Key Retirement Planning Milestones by Stage

Retirement is a major life transition—and planning for it doesn’t happen all at once. Taking proactive steps at every stage can help you secure lasting financial confidence and set the stage for the retirement you’ve imagined.

Here’s a stage-by-stage guide to the most important retirement planning actions to take—beginning a decade before retirement and continuing through your early years of financial independence.

Stage	Key Focus Areas
10 Years Out	Review savings, clarify goals, address taxes & debt, connect with an advisor
5 Years Out	Map income plan, assess healthcare costs, explore Roth strategies
3 Years Out	Prioritize portfolio protection, update estate plan, manage risk
1 Year Out	Finalize income sources, review Social Security & Medicare, evaluate housing
5 Months Out	Prepare for home payoff, organize paperwork, consider next steps
1 Month Out	Submit forms, confirm health coverage, build cash reserves
After Retirement	Activate your plan, monitor spending, schedule annual reviews

10 Years Out

With a decade to go, start with a holistic review of your finances. Are your retirement savings on track? Do you need to ramp up contributions to close any gaps?

Talk openly with your spouse or partner about your shared goals—whether it’s travel, a new business, or a second career. Aligning your vision now can make planning much smoother down the road.

Review your debt situation, especially your mortgage, and start building a strategy to reduce or eliminate what you owe by retirement. Evaluate your tax picture and begin considering how withdrawals from different accounts will affect your future cash flow.

If you don’t already have an advisor, this is a great time to find one who understands your goals and can help you map out your next steps.

5 Years Out

This is the “retirement red zone”—the closer you get, the more important it is to protect what you’ve built. Focus on transitioning from accumulation to reliable monthly income.

Estimate your future expenses and match them to your income sources. Don’t overlook healthcare and long-term care costs. This is also the time to review whether Roth conversions or other tax strategies could benefit you in the long run.

Meet with your advisor to discuss income planning, rollover options, and how to minimize sequence-of-return risk.

3 Years Out

Shift your strategy toward protecting your nest egg. Consider dialing down risk and make sure your portfolio is diversified and well-positioned for income needs.

Start reviewing your estate plan and beneficiary designations. Make sure your legal documents reflect your current wishes and family circumstances. Your advisor can work with you and an estate attorney to ensure everything is up to date.

1 Year Out

Your portfolio should now be tuned for retirement income and inflation protection. Evaluate guaranteed income solutions, such as annuities, to supplement Social Security or pension benefits.

It’s also time to make final decisions about Social Security, Medicare enrollment, and your housing plans. If you’re planning to stay in your current home, aim to have it paid off. If not, explore downsizing or tapping home equity as part of your plan.

Have a thorough review with your advisor to ensure your plan is on track and ready for the transition.

5 Months Out

Fine-tune your strategy and start executing key steps. Organize your paperwork for rollovers and benefit changes. If you’re considering a second act—part-time work or a new career—start putting those plans in motion.

Revisit your home payoff strategy, and consider options for accessing equity if needed. If you have questions about financial products, make sure you’re working with a fiduciary advisor who puts your interests first.

1 Month Out

The countdown is on. Submit any remaining paperwork, confirm your health insurance, and build up a short-term cash buffer to cover expenses during the transition.

If you’re eligible for Medicare, coordinate with an insurance advisor to ensure your coverage begins on time. Double-check your financial “go bag”—so you can enjoy your retirement with confidence.

After Retirement

Congratulations! Now it’s time to put your plan into action. Work with your advisor to activate your income streams and monitor your spending. Set up annual reviews to stay ahead of changes in your life and the financial landscape.

Missed a step or want to adjust your plan? It’s never too late to refine your approach and make sure your money keeps working for you.

Putting a Comfortable Retirement Within View

These milestones form a clear roadmap to help you navigate each phase of the retirement journey with confidence.

Talk with us at Foxcove Financial and fine-tune your personal plan and prepare for what’s ahead. Don’t hesitate to explore alternative strategies—from insurance to income planning—that can offer more security and peace of mind in retirement.