Why This Checklist Matters
Retirement isn’t an age. It’s readiness.
This no-fluff checklist helps you cut through the noise, focus on what matters, and spot gaps before they become expensive—or stressful.
Whether retirement is five years away or right around the corner, this is designed to give you clarity, confidence, and control.
Income & Spending
✅ I know how much I spend monthly (needs vs. wants)
✅ I’ve created a post-retirement budget
✅ I’ve estimated my income sources (Social Security, pension, investments, real estate, side income)
✅ I’ve run retirement income projections (and stress-tested for market dips)
✅ I have a plan for big one-time expenses (travel, home repairs, gifts)
✅ I’ve reviewed any other income or expense factors unique to my situation
✅ I have a cash reserve / income buffer plan (e.g., 6–24 months) to avoid selling in down markets
✅ I’ve set spending “guardrails” (what I’ll reduce/pause if markets drop early in retirement)
Taxes & Retirement Timing
✅ I have a Social Security claiming strategy (including spousal/survivor considerations, if applicable)
✅ I understand how Medicare IRMAA surcharges work and what can trigger them
✅ I have a plan for required minimum distributions (RMDs) and their tax impact
✅ I’ve evaluated Roth conversions during lower-income “gap years” (if appropriate)
✅ I’ve mapped my likely tax brackets over the next 5–10 years (not just this year)
✅ I’ve reviewed any pension decisions (lump sum vs. annuity, survivor options) if applicable
Healthcare & Insurance
✅ I understand my Medicare options and eligibility
✅ I know Medicare enrollment deadlines (and how to avoid penalties)
✅ I’ve considered supplemental (Medigap) or Advantage plans
✅ If retiring before 65, I have a plan for healthcare coverage until Medicare
✅ I’ve planned for long-term care (insurance, savings, or both)
✅ I’ve budgeted for out-of-pocket healthcare costs
✅ I’ve reviewed life insurance needs (if any)
✅ I have an umbrella liability policy and updated home/auto coverage
Investments & Withdrawals
✅ I know which accounts I’ll withdraw from first (tax-smart strategy)
✅ I’ve chosen or reviewed my withdrawal plan (e.g., guardrails, bucket strategy)
✅ I’ve reviewed my asset allocation for retirement
✅ I’ve minimized investment fees where possible
✅ I’ve updated or confirmed my risk tolerance
✅ I’ve identified any other investment considerations unique to my plan (concentrated stock, real estate, business sale)
✅ I’ve run a “retirement stress test” for: (1) a bad first 3–5 years, (2) higher inflation, (3) living to 90–95+
Estate & Legacy Planning
✅ I have a will and/or trust in place
✅ I’ve updated my beneficiaries on all accounts
✅ I’ve ensured beneficiaries align with my will/trust (no conflicts)
✅ I’ve assigned a power of attorney and healthcare proxy
✅ If I have a trust, it’s funded and major accounts/titles are aligned (not just drafted)
✅ I’ve talked with family or loved ones about my wishes
✅ I’ve considered charitable giving or legacy planning
✅ I’ve addressed other estate matters (digital assets, personal property, document location, access info)
Emotional & Lifestyle Readiness
✅ I’ve thought about how I want to spend my time in retirement
✅ I have a plan to stay socially, mentally, and physically engaged
✅ I’ve discussed retirement expectations with my spouse/partner (if applicable)
✅ I’ve planned for purpose—not just finances
✅ I feel emotionally ready to leave full-time work
✅ I’ve considered major “what if” scenarios (loss of a spouse, caregiving needs, cognitive decline)
✅ I’ve thought through housing plans (downsizing/relocation) and the cost/tax implications
Your Retirement Confidence Score
Count your checkmarks ✅:
29–34: You’re well-prepared to retire confidently.
22–28: Solid foundation — focus on your weakest category before making big moves.
0–21: Gaps exist that could cost you money or peace of mind — prioritize a coordinated plan.
Want a second set of eyes? Book a Retirement Clarity Call.