Roth Conversions in Retirement

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JakeyLee
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Roth Conversions in Retirement

Post by JakeyLee »

Hello fine people. I recently retired with a pension and 7 figures in what’s now a traditional IRA (rolled over my 403b/457).

Now that I’ve got my married household income lowered ($170k), I’ve been thinking of converting some of those traditional IRA to a Roth. I’m know that I’d pay taxes on those conversions. Would those taxes just be at my current marginal rate? I’m assuming 22%. I’m also assuming that if I convert too much, it might push me to the next marginal tax bracket (?). I’m 50. I have approximately 150k in cash to pay the taxes on said conversions. I’m wondering if at my age, there’s a big enough benefit to having a chunk of my money sitting in a Roth. Sorry for the ramble. Any advice is appreciated.
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JakeyLee
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Re: Roth Conversians in Retirement

Post by JakeyLee »

Edit: “Conversions “. It would be nice if I could finally learn to spell after 50 years.
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BolderBoy
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Re: Roth Conversians in Retirement

Post by BolderBoy »

JakeyLee wrote: Sat Apr 17, 2021 11:40 am... I’ve been thinking of converting some of those traditional IRA to a Roth. I’m know that I’d pay taxes on those conversions. Would those taxes just be at my current marginal rate? I’m assuming 22%. I’m also assuming that if I convert too much, it might push me to the next marginal tax bracket (?).
Then don't convert too much. And yes, I think there is value in doing Roth conversions in retirement so long as the tax hit is acceptable to you.

BTW, you can't undo Roth conversions.
"Never underestimate one's capacity to overestimate one's abilities" - The Dunning-Kruger Effect
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Wiggums
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Re: Roth Conversians in Retirement

Post by Wiggums »

I would do Roth conversions in the 22% bracket! Even if you spill into the 24% bracket by mistake, you only pay 24% on the amount in the 24% range.

If you have a state tax, they get their share too!

Congratulations on your retirement
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FiveK
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Re: Roth Conversians in Retirement

Post by FiveK »

You can go back and edit the title in the OP if you wish. ;)

But more to the point: see Roth IRA conversion - Bogleheads for some good discussion and references to a couple of good spreadsheet tools that you may find helpful.
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FIREchief
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Re: Roth Conversians in Retirement

Post by FIREchief »

JakeyLee wrote: Sat Apr 17, 2021 11:40 am I recently retired with a pension and 7 figures in what’s now a traditional IRA (rolled over my 403b/457).
With a pension and "7 figures," do you expect to ultimately leave behind a meaningful inheritance for your heirs?
I am not a lawyer, accountant or financial advisor. Any advice or suggestions that I may provide shall be considered for entertainment purposes only.
MrJedi
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Re: Roth Conversians in Retirement

Post by MrJedi »

Something to consider is when the TCJA tax brackets expire, 22%/24% brackets go up to 25%/28%.

If you anticipate staying in that 22% bracket, it may be worthwhile to convert into the 24% bracket rather than get taxed at eventual 25% (from 22%) after the tax cut expiration.
JBTX
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Re: Roth Conversians in Retirement

Post by JBTX »

Let's look at the scenarios:

1. In the future you not likely be in the zero bracket due to rmds and a pension.
2. Worst case scenario you end up in 12% marginal rate in retirement scenario, and those rates are renewed in 2026. Add a couple of points to the 12% given a Roth conversion will increase your tax advantaged and otherwise you'd need to keep the tax paid in a taxable account. So let's say 15%. So worst case you convert at 22% vs 15% in retirement, a loss of about 7%
3. In 2026 the tax 12% bracket becomes 15%, unless a new law overrides it. 15% really would be about 18%, compared to 22% now. Fairly small loss.
4. Add in social security which increases your income, and or increases your retirement marginal rate in non linear ways due to SS taxability. At that point between rmds, pension and social security your rate may very well be higher in retirement.

A lot depends on the amount of pension income. If the pension is large, I'd say converting at 22% has some appeal. If not then it is less attractive, but still could make sense depending on the circumstances.
tibbitts
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Re: Roth Conversians in Retirement

Post by tibbitts »

JakeyLee wrote: Sat Apr 17, 2021 11:40 am Hello fine people. I recently retired with a pension and 7 figures in what’s now a traditional IRA (rolled over my 403b/457).

Now that I’ve got my married household income lowered ($170k), I’ve been thinking of converting some of those traditional IRA to a Roth. I’m know that I’d pay taxes on those conversions. Would those taxes just be at my current marginal rate? I’m assuming 22%. I’m also assuming that if I convert too much, it might push me to the next marginal tax bracket (?). I’m 50. I have approximately 150k in cash to pay the taxes on said conversions. I’m wondering if at my age, there’s a big enough benefit to having a chunk of my money sitting in a Roth. Sorry for the ramble. Any advice is appreciated.
It's a much more complicated question than what you seem to be aware of, but it's also a less precise calculation than most Bogleheads wish it was, due to all the assumptions involved. But you really shouldn't be worried that much about marginal brackets. In any case you won't get any helpful replies without everyone knowing the deferred balance, pension amount, social security, and ages involved (not just yours.)
FireAway
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Re: Roth Conversians in Retirement

Post by FireAway »

iORPhttps://www.i-orp.com/ is a tool you can use to figure out if it makes sense, or how much makes sense.
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TomatoTomahto
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Re: Roth Conversians in Retirement

Post by TomatoTomahto »

tibbitts wrote: Sat Apr 17, 2021 2:00 pm
JakeyLee wrote: Sat Apr 17, 2021 11:40 am Hello fine people. I recently retired with a pension and 7 figures in what’s now a traditional IRA (rolled over my 403b/457).

Now that I’ve got my married household income lowered ($170k), I’ve been thinking of converting some of those traditional IRA to a Roth. I’m know that I’d pay taxes on those conversions. Would those taxes just be at my current marginal rate? I’m assuming 22%. I’m also assuming that if I convert too much, it might push me to the next marginal tax bracket (?). I’m 50. I have approximately 150k in cash to pay the taxes on said conversions. I’m wondering if at my age, there’s a big enough benefit to having a chunk of my money sitting in a Roth. Sorry for the ramble. Any advice is appreciated.
It's a much more complicated question than what you seem to be aware of, but it's also a less precise calculation than most Bogleheads wish it was, due to all the assumptions involved. But you really shouldn't be worried that much about marginal brackets. In any case you won't get any helpful replies without everyone knowing the deferred balance, pension amount, social security, and ages involved (not just yours.)
... and you and your spouse’s health, your bequest motivations, your over/under bets (expectations) of returns on deferred balances, your over/under wager (expectations) of future tax rates for Federal and State, etc
I get the FI part but not the RE part of FIRE.
tibbitts
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Re: Roth Conversians in Retirement

Post by tibbitts »

TomatoTomahto wrote: Sat Apr 17, 2021 2:13 pm
tibbitts wrote: Sat Apr 17, 2021 2:00 pm
JakeyLee wrote: Sat Apr 17, 2021 11:40 am Hello fine people. I recently retired with a pension and 7 figures in what’s now a traditional IRA (rolled over my 403b/457).

Now that I’ve got my married household income lowered ($170k), I’ve been thinking of converting some of those traditional IRA to a Roth. I’m know that I’d pay taxes on those conversions. Would those taxes just be at my current marginal rate? I’m assuming 22%. I’m also assuming that if I convert too much, it might push me to the next marginal tax bracket (?). I’m 50. I have approximately 150k in cash to pay the taxes on said conversions. I’m wondering if at my age, there’s a big enough benefit to having a chunk of my money sitting in a Roth. Sorry for the ramble. Any advice is appreciated.
It's a much more complicated question than what you seem to be aware of, but it's also a less precise calculation than most Bogleheads wish it was, due to all the assumptions involved. But you really shouldn't be worried that much about marginal brackets. In any case you won't get any helpful replies without everyone knowing the deferred balance, pension amount, social security, and ages involved (not just yours.)
... and you and your spouse’s health, your bequest motivations, your over/under bets (expectations) of returns on deferred balances, your over/under wager (expectations) of future tax rates for Federal and State, etc
Good point, there is a lot to consider, but unfortunately there's never any certainty you've made even close to what will turn out to be the optimal decision.
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TomatoTomahto
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Re: Roth Conversians in Retirement

Post by TomatoTomahto »

tibbitts wrote: Sat Apr 17, 2021 2:45 pm
TomatoTomahto wrote: Sat Apr 17, 2021 2:13 pm
tibbitts wrote: Sat Apr 17, 2021 2:00 pm
JakeyLee wrote: Sat Apr 17, 2021 11:40 am Hello fine people. I recently retired with a pension and 7 figures in what’s now a traditional IRA (rolled over my 403b/457).

Now that I’ve got my married household income lowered ($170k), I’ve been thinking of converting some of those traditional IRA to a Roth. I’m know that I’d pay taxes on those conversions. Would those taxes just be at my current marginal rate? I’m assuming 22%. I’m also assuming that if I convert too much, it might push me to the next marginal tax bracket (?). I’m 50. I have approximately 150k in cash to pay the taxes on said conversions. I’m wondering if at my age, there’s a big enough benefit to having a chunk of my money sitting in a Roth. Sorry for the ramble. Any advice is appreciated.
It's a much more complicated question than what you seem to be aware of, but it's also a less precise calculation than most Bogleheads wish it was, due to all the assumptions involved. But you really shouldn't be worried that much about marginal brackets. In any case you won't get any helpful replies without everyone knowing the deferred balance, pension amount, social security, and ages involved (not just yours.)
... and you and your spouse’s health, your bequest motivations, your over/under bets (expectations) of returns on deferred balances, your over/under wager (expectations) of future tax rates for Federal and State, etc
Good point, there is a lot to consider, but unfortunately there's never any certainty you've made even close to what will turn out to be the optimal decision.
I’m pretty sure that I’m making suboptimal choices, but short of solving the beating of a Brazilian butterfly’s wings effect on the analysis, I have chosen to make future Roth 401k account contributions for my wife’s remaining years of employment but do no Roth conversions (beyond backdoor). Since the deferred balance is exclusively bonds and Stable Value, I don’t foresee having the opportunity to meaningfully convert even during a crash.
I get the FI part but not the RE part of FIRE.
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dratkinson
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Re: Roth Conversians in Retirement

Post by dratkinson »

If you will need RMDs to pay retirement living expenses, then no need to do Roth conversions as conversions just pay tax early.

But, if you don't need/want RMDs/taxes, then Roth conversion will turn off unneeded RMDs, and so minimize tax in later retirement.


Problem. If you convert all in one year, you'll jump up several tax brackets. (Been there, done that, don't recommend it.) So you'll want to spread your conversions out over several years to minimize the tax bite.

But you may need to advance tax brackets so you have more tax-bracket headroom each year to finish your conversions before RMDs start. How many tax brackets should you advance?

See: https://www.kitces.com/blog/tax-rate-eq ... nversions/


Problem. By moving your 403b/457 into a tIRA, you have created a prorata problem for your multi-year Roth conversions. Believe most would have suggested converting a little of your 403b/457 each year into a rIRA, and bypass the tIRA step.

See: https://www.bogleheads.org/wiki/Roth_IR ... tributions

Do you have a side job in retirement? Can you start a Solo 401K? And move your tIRA into your Solo 401k? Why? No tIRA = no prorata problem. This is to undo the problem created when you moved your 403b/457 into a tIRA.

Side jobs. Could you tutor students, mow lawns/become a handyman for neighbors,...? Anything that could create self-employment income, to justify the creation of a Solo 401k. (I know nothing of the mechanics of self-employment, so you must learn this for yourself.)


Excel is your friend. Recall many use Excel to model each retirement year (income (pension+SS+conversion), tIRA account balance (+market growth -conversion), tax bracket, tax paid,...).

Since current tax code is to sunset (~2017?), it'd be good to take advantage of current lower tax rates.

Option. If needed to pay tax on conversions.
--Bond (2% growth) should grow less than equities (7% growth), so skew tIRA to bonds to minimize growth/tax, and skew Roth back to equities to maximize growth.
--Do ~75% of annual conversion in Jan to shift more annual growth into your Roth, do remaining ~25% of annual conversion in late Dec, after you have a better tax picture (moving expense, medical expense, yearend distributions,...).
--Believe brokerages will withhold tax on withdrawal/conversion. Call to check. Con: if tax withheld on conversion, less goes into Roth.
--Ask employer to withhold more from pension to pay conversion tax, to get more into your Roth.

All of these pieces-parts (and anything else you can think of) are what you need to model with Excel, for each retirement year, to come up with a retirement conversion game plan.

Use your 2020 tax s/w to model your annual conversions---the future will resemble the present. Since everything should be indexed for inflation, so the answers produced by your tax s/w today should translate okay into the future. (Rerun this exercise each year in retirement with the then current tax s/w as a CYA to tweak the Excel model of your conversion game plan.)

You'll definitely need to rerun the conversion tax simulation when the tax code sunsets.


That's all I can think of.
d.r.a., not dr.a. | I'm a novice investor, you are forewarned.
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FiveK
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Re: Roth Conversions in Retirement

Post by FiveK »

dratkinson wrote: Sat Apr 17, 2021 3:22 pm Problem. By moving your 403b/457 into a tIRA, you have created a prorata problem for your multi-year Roth conversions.
No problem here. The tax cost of converting pre-tax traditional funds to Roth is independent of the tIRA balance. Things would be different if we were talking about the backdoor Roth process.
Excel is your friend.
Agreed!
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dratkinson
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Re: Roth Conversions in Retirement

Post by dratkinson »

FiveK wrote: Sat Apr 17, 2021 3:37 pm
dratkinson wrote: Sat Apr 17, 2021 3:22 pm Problem. By moving your 403b/457 into a tIRA, you have created a prorata problem for your multi-year Roth conversions.
No problem here. The tax cost of converting pre-tax traditional funds to Roth is independent of the tIRA balance. Things would be different if we were talking about the backdoor Roth process.
Thanks for the correction. Don't know how I spaced that. Never mind.
d.r.a., not dr.a. | I'm a novice investor, you are forewarned.
tibbitts
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Re: Roth Conversians in Retirement

Post by tibbitts »

dratkinson wrote: Sat Apr 17, 2021 3:22 pm Problem. If you convert all in one year, you'll jump up several tax brackets. (Been there, done that, don't recommend it.) So you'll want to spread your conversions out over several years to minimize the tax bite.

Problem. By moving your 403b/457 into a tIRA, you have created a prorata problem for your multi-year Roth conversions. Believe most would have suggested converting a little of your 403b/457 each year into a rIRA, and bypass the tIRA step.

See: https://www.bogleheads.org/wiki/Roth_IR ... tributions

Do you have a side job in retirement? Can you start a Solo 401K? And move your tIRA into your Solo 401k? Why? No tIRA = no prorata problem. This is to undo the problem created when you moved your 403b/457 into a tIRA.

Side jobs. Could you tutor students, mow lawns/become a handyman for neighbors,...? Anything that could create self-employment income, to justify the creation of a Solo 401k. (I know nothing of the mechanics of self-employment, so you must learn this for yourself.)


Excel is your friend. Recall many use Excel to model each retirement year (income (pension+SS+conversion), tIRA account balance (+market growth -conversion), tax bracket, tax paid,...).

Since current tax code is to sunset (~2017?), it'd be good to take advantage of current lower tax rates.

Option. If needed to pay tax on conversions.
--Bond (2% growth) should grow less than equities (7% growth), so skew tIRA to bonds to minimize growth/tax, and skew Roth back to equities to maximize growth.
--Do ~75% of annual conversion in Jan to shift more annual growth into your Roth, do remaining ~25% of annual conversion in late Dec, after you have a better tax picture (moving expense, medical expense, yearend distributions,...).
--Believe brokerages will withhold tax on withdrawal/conversion. Call to check. Con: if tax withheld on conversion, less goes into Roth.
--Ask employer to withhold more from pension to pay conversion tax, to get more into your Roth.

All of these pieces-parts (and anything else you can think of) are what you need to model with Excel, for each retirement year, to come up with a retirement conversion game plan.

Use your 2020 tax s/w to model your annual conversions---the future will resemble the present. Since everything should be indexed for inflation, so the answers produced by your tax s/w today should translate okay into the future. (Rerun this exercise each year in retirement with the then current tax s/w as a CYA to tweak the Excel model of your conversion game plan.)

You'll definitely need to rerun the conversion tax simulation when the tax code sunsets.

That's all I can think of.
Well, some of what you identified as problems aren't always issues. For example if you have $1M in your tIRA and a $12k basis that's not really an issue, just a nuisance, and not worth working around by manufacturing a 401k.

The problem with multi-year conversions vs. taking a big bite up front is that if you get unlucky(?) and get a few good years, you can end up with a lot more to convert at the end than you had at the beginning. So saving a few % in marginal tax bracket might not work out. Or admittedly you could get lucky(?) and catch a huge downturn if you procrastinate.

There is likely to be a problem converting from an employer plan to a Roth directly, because while tIRA to Roth is usually a couple of mouse clicks with no time out of market, an employer plan to IRA of any kind is often a convoluted paper process. So there can be an advantage to the extra step of going through a tIRA.
diy60
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Re: Roth Conversians in Retirement

Post by diy60 »

tibbitts wrote: Sat Apr 17, 2021 4:42 pm The problem with multi-year conversions vs. taking a big bite up front is that if you get unlucky(?) and get a few good years, you can end up with a lot more to convert at the end than you had at the beginning. So saving a few % in marginal tax bracket might not work out. Or admittedly you could get lucky(?) and catch a huge downturn if you procrastinate.
This is not universally true for everyone. If you have mostly or all bond-like investments in your 401K plan and you convert into bond-like investments in your Roth then market movement doesn't materially matter relative to the conversion.
tibbitts wrote: Sat Apr 17, 2021 4:42 pm There is likely to be a problem converting from an employer plan to a Roth directly, because while tIRA to Roth is usually a couple of mouse clicks with no time out of market, an employer plan to IRA of any kind is often a convoluted paper process. So there can be an advantage to the extra step of going through a tIRA.
Again, this is not universally true. My 401K funds are at my former employer's custodian. It's a click of a button to have the FBO check sent to my home address, and then I just deposit the check into my Roth account via mobile. It is true I may be out of the market for a week or so for the check to arrive, but it doesn't matter to me. Bonds to bonds.
diy60
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Re: Roth Conversians in Retirement

Post by diy60 »

TomatoTomahto wrote: Sat Apr 17, 2021 3:00 pm Since the deferred balance is exclusively bonds and Stable Value, I don’t foresee having the opportunity to meaningfully convert even during a crash.
Agreed, this is an understated point missed in nearly every Roth conversion thread on this forum I've ever read.
tibbitts
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Re: Roth Conversians in Retirement

Post by tibbitts »

diy60 wrote: Sat Apr 17, 2021 5:04 pm
TomatoTomahto wrote: Sat Apr 17, 2021 3:00 pm Since the deferred balance is exclusively bonds and Stable Value, I don’t foresee having the opportunity to meaningfully convert even during a crash.
Agreed, this is an understated point missed in nearly every Roth conversion thread on this forum I've ever read.
I'd guess that most people start out with a good chunk of equity in deferred accounts, only because of the historical percentage of deferred space available relative to Roth, and the general preference for deferred over taxable. Of course the idea is to convert equity first and fixed only when the equity has already been converted.
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TomatoTomahto
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Re: Roth Conversians in Retirement

Post by TomatoTomahto »

tibbitts wrote: Sat Apr 17, 2021 5:38 pm
diy60 wrote: Sat Apr 17, 2021 5:04 pm
TomatoTomahto wrote: Sat Apr 17, 2021 3:00 pm Since the deferred balance is exclusively bonds and Stable Value, I don’t foresee having the opportunity to meaningfully convert even during a crash.
Agreed, this is an understated point missed in nearly every Roth conversion thread on this forum I've ever read.
I'd guess that most people start out with a good chunk of equity in deferred accounts, only because of the historical percentage of deferred space available relative to Roth, and the general preference for deferred over taxable. Of course the idea is to convert equity first and fixed only when the equity has already been converted.
We had equity in deferred, but once we switched to a Quasi-LMP after having “won the game,” I didn’t want a bunch of bonds in taxable (although I could have used munis). Our $3M+ deferred accounts are a large part fixed income.
I get the FI part but not the RE part of FIRE.
tibbitts
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Re: Roth Conversians in Retirement

Post by tibbitts »

TomatoTomahto wrote: Sat Apr 17, 2021 5:51 pm
tibbitts wrote: Sat Apr 17, 2021 5:38 pm
diy60 wrote: Sat Apr 17, 2021 5:04 pm
TomatoTomahto wrote: Sat Apr 17, 2021 3:00 pm Since the deferred balance is exclusively bonds and Stable Value, I don’t foresee having the opportunity to meaningfully convert even during a crash.
Agreed, this is an understated point missed in nearly every Roth conversion thread on this forum I've ever read.
I'd guess that most people start out with a good chunk of equity in deferred accounts, only because of the historical percentage of deferred space available relative to Roth, and the general preference for deferred over taxable. Of course the idea is to convert equity first and fixed only when the equity has already been converted.
We had equity in deferred, but once we switched to a Quasi-LMP after having “won the game,” I didn’t want a bunch of bonds in taxable (although I could have used munis). Our $3M+ deferred accounts are a large part fixed income.
My deferred accounts are gradually becoming more fixed income as I do more conversions, of course. The advantage is you usually have more modest and predictable returns, so RMDs become more predictable. The disadvantage is you never get a change to get a bargain on conversions during a downturn.
diy60
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Re: Roth Conversians in Retirement

Post by diy60 »

tibbitts wrote: Sat Apr 17, 2021 5:38 pm I'd guess that most people start out with a good chunk of equity in deferred accounts, only because of the historical percentage of deferred space available relative to Roth, and the general preference for deferred over taxable.
I think you're probably correct. I too started out with a disproportionate amount in tax deferred, but switched over to Roth contributions closer to retirement once my pension and SS became a somewhat predictable bet, as well as current aggressive conversions. I just want folks to understand the underlying logic and math, and make decisions based on their own circumstances.
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Eagle33
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Re: Roth Conversians in Retirement

Post by Eagle33 »

diy60 wrote: Sat Apr 17, 2021 7:19 pm
tibbitts wrote: Sat Apr 17, 2021 5:38 pm I'd guess that most people start out with a good chunk of equity in deferred accounts, only because of the historical percentage of deferred space available relative to Roth, and the general preference for deferred over taxable.
I think you're probably correct. I too started out with a disproportionate amount in tax deferred, but switched over to Roth contributions closer to retirement once my pension and SS became a somewhat predictable bet, as well as current aggressive conversions. I just want folks to understand the underlying logic and math, and make decisions based on their own circumstances.
Totally agree. That's why its called personal finance.
Rocket science is not “rocket science” to a rocket scientist, just as personal finance is not “rocket science” to a Boglehead.
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