Retirement Accounts/Taxes/Investment & Withdrawal strategies

Barefootwoman

Level 2 Member
Does any one have a good reference for research goes beyond the basics of describing the various tax advantaged accounts ?

I am looking for something that discusses when to use a Roth 401K versus regular 401k, using the Backdoor Roth, Roth conversions and tax implications/strategies for lowering tax liability when working vs. in retirement etc.?

I have a handle on the basics, just having difficulty finding a book or reliable site (not a broker site) for more than a one page discussion.

Thank you.
 

Matt

Administrator
Staff member
The boglehead wiki is a good sourcehttps://www.bogleheads.org/wiki/Getting_started
Bogle Heads is a great resource, also for @Barefootwoman here's some things

If you understand both of these posts you'll go a long way to understanding the mechanics.

As for working vs retirement that's not the best way to think about it - instead, think about it purely from variable income ranges - while working, think about salary, while in retirement think about pensions (some are taxable, some not) and other things that boost up your income. Traditional IRAs have a RMD which kicks in at 70 1/2 which forces the owner to boost their income by taking the distributions.. so within retirement there is a window where you may have stopped working, but not started taking your pension/SSI/ etc and have a low income, this could be a chance to shift from pretax to post tax (401K to tradIRA and then into Roth for example)

Feel free to ask specific questions to help clarify.
 

Barefootwoman

Level 2 Member
Thank you for the references, the topic appears to be not widely discussed elsewhere, which is interesting. Also was given the name of an expert who has written on the topic - James Lange, if anyone else is looking for resources.

What triggered my interest was a discussion of domicile in retirement and how that impacts taxation - particularly for Roth conversions. I may have mentioned before that soon my domicile will be up for grabs! lol
 

Matt

Administrator
Staff member
Thank you for the references, the topic appears to be not widely discussed elsewhere, which is interesting. Also was given the name of an expert who has written on the topic - James Lange, if anyone else is looking for resources.

What triggered my interest was a discussion of domicile in retirement and how that impacts taxation - particularly for Roth conversions. I may have mentioned before that soon my domicile will be up for grabs! lol
You mean in terms of not having to pay state tax on the 1099-R (the income produced when you convert from pretax to post tax) income?
 

AnxiousRetirement

New Member
The Withdrawal Strategies in the subject line interest me. I'd love to see some sort of fancy, online way of balancing account withdrawals after retirement. For me, I'm envisioning 2 traditional IRAs, one to be used for 72t withdrawals and the 2nd to be periodically converted to a Roth IRA, then eventually spent. Then an HSA for healthcare costs, and Roth IRA principal, tax accounts and savings accounts for regular spending. Tracking the backdoor conversions to keep the multiple 5 year periods straight while balancing total taxable income to shamelessly get cheap health insurance from the Affordable Care Act. Then I have an aneurysm from keeping track of all the numbers.

It's very easy to withdraw money in one way that works and then in another way where you end up destitute. I'd love some fancy (yet cheap) software that would do that for someone.
 

GettingReady

Level 2 Member
Anxiousretirement, have you used TaxCaster? Its interesting to get an estimate on your taxes depending on income sources and to see the effects different moving pieces have.
 

Barefootwoman

Level 2 Member
The Withdrawal Strategies in the subject line interest me. I'd love to see some sort of fancy, online way of balancing account withdrawals after retirement. For me, I'm envisioning 2 traditional IRAs, one to be used for 72t withdrawals and the 2nd to be periodically converted to a Roth IRA, then eventually spent. Then an HSA for healthcare costs, and Roth IRA principal, tax accounts and savings accounts for regular spending. Tracking the backdoor conversions to keep the multiple 5 year periods straight while balancing total taxable income to shamelessly get cheap health insurance from the Affordable Care Act. Then I have an aneurysm from keeping track of all the numbers.

It's very easy to withdraw money in one way that works and then in another way where you end up destitute. I'd love some fancy (yet cheap) software that would do that for someone.
Not affiliated, but several trusted sources use financial planning software - esplanner dot com
 

Matt

Administrator
Staff member
We know cheap is relative, so how do the ACA plans compare to regular commercial plans? roughly speaking
Plans vary in price based on their quality. I had quotes starting at $0 per month to cover our family of 3 (with a little planning...) I would probably elect the $150-200 per month range for us as it has nice levels of copay ($5 for visits etc).

I'm also trying to sneak in a sizeable rollover this year, which means I would COBRA the year end (without paying for it) and pick up the new plan in 2016.
 

Sesq

Level 2 Member
In terms of withdrawal strategies there are a few broad concepts.

1. Prefer Trad over Roth in accumulation if you think you will be able to withdraw or convert at a lower rate.

2. Your retirement withdrawal strategy will intersect with your social security claiming strategy. For example, you may wish to delay claiming SS and allow the payout to grow till age 70 and draw down your nest egg to cover the shortfall. An opposite strategy is that you may claim early to avoid tapping the nest egg, and thus let your capital grow. Perhaps there is a sweetener in the second strategy, like a minor child (second marriage, adoption) that could claim benefits while your benefit is being paid. Or perhaps you are aware of health risks and want to re-invest your ss checks. In general my plan is to delay SS, and draw from my traditional assets to utilize the lower brackets if I am retired between 62 and 70 (hopefully before).

3. Similar to 2 (&1), the presence of a pension can be a factor in your withdrawal strategy as it may grow from delaying draw, may had different options for spousal coverage, and may impact your expected tax rate.

4. When considering the effective tax rate at withdrawal/conversion you need to consider your fully loaded cost. That includes state/local taxes, taxability of SS, means testing, impact on the ACA (if you come under Obamacare pre-medicare).

5. Keep in mind laws change, so its going to be an estimate. The fact that its an estimate does not mean you can't try to come up with plans.

6. Similar to using your brackets, current tax law says you don't have to pay any capital gains taxes if you are in the 15% bracket. So you may need to weigh the "free" cap gains versus the opportunity to do Roth conversions in a lower bracket. Who knows if this perk will be part of the law when you are ready.

7. When thinking about #1 (current rate vs future rate), state taxes make a difference. Say you are in the 39.6% bracket, living in California (12%?) during your working years. If you plan to retire to Texas (no state tax) the traditional IRA/401(k) approach should be attractive based on state tax alone. Works the other way too. In the OP's case TX or FL residence may be appealing for conversion purposes.

8. Laws are subject to change, some folks opine that Roth's won't hold their status forever. I am aware of this but I don't fear it (similar #5, its okay to use your best data available and adjust).

9. Don't die with an HSA being inherited by a non-spouse. Your heirs will pay tax on it even if you had incurred qualifying expenses during your life sufficient to pull the money tax free.


My personal plan is to retire in my 50's and do a mix of conversions and withdrawals of my traditional balance until I reach 70 and draw on SS. I will live on my withdrawals and spend down my taxable accounts. I intend to have my roth balances be my last to draw account for the day-to-day, but be available for big ticket draws if something comes up and I don't want to spike my rate. I am also looking to draw down my HSA, which I am using as an extra retirement account by the time I reach 70. Depending on the status of healthcare I would try to optimize my tax rate and medical subsidies where practical (and perhaps college aid). I wouldn't plan to fall into the medicaid or expanded medicaid plans based on current law as I think (don't know) that having a full plan will result in better care. The final key part of my plan is to arrange to keep my expenses as low as possible (paid off downsize housing being key) once I lose the allmighty paycheck.

I am sure there are more organized responses that cover these points.
 

GettingReady

Level 2 Member
Sesq, your plan is similar to ours. My dh, older and higher wage earner will wait until 70 for his SS. However, he'll file, restrict, and draw on mine when I start at age 62. This will leave the higher survivor benefit for me based on statistical evidence that I'll outlive him. We will also do Roth conversions. Rather than pulling from investments, to bridge pre SS years, we're planning on selling our home. It's too big for us and we're tired of the upkeep. We want to be footloose and fancy free. :)
 

AnxiousRetirement

New Member
In terms of withdrawal strategies there are a few broad concepts.

1. Prefer Trad over Roth in accumulation if you think you will be able to withdraw or convert at a lower rate.
I do agree with everything you wrote. On this one though, I think it would be beneficial to have a bit of balance between the two. I have 12.5times as much tax deferred funds than I do in Roth. Due to an unhelpful employer/HR dept, I don't have access to any Roth products at work. And if it weren't for the backdoor Roth IRA for the past few years, I wouldn't have anything. But it'd be nice to have more.

Thankfully I have no spouse and no state taxes to worry about (spouses...taxes...they are equivalent things). That does make my planning a bit easier.
 

Matt

Administrator
Staff member
I do agree with everything you wrote. On this one though, I think it would be beneficial to have a bit of balance between the two. I have 12.5times as much tax deferred funds than I do in Roth. Due to an unhelpful employer/HR dept, I don't have access to any Roth products at work. And if it weren't for the backdoor Roth IRA for the past few years, I wouldn't have anything. But it'd be nice to have more.

Thankfully I have no spouse and no state taxes to worry about (spouses...taxes...they are equivalent things). That does make my planning a bit easier.
If you are planning an early retirement then his point is valid, you'd do better to have a lot more in a Trad right now.
 

Sesq

Level 2 Member
I do agree with everything you wrote. On this one though, I think it would be beneficial to have a bit of balance between the two. I have 12.5times as much tax deferred funds than I do in Roth. Due to an unhelpful employer/HR dept, I don't have access to any Roth products at work. And if it weren't for the backdoor Roth IRA for the past few years, I wouldn't have anything. But it'd be nice to have more.
I agree having tax diversification is desirable.

Well, the math is somewhat stacked if your expected rate is lower in retirement. That said, the converse, if you expect to have an EQUAL or higher rate (or close enough) then Roth is a winner (locks in your rate, better withdrawal rules, RMD rules, estate taxes). I also think the rate number needs to be fully loaded, potentially including the impact of causing your social security taxes to become taxable and/or means testing for other items.

I am a bit of an anomaly in that I assume my future tax will be around 30% (25 fed +5 state). So I have been willing to fund backdoor roths ans roth 401(k)'s even though I am an AMT taxpayer (so 28% + ~6% as the AMT exclusion phases out). If I hit the band of income when the AMT exclusion fully phased out, but before the 39.6% rate takes over I will consider doing in-plan Roth conversions of my traditional 401(k) balance at the 28% rate. I am baised towards prepaying my taxes, which is why I am okay paying 34% now even though my estimate says 30% is my expected rate. I really should flip back to traditional since the 4% delta is probably too high. I am taking on risk that we will see a lowering of income tax rates with an adoption of a VAT. This I see as a bigger "threat" to Roth's than congress reneging on the tax free status. I think in this instance my retirement rate might be 20% (15+5), but then all my dollars will be subject to a national sales tax.

Speaking of risks, I do think the proposals to cap contributions to retirement accounts once the account reaches a threshhold (ballpark $3M indexed to inflation) is a possibility. But that will lead to an increase of roth dollars since a tax free dollar is more valuable than a tax deferred one. Roth stretch IRA's are crazy valuable, so I am sure that one will be shut down in the next 10 years or so. I am not worried about an Argentina style seizure of accounts.
 

Whitecat

New Member
There are a lot of experts on Boglehead forum and they are all very helpful when you post specific question/follow up questions. You really should check it out. They also help me "stand still" during the market downturn and not pressing that panic sell button to make those typical "buy high sell low" mistakes!!!
 
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