Retirement is an exciting milestone; reaching it with financial confidence is truly something to celebrate. Now that you’re moving on from the workforce, you can finally enjoy the financial freedom you’ve worked so hard for over the years. While your planning has paid off, there’s still a little more to keep an eye on, even as you embrace a more relaxed pace.
Staying connected to your finances is essential, but the good news is that it doesn’t have to take much time. A yearly retirement calendar checklist can help you stay organized and ensure that nothing important slips by unnoticed.
This retirement calendar checklist can help you make the most of each year, staying on top of key dates and responsibilities without missing a beat. We want you to enjoy retirement to its fullest, and with a bit of planning, you can do just that!
January
Start the year off right by taking a fresh look at your finances. Review your income and spending from last year, and see where you stand today. A quick January check-in can help you catch any areas that need a little tweaking before they become more significant issues. This simple step sets a solid foundation for the year ahead.
January is also an important time for tax planning, just as it was during your working years. Taxes don’t take a break in retirement, so now’s a great time to get ready for tax season. Pull together any paperwork, and connect with your financial advisor and accountant to make sure you’re all set for maximum tax advantages and prepared for any upcoming changes.
February
Your financial and physical well-being are closely connected, particularly as you age. That’s why February is a perfect time to focus on health and wellness. Start by reviewing your insurance policies, checking for updates to Medicare plans and benefits, and making sure you’re familiar with your coverage and any adjustments you might need.
This month, schedule those physicals and health screenings you may have been putting off. It’s a good opportunity to discuss any questions or concerns with your doctors. Staying proactive with your health is important to maintaining independence, managing medical costs, and supporting long-term well-being through prevention and early detection. After all, health is wealth!
March
As March arrives, the tax deadline draws near. Now’s a great time to consider whether any last-minute actions are needed, such as making allowable contributions to your retirement accounts or taking advantage of options like Qualified Charitable Distributions (QCDs) if you’re eligible. Remember, you can still contribute to your IRA after retirement and even past age 70½, as long as you have earned income from a part-time job or business. And if your spouse is working, they might also consider making a spousal contribution to your IRA. A quick chat with your advisor can help you plan ahead. [1,2]
March is also a good time to revisit your emergency fund. While job loss may no longer be a concern, it’s still wise to have funds set aside for unexpected expenses. With a potentially limited income, unplanned costs like home repairs or car issues can be more challenging. Preparedness is key, as anything from natural disasters to sudden medication price hikes can happen. Take a look at your savings to see if it’s time to add to your fund or adjust your monthly savings plan.
April
April is tax month, so now’s the time to focus on completing your tax filing. Gather all necessary documents, like 1099s for income, Social Security statements, and any investment earnings. Double-checking your deductions and credits is also a good idea, especially if you made any last-minute contributions in March. If you’re unsure about anything, don’t hesitate to reach out for help from your financial advisor, accountant, or a trusted family member.
If you owe taxes, take steps to prepare for payment or explore setting up a payment plan if needed. It’s also a good moment to start exploring strategies aimed at reducing your tax burden next year.
May
Use the month of May to check on your estate and legal affairs. Life changes—relationships evolve, and loved ones may no longer be with us—which makes it important to update your plans regularly. This month, meet with your attorney and review your wills, trusts, and beneficiary designations. Make sure essential legal documents, like powers of attorney (POA) and healthcare directives, are current and reflect your wishes.
While it’s always a good idea to stay on top of these details as changes occur, dedicating a month to review everything helps ensure nothing is overlooked so you can feel confident that your plans are current when they’re needed most.
June
Summer is a great time to take a step back and reflect on your retirement lifestyle. Are you happy with how you’re spending your days? Think about whether you’re engaged in activities that bring you joy or if there are new interests you’d like to explore. Staying social is enjoyable and beneficial—research shows it can reduce the risk of cognitive decline by 26%. Think about ways to spend more time with family and friends, and remember that it’s never too late to make new friends. [3]
June is also the time to finish planning your summer getaway and start thinking about next year’s adventures. Now that your schedule isn’t tied to a job start checking off those dream destinations on your bucket list. Make it a priority to visit aging family members and friends, creating memories while you have the opportunity. Planning allows you to make the most of these moments, creating lasting memories with loved ones.
July
With the year half over, a mid-year check-in is in order. Use July to review your financial goals, assess your progress, and make any necessary adjustments.
Reassess your spending, savings, and investment performance since your January check-in. Have your priorities or circumstances shifted? If so, consider revisiting your budget or adjusting your withdrawal strategy. Keeping your plan in sync with your retirement goals will help you stay on track for the rest of the year and beyond.
August
In August, check in on your home maintenance and expenses. If you live in an older home, it might be due for some repairs or updates—a new roof, updated windows, or other improvements. By scheduling routine inspections and planning for major repairs, you can help preserve your home’s value and potentially avoid bigger expenses later on. Treat your home as a valuable asset.
This is also an excellent time to check over your property tax bills (use last year’s bill as a guide if this year’s hasn’t been sent yet) and plan for upcoming payments. Rising property taxes can sometimes make it challenging for retirees to stay in their homes, especially in growing neighborhoods. Fortunately, some states offer property tax exemptions or reductions for seniors, so look into those options and talk with your tax professional or financial advisor about other ways to reduce your property taxes. [4]
September
Though your children are likely grown and flown, you may still have educational savings accounts set up for family members. Whether you have 529 plans or Coverdell Education Savings Accounts (ESAs) in place for your grandchildren, nieces, or nephews, take a moment to assess their progress. These tools can offer a tremendous leg up for family members by helping cover the costs of elementary, secondary, or higher education, especially as education expenses continue to rise. [5]
Don’t forget contributing to these accounts may also provide you with tax advantages. Regularly checking in ensures you’re on track to support your loved ones’ futures while making the most of potential savings.
October
As Q4 begins, it’s time to review your year-end financial plans. Look closely at your investments, withdrawals, and overall budget to track your progress. Are there any adjustments you’d like to make so you finish the year strong?
It’s also a smart time to consider any charitable donations you’d like to complete by year-end. Charitable giving can offer valuable tax benefits, so consider options like donating appreciated stock or reviewing your required minimum distributions (RMDs). By preparing now, you can maximize your financial impact while supporting the causes and goals that matter most to you.
November
As November arrives, it’s a good idea to start preparing your holiday budget, covering everything from gifts and travel to food and festivities. Holiday gatherings can become even more meaningful over the years. If your family isn’t nearby, consider connecting with other seniors, inviting friends and neighbors over, or volunteering to support foster children or others in need.
We can’t emphasize enough how much your emotional and financial well-being are intertwined, so prioritizing mental health during the holiday season is essential. Enjoy seasonal activities like holiday concerts and decorated gardens. You don’t need to overspend for a memorable holiday, but planning for some extras can help you enjoy it fully.
December
December is a wonderful month for reflection. Celebrate your accomplishments and acknowledge any challenges you’ve faced. As the year comes to a close, wrap up any outstanding financial tasks, like required minimum distributions (RMDs) or year-end paperwork. Use this time to review your retirement plan one more time, making any adjustments needed to stay on track.
Looking ahead, set updated goals for the new year to help your financial choices continue to align with your retirement vision and support a fulfilling future.
Celebrate Your Past, Present, and Future
As you reflect on another year of retirement, take pride in the journey you’ve navigated and the lifestyle you’ve built. Staying engaged with your finances and personal goals empowers you to make the most of your golden years, enjoying each moment with confidence. Remember, retirement is an ongoing adventure, and you’re in control of shaping a fulfilling future.
If you have any questions or concerns about the topics covered here, we’re just a call or message away. Our team is ready to provide personalized guidance and support to help you make the most of your retirement journey.
Sources:
- https://www.irs.gov/newsroom/qualified-charitable-distributions-allow-eligible-ira-owners-up-to-100000-in-tax-free-gifts-to-charity
- https://www.bankrate.com/investing/ira/contributing-to-an-ira-during-retirement/
- https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11401599/
- https://www.aarp.org/money/budgeting-saving/info-2023/ways-to-reduce-your-property-taxes.html
- https://www.irs.gov/taxtopics/tc310
Kevin Stoddard, CFA® is the founder and president of Stoddard Financial, LLC. He holds the designation of Chartered Financial Analyst® (CFA®) and is a veteran in the financial services business with over three decades of experience. In 2004, Kevin founded Stoddard Financial, LLC. to help clients use their company benefits to improve their financial situation and leverage those and other assets to pursue and manage financial independence. Using his in-depth knowledge of portfolio management, he helps people transition from building wealth to using that wealth in seeking to create income and recognize what that looks like from an asset, income, and tax perspective.
The opinions voiced in this material are for general information only and are not intended to provide specific advice or recommendations for any individual.
This material was prepared by Crystal Marketing Solutions, LLC, and does not necessarily represent the views of the presenting party, nor their affiliates. This information has been derived from sources believed to be accurate and is intended merely for educational purposes, not as advice.