🏖️ Retirement Readiness: No-Fluff Checklist

Why This Checklist Matters

Retirement isn’t just about age—it’s about readiness. This no-fluff checklist helps you cut through the noise, focus on what matters, and assess whether you’re truly prepared for life after work.

Whether retirement is 5 years away or right around the corner, this checklist 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 hustles)
✅ 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 for any other income or expense factors unique to my situation

Healthcare & Insurance

✅ I understand my Medicare options and eligibility
✅ I’ve considered supplemental or Advantage plans
✅ I’ve planned for long-term care (insurance or savings)
✅ I’ve budgeted for out-of-pocket healthcare costs
✅ I’ve reviewed my life and disability insurance needs
✅ I’ve addressed any other health-related or insurance gaps

Investments & Withdrawals

✅ I know which accounts I’ll withdraw from first (tax-smart strategy)
✅ I’ve chosen or reviewed my withdrawal plan (e.g., 4% rule, 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 for my plan

Estate & Legacy Planning

✅ I have a will and/or trust in place
✅ I’ve updated my beneficiaries on all accounts
✅ I’ve assigned a power of attorney and healthcare proxy
✅ I’ve talked with family or loved ones about my wishes
✅ I’ve considered charitable giving or legacy planning
✅ I’ve ensured other estate matters are addressed (digital assets, personal property, etc.)

Emotional & Lifestyle Readiness

✅ I’ve thought about how I want to spend my time in retirement
✅ I have a plan to stay socially and mentally engaged
✅ I’ve discussed retirement expectations with my spouse/partner
✅ I’ve planned for purpose—not just finances
✅ I feel emotionally ready to leave full-time work
✅ I’ve addressed any other personal or lifestyle factors important to my happiness

Your Retirement Confidence Score

Count your checkmarks ✅

20–25: You’re well-prepared to retire confidently.

14–19: Solid foundation — focus on your weakest category before making big moves.

Under 14: Gaps exist that could cost you money or peace of mind — get a coordinated plan in place now.

Let’s Make It Happen

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© 2025 MVP Money Moves. InFocus Wealth Strategies and MVP Money Moves are marketing brands of DeWitt Investment Research & Management, Inc., doing business as DeWitt Capital Management. Investment advice is offered through DeWitt Capital Management, a Registered Investment Adviser. This website is for informational purposes only and does not constitute a solicitation or offer of investment advice.

Disclaimer: The information provided on this site and its blogs is for educational and informational purposes only. It does not constitute financial, legal, or tax advice. Always consult with a qualified professional for guidance tailored to your individual circumstances. The examples, illustrations, and sample checklists are intended for general reference and are not meant to reflect any individual or family's specific needs or outcomes. They are provided to demonstrate concepts and do not guarantee future results. All investing involves risk, including possible loss of principal. Past performance is not indicative of future results.