Retirement Readiness Check-Up: 5 Questions to Ask Before Year-End
By Mike Perros
The Importance of an Autumn Check-In
The arrival of October signals the beginning of the year’s final stretch. For many, it is a season of routines returning, cooler evenings, and thoughts of the holidays just around the corner. It is also the perfect moment to pause and review your retirement plan. There is still time to make adjustments before the year closes, and those adjustments can carry meaningful benefits.
A retirement check-up does not have to be complicated. The right questions can guide a thoughtful conversation that ensures your plan is not only intact but thriving. These questions invite reflection on both financial numbers and personal goals.
Question One: Am I Managing My Retirement Distributions Wisely?
For those already retired, required minimum distributions (RMDs) remain a key priority. Missing an RMD deadline can create unnecessary penalties. Reviewing distribution strategies in October allows time to confirm that withdrawals are on track and tax efficient.
If you are not yet retired, consider whether you are contributing enough to retirement accounts. There is still time to maximize 401(k) or IRA contributions before year-end. Even a few extra contributions now can compound significantly over time.
Question Two: Is My Investment Allocation Still Right for Me?
Market conditions shift, and so does personal comfort with risk. A retirement plan is not a one-time setup; it is an evolving strategy. Ask whether your allocation reflects your current life stage, your income needs, and your ability to weather market fluctuations without undue worry.
Diversification remains a central tool. Too much concentration in one area may increase volatility, while over-diversification may dilute growth. The balance depends on your goals, and reviewing this balance each fall ensures your investments remain in sync with your needs.
Question Three: Am I Prepared for Healthcare Costs?
Healthcare is one of the largest expenses in retirement, and costs rarely stay static. Medicare open enrollment begins in October, making this the ideal month to review your coverage.
Ask whether your plan still meets your needs, whether supplemental coverage is worth considering, and how future healthcare costs fit into your overall budget. Addressing these questions now avoids surprises later and builds peace of mind around one of retirement’s most significant expenses.
Question Four: Have I Considered Charitable Giving or Gifting?
The final months of the year often inspire generosity. Whether you wish to support a favorite cause or assist family members, October is the right time to explore gifting strategies.
Qualified charitable distributions from IRAs can satisfy RMD requirements while supporting charities. Gifting to children or grandchildren may align with tax-efficient strategies. Each decision should reflect both your financial capacity and your personal values. Early planning avoids rushed decisions in December and ensures your giving has both impact and intention.
Question Five: Is My Estate Plan Up to Date?
Estate planning is not a one-time event. Family circumstances, tax laws, and personal priorities evolve. Review whether wills, trusts, and beneficiary designations reflect your current wishes. Consider whether power of attorney documents remain appropriate.
This step is often overlooked, yet it can be one of the most meaningful. Ensuring that your legacy is protected and clearly communicated removes uncertainty for loved ones and strengthens your overall financial readiness.
The Emotional Side of Retirement Readiness
Retirement is not only about money. It is also about purpose, identity, and lifestyle. These five questions touch on numbers, but beneath them is a deeper reflection: Am I living the retirement I imagined? Do my financial choices reflect what matters most?
These questions often spark emotional conversations. Clients share worries about healthcare, excitement about travel, or concerns about leaving a meaningful legacy. A retirement check-up is not about judgment. It is about listening carefully to your own story and making sure your plan supports it.
Practical Steps to Take in October
For many clients, October becomes the month of clarity. Here are practical steps that flow from the five questions:
Schedule a review with your advisor to confirm RMDs and contributions.
Review investment statements and confirm your allocation matches your goals.
Explore Medicare options during open enrollment.
Identify charitable gifts and complete them before year-end.
Update estate documents and beneficiaries if needed.
Taking these steps now means December can be spent with family and reflection, not financial deadlines.
A Personal Perspective
I remember meeting with a couple who, after years of careful saving, had finally retired. Each October we would sit down for a check-up. They told me they valued these fall meetings not only for the financial clarity but for the sense of reassurance. They knew where they stood, what adjustments were needed, and that their plan was built to support their lifestyle.
They often said the check-up allowed them to enjoy the holidays with peace of mind. That is what October readiness can provide - a calm assurance that your plan is not just functioning but flourishing.
Looking Ahead
October is not just another month on the calendar. It is a strategic checkpoint that invites reflection, action, and alignment. Retirement readiness is not about predicting markets or reacting to headlines. It is about asking the right questions and ensuring your plan reflects your goals and your values.
If you find yourself uncertain about any of these five questions, now is the time to explore them. The answers do not need to be perfect, but they should be clear. Clarity creates confidence, and confidence is one of the greatest assets in retirement.
