The end of the year has a way of arriving quickly. One minute it’s September, and the next you’re looking at holiday plans, year-end statements and a calendar that suddenly feels very full.
Financial planning can feel the same way. Throughout the year, you make decisions one at a time. You take a distribution from an IRA. You help a grandchild with college. You replace a car. Perhaps you retire, change your Medicare coverage or begin collecting Social Security.
A year-end financial planning meeting gives you a chance to step back and look at those decisions together. You don’t need a long list of financial terms or a folder full of spreadsheets. A few good questions can lead to a much more useful conversation.
What Should You Ask at a Year-End Financial Planning Meeting?
1. How Could the Changes in My Life This Year Affect My Financial Plan?
This is often the best place to start. Think about what has changed in your life over the past 12 months, then ask your advisor whether any of those changes should affect your financial plan.
Maybe your income changed. Perhaps you retired, sold a property, received an inheritance, made a large purchase or began helping a family member financially.
Changes that don’t seem strictly financial can matter, too. A marriage, death in the family, health issue or move may affect beneficiary designations, insurance needs, estate documents or cash-flow planning.
If you’re retired, compare what you actually spent this year with what you expected to spend. If withdrawals were higher than planned, understanding why is more useful than simply noticing that an account balance changed. If retirement is approaching, this may be the right time to update your retirement date, expected expenses and income plan.
Good retirement planning changes as your life changes. A year-end meeting is a chance to make sure your plan still reflects the life you are living now.
2. Are There Decisions I Should Make Before December 31?
Some planning decisions are flexible. Others are tied to the calendar.
Ask whether anything in your situation deserves attention before year-end. Depending on your circumstances, that conversation might include workplace retirement plan contributions, required minimum distributions, charitable giving, portfolio gains and losses, Roth conversions, or the timing of income and withdrawals.
The point isn’t to make a financial move simply because the calendar says December. It’s to understand whether an opportunity or obligation applies to you and how it fits into the larger plan. A Roth conversion, for example, may affect taxable income, future required distributions and Medicare premiums. Selling an investment for tax reasons should still make sense within the portfolio.
This is also where coordination can help. Your financial advisor can address the investment and retirement implications of a decision, while your tax professional can advise on the tax consequences and your attorney can address legal or estate matters.
3. Is My Investment Strategy Still Appropriate for Where I Am Today?
It’s easy to judge a portfolio by one number: whether it went up or down. A better year-end discussion goes further.
Ask whether your current mix of investments still fits your goals, income needs, time horizon and comfort with market risk. That question becomes especially important around retirement. A portfolio designed primarily to accumulate assets during your working years may need to serve a different purpose once you begin drawing income from it.
If you’re already retired, ask where the money you expect to spend over the next few years will come from. How much is held in cash or short-term investments? Which accounts will fund withdrawals? How could an extended market decline affect that strategy?
The goal isn’t to predict what markets will do next year. It’s to make sure your plan doesn’t depend on getting that prediction right.
4. What Should I Be Preparing for Next Year?
Year-end planning should look forward as well as backward.
If you receive Social Security, benefits will increase 3.6% in 2027 under the cost-of-living adjustment announced by the Social Security Administration. The agency estimates that the average retired worker will receive about $75 more per month beginning in January.¹
That’s useful information, but the planning conversation should go beyond the headline. How will the change affect your household income? Does your spending plan need to change? Are there upcoming withdrawals, major purchases or charitable gifts that should be included in next year’s cash flow?
Medicare deserves attention, too. Income-related adjustments to Medicare Part B and Part D premiums generally use tax-return information from two years earlier. Ask whether a Roth conversion, capital gain or other increase in taxable income could affect future premiums, and remember that final 2027 premium amounts had not yet been announced as of October 22, 2026.
If retirement is approaching, this is also a good time to discuss when to claim Social Security, how to handle health insurance before or after Medicare eligibility, and where retirement income will come from. Looking ahead now gives you more time to make thoughtful decisions instead of reacting later.
5. Is My Financial Life Organized and Protected?
Not every important year-end question involves investments.
Ask whether your beneficiary designations are current. Make sure your advisor knows about financial accounts held elsewhere. Review whether the right people know whom to contact if something happens to you.
This is also a good time for a cybersecurity check. Review how you protect your financial accounts. Strong, unique passwords and multifactor authentication are good starting points. Make sure you and your family know to pause before acting on an unexpected request to send money, share a verification code or disclose sensitive information.
For families, consider one more question: Would someone else know what to do if I could not handle our finances tomorrow?
That doesn’t mean giving family members access to everything. It means making sure the right people know that a plan exists, where important information can be found and which professionals to contact.
What Should You Bring to a Year-End Financial Planning Meeting?
You usually don’t need to arrive with every financial document you own. Start with anything that changed. Helpful items may include:
- Recent investment and retirement account statements
- Updated income and spending information
- Social Security or Medicare notices
- Changes to insurance coverage or estate documents
- Charitable giving records
- Details about a major purchase, sale, inheritance or family event
Most importantly, bring your questions. If something has been on your mind, it belongs in the conversation.
A Good Year-End Meeting Should Leave You With Clarity
You don’t need to make a change simply because another year is ending.
Sometimes a year-end review uncovers something that needs attention before December 31. Other times, it confirms that the plan you already have remains appropriate. Both can be valuable outcomes.
The purpose of a year-end planning meeting is to understand where you stand, what has changed and what deserves your attention next. You may leave with a few actions to take before December 31, or simply with greater confidence that your plan remains on track. Either way, the goal is clarity about what comes next.
Source: Social Security Administration, “2027 Cost-of-Living Adjustment (COLA) Fact Sheet,” October 2026.
The information contained in this blog is provided for educational purposes only and does not purport to be a complete description of the matters discussed. The information has been obtained from sources considered reliable, but Aspire Wealth Group and Raymond James do not guarantee that it is accurate or complete. This material is not intended to provide legal or tax advice. You should discuss your individual circumstances with the appropriate professional.
Have questions about your financial plan?
Every financial situation is unique. If you’re wondering how the ideas in this article apply to your own goals, we’re here to answer your questions and discuss how we may be able to help.
Explore More Insights
The Final 5 Years Before Retirement Guide
The final years before retirement may be among the most important planning years of your financial life. They deserve to be used well.
Read More >
By Tax Season, Some of Your Best Tax Planning Opportunities Are Gone
Discover why some tax planning opportunities expire at year-end and which financial decisions may deserve attention before December 31.
Read More >
RMDs, Roth Conversions, and QCDs: What Retirees Should Know
Learn how RMDs, Roth conversions, and Qualified Charitable Distributions may affect retirement taxes, charitable giving, Medicare premiums, and the assets you leave to your family.
Read More >
