Retirement · Checklist
The retirement checklist.
Retirement is not a single decision. It is dozens of decisions made over several years. Below are the categories worth thinking through.
Insurance and health care
Medicare enrollment timing. Advantage vs. Supplement. Part D drug coverage. Long-term care planning. Health savings account decisions. See the Turning 65 Checklist for the detailed timeline.
Income and Social Security
When to claim Social Security. Whether and how to coordinate with a spouse. How working past 65 affects benefits. Required minimum distributions from retirement accounts. We are not financial planners and refer clients to specialists for these conversations, but we make sure the timing aligns with Medicare decisions.
Housing and location
Whether to stay in your current home, downsize, relocate, or split time between Florida and another state. Each path has tax, insurance, and Medicare implications. See the snowbird guide if you are considering splitting time.
Estate and legacy
Wills, trusts, beneficiary designations, life insurance, and how you want assets to flow when you die. We help with the insurance portion and refer to estate attorneys for the legal work.
Day-to-day financial flexibility
Building an emergency fund inside retirement, managing predictable monthly expenses, and making sure cash flow can absorb a bad year without forcing decisions you would not otherwise make.
Next step
Walk through the checklist with us.
We focus on the insurance and Medicare pieces, but we know who to refer you to for everything else. The full checklist is what we cover in the consultation.