Countdown to Retirement: Important Checkpoints

Posted by Creekmur Wealth Advisors on 10:55 AM on April 10, 2025

Whether retirement feels like a distant goal or is fast approaching, staying aligned with key financial checkpoints can help you move forward with clarity and purpose. These steps act as a helpful framework to stay prepared, evaluate your strategy, and make informed decisions as you age.

This decade-by-decade guide offers practical insights to help you approach retirement with greater confidence and structure.

Your 50s – The Foundation Decade

With retirement on the horizon, this is a critical time to solidify your financial foundation. Strategic actions now can have a meaningful impact in the years ahead.

Maximize Your Retirement Contributions

Turning 50 opens the door to “catch-up contributions” for retirement accounts like 401(k)s and IRAs. These additional contributions provide an opportunity to enhance your savings. Consider whether your current savings plan is aligned with your retirement goals.

Evaluate Health Insurance

If you retire before becoming eligible for Medicare at 65, health coverage gaps may arise. Take time to review your current insurance and explore options such as long-term care coverage. Early planning may help you manage future healthcare expenses more effectively.

Check Your Social Security Projections

Access your Social Security statement online to verify your earnings and review your estimated benefits. Understanding how timing affects your payout can help guide your retirement income planning.

Draft a Preliminary Budget

Begin estimating your expected retirement expenses, from housing and utilities to healthcare and leisure. While it’s impossible to predict everything, a working budget helps set realistic expectations and informs your savings strategy.

Tip: Bring your vision for retirement into focus by imagining your lifestyle in 20 years. Are you traveling? Downsizing? These choices affect your savings strategy today.

Your 60s – The Pivotal Decade

As you approach or enter retirement, your focus may shift toward income planning and refining your overall financial strategy.

Social Security Decisions

While benefits can begin at 62, delaying until full retirement age—or beyond—can increase your monthly benefit. Each option has trade-offs, so evaluate your situation carefully, ideally with guidance from a qualified professional.

Enroll in Medicare

At age 65, you become eligible for Medicare. Missing the initial enrollment window can lead to penalties, so it’s important to mark key dates and review your coverage options, including supplemental plans like Medigap or Medicare Advantage.

Create a Withdrawal Strategy

Creating a structured approach to draw down retirement savings is essential. Some retirees use a “bucket strategy,” segmenting assets by timeline to better manage risk and liquidity. Tax implications, investment mix, and required withdrawals should all be considered.

Adjust Your Portfolio

As you near retirement, reducing portfolio volatility becomes more important. Rebalancing toward more conservative holdings can help preserve capital while still supporting modest growth.

Plan for the Unexpected

From market shifts to healthcare surprises, having contingency plans for the unexpected adds resilience to your financial approach.

Beyond Your 60s – Retirement Evolution

Retirement is not a one-time event—it evolves. Adapting to changes in health, spending, and lifestyle is part of staying financially secure in later years.

Start Required Minimum Distributions (RMDs)

Starting at age 73, most retirees must begin taking RMDs from qualified retirement accounts. Without proper planning, these withdrawals can affect your taxable income. A coordinated tax strategy may help manage the impact.

Plan for Longevity

Lifespans are increasing, so it’s important to assess whether your withdrawal rate and asset allocation can support a multi-decade retirement. Diversified income sources and disciplined spending may help sustain your lifestyle longer.

Revisit Estate and Legacy Plans

Ensure your legacy aligns with your values and goals. Consider updating your will, beneficiary designations, and exploring strategies such as lifetime gifting or qualified charitable distributions (QCDs) to support your intentions.

Reminder: Retirement planning doesn't end when you stop working. Regularly reviewing your plan helps ensure it continues to serve your evolving needs.

Across All Decades – Financial Education and Flexibility

Laws change. Markets shift. Life happens. Ongoing education and regular plan reviews can help keep you on track, regardless of where you are in the journey.

Consider scheduling periodic reviews with a financial professional to assess progress and make adjustments based on new developments in your life or in the broader financial landscape.

Actionable Steps to Secure Your Retirement

Breaking retirement planning into clear, decade-based goals can make the process more manageable. With the right framework, you can move forward more clearly and confidently.

If you’re looking to take the next step—whether that’s refining your savings plan, structuring income withdrawals, or exploring estate planning strategies—consider connecting with a trusted professional to discuss your unique needs.

The best time to plan is now. Take action today to stay on track for tomorrow.

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