What Issues Should I Consider Before I Retire?

Retirement isn’t a single decision — it’s a series of trade-offs that compound over time. This checklist helps you think through the big issues most people overlook before they retire, across cash flow, taxes, healthcare, Social Security, investments, and estate planning — before small mistakes turn into expensive ones.

✅ What You’ll Get:

• A concise retirement readiness checklist covering the decisions that matter before you stop working

• Clear prompts around Social Security timing, early retirement trade-offs, and spousal strategies

• Healthcare planning considerations, including Medicare timing, COBRA, ACA credits, and IRMAA exposure

• Tax planning flags like RMDs, Roth conversions, deferred compensation, and large one-time income events

Most retirement mistakes aren’t caused by bad investments. They’re caused by missing a decision you didn’t know you needed to make.