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Which Assets Should You Spend First in Retirement?

Self Improvement Books

Which assets should you spend first in retirement?  When I was just a few years into my medical career, I didn’t once consider how or when I might access the money I was saving. I was just saving for a later date and figured I’d sort out the details later.

Dr. Jim Dahle, on the other hand, read a book on the subject and created an excellent critique full of caveats and what-ifs.

As I’ve inched closer and closer to my own early retirement, I’ve thought a lot more about how this is going to look. I shared my drawdown strategy a while back and recently talked about the epochs of early retirement and the monies available in them.

Today’s post fills in the gaps, discussing additional potential sources of spending money, including pensions, annuities, and cash value life insurance. This post originally appeared at The White Coat Investor.

Which Assets Should You Spend First in Retirement?


In his elegant book, Retire Secure!, James Lange, JD, CPA, argues strongly for a specific spending order of your assets. His recommended order is this:

James Lange’s Recommended Spending Order of Assets in Retirement


#1 After-Tax Assets Generated by Income Sources


This includes:

  • Pension distributions
  • Interest
  • Dividends
  • Capital gains distributions from your mutual funds or generated by mandatory activities like rebalancing
  • Social Security
  • Any required minimum distributions (RMD) from tax-deferred accounts or Roth 401(k)s.
  • Rent from investment real estate
  • “Retirement job” income


#2 After-Tax Assets


Lange wisely advises you to liquidate your assets with a loss first, then assets with minimal gain, and finally assets with significant gains.


#3 Tax-Deferred Assets


This includes your 401(k) and IRA. We’re talking about withdrawals above and beyond your RMDs.


#4 Tax-Free Assets


This includes withdrawals from your Roth IRA and any withdrawals above and beyond the RMD in your Roth 401(k).

While I agree with his general sentiment, I don’t think this is nearly as hard and fast a rule as he makes it out to be for a number of reasons. There are so many exceptions to this rule of thumb, that I’m not even sure it ought to be a rule of thumb. I was also disappointed that he didn’t address when to borrow from any permanent life insurance policies or annuities you may have been suckered into buying. I’d like to try to fill in the gaps with this post.



Obviously, Spend Income First


His first rule, that you should spend your income first, is obviously true. I can think of no exceptions to this. Even if you have taxable account investment losses, you probably ought to spend your income and just tax loss harvest the losing investments.


8 Exceptions to Lange’s Order of Spending


Exception #1 Don’t Generate Unnecessary Capital Gains On Your Death Bed


Mr. Lange’s second rule, to always spend your taxable assets before your tax-deferred assets, has several exceptions to it. The general rule exists because the longer you wait to pay taxes, the more time the investment spends in a tax-protected account, boosting its growth (and asset protection in most states.)

The first exception to the general rule is that if you are on your death bed with low basis taxable assets. According to the rule of thumb, you should spend that money instead of raiding a traditional IRA. However, that IRA is going to get taxed at some point, whereas those taxable assets get a step-up in basis at death. Better to pay a tax that must be paid eventually, than to pay one, even at a lower rate, that can be avoided altogether.


Exception #2 Beware the SEPP Penalty


The second exception is if you are in a Substantially Equal Periodic Payments program. This is when you want to raid your retirement accounts before age 59 1/2 without paying the 10% withdrawal penalty.

Once you start the program, you have to take out the payment every year until you turn 59 1/2 or you will pay an unnecessary penalty. Although it is possible that decades of compounding in a tax protected account will make up for that penalty, that seems unlikely to me for someone who is already into their retirement accounts in their 50s.


Exception #3 Donating Appreciated Shares


The third exception is when you have a good reason to have a taxable account. One of these is donating appreciated shares to charity. No sense in paying a tax that you can avoid altogether.



Exception #4 Don’t Pay Estate Taxes on the Government’s Portion of your IRA


The fourth exception involves those who actually have an estate tax problem (estate larger than the Federal exemption of $11.4 Million ($22.8Million Married), or in a state with a lower exemption). If you have an estate tax problem, it is helpful to have some taxable money to use to pay the estate taxes without having to pay both estate taxes and income taxes at the same time.

Although that is a relatively weak argument by itself, if you are over the estate tax exemption this can have a dramatic effect. Remember, tax-deferred money belongs to both you and the government. Wouldn’t it suck to pay estate taxes on the government’s portion of the money?

A great way to reduce your estate is to take money out of your retirement account, gift it to an irrevocable trust, and buy permanent life insurance with it. Now you’re not paying estate tax on either the government’s portion of your IRA, or on the amount you gifted to the trust. Plus, neither the trust nor its eventual beneficiaries have to pay any income tax on life insurance.


Exception #5 Whose Tax Rate Is Higher?


Mr. Lange’s third rule is to basically spend all of your tax-deferred money before any of your Roth money. While I don’t disagree that I would rather inherit a Roth IRA than a traditional IRA, the family may pay less tax overall if your heirs in lower tax brackets pay the tax rather than you.

Plus, if the government ever changes the rules (changes the income tax to a value-added tax or sales tax for instance), no sense in pre-paying your taxes.



Exception #6 What About Tax Diversification?


This is my biggest beef with the order of accounts presented by Mr. Lange. One of the biggest benefits of having both tax-deferred and tax-free accounts in retirement is to have some “tax diversification.” That basically allows you to determine your tax rate in retirement.

The theory is that you fill up the lower tax brackets (0%, 10%, 12%, 22%, and maybe even 24%) with tax-deferred account withdrawals (and later Social Security). Then, if you need more money than that, you pull it from the tax-free accounts. This allows you to save money at 32%, 35%, or even 37% when contributing to your tax-deferred accounts, while paying taxes at an effective rate well under 20% upon withdrawing it.

This “arbitrage” is one of the biggest benefits of using tax-deferred accounts to save for retirement.

But if you actually plan to spend all or most of your retirement savings in retirement, Lange’s plan would have you not only pay all the taxes up front (what happened to “Pay Taxes Later”) but to pay them at a higher rate than you would have to if you had been tapping both accounts at the same time. I don’t think the right answer to “Tax-deferred or Tax-free first?” is tax-deferred; I think it’s both.


Exception #7 Permanent Life Insurance Omission


Mr. Lange didn’t address when to tap the cash value of permanent life insurance policies in his book. In fact, I don’t think I’ve ever seen a serious work that did (if you know of one, please post it in the comments).

I’ve done some thinking about it. While you could use cash value like a Roth for some tax diversification, there is a significant difference between a Roth and permanent life insurance cash value. Roth withdrawals are tax-free and interest-free. Life insurance is a little more complex.

Initial insurance withdrawals (partial surrenders) are tax-free and interest-free, up to the amount paid in premiums. Beyond that, gains are taxed at your ordinary interest rate (not the lower capital gains rate.) You can also borrow from the policy. These funds are tax-free, but not interest-free. You’re essentially borrowing money from the insurance company using the cash value of the policy as collateral.

If you’re planning to borrow much out of your life insurance policy, it is probably best if it is a non-direct recognition policy. That means that if you had $100K in cash value, the company would loan you $90K, but it would still use the entire $100K when calculating the dividends paid.

With a direct recognition policy, the company would base your dividends on just $10K. It would also be helpful if the interest rate charged for the loan (including any fees) were similar to or lower than the dividend rate.



I would rather inherit a Roth IRA than the proceeds of a life insurance policy, but what about a traditional IRA? A traditional IRA beats cash/taxable account/life insurance proceeds IF it can be stretched out over many, many years where the tax-protected growth can make up for the fact that the government owns part of the account.

Where that break-even point lies is complicated and will change with future tax law and income changes. But if the money is going to be spent this year, a Roth IRA and cash/taxable account/life insurance proceeds are pretty much equivalent.

All of this makes it really hard to determine where in your distribution plan life insurance cash value should fall. Neither tax-free, interest-free policy surrenders up to the basis nor tax-free loans are a free lunch. They are both subtracted from your death benefit. You don’t get both the cash value and the death benefit. So it really depends on what you plan to do with the death benefit.

While I haven’t run the numbers, I suspect the right answer is to hold the cash value in reserve, tapping it only if you end up running out of all your other assets, and if unneeded, simply passing it on to your heirs as a death benefit. An exception, of course, would be made if the alternative is to pay an unnecessary capital gains tax on highly appreciated taxable assets.

It may also be worth tapping cash value prior to both IRA and especially Roth IRA money if your heirs are very young and can be relied upon to maximize the stretch benefits. No wonder Lange didn’t include it in his list. The devil is in the details.


Exception #8 What About Annuities?


While we’re on the subject of insurance-based investing products you probably shouldn’t have bought in the first place, let’s talk about annuities. With life insurance surrenders, the tax treatment is “first-in, first out” (FIFO) meaning you get the premiums paid back out first. With the surrender of/withdrawal from an annuity, it’s “last-in, first-out” (LIFO). That means the first dollars you get out of the annuity are fully taxed at your regular income rate.

Perhaps the best way to get reasonable tax treatment on an annuity is to actually annuitize it, then at least a portion of the first payments you get is tax-free. (Annuitized payments come out pro-rata between the basis and the earnings.) That is what I would do, then just throw the annuity payments in with Lange’s first category of after-tax assets generated from income sources.


Lange’s Order is Good But Not a Reliable Rule of Thumb


Again, like life insurance and even retirement account withdrawals, I would make annuity withdrawals before cashing in highly-appreciated taxable assets if life expectancy were short in order to take advantage of the step-up in basis at death.

In short, while Mr. Lange’s list provides a good starting point, I think he has broken Einstein’s rule with this one. Einstein said, “Make things as simple as possible, but no simpler.” I fear he has made this complex decision far too simple with his recommended list. I don’t think this subject lends itself to a reliable rule of thumb at all. Spending significant time analyzing your own situation with or without a talented financial planner is probably worthwhile.



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What do you think about which assets to spend first? Did Mr. Lange nail it? How do you plan to tap your retirement assets? Will you spend all your tax-deferred before your Roth?

Or will you go for tax diversification? If you own a permanent life insurance policy or annuity, when and how do you plan to use the cash value? Comment below!

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7 thoughts on “Which Assets Should You Spend First in Retirement?”

  1. Perceptive critique of a powerful book. Lange is a very thoughtful planner, and I highly recommend Retire Secure for anyone starting to plan the drawdown phase of financial life. But I too was somewhat nonplussed at his order of drawdown, especially over the tax diversification issue. Your analysis is thought provoking. Well done!

  2. Subscribe to get more great content like this, an awesome spreadsheet, and more!
  3. Thank you for Exception #6. These boilerplate “order of consuming money in retirement” advice nuggets seem to always ignore the tax diversification possibilities offered by having a mix of pre-tax and Roth retirement accounts. When I first opened a Roth, I did so with my eye on future tax diversification!

    And some advice nuggets simplify it ever further (in error) by stating your retirement money from pretax 401K or IRAs will be taxed at x%, where x is the top tier tax bracket you’re in, not your effective tax rate. This totally ignores how our US tax system is structured, and grossly misleads the general public reading these articles.

    • I agree. Retirement is not a single thing, but an unfolding of life as dynamic as life during accumulation. My retirement is structured in epochs and the epochs are structured to hand shake with each other. What happens from age 60-70 is designed to augment what happens say from 70-80 and 50-70 and 70-80 handshake with the end of life epochs for each spouse, and the tax implications once a spouse dies for the surviving spouse are not trivial. Artificial rules that look at static concepts like which account first, completely misses the dynamics of living and the continued need to plan almost yearly for the future in retirement.

      For example: I am retired. I’m Roth converting according to a specific schedule to conclude at age 70, then the next epoch begins. There is new tax law on the horizon which may push RMD back from 70 to 72, giving a longer period of RMD, allowing a smaller per year RMD and a lower tax bill. Change of plan. To make that longer period happen, I needed to rustle some more living expense from the brokerage and extend the age 70 hand off to an age 72 hand off. I needed to rustle up that dough now because the market is at an all time high and the rule is “sell high”. My retired life is dynamic and not suitable to control by someone’s idea of irrelevant bullet points.

  4. How would you incorporate non governmental 457?
    I would likely withdraw it first a little lower then expected needs and then use taxable to top it off.
    Again highly dependant on the situation.

    • Personally, I plan to draw mine down before the current tax rates sunset in 2025. So I plan to set up a withdrawal rate that will deplete the account over about 5.5 years starting next spring.

      • 457 drawdowns are also somewhat plan dependent. In particular, the plan defines the options for how much can or must be withdrawn over a given period. In some cases it is immediate, but my own plan allows withdrawals to stretch over 15 years. And don’t forget the nongovernmental 457s are subject to your employers creditors, so you might factor that in and withdraw sooner rather than later. I’m spending mine as a bridge to SS.

  5. A great review by Jim.

    Another time you might want to tap your Roth account early is if you want to minimize your taxable income for a specified reason. This could be to get ACA subsidies for insurance before 65, or to decrease the surcharges on Medicare part B. IRMAA is a consideration for high income retirees, as is taxation of social security for low income.

    Legacy goals are important too. If you have charitable goals rather than legacy, take the minimum from your pre-tax accounts and spend the rest.

    I suggest cash value life insurance is a good Buffer Asset for sequence of return risk mitigation.


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