Cheat Sheet

Withdrawal Order Cheat Sheet: Taxable Tax-DeferredTax-Free (With Smart Exceptions)

Use this printable cheat sheet to decide which account to draw from first in retirement—and when to deviate. It pairs a simple baseline with practical exceptions for tax brackets, IRMAA, RMDs, and Roth conversions.

  • The baseline sequence explained
  • Smart exceptions (when to deviate)
  • IRMAA & bracket guardrails
  • One-page decision flow

Educational only—not tax or legal advice.

Cheat Sheet

Withdrawal Order Cheat Sheet: Taxable Tax-DeferredTax-Free (With Smart Exceptions)

Use this printable cheat sheet to decide which account to draw from first in retirement—and when to deviate. It pairs a simple baseline with practical exceptions for tax brackets, IRMAA, RMDs, and Roth conversions.

  • The baseline sequence explained
  • Smart exceptions (when to deviate)
  • IRMAA & bracket guardrails
  • One-page decision flow

Educational only—not tax or legal advice.

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What's Inside the Cheat Sheet

Baseline Sequence

The default order: taxable → tax-deferred → tax-free (Roth), and why it works for most retirees.

Smart Exceptions

When to deviate: bracket-fillers, Roth conversions, RMD years, and capital gains timing.

IRMAA Guardrails

How withdrawals affect Medicare surcharges (2-year lookback) and when to size conversions carefully.

Taxable Account Tips

Order for capital gains vs. dividends, and specific-lot strategies to control taxes.

Decision Flow

A one-page visual you can keep by your desk to guide withdrawal decisions.

The Baseline Sequence

This is the default order—but exceptions often apply.

1

Taxable Accounts First

Spend down cash, interest, and tax-efficiently harvest gains as needed. Refill cash with dividends if aligned to your plan (or reinvest and sell lots intentionally).

Account types: Brokerage, savings, CDs

2

Then Tax-Deferred

Traditional IRA, 401(k), 403(b) withdrawals are ordinary income. Pace them to fit your tax plan and RMD timeline.

Account types: Traditional IRA, 401(k), 403(b)

3

Then Tax-Free (Roth)

Keep Roth dollars for later years, longevity, or heirs—unless an exception fits. Qualified withdrawals are completely tax-free.

Account types: Roth IRA, Roth 401(k)

Smart Exceptions
(When to Deviate)

Bracket-Filling from IRA

Take enough tax-deferred income to fully use your current bracket. Don't leave "free" tax space on the table.

Roth Conversions in "Gap Years"

Convert Traditional → Roth in years with lower income, staying inside chosen tax/IRMAA guardrails.

Capital Gains Management

Realize gains in 0%/lower capital-gains years; avoid stacking gains that bump brackets unexpectedly.

IRMAA Awareness

Model how withdrawals/conversions affect Medicare brackets (2-year lookback).

RMD Years

RMDs must be taken regardless of baseline. Coordinate so they fund your cash-flow target.

Sequence-of-Returns Buffer

In down markets, fund cash needs from bonds/taxable instead of selling equities at lows.

Taxable Account Ordering (Quick Tips)

Spend cash & interest first → then consider qualified dividends → then LT capital gains (use specific-lot sales to control taxes).

Keep lots with large embedded gains for later years or charitable gifting strategies.

Note: We coordinate charitable strategies with your attorney/CPA; legal/tax work is separate.

Download the printable one-page decision flow to keep by your desk.

Download the Cheat Sheet

Frequently Asked Questions

Is taxable → tax-deferred → tax-free always best?

No. It's a starting point. Bracket-filling, Roth conversions, RMD timing, and IRMAA planning often justify deviations. We model options and document the "why" so your withdrawal strategy is coordinated with your overall tax plan.

Should I convert to Roth every year?

Not necessarily. Conversions help when today's tax cost likely beats tomorrow's—and when IRMAA/tax bracket impacts are acceptable. We size conversions to guardrails based on your specific situation, income sources, and time horizon.

Where do dividends fit?

Use dividends to support cash needs if tax-efficient; otherwise reinvest and sell the most favorable lots when you actually need cash. Qualified dividends are taxed at preferential rates, so timing matters less than with ordinary income.

What if markets drop right after I retire?

Use your planned cash buffer and conservative assets to cover near-term withdrawals, then rebalance when markets stabilize. Avoid panic-selling long-term holdings at depressed prices—this is exactly why we build cash reserves into retirement income plans.

How does this connect to RMDs?

Once RMDs start, you must take them regardless of your preferred withdrawal order. Smart planning means using RMDs as part of your cash-flow—not in addition to it—and potentially doing Roth conversions before RMDs begin to reduce future required distributions.

Want a Personalized Withdrawal Strategy?

Our cheat sheet is a starting point. For personalized modeling of withdrawal sequences, Roth conversion opportunities, and tax bracket optimization, schedule a 20-minute introductory call.

Or call us directly: (480) 597-1743

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