Retirement planning checklist: income, health and timing

Good retirement planning comes down to four questions: when you will stop working, how you will cover health care until and after 65, where your monthly income will come from, and how you will protect it from the big risks. Social Security is the foundation for most people, but for an average earner it replaces only about 40% of pre-retirement earnings, so pensions, savings and other income have to fill the rest. This checklist walks through each step in order. A no-cost retirement planning review with me covers the insurance side of these decisions; for tax and securities questions, work with your tax professional or a licensed financial adviser.

Five or more years before you retire

• Create a my Social Security account at ssa.gov and check your earnings record for mistakes.
• Estimate your retirement budget: essentials (housing, food, insurance, health care) and wants (travel, gifts).
• List every income source you expect: Social Security, pensions, retirement accounts, part-time work, rental income.
• Decide whether you might retire before 65, because health coverage becomes the biggest planning question if you do.
• Review life, disability and supplemental coverage while you are still working and insurable.

Social Security timing

Your benefit is based on your highest 35 years of earnings, so a few more working years can matter if you have gaps. If you worked for a government employer that did not withhold Social Security, the Social Security Fairness Act, signed in January 2025, ended the Windfall Elimination Provision and Government Pension Offset, which had reduced many of those benefits.

Health coverage: before 65 and at 65

• Retiring before 65? Plan for COBRA or a Connect for Health Colorado plan, and manage your income around the 400% of poverty level line for tax credits. Our early retiree guide explains how.
• Your Medicare Initial Enrollment Period is the seven months around your 65th birthday month. If you are working with employer coverage, the rules for delaying Part B are different; see our working past 65 guide.
• If you have an HSA, plan to stop contributions about six months before you enroll in Medicare.
• Budget for Medicare costs: the 2026 standard Part B premium is $202.90 a month and the Part B deductible is $283, with higher premiums (IRMAA) for higher incomes based on your tax return from two years earlier.
• Remember what Medicare does not cover: most dental, routine vision, hearing aids and long-term custodial care.

Turning savings into income

• Separate essential expenses from discretionary ones. Many people like essential expenses covered by income that lasts for life, such as Social Security, a pension or an annuity payout.
• Know your required minimum distributions: for most people they begin for the year you reach 73 (75 for those born in 1960 or later), with the first one due by April 1 of the following year.
• Keep an emergency reserve so a bad month does not force you to sell at the wrong time or take a large taxable withdrawal.
• Think about taxes across accounts: traditional, Roth and taxable accounts are taxed differently, which also affects Medicare IRMAA and marketplace tax credits.

Protecting what you have built

Every year after you retire

• Review your Medicare plan during the October 15 to December 7 Annual Enrollment Period, because costs, networks and drug lists change every year.
• Revisit your budget and withdrawal amounts.
• Check beneficiaries on life insurance, annuities and retirement accounts.
• Keep your important documents (will, powers of attorney, policies) in one known place.

Useful official calculators

• SSA Retirement Estimator and the my Social Security account, for your own benefit estimates.
• SSA life expectancy calculator, to think about how long your money needs to last.
• Medicare.gov Plan Finder, for Medicare plan comparisons.
• Connect for Health Colorado's quick cost and plan estimator, if you will retire before 65.

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The bottom line

You do not have to solve retirement in one sitting. Start with the dates (your Social Security age, your Medicare month, your RMD year), then match each income source to a need, then cover the risks you cannot afford to carry yourself. My no-cost retirement planning review covers the health insurance, Medicare and insurance protection pieces. Send Lisa a message or call (303) 887-8584.