Retirement Planning Checklist: Preparing for a Successful Transition

Retirement is one of the most significant financial transitions you will experience. A successful retirement requires coordination across income planning, taxes, healthcare, estate planning, and your vision for the years ahead.

Ideally, retirement planning begins well before your retirement date. In the early stages, focus on defining what you want retirement to look like and determining how your resources will support that lifestyle. As retirement approaches, shift your focus toward implementation: coordinating income sources, evaluating tax strategies, reviewing healthcare decisions, and stress-testing your plan. Starting early provides time to evaluate your financial readiness, make strategic decisions, and adjust your plan before important deadlines arrive.

Because these decisions are interconnected, and because no two retirements look alike, this checklist is meant to be a starting point.  As you work through the areas below, our team is here to help you sort through the complexity, weigh the tradeoffs specific to your situation, and turn this checklist into an actionable plan.

A comprehensive retirement plan should address the following areas:

1. Define Your Retirement Vision

Financial planning is only one part of retirement readiness. A successful retirement also requires clarity around how you want to spend your time, and the best retirement plans connect your financial resources with the life you want to create. Start reviewing the following questions 5-10 years out from retirement: 

• Where do you want to live?
• Do you want to relocate or downsize?
• How will you structure your days?
• What role will travel, family, philanthropy, volunteering, or consulting play?
• What experiences or goals do you want to prioritize?

2. Develop Your Retirement Income Plan

The foundation of a successful retirement is understanding how your assets and income sources will support your lifestyle over time.

Review Employer Benefits and Retirement Options

Before leaving an employer, evaluate decisions that may have long-term implications, including:

• Deferred compensation elections: Review timing, payout options, and tax implications alongside other income sources.
• Employer retirement accounts: Evaluate the benefits of keeping assets in an employer plan versus rolling assets into an IRA or Roth IRA.
• Employer stock: Review stock options, restricted stock units (RSUs), employee stock purchase plans (ESPPs), and net unrealized appreciation (NUA) opportunities. Consider both tax implications and overall portfolio concentration.
• Unused benefits: Determine how to maximize unused vacation, sick leave, and other available benefits.
• Life insurance coverage: Review whether your insurance needs change in retirement and whether employer coverage remains appropriate.

Many of these decisions are time-sensitive and may not be reversible after retirement.

Understand Your Retirement Income Sources

Create an inventory of all expected retirement income sources, including:

• Fixed income sources such as Social Security, pensions, and annuities
• Variable income sources such as deferred compensation, business income, installment payments, and rental income
• Portfolio income from dividends, interest, and capital gains
• Retirement account distributions, including required minimum distributions (RMDs)
• Work income, such as part-time, consulting, or other earned income

Consider when income begins, how long it will last, and the tax impact. The timing of income sources can be a valuable planning tool to help manage taxes over time.

For married couples, Social Security and pension decisions should be evaluated jointly. Claiming strategies, survivor benefits, and timing decisions can significantly impact lifetime income.

Build a Realistic Retirement Spending Plan

Retirement spending can change significantly throughout retirement, so make sure that your plan accounts for these fluctuations. 

• Early Retirement (“Go-Go Years”)
   Many retirees spend more on travel, hobbies, entertainment, and lifestyle experiences. Expenses related to commuting, professional clothing, and work-related costs may decline.
• Middle Retirement (“Slow-Go Years”)
   Travel and discretionary spending may decrease, while healthcare and support expenses may increase.
• Later Retirement (“No-Go Years”)
   Lifestyle spending may decline further, but medical, caregiving, and support costs may become more significant.

A strong retirement plan should also account for unexpected expenses, including home improvements, family support, healthcare needs, or other one-time costs. Understanding how your plan responds to higher-than-expected spending can help you make informed decisions.

3. Review Your Investment Strategy

Your investment strategy should evolve as you transition from accumulating wealth to managing and preserving it.

Key considerations include:

• How much investment risk can you comfortably take?
• How much liquidity do you need?
• How will your portfolio support future income needs?
• Do you have an appropriate cash reserve?
• Is your asset allocation aligned with your retirement goals?

Retirement introduces a new risk: sequence of returns risk. Selling investments during periods of market volatility, especially early in retirement, can significantly impact long-term outcomes.

Your portfolio should be designed around your spending needs, time horizon, and broader financial goals. 

4. Create a Tax-Efficient Withdrawal Strategy

Taxes are likely to be one of your largest expenses throughout retirement, yet many retirees do not have a proactive strategy to manage them.

Important considerations include:

• Which accounts to withdraw from and when
• Managing tax brackets over time
• Roth conversion opportunities
• Capital gains planning
• Charitable giving strategies
• Timing of income sources
• State tax considerations if relocating or maintaining multiple residences

Many retirees experience significant changes in taxable income after leaving the workforce. Strategic planning before and during retirement can create opportunities to manage lifetime tax exposure and improve flexibility.

5. Plan for Healthcare Costs

Healthcare is one of the largest unknown expenses in retirement and requires advance planning.

Consider:

• How retirement timing aligns with Medicare eligibility and options if you retire before this date 
• Whether employer-sponsored coverage through a spouse may be available
• The impact of Medicare income-related premiums
• Health savings account strategies
• Long-term care planning

Long-term care expenses can have a significant impact on even well-funded retirement plans. Evaluate whether your preferred approach is:

• Self-funding costs
• Purchasing traditional long-term care insurance
• Using a hybrid insurance solution
• Incorporating other planning strategies

6. Update Your Estate Plan

Retirement is an important time to confirm your estate plan reflects your current goals and family circumstances.

Review:

• Wills and trusts
• Beneficiary designations
• Powers of attorney
• Healthcare directives
• Trusted contacts on financial accounts

Beyond documents, consider discussing your intentions and wealth transfer goals with your family to help create clarity and alignment.

7. Stress-Test Your Financial Plan

A retirement plan should be flexible enough to withstand uncertainty.

Consider modeling market downturns, increased inflation, and a longer life expectancy, among others.

A key question to ask is: What circumstances could cause my retirement plan to fall short, and what steps can I take today to improve my flexibility?

Understanding potential challenges before retirement allows you to make informed decisions while you still have options.

Conclusion

Retirement planning is not a one-size-fits-all process. The most successful retirement strategies balance financial security with the flexibility to pursue the lifestyle you envision.

Retirement decisions are interconnected, and income planning, investment strategy, taxes, healthcare, and estate planning should be evaluated together. Working with a coordinated advisory team helps ensure these decisions are evaluated together so tradeoffs in one area don’t create unintended consequences in another.

If you’re approaching retirement, or want a second opinion on a plan already in place,  we invite you to talk with our team. We’ll help you work through this checklist together, prioritize the areas most relevant to your circumstances, and build a retirement strategy designed around your goals. Reach out today to schedule a conversation.

DISCLOSURE: This material has been prepared or is distributed solely for informational purposes only and is not a solicitation or an offer to buy any security or instrument or to participate in any trading strategy. Any opinions, recommendations, and assumptions included in this presentation are based upon current market conditions, reflect our judgment as of the date of this presentation, and are subject to change. Past performance is no guarantee of future results. All investments involve risk including the loss of principal. All material presented is compiled from sources believed to be reliable, but accuracy cannot be guaranteed and Evergreen makes no representation as to its accuracy or completeness. Securities highlighted or discussed in this communication are mentioned for illustrative purposes only and are not a recommendation for these securities. Evergreen actively manages client portfolios and securities discussed in this communication may or may not be held in such portfolios at any given time.