r/DIYRetirement

Financial planner recommendations not making sense

My wife and I are planning to retire in our early 50s (fingers crossed), but without any taxable accounts, accessing the money is going to be a challenge before 59.5.

Our financial advisor (used as a second opinion - paid hourly fwiw) put together a rough bridge plan that includes withdrawals from our 457(b) and then possibly some combination of SEPP and Roth contributions.

Then he said something that made me pause - "go very conservative in your Roth"

Our overall AA is 80/20, and he was recommending that the Roth account should be more like 60/40 or 50/50.

Why? I'm really not sure. Can anyone think of a good reason to do this? I'm sure I'm missing something.

The only thing I can think of is that he was wanting to conserve our Roth contribution basis because we might need to tap into some of that, but the contributions only make up 1/3 of the account, so it would need to suffer EXTREME losses to not be able to pull contributions out if I needed to.

For the record, Roth contributions would likely be the third rail for the withdrawals - I'd try to limit those as much as possible before 59.5.

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u/Primordial_Beast — 17 hours ago
▲ 11 r/DIYRetirement+2 crossposts

Any reason to covert to Roth?

I’m recently retired - my nonprofit board’s decision, not my plan - and turning 69 soon. I have enough in a taxable account to hold off applying for SS until I’m 70, when it’ll be worth another $450 per month, and likely to get us to my required RMDs. My wife is collecting her SS and a couple years younger. We have no heirs, the taxable account and home are both jointly in our names, and we are primary beneficiaries on each other’s IRAs. I know I have a short window to convert anything to a Roth. Is there any real benefit to converting? I don’t envision RMDs will raise my tax bracket. I’ve roughly calculated I could convert 10-12% of my IRAs in the next 4 years.

Also, any recommend software to work out the tax scenarios? After years of creating spreadsheets, I’m enjoying not having to use Excel or looking to not recreate the wheel. TIA.

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u/Alterkaka — 2 days ago
▲ 6 r/DIYRetirement+1 crossposts

Try Out My FREE Retirement Travel Planner - WanderList

Hi fellow DIY Retirement planners. I have something more 'retirement life' and less 'retirement finance' I want to share with you. If you are like my wife and I, travel is a big part of your retirement plans and there is likely a list of dream trips/vacations you want to try and fit into your early and go-go retirement years. I recently coupled my desire to leverage AI to code for me and my desire for a more macro trip planner that let my wife and I...

  • manage our dream trip list in one place
  • preliminarily slot or schedule these trips across the upcoming years

...to produce a new solution I call WanderList (a place to plan your wanderlust!) and think it ready for prime time now.

The solution lives as a website ( https://trip-planner-chi-sage.vercel.app/ ) and is really designed to be viewed on a laptop or desktop (i.e., not a mobile app). It's free and I am looking to share it with you to ascertain if there is any need for such a tool and, if so, how to make it better.

With the tool you can identify your bucket list of trips and start scheduling them across the upcoming years. You can manage key trip details as desired and even go so far as to manage trip budgets against an overall retirement travel budget if you like. Define blackout periods where no travel should be planned and invite friends & family to collaborate on trip planning as you see fit.

The tool's intent, to be clear, is not to be a detailed trip planner for any one trip, but rather a way to start slotting trips for that level of detailed planning. Hopefully, the tool addresses the "problem" of seeing how one can fit (and pay for) all the travel they have envisioned in their retirement years.

I'll stop here and simply invite you to give the website/tool a spin.

Let me know what you think by DMing me back. Thanks!

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u/Aggravating_Profit71 — 2 days ago
▲ 0 r/DIYRetirement+1 crossposts

55 y/o M single w/ no dependents, $4.5M NW w/ $1.5M in IRA, 500k taxable, $2M in RE generating ~$30-40K a year… Boldin says I can retire now, but I’m still hesitant… unsure if I should do Roth conversions now or spend big? Sell the RE for better returns in index funds?

I made 160k a year before I was impacted by a layoff - now deciding if it’s time I hang it up for good. Put in my numbers in Boldin and it looks rosy (age 90 shows $11M NW w/ average returns). I went conservative with 6% asset appreciation, and heavier spending (up to$140K/yr) until 65 for travel and even added an additional $200k for an immediate purchase of my dream car! Not planning on leaving much for any heirs, and Boldin is still showing 99% chance of not running out of money without doing Roth conversions. I also feel I have my RE to cash out of if I need liquid funds. Still, I feel hesitant in stopping work altogether, but I know I have the flexibility to work again (part time / contract) if needed, albeit harder as I get older to find work as a tech PM, and should the market crash for a few years. LMK your thoughts on my situation thanks in advance!

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u/Ok_Blackberry_3301 — 3 days ago

Do Roth conversions matter if you have no heirs?

I have no children and I really don’t care what happens to my money when I die. My sole concern is running out of money. It seems to me that if you have enough wealth to be worried about the tax implications of RMDs then you probably aren’t at risk of running out of money, it’s solely a legacy concern.

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u/meezun — 4 days ago

Am I there? I think I am ready to ease in to retirement

60F, single, primary residence TN. I think I'm there, and could semi-retire. I would be able to freelance hourly for my current job and taper back. I have the following:

~ $500,000 in CDs, emergency fund and HYS. Most of the cd's will mature at avg 4.5% later this year, so I need to do something with those when they do. Thinking SGOV <??>

~ $370,000 across SEP IRA, Roth, Rollover IRA and taxable brokerage (convert all to Roth?)

~ $60,000 HSA, invested. I max it out every year

~ Long term care insurance (current premium is about $1k a year - I bought early)

~ AFLAC personal policies for both Cancer specific and "Major Event" (heart etc)

~$30k left on mortgage @ 3.35% - will probably pay it off this summer depending on what interest rates do. House is worth about $400,000

~ 4 yrs left of receiving alimony payments = appx $130k total, but taxable

estimated SS at full retirement would be around $2500 as I have been self-employed for 20 years and some years were low due to write-offs

I will also inherit a commercial property and my mother's residence (she is 90) which will = about $500,000 in re-sale value, and appx $300K cash, assuming already 2-3 years in long term care facilities for her.

Retirement spend, probably on the low side, $60k a year ish? I am not a big spender

I have no heirs, so am not concerned with a legacy, just not running out! Any advice is greatly appreciated !

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u/tastebud413 — 4 days ago
▲ 31 r/DIYRetirement+1 crossposts

Worth it to keep paying for retirement planning software?

Hi All: I've been struggling with the decision to continue paying for software like Boldin and/or Projection Lab. I've been retired for 2 years now (as of today!), and I've been using Boldin for a little over 2 years. Regardless of what I do to my plan to stress-test it, my chance of success is always 99%. I have to basically double my annual spending to get the plan to drop below 99%.

Not saying any of that to brag, but it makes me wonder why I need to continue paying for Boldin just to update my account values each quarter or year just to look at the new numbers.

As far as tax planning, Roth conversions, Social Security strategy, etc, it seems like there are so many other free tools out there for doing those things. In fact, I find it very confusing to use Boldin for those things because Boldin doesn't really know all my exact investments and/or nuances of how we spend and move money around. It all seems based on estimates, averages, and best guesses. I'd tried using the Roth conversion explorer in Boldin, but it never seems to meet my needs. I'm trying to do small Roth conversions each year while also staying under a certain MAGI for ACA subsidies. If I'm careful and intentional, I can actually do Roth conversions while owing very little or zero tax each year, which still getting a pretty high subsidy.

To do that in Boldin, I feel like I have to jump through a bunch of hoops to get it to match up with that I'm trying to accomplish. But I can figure it out myself using a basis spreadsheet.

Anyway... I'm rambling. Just wondering what other retired folks think about continuing to pay for tools like Boldin when your retirement plan is already pretty solid. Is it worth it? Would other free tools like Empower, Fidelity's retirement planner, FiCalc, or others serve pretty much the same purpose?

I've looked for information such as a "day in the life" of a retired Boldin user to get better insights into how folks are using it. 🙂

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u/BarefootMarauder — 5 days ago
▲ 2 r/DIYRetirement+1 crossposts

Heading into semi-retirement: Q re Roth 403b/457b contributions?

60M, widowed, going part-time in late summer. Retirement-wise, I have two goals for the next year: (a) make sure my projected budget really is my spending; and (b) take advantage of catch-up on the Roth side of my employer's 403b/457b voluntary options.

My question for the subreddit is about (b): my plan is to use cash to provide part of my living expenses while my net paycheck drops dramatically, both from lower salary and the catch-up post-tax deductions. (14% goes to a 401k, half my employer's contributions. 403b/457b is extra, all mine.) I *think* that what I'm doing is effectively converting what could be brokerage investments into Roth assets so I get the tax advantage gratis, just substituting existing cash for what would have been more paycheck deposits.

Am I missing anything?

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u/TempeGrumble — 3 days ago

Roth Conversion, can this really be true? $1m more at end of life vs non conversion.

I've been running spreadsheets to determine the benefits of doing a Roth Conversion on approximately $550k in IRAs over the next 14 years.

I've tried to make it as granular as possible, accounting for 4% annual growth in investments, 3.5% annual inflation, an increase of 3% annually with expenses, 2% annual cost of living increase for pension and social security. And determined taxes down to the dollar for state and federal.

When I run each scenario, the results surprised me.

Standard drawdown, where we withdraw only the amount needed to make up annual expense difference, that pension and social security doesn't cover. We don't touch any other investments (roth, brokerage, real estate). At the end of 14 years, the IRA's essentially remain the same. Not a big surprise as pension and SS cover roughly half of annual expenses.

The Roth Conversion drawdown, where we do the same as above, but we also withdraw up to our AGI (to keep us in the 12% bracket) from IRAs every year, until they are depleted. At the end of 14 years, we have withdrawn more vs the Standard scenario, but that's to be expected.

Where the surprise happens is when you extrapolate years 15 through 40. When RMDs start at age 75, and taxes start to ramp up. With the Standard drawdown, we hit zero at age 100. With the Conversion scenario, we have over $1million left at age 100. We would be paying an extra $42k in taxes over that time period, and the net difference in balance is $79k less at the end of 14 years.

I understand that taxes today, may not be taxes in 15 years (even taxes 10 years ago were different from today's). And I realize that tax brackets may change, but I only see them increasing. So, the funding of the Roth account could happen sooner than 14 years.

I've heard that Roth conversions are the way to go, but it's hard to see the true effects unless you drill down and see the numbers. Unless, I missed something and my spreadsheet is FUBAR. We are planning to meet with a flat fee fiduciary in the near future.

Can these numbers be true? Anything I might be missing?

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u/snotick — 6 days ago
▲ 12 r/DIYRetirement+1 crossposts

10 Year Rolling Returns

Just for my "hobby" of dreaming up things to do with AI and a thought from one of Rob Berger's comments this week. This is the 10 year cumulative stock market returns gross and net of inflation. I was pretty surprised how high they were, mostly.

10-Year Period Cumulative Gross Return Cumulative Inflation Cumulative Net Return
1920 - 1929 +194.90% -1.11% +198.22%
1921 - 1930 +230.06% -16.77% +296.55%
1922 - 1931 +65.91% -14.90% +94.95%
1923 - 1932 +25.12% -18.62% +53.74%
1924 - 1933 +99.14% -24.22% +162.77%
1925 - 1934 +55.58% -21.88% +99.14%
1926 - 1935 +76.72% -21.72% +125.76%
1927 - 1936 +112.03% -21.64% +170.60%
1928 - 1937 +0.19% -17.17% +20.96%
1929 - 1938 -8.52% -17.84% +11.35%
1930 - 1939 -0.52% -18.91% +22.68%
1931 - 1940 +19.51% -16.08% +42.40%
1932 - 1941 +86.48% -3.18% +92.60%
1933 - 1942 +144.42% +19.70% +104.19%
1934 - 1943 +99.84% +33.84% +49.31%
1935 - 1944 +142.80% +31.39% +84.80%
1936 - 1945 +124.34% +31.00% +71.24%
1937 - 1946 +54.00% +40.73% +9.43%
1938 - 1947 +150.56% +55.25% +61.39%
1939 - 1948 +101.60% +70.62% +18.16%
1940 - 1949 +140.47% +71.14% +40.51%
1941 - 1950 +251.06% +71.82% +104.32%
1942 - 1951 +392.46% +76.39% +179.18%
1943 - 1952 +384.40% +62.72% +197.69%
1944 - 1953 +280.94% +54.73% +146.19%
1945 - 1954 +385.50% +52.75% +217.83%
1946 - 1955 +368.14% +48.87% +214.46%
1947 - 1956 +442.64% +39.27% +289.64%
1948 - 1957 +357.99% +25.75% +264.19%
1949 - 1958 +522.34% +19.92% +418.98%
1950 - 1959 +486.56% +22.44% +379.08%
1951 - 1960 +347.44% +22.92% +264.01%
1952 - 1961 +357.79% +15.17% +297.48%
1953 - 1962 +252.98% +13.93% +209.81%
1954 - 1963 +337.80% +14.39% +282.73%
1955 - 1964 +234.13% +15.53% +189.22%
1956 - 1965 +185.59% +17.73% +142.59%
1957 - 1966 +141.05% +19.47% +101.77%
1958 - 1967 +234.96% +18.89% +181.74%
1959 - 1968 +159.49% +20.74% +114.91%
1960 - 1969 +112.07% +26.02% +68.28%
1961 - 1970 +119.54% +31.36% +67.13%
1962 - 1971 +97.78% +35.52% +45.94%
1963 - 1972 +157.83% +38.33% +86.38%
1964 - 1973 +79.18% +45.17% +23.43%
1965 - 1974 +13.11% +59.21% -28.96%
1966 - 1975 +38.00% +70.96% -19.28%
1967 - 1976 +90.02% +75.44% +8.31%
1968 - 1977 +42.26% +81.76% -21.73%
1969 - 1978 +36.50% +87.51% -27.21%
1970 - 1979 +76.69% +97.82% -10.68%
1971 - 1980 +124.95% +112.21% +6.00%
1972 - 1981 +87.12% +124.42% -16.62%
1973 - 1982 +91.17% +130.51% -17.07%
1974 - 1983 +174.54% +123.99% +22.57%
1975 - 1984 +296.78% +110.28% +88.69%
1976 - 1985 +280.96% +99.49% +90.97%
1977 - 1986 +265.06% +92.32% +89.82%
1978 - 1987 +313.95% +87.26% +121.05%
1979 - 1988 +352.99% +81.17% +150.03%
1980 - 1989 +403.66% +70.59% +195.25%
1981 - 1990 +268.56% +58.42% +132.65%
1982 - 1991 +405.69% +49.66% +237.90%
1983 - 1992 +347.74% +45.28% +208.18%
1984 - 1993 +302.15% +45.00% +177.34%
1985 - 1994 +283.41% +42.64% +168.80%
1986 - 1995 +300.44% +41.67% +182.65%
1987 - 1996 +314.92% +43.06% +190.02%
1988 - 1997 +425.73% +41.13% +272.51%
1989 - 1998 +479.70% +37.74% +320.86%
1990 - 1999 +432.82% +34.33% +296.66%
1991 - 2000 +399.83% +31.78% +279.30%
1992 - 2001 +237.55% +30.01% +159.64%
1993 - 2002 +144.33% +28.24% +90.53%
1994 - 2003 +185.61% +27.37% +124.24%
1995 - 2004 +212.56% +27.49% +145.16%
1996 - 2005 +138.34% +28.24% +85.86%
1997 - 2006 +124.44% +28.61% +74.52%
1998 - 2007 +77.54% +29.36% +37.24%
1999 - 2008 -13.01% +32.17% -34.18%
2000 - 2009 -9.12% +28.80% -29.44%
2001 - 2010 +15.04% +26.56% -9.10%
2002 - 2011 +33.32% +27.05% +4.93%
2003 - 2012 +98.52% +27.68% +55.49%
2004 - 2013 +104.25% +26.68% +61.23%
2005 - 2014 +109.42% +25.32% +67.11%
2006 - 2015 +102.37% +21.32% +66.81%
2007 - 2016 +95.68% +19.09% +64.31%
2008 - 2017 +125.99% +18.16% +91.25%
2009 - 2018 +243.00% +16.57% +194.25%
2010 - 2019 +256.65% +19.15% +199.34%
2011 - 2020 +267.00% +18.68% +209.25%
2012 - 2021 +362.60% +20.40% +284.22%
2013 - 2022 +226.58% +27.36% +156.42%
2014 - 2023 +211.53% +30.62% +138.50%
2015 - 2024 +242.57% +32.29% +158.95%
2016 - 2025 +298.33% +35.60% +193.76%
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u/Evening_Warthog — 6 days ago
▲ 4 r/DIYRetirement+1 crossposts

Want to be on the right track for Retirement

I feel more anxious day by day as I am three years out to retirement. I feel like a headless chicken, not sure where I should go with the portfolios. I know my portfolios are too risky and I am concerned about the market and I properly not make the money work as hard as it should either. I also worry about being hit by a big tax bill. I need help from all your wise and savy planners. Here is the big picture of my finance:

60F, total net assets are around $2M: DC 457 $1.3M, Fidelity +Schwab $640K, Annuity $72K, Treasury $11K. The current allocation is 44% in US stocks, 17% in Intl Stocks, 17% US bonds, 0.34% Intl Bonds and 18% Cash (Stable Value, Money Market, cash etc.). Among all the accounts, only $110K is in Roth. I am not very knowledgeable about investing and mostly just throw the darts in the dark. I do know two things: diversification and consistently savings. I had a financial advisor in charge of the Fidelity account for a year, they invested ETFs. I am looking for a new one who charges less fees.

I am eligible to cash out my DC457 (B). My pension would be $57K per year at 63yr and SS payment would be $44K at 67yr. Single, no dependents if that helps. Thanks for any input.

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u/No-Potential-85 — 7 days ago

Questions for using the models: Claude, Gemini, et al

I appreciate the helpful responses I got regarding my last post, i.e. fin planning after retirement.

I have engaged the services of a CFP, but also will be using the other methods mentioned - i.e. Gemini, Claude, etc.

Until now, I have only used these for simple questions that I plug into the chat box....seems that financial analysis with all of the factors involved, shouldn't I upgrade to the paid versions of these platforms?

Do you just cut and paste all your analysis information into the chat box? seems simplistic, but maybe I am overthinking it? and then you download the results?

Just trying to maximize the results and hoping for accuracy. Just trying to look at logistics, thanks

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u/Delicious_Mess7976 — 7 days ago

Question: Financial Planning Advice for After Retirement?.

I am treading water, but need to swim. The short of it is that I worked long and hard for decades, never came up for air. Then I retired a couple years ago and I have been like a bird let out of a cage - traveling, spending time with family, sleeping more, exercising more...barely look at the market news - this after decades of daily watching.

DIY personal finance was a breeze in the accumulation phase - spend below income, invest the rest according to plan, set and forget until one day you wake up and have a big pile.

Since retirement? I have actually been just living from withdrawals from my savings account...yikes. Just signed up for Medicare so now it's time to get serious:

- when to take Social Security

- how to develop a withdrawal strategy - based on taxable vs. nontaxable vs. tax deferred

- what about IRMAA?

- are my Roth Conversions on the right path?

- what should I know about RMDs?

- how do I max out withdrawals without running out of $?

Those are the kind of questions that I am late to answer.

I have been recommended to a fee only advisor for an initial no obligation consult, so will see how that goes.

Would one of the software programs be helpful as well? I am a low tech person, so a bit intimidated.

I understand the limitations of intelligence platorms, but is one of them better than the others for helping me run scenarios?

Thoughts? retirees here? any advice or suggestions? Any good books for retirees on these topics? Many thanks.

-

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u/Delicious_Mess7976 — 8 days ago

DIY retirement programs - where to start?

Been watching videos and reading reviews about Bolden, ProjectionLab, Pralana.

Sure, I have scenarios in mind:

  • retire at 55
  • retire at 59.5
  • retire at 60 (bonuses are paid in q1)
  • retire at 62 - if the market takes a big hit

Sure, I’ve read about ACA (400 %), IIRMA, required distributions.

But, I’m looking for a program that will tell me what I’m not thinking about.

And yes, I want to think about potential windfalls like suddenly a big real estate inheritance or heck, even a 60k inheritance.

What program do you recommend to start?

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u/RetireYoung72 — 8 days ago
▲ 0 r/DIYRetirement+1 crossposts

VTxxx and cash

Just curious if any on here is doing a VTI, VOO, VTSAX, etc and say some HYSA cash as their fixed position to make the set up short and sweet.

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u/michjg — 7 days ago

Financial Planner - advice only help

I am ashamed to say that after realizing that Ameriprise was siphoning our funds away, my husband and I (both age 50) fell into an Edward Jones trap for the last 2 years. I am sure I dont need to get into the gory details that led us here.

I want to DIY but he is hesitant. We are starting on Rob's book and found a couple of advice only advisors in the Garrett network we are meeting with next week.

Obviously I am terrified of making yet another error in judgement ( I am quick to trust and he is even less inclined to question things-he self admittedly is a novice). I could probably do Boldin but dont have the knowledge nor the time to study taxes in depth.

Is there anything we should ask specifically of these two people? Both are CFP and CPAs and are either hourly or project based.

We want to know if we can retire by age 62 and where to put our $ that is tax efficient and minimze fees.

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u/PrincessDragonfly25 — 9 days ago

Should taxable accounts be depleted to fund Roth conversions?

I currently have 4.3m in a Traditional IRA account. I am retired at age 58 and will start Social Security Survivor Benefits in two years. The account is composed of VBTLX, VTI, and VXUS. I am planning on using all future dividends in that account to purchase more VBTLX. I was also planning on moving VTI and VXUS shares into the Roth IRA by doing Roth conversions. I know that it is best to pay the taxes for the Roth conversion using the funds from taxable accounts. Is it a good idea to sacrifice the taxable accounts (run down to almost zero) to fund the Roth conversions? If I do Roth conversions to the top of the 32% tax bracket for a couple of years, I would be running down the principal in my taxable accounts. Right now I don't have enough passive income and Social Security to fund all of my living expenses.

Update: I plan to perform Roth conversions up to the 24% tax bracket limit for the next three years (while I am HOH tax filing status) and will pay the taxes from my taxable accounts. I plan to use QCDs starting at age 70.5. I will reevaluate annually whether or not more Roth conversions are needed.

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u/DragonflyUseful9634 — 10 days ago

Another Roth Conversion Perspective

Like many here, I have watched many YouTube videos on conversions and my perspective is there is a lot voodoo math and pretty graphs with huge tax savings in the future. The Widow tax is real and trying to pass money tax free to heirs are certainly some of the stronger reasons for conversions.

However, too many people complaining about taxes as if Rmds are going to be taxed at higher rates than ordinary income. They will not. By the time rmds are due, the government has given you a 50 year tax free loan. During that time you had use of that money and earned significant market returns all at that coursty of the US government.

Be thankful for living in the greatest country in world and in what has been strong market returns. Our kids may not be as lucky.

If you are worried about rmds, you have a lot of money. Live your life, spend as much as you can while healthy enough to do so. I having been saving my whole life for the future and my future is now. I am not worried about break even on a Roth at 90. Sure, be smart and take advantage of conversions at lower tax rates.

As they say, there are two certainties in life- death and taxes.

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u/Crafty_Future4829 — 12 days ago

Anyone dig into the McQuarrie study into Roth conversions?

In another thread I started to ask about "wash" Roth converesions, I was pointed to this document by Edward McQuarrie https://www.financialplanningassociation.org/learning/publications/journal/MAY23-arithmetic-roth-conversions-OPEN

This paper famously paints Roth conversions as being of limited value. I had seen this paper referenced in the past, but didn't know enough about the workings of Roth conversions to really understand the math. Looking at it again, it made a little more sense, and I tried making a simple spreadsheet to better follow how the math worked (the math in the paper is relatively straightforward and easily translated into a spreadsheet). I certainly don't have the mathematical rigor that Mr. McQuarrie used, but I think I found a problem with the reasoning behind the arithmetic. I'm going to sketch out my thinking, hoping for someone to point out the error in my thinking, or maybe confirm a known issue. I'll try to keep this simple, but its a little long - feel free to skip ahead to the conclusions if the math is too heavy.

The paper starts out showing the difference between withdrawing the taxes from the conversion to pay the tIRA taxes, and using outside money to pay the taxes. The example is converting $100K in a 25% tax bracket, where the tax will be $25K. Taking the taxes from the conversion results in $75K in the Roth, while using $25K in outside money results in $100K in the Roth. Assuming the funds are invested in the same equities and compound at the same rate, the one with outside money will clearly always be way ahead going forward.

The example looks at the case where both the conversion and distribution taxes are the same rate. And indeed, the distribution tax rate never enters the outome of a conversion, it only comes into play in modeling the no-conversion case, where tIRA funds are taken directly and incur the distribution tax.

The paper then points out that the $25K outside money has an opportunity cost. If instead of using it to the pay taxes on the conversion, it was invested (in a taxable account), it would compound, and generate LTCG taxes on the earnings. The paper models the invested outside money as a rather tax-inefficient investment where the gains are taxed every year (interestingly enough, the example is very similar to that used in the Vanguard BETR study). Because of the tax drag, this hypothetical outside investment generates less growth than if it were compounding with tax-free-gains in the Roth; every year the Roth balance would grow bigger than the alternative of withdrawing taxes from the conversion and investing the $25K in a taxable account. This is exactly what the various conversion advocates suggest: using outside funds is a win over withdrawing the taxes from the conversion (I'll get to how big the difference is in the conclusions).

Here is where I think the problem is (and the paper does not show a detailed example of the numbers, so I may be confused). The average retiree won't have a "spendable" $25K sitting in a low-interest bank account or stuffed in their mattress to pay conversion taxes or invest; more likely we will get the funds from selling investments in a taxable account and paying LTCG taxes. To get that $25K, we might have to sell as much as $29K in stock, paying an extra $4K to the IRS. Mr. McQuarrie sees that extra $4K as an additional cost of the conversion; he subtracts the entire $29K from the Roth balance using outside money and finds a lower balance than just discounting the $25K conversion taxes from the converted amount. There is still $100K in the outside-money Roth generating more growth that will eventually cover the $4K, and the paper defines this as the "break even" point - which with typical ROIs and tax-rates could be 10+ years!

The problem is, I think it is wrong to include the taxable-taxes as part of the cost of the conversion. Yes, the person converting took $29K from their taxable account, but that was never all of their own money; the government was already owed a piece of that $29K that the tax-payer would never receive. Selling $29K of equities was simply necessary to generate $25K in un-encumbered (what I think of as "spendable") money to pay the conversion taxes (the IRS always wants paid with "spendable money"). If we turned this around, and left the $29K invested, the spendable funds it would generate over time would be exactly the same as if we had invested $25K of spendable funds.

If you use this interpretation, the Roth balance when paying conversion taxes with outside money from selling taxable investments is never less than withdrawing the tax from the conversion, and as suggested above can give a slight advantage in spendable-dollars every year following the conversion. This seems like a pretty important distinction, since it suggests that conversions can never hurt - that you never have to wait multiple years just to avoid losing money on a conversion.

I played around with the knobs in my little spreadhseet and discovered something that should have been obvoius: the examples in the paper assume that both the Roth investments and the taxable account investments have the same ROI. This is somewhat reasonable; if you had an investment in one account with a better ROI, why wouldn't you change the other account to have the same investment? In practice, that isn't always possible or wise; it might make your portfolio less diverse, or generate a taxable event to move funds. Taking advantage of a conversion to sell off poor performing investments can make the conversion much more valuable, and conversely if your taxable account is doing well - and has minimal tax drag - you might want to leave it alone, as converting it has little impact on the Roth.

Conclusion (based on my re-interpretation of the paper): there is no real downside to converting even in a "wash" scenario; there is no real break even period (converting at a lower tax rate than withdrawing is even better). Here's the bad news: while converting with the proceeds from selling taxable equities is always positive, the difference is very small over reasonable time-scales. After 10 years, a $100K conversion may be ahead $4K versus taking the money from the conversion and $16K versus not doing a conversion. Dealing with estimated tax payments to use outside money may not be worth the few percent gain; its not nothing, but you're not going to buy a second-hand Ferrari with the difference. I think the impact on RMDs may be more significant, but I need to think about those some more - but converting tIRA funds will always reduce the tIRA balance and reduce future RMDs. All of these estimates are based on lots of guesses as to ROIs and tax-rates., so YMMV.

Does this make sense - or (won't be the first time) am I missing some subtle issue?

u/Puzzleheaded-Gas-398 — 11 days ago