Eian Lomash
August 14, 2026

Retirement planning is not a one-time event. The decisions that matter most often change as

you move through different stages of life. What makes sense at age 50 may be very different

from the priorities you face at 60 or 70.

A successful retirement planning process involves more than simply saving money. It requires

coordinating retirement accounts, investment strategies, taxes, income sources, healthcare

planning, and estate considerations over several decades.

This retirement planning checklist outlines key financial actions to consider in your 50s, 60s, and 70s based on guidance from reputable sources, including the Internal Revenue Service (IRS),Social Security Administration (SSA), Financial Industry Regulatory Authority (FINRA), andmajor retirement planning research from institutions such as Fidelity Investments.

Your 50s: Finish Building the Foundation

Your 50s are often considered the "retirement red zone"—the period when retirement begins to

feel real and the financial decisions you make can have a significant impact on your future.

Rather than starting from scratch, this decade is typically about finishing the foundation you've

spent years building. It's often the last opportunity to maximize retirement savings, strengthen

your retirement account strategy, and address potential gaps before retirement income becomes

a reality.

1. Maximize Retirement Account Contributions

One of the most effective ways to strengthen retirement readiness is to fully utilize

tax-advantaged retirement accounts.

This may include:

  • 401(k) retirement plan contributions
  • Traditional IRA contributions
  • Roth IRA contributions (if eligible)
  • Employer matching opportunities
  • Catch-up contributions available after age 50

For many workers, increasing contributions during their 50s can significantly improve long-term retirement income potential.

When evaluating the best retirement savings opportunities, maximizing tax-advantaged

accounts is often one of the first places to start.

2. Evaluate Whether Your Investments Match Your Timeline

As retirement approaches, portfolio allocation deserves closer attention.

Many investors accumulate investments over decades without periodically reviewing whether

their risk exposure still aligns with their goals.

Questions to consider include:

  • Is the portfolio appropriately diversified?
  • Does it balance growth and risk?
  • Will it support future retirement income needs?
  • Does the investment strategy reflect your retirement timeline?

The goal is not necessarily to become conservative, but to ensure your investment allocation

reflects your long-term retirement objectives.

3. Estimate Future Retirement Income Sources

Begin identifying potential income sources, including:

  • Social Security benefits
  • Pension plan benefits
  • Retirement annuity income
  • Investment accounts
  • Personal savings

Understanding these income sources early can help identify potential shortfalls while there is

still time to make adjustments.

4. Begin Preliminary Tax Planning

Many individuals focus on saving while giving little attention to future taxes.

However, retirement income may come from accounts with very different tax treatments

Examples include:

  • Tax-deferred 401(k)s and Traditional IRAs
  • Roth accounts that may provide tax-free qualified distributions
  • Taxable brokerage accounts

Early planning can help create more flexibility later when minimizing taxes in retirement

becomes a priority.

Your 60s: Transition From Saving to

Income Planning

Your 60s are often when retirement planning shifts from accumulation to distribution.

The focus becomes less about growing assets and more about converting savings into

sustainable income.

1. Create a Retirement Income Strategy

Many retirees spend years building assets but very little time planning how those assets will be

used.

Key questions include:

  • Which accounts should be withdrawn from first?
  • How much can be safely withdrawn?
  • How should market volatility be managed?
  • How will income be coordinated with taxes?

A retirement plan should address both investment growth and income sustainability.

This stage is where many individuals seek guidance from a certified financial planner or

fiduciary retirement planner.

2. Review Your 401(k) and Rollover Options

As retirement approaches, many workers leave an employer and must decide what to do with

their workplace retirement plan.

Potential options may include:

  • Leaving assets in the employer plan (if allowed)
  • Rolling assets into an IRA
  • Consolidating multiple retirement accounts

For individuals with Roth 401(k) assets, a rollover Roth 401(k) to Roth IRA may provide

additional flexibility and simplify account management.

Some retirees may also evaluate whether it makes sense to convert 401(k) to Roth IRA assets

through a Roth conversion strategy. Because conversions generally create taxable income,

these decisions should be evaluated carefully as part of a broader retirement income plan.

3. Develop Tax Planning Strategies for Retirement

The years immediately before retirement often present valuable tax planning opportunities.

Potential strategies may include:

  • Roth conversions
  • Managing taxable income levels
  • Coordinating withdrawals among account types
  • Reducing future Required Minimum Distributions
  • Creating a more tax-efficient retirement income strategy

These years may provide opportunities to build future tax-free retirement plan income sources

while reducing future tax exposure.

4. Build a Healthcare Funding Strategy

Healthcare expenses often represent one of the largest retirement costs.

Planning should include:

  • Medicare enrollment decisions
  • Supplemental insurance evaluation
  • Long-term care considerations
  • Out-of-pocket healthcare projections
  • Emergency healthcare reserves

A comprehensive retirement planning process should account for healthcare costs alongside

investment and income planning.

Your 70s: Focus on Distribution, Taxes,

and Legacy Planning

By your 70s, retirement planning priorities often shift again.

The emphasis frequently moves toward retirement income management, taxes on retirement

income, healthcare planning, Required Minimum Distributions (RMDs), and legacy

considerations.

1. Manage Required Minimum Distributions (RMDs)

Most traditional retirement accounts eventually become subject to Required Minimum

Distribution rules.

RMDs can:

  • Increase taxable income
  • Affect Medicare premiums
  • Influence taxation of Social Security benefits
  • Impact overall retirement cash flow

Failure to plan for these distributions may result in larger-than-expected tax obligations.

2. Evaluate Taxes on Retirement Income

Many retirees discover that taxes remain an important part of retirement.

Potential taxable income sources include:

  • Traditional IRA withdrawals
  • 401(k) distributions
  • Pension plan payments
  • Investment income
  • Certain Social Security benefits

Understanding taxes on retirement income can help retirees make more informed withdrawal

decisions and support the goal of minimizing taxes in retirement.

3. Plan for Healthcare and Long-Term Care Needs

By your 70s, healthcare planning often becomes one of the most important components of

retirement planning.

Healthcare expenses can represent a significant portion of retirement spending, particularly as

individuals age.

Areas to review include:

  • Medicare coverage and supplemental policies
  • Prescription drug costs
  • Potential long-term care needs
  • In-home care options
  • Assisted living or nursing care expenses
  • Healthcare inflation

Many retirees assume Medicare will cover most healthcare expenses. However, Medicare

generally does not cover extended custodial long-term care services.

Because long-term care costs can significantly affect retirement savings and legacy goals,

periodic reviews can help determine whether existing assets, insurance coverage, or income

sources are sufficient to support future care needs.

Healthcare planning should be integrated into the broader retirement planning process rather

than treated as a separate issue.

4. Reassess Income Sources

Retirement spending often evolves over time.

Review whether income sources remain appropriate, including:

  • Investment withdrawals
  • Pension benefits
  • Retirement annuity payments
  • Social Security benefits

Periodic reviews can help ensure income strategies remain aligned with current needs.

5. Review Estate and Beneficiary Plans

Retirement planning extends beyond investment management.

Important items to review include:

  • Beneficiary designations
  • Wills and trusts
  • Powers of attorney
  • Healthcare directives

Keeping documents updated can help ensure assets are distributed according to your wishes.

Common Mistake: Treating Retirement

Planning as a One-Time Event

One of the biggest misconceptions about retirement planning is that it ends once retirement

begins.

In reality:

  • Tax laws change
  • Markets fluctuate
  • Spending needs evolve
  • Healthcare costs increase
  • Family circumstances shift

Retirement planning should be viewed as an ongoing process rather than a one-time decision.

Periodic reviews can help ensure your strategy remains aligned with your goals and changing

circumstances.

Bringing It All Together

The most effective retirement plans typically evolve through three distinct stages:

In Your 50s

  • Maximize retirement savings
  • Strengthen your retirement account strategy
  • Review investment allocations
  • Begin tax planning
  • Address potential retirement income gaps

In Your 60s

  • Develop retirement income strategies
  • Evaluate rollover and Roth conversion opportunities
  • Implement tax planning strategies for retirement
  • Prepare for healthcare expenses
  • Transition from accumulation to distribution planning

In Your 70s

  • Manage Required Minimum Distributions (RMDs)
  • Monitor taxes on retirement income
  • Review healthcare and long-term care planning
  • Reassess retirement income sources
  • Update estate and beneficiary plans

Each stage presents unique opportunities and challenges, which is why many individuals seek

guidance from retirement planning firms, retirement planning companies, certified financial

planners, or fiduciary retirement planners.

Retirement Planning Guidance in Northern

Virginia

At Legacy Wealth Management, we help individuals and families navigate every stage of the

retirement planning process.

Our team works with clients on:

  • Retirement planning information and education
  • Retirement account strategies
  • 401(k) retirement plan reviews
  • Roth conversion and rollover analysis
  • Tax planning strategies for retirement
  • Minimizing taxes in retirement
  • Retirement income planning
  • Long-term savings planning

Whether you're searching for retirement planning near me, evaluating retirement planning firms, or looking for guidance from a certified financial planner, our goal is to help create a retirement strategy that aligns with your long-term financial objectives.

If you'd like help reviewing your retirement strategy, retirement accounts, tax planning

opportunities, or retirement income plan, you can schedule a complimentary meeting by visiting

www.lwealthmanagement.com/contact or calling (877) 650-4738.

As a fiduciary-focused wealth management firm serving retirees and pre-retirees, we help

individuals and families navigate the retirement planning process with strategies designed to

align investments, income, taxes, and long-term financial goals.

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