Optimizing taxes in ER

kevink

Full time employment: Posting here.
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Thought I'd share this new post from the estimable John Greaney, who I think of as more-or-less the pioneer of writing about ER since he's been blogging about the topic since 1996 (and, delightfully from my perspective, his web site looks the same now as it did then). It took him 25 years but he's now reached "real" retirement age but hasn't lost a bit of his dry wit or number-crunching skills.

https://retireearlyhomepage.com/tax_management.html
 
What I've found after doing this for over 25 years now, is that you're better off with money in varied accounts (i.e., taxable, traditional IRA, and Roth.)
The best strategy probably leaves you with some in each account. But clearly you are best off with all of your money in a Roth that has passed the tests for tax and penalty free withdrawals. It bugs me when people talk about tax diversity in their accounts as a goal. The goal should be to optimize your wealth and spending money, which probably equates to paying the least taxes in your life (inflation indexed). If you're able to efficiently convert your entire tax deferred accounts, you should do it.
 
Thought I'd share this new post from the estimable John Greaney, who I think of as more-or-less the pioneer of writing about ER since he's been blogging about the topic since 1996 (and, delightfully from my perspective, his web site looks the same now as it did then). It took him 25 years but he's now reached "real" retirement age but hasn't lost a bit of his dry wit or number-crunching skills.

https://retireearlyhomepage.com/tax_management.html

I recall in ‘96 or ‘97 putting “early retirement” into a search engine (don’t even think Google was around then - it was probably Netscape) and finding the Retire Early Home Page. That’s what got me really digging in to how to make it work. Good to see “intercst” is still active!
 
My goal is to minimize taxes.
 
The author didn't have the option of a Roth account when he retired.

Today ERs can convert traditional (pre-tax) to Roth which if they can manage their income to stay in the lower tax brackets while doing so is a great hedge against forced RMDs from pre-tax accounts starting at age 72...hopefully raised to age 75 in the not-too-distant future.

Which is what I'll be doing over the next several years...hoping to grow the converted amounts in my Roth over the next ~30 years for my heirs.
 
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My goal is to minimize taxes.
My goal is to maximize spending and income. That means that I may pay more in taxes and realize more income than I need early on in ER, but when you have RMDs and SS kick in, you're not going to be faced with a much higher tax bracket. Most here focus on paying the least taxes over their projected lifespan, not just minimizing taxes in your earlier years.
 
The best strategy probably leaves you with some in each account. But clearly you are best off with all of your money in a Roth that has passed the tests for tax and penalty free withdrawals. It bugs me when people talk about tax diversity in their accounts as a goal. The goal should be to optimize your wealth and spending money, which probably equates to paying the least taxes in your life (inflation indexed). If you're able to efficiently convert your entire tax deferred accounts, you should do it.

Yes I agree. Paying higher taxes in order to gain tax diversity seems like a mistake. Of course if you have a lot in tax deferred you can achieve tax diversity at any time.
 
The best strategy probably leaves you with some in each account. But clearly you are best off with all of your money in a Roth that has passed the tests for tax and penalty free withdrawals. It bugs me when people talk about tax diversity in their accounts as a goal. The goal should be to optimize your wealth and spending money, which probably equates to paying the least taxes in your life (inflation indexed). If you're able to efficiently convert your entire tax deferred accounts, you should do it.

Disagree. I agree with the scenario of having investments in each of the 3 varied accounts.....taxable; tax deferred ; and tax free and then withdraw from the one that gives the most tax efficient result.

One reason we want to have some money in a Trad IRA and not convert all of it is we may find ourselves with high medical expenses later in life and need money for nursing home / assisted living expenses. Assuming ( and I know it is an assumption) that one will still be able to deduct medical/dental expenses on Sch. A of a tax return; one could offset taxes due on Trad IRA withdrawals with these medical expenses. Especially as these expenses will be astronomical in future years.
 
Disagree. I agree with the scenario of having investments in each of the 3 varied accounts.....taxable; tax deferred ; and tax free and then withdraw from the one that gives the most tax efficient result.

One reason we want to have some money in a Trad IRA and not convert all of it is we may find ourselves with high medical expenses later in life and need money for nursing home / assisted living expenses. Assuming ( and I know it is an assumption) that one will still be able to deduct medical/dental expenses on Sch. A of a tax return; one could offset taxes due on Trad IRA withdrawals with these medical expenses. Especially as these expenses will be astronomical in future years.
Maybe that will work out, maybe not. You may never need LTC, so you're just stuck with RMDs on top of SS, perhaps a pension, and whatever other income you have. And if it matters to you, your heirs will have to drain (and pay taxes on) the IRA within 10 years, quite possibly in what may be their highest income years.

Even if you do need LTC, that probably won't come until years after age 72, so you've got RMDs for a number of years until you have the medical expenses to deduct from your income. I would model this to see if it's worthwhile to hold back tax deferred money vs converting at a lower rate earlier. This may improve if the RMD date moves out to 75 as has been considered.

My plan, if I need LTC later in life, is to sell my holdings with high capital gains to use the medical expense deduction. Others may not have enough in taxable to use this strategy, so I'm not claiming this is the best way for everyone.

I think the potential for LTC expenses is a factor in Roth conversions, not a hard requirement to leave some in the tIRA. Suppose I could convert all of my tIRA at 0%; I would rather do that and have all that money in a Roth rather than leaving some in a tIRA for the LTC case. This is my point. Leaving some in a tIRA should not be a goal in of itself, but it might very well be the outcome of the best strategy.

Another factor for leaving money in a tIRA is charitable giving, through QCDs and/or through your estate. But again, if I can convert for free, I would do so and donate appreciated stocks from taxable instead. The likelihood is that I can't convert all with 0% taxes, so the outcome of the best strategy is probably leaving some in the tIRA for giving.

Now that I've hopefully convinced you that fully converting your Roth at 0% would be better than leaving some to write off LTC expenses, it follows that fully converting at a relatively low tax rate might be a better strategy than leaving some in the tIRA for those expenses. It's worth running some numbers to see which works best.

And by the way, you don't get to deduct medical expenses dollar-for-dollar against taxable income. The first 7.5% of income is excluded from the deduction. The more income you add, the more expenses are excluded. Factor this in too.
 
Maybe that will work out, maybe not. You may never need LTC, so you're just stuck with RMDs on top of SS, perhaps a pension, and whatever other income you have. And if it matters to you, your heirs will have to drain (and pay taxes on) the IRA within 10 years, quite possibly in what may be their highest income years.

Even if you do need LTC, that probably won't come until years after age 72, so you've got RMDs for a number of years until you have the medical expenses to deduct from your income. I would model this to see if it's worthwhile to hold back tax deferred money vs converting at a lower rate earlier. This may improve if the RMD date moves out to 75 as has been considered.

My plan, if I need LTC later in life, is to sell my holdings with high capital gains to use the medical expense deduction. Others may not have enough in taxable to use this strategy, so I'm not claiming this is the best way for everyone.

I think the potential for LTC expenses is a factor in Roth conversions, not a hard requirement to leave some in the tIRA. Suppose I could convert all of my tIRA at 0%; I would rather do that and have all that money in a Roth rather than leaving some in a tIRA for the LTC case. This is my point. Leaving some in a tIRA should not be a goal in of itself, but it might very well be the outcome of the best strategy.

Another factor for leaving money in a tIRA is charitable giving, through QCDs and/or through your estate. But again, if I can convert for free, I would do so and donate appreciated stocks from taxable instead. The likelihood is that I can't convert all with 0% taxes, so the outcome of the best strategy is probably leaving some in the tIRA for giving.

Now that I've hopefully convinced you that fully converting your Roth at 0% would be better than leaving some to write off LTC expenses, it follows that fully converting at a relatively low tax rate might be a better strategy than leaving some in the tIRA for those expenses. It's worth running some numbers to see which works best.

And by the way, you don't get to deduct medical expenses dollar-for-dollar against taxable income. The first 7.5% of income is excluded from the deduction. The more income you add, the more expenses are excluded. Factor this in too.

Converting tIRA to Roth at 0% tax rate is a no brainer. However, the problem that many people face is to pay tax (and how much) by converting or by withdrawing at RMD, that should be considered. So leaving some money in tIRA is not a bad idea if you have to pay higher tax rates in converting to Roth. At RMD, you still need some withdrawals to fill up the lower tax brackets.
 
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