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As another year draws to a close, it's natural to reflect on the months behind us and look ahead to what's coming. For those of us in or approaching retirement, the turn of the year isn't just about resolutions—it's a valuable opportunity to ensure our financial house is in order and our plans remain aligned with what matters most.
Think of this annual review not as a chore, but as a gift to yourself and your loved ones. Just as you wouldn't let your home fall into disrepair, your financial and estate plans need regular maintenance to serve you well. Here are five critical areas to examine before December 31st.
1. Your Estate Planning Documents: When Was the Last Time You Looked?
Life has a way of changing in ways we don't always anticipate. Yet many of us created our estate planning documents years ago and haven't revisited them since.
Pull out your trust, will, healthcare documents, and powers of attorney. Do the named executors and trustees still make sense? Have you moved states, which might affect the validity or efficiency of your documents? Were any new grandchildren born? If your documents are more than three to five years old, or if you've experienced major life changes—a death in the family, a divorce, a significant change in assets—it's time to schedule a review with your estate planning attorney. A simple update now can prevent family confusion or conflict later.
2. Your Tax Picture: Opportunities Before the Clock Runs Out
Year-end is prime time for tax planning, and there are several moves worth considering before December 31st.
If you're 73 or older, have you taken your Required Minimum Distribution (RMD) from your retirement accounts? Missing this deadline triggers a hefty penalty. Even if you don't need the money, you must take it. Consider directing some or all of your RMD to charity through a Qualified Charitable Distribution (QCD)—it counts toward your requirement and can reduce your taxable income.
Review your investment accounts for tax-loss harvesting opportunities. If you have investments that have declined in value, selling them can generate losses that offset gains elsewhere in your portfolio. At the same time, consider whether it makes sense to realize gains in a lower tax bracket year.
For those with substantial estates, the annual gift tax exclusion allows you to give a certain amount per person without filing a gift tax return or using your lifetime exemption. If supporting children or grandchildren financially is part of your plan, year-end gifts can be both generous and tax-efficient. Just remember: once the year ends, that year's exclusion is gone.
3. Your Investment Strategy: Does It Still Fit?
Market conditions shift, and so do our needs. When you review your investment portfolio, you're not trying to predict the market or chase performance—you're ensuring your asset allocation still aligns with your goals and risk tolerance. Rebalancing isn't about perfection; it's about maintaining the disciplined approach that serves your long-term objectives.
This is also an excellent time to review investment fees. High fees compound over time, eating into returns you could be enjoying. Small adjustments can mean thousands of dollars over the course of your retirement.
4. Your Insurance Coverage: Still Adequate, or Paying for What You Don't Need?
Insurance needs may evolve throughout retirement. Term life insurance policies may be expiring. Long-term care situations may have changed. Medicare coverage decisions loom during open enrollment.
If you're approaching 65 or already enrolled in Medicare, review your coverage during the annual enrollment period (October 15 - December 7). Are your prescriptions still covered at reasonable costs? Does your network include your current doctors? Would a different Medicare Advantage plan or supplemental policy better suit your needs?
For homeowners, ensure your property insurance adequately covers your home's current value and contents. With property values fluctuating and construction costs rising, you don't want to discover you're underinsured when you need to file a claim.
5. Your Daily Life: Are You Living the Retirement You Imagined?
Here's a question that has nothing to do with account balances or policy documents, yet everything to do with a successful retirement: How did you actually spend this past year?
It's easy to spend decades planning financially for retirement while giving far less thought to what we'll actually do with our days once we get there. The transition from working life can be jarring. The structure, social connections, and sense of purpose that work provided don't automatically get replaced. For some, the newfound freedom is exhilarating. For others, days can start to feel unmoored, drifting by without intention.
Take an honest inventory. Did you spend meaningful time with your kids and grandchildren, or did the months slip away with vague promises of "we should get together soon"? Did you pursue that hobby you've been meaning to explore, or is it still sitting on a mental shelf labeled "someday"? Are you staying connected with friends, or have you found yourself increasingly isolated? Did you contribute to causes or communities you care about, or have you withdrawn from engagement?
This isn't about judgment—it's about awareness. Retirement is your opportunity to intentionally design how you spend your time, but it requires just that: intention. Days that lack purpose can stretch into years marked by regret.
As you look toward the new year, consider what would make it meaningful. Perhaps it's committing to a regular weekly lunch with a grandchild. Maybe it's finally signing up for that class, joining that club, or volunteering for that organization. It might be as simple as establishing a routine that includes physical activity, social connection, and mental stimulation.
Purpose doesn't have to be grand. It can be found in teaching a grandchild to fish, tending a garden, mentoring someone in your former field, or becoming a regular at the local coffee shop where the barista knows your name. What matters is that you're actively participating in life rather than passively watching it go by.
The time we have is finite and precious. Financial planning ensures you have the resources to live well. But only you can decide what "living well" actually means and make the choices that bring that vision to life.
Moving Forward with Confidence
A successful retirement isn't just about accumulating resources—it's about organizing them thoughtfully and ensuring your days reflect your values and aspirations. You cannot control everything that will happen in the coming year, but you can control how prepared you are financially and how intentionally you live.
These year-end reviews needn't be overwhelming. Start with one area, schedule the necessary appointments, and work through the list methodically. And as you review the financial elements, don't neglect the most important review of all: taking stock of how you're actually living and whether it aligns with the retirement you envisioned.
As you turn the calendar to a new year, you'll do so with the confidence that comes from knowing your affairs are in order and your days are filled with purpose—the true hallmarks of security and well-being in retirement.
Disclaimer: This blogpost provides general information about estate and financial planning and is not intended as legal or financial advice. It’s essential to consult with a qualified estate planning attorney and financial advisor to discuss your specific needs and create a plan that’s right for you.
