Capital Wealth
Capital Wealth · Planning · Estate & Tax
The WithdrawalOrder

Two retirees, the same $2 million portfolio, a $150,000 difference in lifetime taxes — decided entirely by which account they drew from first.

The conventional wisdom — taxable first, Roth last — was written before RMDs at 73 and before the SECURE Act, and following it builds a tax bomb with a fuse set to your seventy-third birthday. The smarter rule is duller and richer: fill your bracket from the tax-deferred bucket, every year, on purpose. This page lays out the three buckets, the four tax boxes every account in America lives in, and the sequencing that turns the same portfolio into three to five more years of income.

01At a GlanceWhat sequencing alone is worth
Portfolio Life
3–5yrs

The typical extension in portfolio longevity from re-sequencing withdrawals — same assets, same returns, different order.

Lifetime Tax Savings
$150K

What a well-sequenced plan typically saves against the old “taxable first” rule on a $2M portfolio.

RMD Start Age
73

For 2026. Rises to 75 for those born 1960 or later, starting 2033 (SECURE 2.0).

Missed-RMD Penalty
25%

Excise tax on the amount not withdrawn — reduced to 10% if corrected within two years.

02The Buckets & BoxesKnow what you own before you sequence it

Three buckets, four boxes. Every dollar you own lives in one.

Start with the three buckets, because the whole strategy is a conversation between them. The taxable bucket — brokerage, savings, CDs — pays capital gains at 0/15/20%, has no RMDs, and gets a step-up in basis at death. The tax-deferred bucket — Traditional IRA, 401(k), 403(b) — pays ordinary income tax on every dollar out, and RMDs begin at 73 (75 for those born 1960 or later). The tax-free bucket — Roth IRA, Roth 401(k), HSA for medical — pays nothing on qualified withdrawals, with no RMDs on Roth IRAs.

Three buckets is the working model. The full taxonomy is four boxes — defined by how money is treated going in, while it grows, and coming out — and it is worth five minutes, because most people are paying tax three separate times on Box 1 money without ever having decided to.

Before you decide the order to draw from, you need to know how each account is taxed at three points: when you put money in, while it grows, and when you take it out. Every retirement vehicle in America fits into one of these four boxes. Most people don't realize they're paying tax three times on Box 1 money — contribution, every year of interest, and the spread on any capital gains — while Box 4 money never gets taxed again after the initial contribution.

Taxable Now, Taxable Later

  • In: after-tax contributions
  • Grow: interest taxed yearly
  • Out: principal non-taxable
What's in this boxBank accounts · CDs · Money market · Most bond funds · Government securities · Treasury bonds
1

The Goal: Never Taxed Again

  • In: after-tax contributions
  • Grow: tax-free
  • Out: tax-free (if qualified)
What's in this boxRoth IRA · Designated Roth 401(k) · Municipal bonds · Cash-value life insurance (qualified withdrawals & loans) · 529 plans · Coverdell · HSA (medical)
4

Deferred Growth, Taxed Later

  • In: after-tax contributions
  • Grow: tax-deferred
  • Out: gains taxed as ordinary income
What's in this boxFixed & variable annuities · Non-deductible IRAs · Non-deductible excess 401(k) · U.S. Savings Bonds (EE/I)
2

The Big Deferral (IRS's Favorite)

  • In: pre-tax contributions
  • Grow: tax-deferred
  • Out: every dollar taxable as ordinary income
What's in this box401(k) · 403(b) · Pension plans · Profit-sharing · SEP-IRA · SIMPLE IRA · Deductible Traditional IRA · Keogh
3

Direct real estate, common stocks, and some mutual funds are hybrid — a portion of their gains may qualify for the lower long-term capital gains rate rather than ordinary-income treatment.

Hypothetical Illustration — the Compounding Cost of Each Box

What $10,000 a year actually becomes after 30 years, comparing all four tax boxes at a hypothetical 6% return and 28% tax bracket. Numbers are end-of-year values; the After-Tax Income column assumes you stop contributing and start drawing at 6% of the account balance.

Contribution$10,000/yr Return6% Tax bracket28% Distribution rate6%

Box 1 — Taxable

Bank · CD · Brokerage Interest
1
YearAccount ValueAfter-Tax Income
1$7,511
5$40,943$1,769
10$91,528$3,954
15$154,025$6,654
20$231,239$9,990
25$326,635$14,111
30$444,497$19,202
Yr 30 Balance
$444,497
Lump Sum After Tax
$444,497

Box 4 — Never Taxed Again

Roth IRA · Roth 401k · Cash-Value Life
4
YearAccount ValueAfter-Tax Income
1$7,632
5$43,022$2,581
10$100,596$6,036
15$177,642$10,659
20$280,748$16,845
25$418,726$25,124
30$603,372$36,202
Yr 30 Balance
$603,372
Lump Sum After Tax
$603,372

Box 2 — Deferred, Taxed Later

Annuities · Non-Deductible IRA · Savings Bonds
2
YearAccount ValueAfter-Tax Income
1$7,632
5$43,022$1,859
10$100,596$4,346
15$177,642$7,674
20$280,748$12,128
25$418,726$18,089
30$603,372$26,066
Yr 30 Balance
$603,372
Lump Sum After Tax
$494,908

Box 3 — Pre-Tax Deferral

401k · 403b · Pension · Deductible IRA
3
YearAccount ValueAfter-Tax Income
1$10,600
5$59,753$2,581
10$139,716$6,036
15$246,725$10,659
20$389,927$16,845
25$581,564$25,124
30$838,017$36,202
Yr 30 Balance
$838,017
Lump Sum After Tax
$603,372

Hypothetical only. Does not reflect the performance of any specific investment, insurance contract, or financial product. Box 3 shows the highest lump-sum account value because pre-tax contributions let more money compound, but once you apply 28% income tax on distribution, the net after-tax lump sum converges to Box 4. Lower capital-gains rates would narrow Box 1's disadvantage; changes in tax brackets over your lifetime can shift these comparisons meaningfully — which is exactly why the withdrawal-order decisions below matter so much.

The Takeaway

Over 30 years of $10K/yr at 6%, the gap between Box 1 (fully taxable) and Box 4 (never taxed again) is $158,875 — on the same contributions and the same returns. That’s not investment skill; that’s tax structure. Which box your next dollar lands in matters as much as what it’s invested in.

03The SequenceThe old rule, the smarter rule, and the math between them

The old rule built a tax bomb. The new rule defuses it annually.

The old rule, now outdated. Decades of planning guides said: taxable first, Traditional second, Roth last — let the tax-advantaged accounts keep compounding. It sounds right, and it quietly sets a fuse.

The problem with spending taxable first is that at age 73 the RMDs on your untouched Traditional IRA balloon into the highest brackets — exactly when you can’t avoid them.

The smarter rule: fill the bracket. Between roughly 62 and 72 — after the paycheck stops, before RMDs start — most retirees sit in a low bracket, often 12% or 22% after the standard deduction. Those are the gap years, and the move is to deliberately draw from the Traditional IRA to fill the low brackets every year. Each dollar out at 12–22% is a dollar that will never be forced out at 32%. The figure below is the whole idea on one chart.

fig.01

Fill the Bracket — The Gap Years vs. the RMD Spike

12% 22% 32% OLD RULE · IRA UNTOUCHED, THEN THE SPIKE RMDs force 32%+ AGE 73 · RMDs BEGIN THE GAP YEARS · 62–72 RMD YEARS · 73+ FILL THE BRACKET · draw + convert to the top of 22% each year RMDs stay inside 22% Same portfolio, same spending. Blue pays the tax early at 12–22%; red defers it all and pays at 32%+ on the IRS’s schedule.
Illustrative — bracket heights not to scale. Bracket thresholds per the 2026 tax numbers.Capital Wealth

The worked example. Same household, same $80K of spending at 65 — the only difference is which bucket funds it:

ScenarioOld Rule (Tax Last)New Rule (Fill Bracket)
Age 65 income$80K from brokerage (low tax)$80K mix: $40K IRA + $40K brokerage
Age 73 RMD amount$95,000 (huge tax)$52,000 (manageable)
Marginal bracket at 7532%22%
Lifetime taxes paid$520,000$375,000
Savings$145,000

RMD basics, 2026 rules. The first RMD is due by April 1 of the year after you turn 73 — then December 31 every year after, which means waiting on the first one doubles up year two. Those born in 1960 or later start at 75 instead (SECURE 2.0, from 2033). The formula is the prior December 31 balance divided by the IRS Uniform Lifetime Table factor; the penalty for missing one is a 25% excise tax, reduced to 10% if corrected within two years.

AgeFactorAgeFactorAgeFactor
7326.58020.28714.4
7425.58119.48813.7
7524.68218.58912.9
7623.78317.79012.2
7722.98416.89210.8
7822.08516.0958.9
7921.18615.21006.4

IRS Uniform Lifetime Table, key ages. Divide the prior year-end balance by the factor for that year’s RMD.

Roth conversions — the biggest lever in the toolbox. The gap years are also the conversion window: from the year after you retire through the year before RMDs start, you can move Traditional IRA dollars to Roth at low brackets. Pay the tax now at 12–22%, skip the bigger bill later, and leave tax-free money to heirs — which, after the SECURE Act put non-spouse beneficiaries on a ten-year drain clock, is worth more than it used to be. The discipline: convert enough each year to fill the 12% and 22% brackets without spilling into 24%.

2026 BracketMarried Filing Jointly Income
10%$0 – $24,800
12%$24,800 – $100,800
22%$100,800 – $211,400
24%$211,400 – $403,550
32%$403,550 – $512,450

2026 federal brackets, married filing jointly — full tables for every filing status are on the 2026 tax numbers page.

Qualified Charitable Distributions. From age 70½, you can send up to $100,000 a year directly from an IRA to charity. It counts toward the RMD but never touches your AGI — which trims Medicare IRMAA surcharges, Social Security taxability, and state income tax in a single move. If you give to charity anyway, this is the most efficient dollar you own.

The Takeaway

The order of withdrawals is a decision, and not making it is also a decision — one the IRS makes for you at 73. Fill the bracket in the gap years, convert what the 22% bracket will hold, point charity at the IRA, and save the low-basis stock for the step-up. Same portfolio; three to five more years of income.

A single check on a desk — which account funds it decides the tax
Capital Wealth · One paycheck · three buckets
Where this fits Bubble Map: Taxes· POLARIS: Step 4 · Align Framework
POLARIS · Step 1 · Personal Approach

Get a multi-decade tax map.

We build a year-by-year withdrawal plan from 62 to 95 — tax owed, RMD, bracket, and the Roth conversion room in each year. Most clients save 5–8% of lifetime taxes from re-sequencing alone. Fifteen minutes starts the conversation, at whatever pace suits you.

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All figures reflect 2026 federal tax law as of August 2026 and are subject to change; bracket thresholds per the house 2026 tax reference. Hypothetical illustrations do not reflect the performance of any specific investment or product and assume constant rates of return and tax brackets. Not individualized investment, tax, or legal advice — consult your tax advisor before executing conversions or distributions. Disclosures · Privacy