Kiplinger

Retirement Decisions for the First Year

Five key financial choices to make in your first year of retirement.

Nov 7, 2026

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Retirement Decisions for the First Year

Five key financial choices to make in your first year of retirement.

In brief

Five key financial choices to make in your first year of retirement. Retirees should decide where retirement income comes from, manage new tax routines, time Social Security claims, cover healthcare, and prepare for market downturns. Originally reported by Kiplinger.

Where retirement income comes from

Senior businessman carrying box and office supplies as he leaves work

Retirees must decide where monthly income comes from after leaving work.

Tax routine adjustments

Tax routine adjustments

Retirees face new tax rules with multiple income sources and withholding options.

Social Security claiming timing

Senior businessman carrying box and office supplies as he leaves work

Retirees must choose when to claim Social Security benefits to maximize income.

Healthcare coverage options

Retirees need coverage before Medicare starts, including COBRA or marketplace plans.

Market downturn preparedness

Retirees should plan for sequence of returns risk during market declines.

First-year financial review

Retirees compare actual spending with plans and adjust tax and withdrawal strategies.

Tax credits and healthcare costs

Marketplace health insurance premiums depend on retirement income and tax credits.

Social Security benefits

Claiming Social Security early reduces monthly benefits but can lower future tax burdens.

Medicare enrollment

Retirees must enroll in Medicare during the initial seven-month period to avoid penalties.

Roth conversions

Roth conversions can reduce future required minimum distributions and tax burdens.

Health savings accounts

Health savings accounts can cover qualified medical expenses for retirees.

Withdrawal strategy impact

Withdrawals from different accounts affect tax consequences and portfolio longevity.

Market sequence risk

Poor returns early in retirement can be especially damaging with ongoing withdrawals.

First-year review

Retirees should compare actual spending with plans and adjust strategies accordingly.

Social Security delay benefits

Delaying Social Security claims increases monthly benefits but requires careful planning.

Healthcare costs

Retirees must track healthcare costs to ensure they fit within retirement budgets.

In short

Retirees should decide where retirement income comes from, manage new tax routines, time Social Security claims, cover healthcare, and prepare for market downturns.

Read the original on Kiplinger

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