Your 8-Step Retirement Roadmap: What You Need to Do Between Ages 50 and 65
If you’re between the ages of 50 and 65, retirement is no longer an abstract concept—it’s a real milestone that’s quickly approaching. The decisions you make during these years can have a greater impact on your retirement security than almost any other period in your life.
The good news? With the right strategy, this window of time can be incredibly powerful.
This 7-year retirement roadmap outlines the most important steps pre-retirees should take to prepare for retirement, reduce risk, and create sustainable income—before the transition from work to retirement begins.
Why Ages 50–65 Are Critical for Retirement Planning
Your 50s and early 60s are often your highest earning years, which will affect your Social Security payouts. You also gain access to planning tools that weren’t available earlier, such as catch-up contributions and more flexible retirement strategies.
This is the stage where retirement planning shifts from accumulation to coordination—aligning savings, investments, taxes, Social Security, and healthcare into a unified plan.
Without a roadmap, many retirees make decisions in isolation. With one, every move supports the bigger picture.
Step 1 (Ages 50–55): Get Clear on Your Retirement Starting Point
The first step in preparing for retirement is understanding exactly where you stand today.
Key questions to answer:
- How much have you saved for retirement?
- Which accounts hold your assets (401(k), IRA, brokerage, Roth IRA)?
- What debts remain, and when will they be paid off?
- What does your current spending look like?
- Are there large purchases ahead (remodel, epic vacation, etc.)?
This clarity allows you to set realistic goals and identify gaps early—while there’s still time to adjust.
Step 2: Maximize Retirement Contributions and Catch-Up Savings
Once you turn 50, you’re eligible for catch-up contributions to retirement accounts. These additional savings opportunities can significantly boost retirement readiness.
Prioritize:
- Maximizing 401(k) or 403(b) contributions
- Catch-up IRA contributions
- Health Savings Accounts (HSAs), if eligible
Even small increases during your peak earning years can compound meaningfully before retirement.
Step 3 (Ages 55–60): Align Investments with Your Retirement Timeline
As retirement gets closer, investment strategy becomes less about chasing returns and more about balancing growth and risk.
This stage is ideal for:
- Reviewing asset allocation
- Reducing unnecessary concentration risk
- Ensuring that diversification supports long-term income needs
- Stress-testing portfolios for market volatility
The goal isn’t to eliminate risk—but to manage it intentionally.
Step 4: Shift the Focus from Saving to Retirement Income Planning
Many people spend decades saving without ever mapping out how income will actually be generated in retirement.
Retirement income planning answers questions like:
- How much income will you need each year?
- Which accounts should income come from—and when?
- How do taxes affect withdrawal strategies?
- Will income adjust over time?
A clear income plan helps turn savings into a reliable paycheck.
Step 5 (Ages 60–65): Make Smart Social Security Decisions
Social Security is one of the most important—and irreversible—retirement decisions you’ll make.
Planning ahead allows you to:
- Compare claiming strategies at different ages
- Coordinate benefits for married couples
- Understand tax implications
- Integrate Social Security into a broader income plan
Optimizing Social Security can add tens—or even hundreds—of thousands of dollars in lifetime benefits.
Step 6: Plan for Healthcare, Medicare, and Long-Term Care
Healthcare is one of the largest expenses in retirement—and one of the most overlooked.
Preparation should include:
- Understanding Medicare enrollment timelines
- Estimating out-of-pocket healthcare costs
- Using HSAs strategically. There is more to an HSA than meets the eye!
- Evaluating long-term care planning options
Addressing healthcare early helps protect retirement assets later.
Step 7: Proactively Manage Taxes in Retirement
Taxes don’t disappear in retirement—and for many households, they become more complex.
Strategic tax planning may include:
- Coordinating withdrawals across account types
- Evaluating Roth conversion opportunities
- Managing future required minimum distributions (RMDs)
- Reducing taxes on Social Security and Medicare premiums
Effective tax planning helps extend the life of your retirement portfolio.
Step 8: Update Estate and Legacy Planning
Your retirement roadmap should also reflect what happens beyond your lifetime.
Key considerations include:
- Updated wills and powers of attorney
- Beneficiary reviews
- Legacy and charitable goals
- Coordinating estate and tax strategies
Estate planning provides clarity and confidence—for you and your family.
The Bottom Line: Retirement Planning Works Best with a Roadmap
Preparing for retirement between ages 50 and 65 isn’t about guessing—it’s about planning with intention.
A clear retirement roadmap helps you:
- Make confident decisions
- Avoid costly mistakes
- Reduce uncertainty
- Turn savings into sustainable income
Working with a retirement-focused advisor can help coordinate every moving part into a cohesive strategy—so when retirement arrives, you’re ready.
Ready to See Where You Stand?
At HCM Wealth Advisors, we help pre-retirees create personalized retirement roadmaps that integrate investments, income, taxes, and long-term planning.
📅 Schedule a Retirement Readiness Review and take the next step toward clarity and confidence.