Retirement checklists
Know exactly where you stand at every stage
Retirement planning is not a single event — it is a series of decisions made over decades. These checklists keep you on track at every stage.
A checklist for every stage of the journey
The decisions you make in your 50s affect your options in your 60s. The actions you take in the year before retirement determine how smoothly the transition goes. These checklists give you a clear, actionable roadmap — so nothing falls through the cracks.
In your 50s
Build the foundation
- Maximize contributions to 401(k) and IRA (catch-up contributions allowed at 50+)
- Review and update all beneficiary designations
- Create or update your will, power of attorney, and healthcare directive
- Evaluate long-term care insurance options while still insurable
- Estimate your Social Security benefit at different claiming ages
- Build a personal financial inventory (all accounts, policies, debts)
- Pay down high-interest debt aggressively
- Begin projecting retirement income needs and gaps
In your early 60s
Prepare for the transition
- Develop a detailed retirement income plan (all sources, timing, tax treatment)
- Model Social Security claiming scenarios for you and your spouse
- Evaluate Roth conversion opportunities before RMDs begin
- Review Medicare enrollment timeline and coverage options
- Assess pension options (lump sum vs. monthly payments)
- Review and rebalance investment portfolio for retirement income needs
- Finalize long-term care plan (insurance, self-insurance, or hybrid)
- Identify healthcare coverage for the gap before Medicare (if retiring before 65)
The year before retirement
Final preparations
- Confirm your retirement date with your employer and HR department
- Enroll in Medicare (if turning 65 within 3 months)
- Decide when to claim Social Security
- Roll over or consolidate old 401(k) accounts
- Establish your retirement income withdrawal plan
- Build a 12-month cash reserve for living expenses
- Review and finalize estate planning documents
- Notify your financial institutions of your retirement plans
Your first year of retirement
Settle in and optimize
- File for Social Security if you have not already
- Confirm Medicare coverage is active and correct
- Set up your retirement income distribution system
- Adjust tax withholding or set up quarterly estimated tax payments
- Track actual spending vs. your retirement budget
- Review your investment allocation for retirement income needs
- Update your estate plan to reflect your new financial situation
- Schedule an annual financial review with your advisor
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Not sure where you stand on your checklist?
Schedule a no-cost conversation with David O'Bryan, CPA. We will review your situation and identify the most important steps to take right now.
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