Preparing to retire and I've looked at a lot of info on the internet and it all says the same thing: pull money out of your high taxed brokerage account first so you leave all that tax deferred money in your IRA alone. But, I think that's only correct if you have short term investments (that would generate lots of taxes). All mine are long term. Thus, I don't pay taxes on them until I sell and, when I sell, the capital gains tax is low. Instead, I think people in this situation should pull money of the the IRA first.

So, am I missing something, or is the internet "conventional wisdom" making assumptions that make that incorrect for my situation?

(In case someone brings this up, 2/3 of my brokerage account's dividends are qualified which makes them tax friendly).

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    I'm not sure what you mean by "high taxed brokerage account". Conventional wisdom usually focuses on moving your money out of high-risk assets like stock into low-risk assets. Once you retire, you should be more concerned about your investments losing value than in how much they'll increase. Qualified dividends may be tax-friendly, but that won't help you much if the value of the stock itself crashes.
    – chepner
    Commented Feb 9, 2021 at 16:42
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    What I mean is if you're stocks are all short term, you're generating lots of taxes.
    – Jim
    Commented Feb 9, 2021 at 19:35
  • Yet another "what is a "high taxed brokerage account?" question. Did you really mean "taxable brokerage account* (unless you live in CA, NY, Taxachusettes, etc)?
    – RonJohn
    Commented Feb 9, 2021 at 19:38
  • I don't think there's one rule for everyone. For instance if you're before the age where you have to take minimum required distributions, and you don't spend a lot (say you have a paid-off house and inexpensive hobbies), then it probably makes sense to pull money out of the IRA at a low tax rate.
    – jamesqf
    Commented Feb 9, 2021 at 23:50

5 Answers 5


Your primary focus in retirement should be preservation of assets. Assuming that's resolved, despite popular wisdom, I would withdraw the assets that incur the lowest amount of taxation with the intent of having the highest taxed assets going to my heirs with a stepped up basis (no taxation).

In addition, if you minimize the tax bite of a withdrawal (for example, LIFO in a non sheltered account?), you reduce the amount that you have to withdraw, leaving more assets available for growth.

The above is a generalization. What's best will depend on how much you need to withdraw, the amount of capital gain on assets sold, and what tax bracket you're in along with the amount of tax due. You should run both scenarios and see which one best suits your situation.

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    I agree if your intent is to bequeath as much money as possible to heirs. However, I intend to "die broke" (read an article with that title years ago) :).
    – Jim
    Commented Feb 9, 2021 at 19:17
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    I changed my mind after thinking about this more. You make an interesting point. You need to pull less money out if you're paying less taxes on it, leaving more to earn interest (or leave behind, if you don't spend it all).
    – Jim
    Commented Feb 9, 2021 at 19:25
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    The more I think about this answer, the more I like it. I'm going to upvote it, but I'll wait to read other comments/answers before I select it as the answer--you never know what ideas people have (which is why I posted). Thanks.
    – Jim
    Commented Feb 9, 2021 at 19:39
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    @Jim If you know exactly when you will be dropping dead, it's a relatively simple math problem. What if you end up living longer by 10 or 20 years or more? Commented Feb 10, 2021 at 17:31
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    @Michael R: Back in 2003/04 I met a guy who had retired...and then outlived his retirement income, and was going back into the workforce in his mid-70s. I don't want to be that guy.
    – Petro
    Commented Feb 10, 2021 at 21:19

Preparing to retire and I've looked at a lot of info on the internet and it all says the same thing: pull money out of your high taxed brokerage account first so you leave all that tax deferred money in your IRA alone.

Do they say to pull all of your money immediately out of all your taxable accounts??

No, they don't.

  1. Sell long-term investment first,
  2. only what you "need" (for varying definitions of "need"),
  3. on a schedule (monthly, quarterly, etc), and
  4. in a year or so any short term investments are now long-term investments...

I've not mentioned selling your risky equity investments, since I take for granted that you've been slowly moving them into safer investments over the past 10 years.

  • not sure if this is suitable for a separate question, but... your last sentence has me intrigued - is it still reasonable to move to safer investments during your last 10 years before retirement if it's obvious that doing so will mean you won't be able to retire? (for instance, suppose you need to increase your retirement portfolio by 10x to have enough to meet the 4% rule) Do you go for broke and invest in higher risk/return asset classes for a chance at a decent retirement or none, or switch to safer investments for a more certain chance at a poor retirement?
    – user12515
    Commented Feb 11, 2021 at 6:27
  • @Michael spreadsheets are so darned useful. Since I follow a budget, I am able to run that forward at any inflation rate I want (adjusting the Medicare part for higher inflation rate) to estimate how much I'll need to retire at 62, 65, 67, what my investment portfolio will be then, and how many years the portfolio will last. With or without SS, it's really not that much.
    – RonJohn
    Commented Feb 11, 2021 at 13:57

You could look at it both ways - would you rather pay "income" tax by pulling money out of your IRA now and pay less taxes from your brokerage gains later, or pay less tax now and defer the higher taxes to later (or possibly avoid them altogether if the IRA is bequeathed to your heirs).

Most people in retirement are in a low tax bracket because by definition they have less income, so pulling out of an IRA is not as big of a tax burden. But everyone's situation is different- if you require so much that it would push you into higher tax brackets, then perhaps tapping your investment accounts first is a better move. Or if you'd have a lot of short term gains and want to keep them until they become long term gains, then tapping the IRA first may be optimal.

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    Thanks. Interesting observation in first paragraph--I will think that over. Concerning second paragraph, I'm a bit confused. You might be advocating pulling money out of IRA if you're in a lower tax bracket when you retire. But even if you're in a lower tax bracket, in general, the tax on long term capital gain is still going to be less.
    – Jim
    Commented Feb 9, 2021 at 19:13
  • I'm not saying one is better in all cases - certainly long term gains will always be taxed at a lower rate than income (and you're only taxed on the gain, not the whole amount unlike IRA withdrawals), so it's generally better. What I was saying is that if you have only short-term gains (which it sounds like you do), then pulling out of an IRA first may be optimal but still may not be a huge burden.
    – D Stanley
    Commented Feb 9, 2021 at 19:41

It’s impossible to say which funds you should spend first without knowing your total financial picture and life circumstance. The best way to get an answer based on actual facts and numbers is to hire a certified financial planner on a fee-for-service basis and disclose the details of your holdings, your income from pensions and Social Security, your expenses, your debts, your age and life expectancy and your long term goals.

A good financial planner will have access to one or more software packages such as Money Guide Pro that can take all your numbers and details and run them through Monte Carlo simulations: thousands of iterations of “what if” scenarios that include random factors that account for ranges of possible outcomes. The planner can run different total-picture scenarios that differ only in which funds are spent first. Then you'll know.

It definitely makes a difference, so paying for professional advice can reap big rewards in the long term. Any good financial planner has performed this service for many clients and should be able to give you a ballpark estimate of cost before you commit to anything.


Understanding that you wish to aim for a zero balance at death,b and not knowing if you are single or married, I'm using MFJ numbers.

Having a mix of pretax (traditional 401(k)/IRA) and other investments is ideal at retirement. 100% traditional or 100% Roth missed a bit of tax savings.

(Keep in mind, without knowing the numbers, this is an example of my thought process)

Say you need $120K to live on this year. $24,800 std deduction. $95,200 would be taxed. The 12% bracket ends at $81,050 so I'd want $14,150 to come from my Roth/Cash account, and the rest can be withdrawn from my pretax money.

In general, I'm looking at a combination of taking advantage of the 10/12% brackets while not pushing into 22%. For the member retiring on, say $60K/yr, I'd just be mindful of the interaction of Social Security taxation and your other retirement income. Possible that topping off the 12% bracket via Roth conversion can save big on the tax bill when one start taking the Social Security benefit.

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