Would you like help turning this checklist into a real plan?
Book a Free 1-on-1 Retirement Readiness SessionRetirement Readiness Checklist
Your Checklist for Financial, Healthcare, Legal & Lifestyle Readiness
Build a Retirement Plan That Gives You Confidence to Spend, Adapt, and Enjoy Life
Retirement isn't just about reaching a number. It's about creating a plan that supports the life you actually want to live, without second-guessing every decision along the way.
This checklist will help you prepare for the financial, emotional, and strategic decisions that define a successful retirement.
Use this checklist to help you:
- Get organized around your finances and future income
- Spot potential gaps in healthcare and long-term care planning
- Review and update your legal and estate documents
- Start preparing for the emotional and social transition ahead
Would you like help turning this checklist into a real plan?
Book a Free 1-on-1 Retirement Readiness SessionDefine Your Retirement Vision
Before making financial decisions, get clear on what retirement looks like for you.
- Where do you want to live? Will you downsize, relocate, or stay put?
- What will your days look like without work on the calendar?
- What role will travel, hobbies, or family play in your life?
- Are your goals aligned with your spouse or partner?
Writing things down brings clarity and ensures your money is working toward something specific.
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Book a Free 1-on-1 Retirement Readiness SessionOrganize and Simplify Your Financial Life
Retirement planning gets messy when you're dealing with a scattered financial picture. Organizing your assets helps you see what you have and how to use it more effectively.
- List all accounts: 401(k)s, IRAs, pensions, brokerage, HSAs, annuities, insurance policies
- Categorize each by tax treatment: taxable, tax-deferred, or tax-free
- Identify accounts that are redundant or unnecessarily complicated
- Consolidate where appropriate to reduce noise and make your income plan easier to manage
A streamlined setup makes the rest of the planning process more efficient and less error-prone.
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Book a Free 1-on-1 Retirement Readiness SessionBuild a Personalized Income and Withdrawal Plan
This is where a theoretical retirement becomes a real one. The focus shifts from growing wealth to using it wisely.
- Separate your spending into essentials (housing, food, insurance) and discretionary (travel, hobbies, gifts)
- Fund essential expenses with reliable income sources like Social Security, pensions, or annuities
- Use a guardrails-based system to adjust discretionary spending based on market performance
- Take advantage of Roth conversions during low-income years to reduce future tax exposure
- Sequence withdrawals tax-efficiently to avoid higher brackets and minimize the long-term tax bill
The right income strategy should give you structure, flexibility, and peace of mind without relying on guesswork.
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Book a Free 1-on-1 Retirement Readiness SessionReview and Realign Your Investments
Your portfolio has a different job in retirement. It needs to provide growth, income, and protection, all without taking on the wrong kind of risk.
- Assess how much market volatility you're comfortable with and how much liquidity you need to feel secure
- Place yourself on a grid that accounts for both risk tolerance and liquidity preferences, not just one or the other
- Adjust your allocation based on where you fall. Some clients need more stable income sources. Others can afford more flexibility
- Make sure your portfolio is stress-tested to handle a major bear market in the first five years of retirement
- Structure assets into time-based buckets for near-, mid-, and long-term needs
- Prioritize tax location. Income assets typically belong in tax-deferred accounts; growth assets are often better in Roths
- Consider tail risk hedging strategies to reduce exposure to catastrophic losses
- Some risks are worth taking. Others just increase the chance of loss without improving your outcome. Be cautious of investments that add risk without adding enough benefit.
Ultimately, your portfolio shouldn't be too aggressive or too conservative. Like Goldilocks, it needs to be just right — aligned with your specific goals, timeline, and temperament.
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Book a Free 1-on-1 Retirement Readiness SessionPrepare for Healthcare and Long-Term Care
Healthcare planning is one of the most overlooked parts of retirement and one of the most expensive.
- Understand how Medicare works: Parts A, B, D, plus Medigap and Advantage plans
- If retiring before 65, make sure you have a plan for coverage until Medicare kicks in
- Budget for out-of-pocket healthcare costs. The average 65-year-old couple can expect to spend at least $165,000 during retirement
- More than half of retirees will need some form of long-term care, which can cost over $100,000 per year
- Consider hybrid long-term care insurance, earmarked reserves, or other funding options
Waiting until you need care is too late. Planning ahead means more options and fewer financial surprises.
Would you like help turning this checklist into a real plan?
Book a Free 1-on-1 Retirement Readiness SessionGet Your Legal Docs in Order
A good financial plan includes making sure your wishes are clearly documented and easy to carry out.
- Review and update your will, powers of attorney (financial and medical), and healthcare directive
- Double-check beneficiary designations on retirement accounts, life insurance, and bank accounts
- Store these documents securely and make sure someone you trust knows how to access them
- Consider whether a trust makes sense based on your goals, family situation, or state laws
This isn't just about legacy. It's about making sure the right people can step in if something happens.
Would you like help turning this checklist into a real plan?
Book a Free 1-on-1 Retirement Readiness SessionPrepare for the Emotional and Social Transition
The emotional side of retirement is real. You're not just leaving a job. You're entering a new phase of life.
- Think about how you'll spend your time once the structure of work is gone
- Explore purpose-driven activities like volunteering, travel, mentoring, or family involvement
- Build social connections outside of your professional identity
- Talk with your spouse or family about how your new routines might affect shared responsibilities or schedules
Retirement success depends just as much on your mental and social wellbeing as it does on your finances.
Would you like help turning this checklist into a real plan?
Book a Free 1-on-1 Retirement Readiness SessionAvoid the Mistakes That Derail Good Plans
It's not usually one big error that ruins a retirement plan. It's a series of avoidable missteps.
- Holding the wrong kinds of risk at the wrong time or thinking diversification alone is enough
- Overlooking the long-term impact of taxes, especially when it comes to RMDs and IRMAA thresholds
- Chasing returns instead of optimizing income, cash flow, and tax efficiency
- Treating your financial plan as static instead of something that evolves with you
A good plan adjusts. A great one makes those adjustments before they're necessary.
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Book a Free 1-on-1 Retirement Readiness SessionDon't Wing This. Work with a Pro
This checklist gives you a foundation, but real retirement planning is more than checking boxes.
It's about coordinating all the moving parts—taxes, income timing, healthcare, legal risk, emotional shifts—into a strategy that works for you.
Working with a financial professional helps you:
- Optimize your Social Security strategy and withdrawal order
- Run side-by-side comparisons for Medicare and LTC coverage
- Identify tax traps and Roth conversion windows
- Advanced tax planning techniques like valuation discounts to turbocharge Roth conversions
- Custom withdrawal sequencing to improve outcomes and reduce RMD-related tax spikes
- Stress testing across multiple scenarios, including market volatility and inflation surprises
- Integrated planning that connects income, investments, taxes, and estate goals into a clear roadmap
- Catch blind spots most DIY plans miss
Most people don't retire with too little. They retire with too much uncertainty. We help you fix that.
Would you like help turning this checklist into a real plan?
Book a FREE 1-on-1 Retirement Readiness Session
To schedule your free consultation, please use the link below:
Schedule Your Free SessionOr call us directly at (317) 210-3727
Steven Neeley, CFP®
Fortress Capital Advisors
Sources
- AARP, 2025 [https://www.aarp.org/money/retirement/find-forgotten-401k-and-other-money.html]
- EBRI, 2024 [https://www.ebri.org/content/2024-spending-in-retirement-study-uncovers-concerning-trends-on-dampened-spending-expectations-due-to-lack-of-sufficient-savings--inflationary-pressures-and-rising-credit-card-debt]
- Morningstar, 2024 [https://www.morningstar.com/retirement/how-retirement-income-guardrails-can-ease-clients-worries]
- IRS, 2025 [https://www.irs.gov/pub/irs-pdf/p590b.pdf]
- ThinkAdvisor, 2024 [https://www.thinkadvisor.com/2024/08/09/heres-how-much-retiring-clients-can-expect-to-pay-for-health-care-fidelity/]
- Money.com, 2025 [https://money.com/long-term-care-rising-needs/]
- CNBC, 2025 [https://www.cnbc.com/2025/03/20/retirees-sequence-of-returns-risk.html]
- LegalZoom, 2025 [https://www.legalzoom.com/articles/top-10-reasons-to-update-your-estate-planning-documents]
- AARP, 2025 [https://www.aarp.org/money/personal-finance/most-common-underestimated-expenses/]
- Morningstar, 2024 [https://www.morningstar.com/personal-finance/preparing-retirement-requires-more-than-financial-plan]
Risk Disclosure: Investing involves risk including the potential loss of principal. No investment strategy can guarantee a profit or protect against loss in periods of declining values. Past performance does not guarantee future results.
This material is for information purposes only and is not intended as an offer or solicitation with respect to the purchase or sale of any security. The content is developed from sources believed to be providing accurate information; no warranty, expressed or implied, is made regarding accuracy, adequacy, completeness, legality, reliability, or usefulness of any information. Consult your financial professional before making any investment decision. For illustrative use only.
This information is not intended to be a substitute for specific individualized tax advice. We suggest that you discuss your specific situation with a qualified tax professional.
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