Retirement Planning

Retirement Readiness Checkpoint (40s and 50s)

Published February 27, 2026 • 9 min read

Retirement readiness is less about a single "magic number" and more about cash flow durability. This checkpoint helps you evaluate if your plan survives real-life variation.

Step 1: Define target spending

Start with current spending, then remove temporary expenses and add likely retirement costs like health premiums, travel, or family support.

Step 2: Map guaranteed income

The gap between spending and guaranteed income is what your portfolio must fund.

Step 3: Model withdrawal pressure

Estimate portfolio draw rates under normal, poor, and strong market sequences. Sequence-of-returns risk matters most in the first 10 years.

Key checkpoint: if your plan only works under optimistic returns, it is not yet retirement-ready.

Step 4: Review tax strategy

Blend account withdrawals intentionally: taxable, tax-deferred, and Roth assets each behave differently for tax and Medicare impacts.

Step 5: Define adjustment levers

  1. Retire 1 to 2 years later
  2. Reduce first-decade discretionary spending
  3. Raise savings now
  4. Delay Social Security strategically

Estimate Retirement Outcome

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