my RMD and Cindie has to take her RMD before I can convert any additional traditional IRA assets to my ROTH. Perhaps I should have thought more deeply about this before now. In any case, perhaps you might want to start thinking about it now, rather than later.

Taxes: Reevaluating My ROTH Conversion Strategy (6)
Taxes: Reevaluating My ROTH Conversion Strategy (7)

In a future post, or posts, I hope to be able to explain what I did and why I did it. I also plan to share some links for various resources applicable for those who are interested in their own tax situation. Schwab provides a free useful RMD tool. LINK

Taxes: Reevaluating My ROTH Conversion Strategy (2024)

FAQs

What is the best way to pay taxes on a Roth conversion? ›

The ideal option is usually to pay the tax liability with money that is not in a tax-advantaged account. This could be cash savings in a checking account, a maturing CD, or money in a taxable brokerage account.

Do I pay taxes twice on Roth conversion? ›

Ideally, a nondeductible (after-tax) traditional IRA that gets converted into a Roth IRA would not be subject to any taxes, so the funds would not be taxed twice. To be clear, no converted funds would get double-taxed, but some circ*mstances can result in a taxable transaction.

What is the downside of Roth conversion? ›

Since a Roth conversion increases taxable income in the conversion year, drawbacks can include a higher tax bracket, more taxes on Social Security benefits, higher Medicare premiums, and lower college financial aid.

Why am I being taxed on backdoor Roth conversion? ›

A “backdoor” Roth IRA allows high earners to sidestep the Roth IRA's income limits by converting nondeductible traditional IRA contributions to a Roth IRA. That typically requires you to pay income taxes on funds being rolled into the Roth account that have not previously been taxed.

Should I pay estimated taxes on Roth conversion? ›

You'll owe income tax on the entire amount that you convert from a traditional IRA into a Roth IRA in the year you make the switch. The amount of tax will depend on your income tax bracket and income tax rate—between 10% and 37%. 1 The money you convert is added to your gross income for the tax year.

How do I convert to Roth without paying taxes? ›

In summary, if you have ever made after tax contributions to an IRA and you currently participate in a 401(k) plan or WRP where your employer allows the rollover of IRA funds, your situation would allow you to convert your after tax IRA contributions to a Roth completely free of federal income tax (after having rolled ...

Why am I being taxed on Roth IRA conversion? ›

You'll owe income tax on the amount you convert from a traditional IRA or 401(k) to a Roth IRA, since you've never paid tax on that income. The amount you convert is added to your gross income for that tax year. The higher the conversion amount, the more you'll owe in taxes.

Is the backdoor Roth going away in 2024? ›

Yes. Backdoor Roth IRAs are still allowed in 2024. However, there has been talk of eliminating the backdoor Roth in recent years. And the future is, of course, difficult to predict.

What is the backdoor Roth 5 year rule? ›

Accessed Apr 8, 2022. You'll need the money in five years or less. Money converted from an IRA to a Roth IRA falls under a Roth five-year rule: If you don't wait five years to withdraw it, you could owe taxes and a 10% penalty. The withdrawal from your IRA will push you into a higher income tax bracket.

At what age should I stop doing Roth conversions? ›

However, there are no limits on conversions. A taxpayer with a pre-tax IRA can convert any amount of funds in a year to a Roth IRA. Roth IRAs also are exempt from required minimum distributions (RMDs). These mandatory withdrawals from retirement accounts begin at age 72 and can create a tax burden on affluent retirees.

Is it better to do a Roth conversion when the market is up or down? ›

The Five-Year Rule

The best time to convert from a traditional to a Roth IRA is generally when the market is down and your traditional IRA has lost value, and/or your income is unusually low, and/or your itemized deductions for the year have increased.

How much tax should I withhold on a Roth conversion? ›

You must report any amount converted from a tradi- tional to a Roth IRA on your federal income tax return. Unless you choose otherwise, the IRS requires 10% of the conversion amount be withheld by URS for federal income tax purposes.

What is the pro rata rule for Roth conversion? ›

The IRS' pro-rata rule requires you to include all of your traditional IRA assets—that means your IRAs funded with pretax (deductible) contributions as well as those funded with after-tax (nondeductible) contributions—when figuring the conversion's taxes.

Is there a limit to Roth conversions? ›

No. You may convert just a portion of your assets, and there is no limit to the number of conversions. To help manage the taxes due on each conversion, you may convert smaller amounts over several years.

Should I have taxes withheld from my Roth conversion? ›

You must report any amount converted from a tradi- tional to a Roth IRA on your federal income tax return. Unless you choose otherwise, the IRS requires 10% of the conversion amount be withheld by URS for federal income tax purposes. You may elect to have no taxes withheld or elect to have more than 10% withheld.

How do I pay taxes on a Roth 401k conversion? ›

You'll owe income tax on any money you convert. 15 For example, if you move $100,000 into a Roth 401(k) and you're in the 22% tax bracket, you'll owe $22,000 in taxes. Make sure you have the cash elsewhere to cover the tax bill, rather than using money from your 401(k) to pay it.

How do I offset Roth conversion taxes? ›

  1. Make the most of a business-related loss. ...
  2. Significant medical expenses. ...
  3. Charitable contributions.

How do I pay taxes on my Roth? ›

Contributions to a Roth account are made on a “post-tax” basis. You pay taxes up-front and contributions cannot be deducted from your yearly income, but when you reach retirement age both the earnings and contributions can be withdrawn tax-free.

Top Articles
Assington Cashmere Linen Sweatshirt | Alan Paine UK
25+ Unusual Side Hustles To Make Extra Money - Insane Freedom
Katie Pavlich Bikini Photos
Gamevault Agent
Pieology Nutrition Calculator Mobile
Hocus Pocus Showtimes Near Harkins Theatres Yuma Palms 14
Free Atm For Emerald Card Near Me
Craigslist Mexico Cancun
Hendersonville (Tennessee) – Travel guide at Wikivoyage
Doby's Funeral Home Obituaries
Vardis Olive Garden (Georgioupolis, Kreta) ✈️ inkl. Flug buchen
Select Truck Greensboro
Things To Do In Atlanta Tomorrow Night
Non Sequitur
How To Cut Eelgrass Grounded
Pac Man Deviantart
Alexander Funeral Home Gallatin Obituaries
Craigslist In Flagstaff
Shasta County Most Wanted 2022
Energy Healing Conference Utah
Testberichte zu E-Bikes & Fahrrädern von PROPHETE.
Aaa Saugus Ma Appointment
Geometry Review Quiz 5 Answer Key
Bible Gateway passage: Revelation 3 - New Living Translation
Yisd Home Access Center
Home
Shadbase Get Out Of Jail
Gina Wilson Angle Addition Postulate
Celina Powell Lil Meech Video: A Controversial Encounter Shakes Social Media - Video Reddit Trend
Walmart Pharmacy Near Me Open
A Christmas Horse - Alison Senxation
Ou Football Brainiacs
Access a Shared Resource | Computing for Arts + Sciences
Vera Bradley Factory Outlet Sunbury Products
Pixel Combat Unblocked
Cvs Sport Physicals
Mercedes W204 Belt Diagram
'Conan Exiles' 3.0 Guide: How To Unlock Spells And Sorcery
Teenbeautyfitness
Where Can I Cash A Huntington National Bank Check
Facebook Marketplace Marrero La
Nobodyhome.tv Reddit
Topos De Bolos Engraçados
Sand Castle Parents Guide
Gregory (Five Nights at Freddy's)
Grand Valley State University Library Hours
Holzer Athena Portal
Hampton In And Suites Near Me
Hello – Cornerstone Chapel
Stoughton Commuter Rail Schedule
Otter Bustr
Selly Medaline
Latest Posts
Article information

Author: Amb. Frankie Simonis

Last Updated:

Views: 6354

Rating: 4.6 / 5 (76 voted)

Reviews: 83% of readers found this page helpful

Author information

Name: Amb. Frankie Simonis

Birthday: 1998-02-19

Address: 64841 Delmar Isle, North Wiley, OR 74073

Phone: +17844167847676

Job: Forward IT Agent

Hobby: LARPing, Kitesurfing, Sewing, Digital arts, Sand art, Gardening, Dance

Introduction: My name is Amb. Frankie Simonis, I am a hilarious, enchanting, energetic, cooperative, innocent, cute, joyous person who loves writing and wants to share my knowledge and understanding with you.