A Financial Calendar to Help You Plan Your Finances All Year Long


Calendars, checklists and a big to-do desk pad have long been part of my organizational tool kit. In terms of usefulness, I’d rank them right up there with spreadsheets. (You might not remember Lotus 1-2-3, a discontinued spreadsheet program from the 80s, but I do!)

As a Type-A financial planner, I’m always willing to give new strategies for keeping my ducks in a row a test run. I’ve done my research over the years, and here’s what I’ve learned: For the big picture, nothing works better at keeping you on track than a financial calendar.

Ready to get organized? Here’s your perfect month-by-month framework that includes a money must-do, a few financial reminders and key dates. It’s as easy as 1-2-3.  


Each January gives us a fresh beginning. Take advantage of the motivation, energy and commitment that comes with a new year, and channel it into positive change.

  • Money must-do: Assess where you stand.

Whether you’re trying to dig out of debt, get a handle on your budget or build for the future, start by taking a close look at your current situation. This financial snapshot should include your income, expenses, assets and liabilities.

  • Don’t forget: Check your credit report; update your financial goals.
  • Key dates: Jan. 1–Feb. 14 (time frame for switching from Medicare Advantage to original Medicare)


Buried in the gloomiest part of the year, Valentine’s Day brings a glimmer of heart-shaped hope and happiness. There are also plenty of financial tasks waiting to be tackled. While you’re huddled up inside, why not dig in?

  • Money must-do: Schedule a team talk.

I don’t suggest this for Valentine’s Day, but if you haven’t already got a “money talk” routine, set one up with your spouse or partner. Dedicating a few minutes each month or week — yes, I’ve even seen couples do it every day — to talk about your financial objectives and challenges can help you stay on the same page as you work toward your shared goals.

  • Don’t forget: Adjust tax withholdings by updating your W-4 with your employer. Modify your budget to reflect last month’s assessment and takeaways from your team talk. If you’ve had a pay raise, consider using the extra money to pay down debt or boost your emergency fund, IRA, 401(k), or other employer plan contributions.
  • Key dates: Last week of February (America/Military Saves Week)


Here in San Antonio, we remember the Alamo. But for the rest of the world, St. Patrick’s Day reigns supreme. In that context, I’ll focus on good luck.

  • Money must-do: Make the most of your “green.”

If you’re getting a windfall tax refund, plan first to pay down debt, second to add to your savings and then to invest for your future. (It’s OK to build a little fun into your plan so you can balance prudent planning with enjoying life!)

  • Don’t forget: Discuss the difference between Roth and Traditional IRAs with your tax advisor.


Taxes, taxes, taxes. OK, April Fool’s Day, start of the baseball season … and taxes. Because of last year’s Tax Cuts and Jobs Act, you may have changes in your filing routine.

  • Money must-do: Spring clean your tax files.

Year ago, an elderly client shared her financial records with me and asked for some advice on what to keep and what to throw away. I was shocked by the hundreds of boxes of cancelled checks, receipts and other tax files she’d kept over the years. The IRS advises that we keep tax files dating back three years. I told her the same … but I think the boxes are still in her basement.

  • Don’t forget: Talk with your tax advisor about adjustments you might need to make based on the new tax law.
  • Key dates:  April 1 (deadline for the year’s first Required Minimum Deduction), April 15 (tax filing deadline)


For many students, May marks the end of the school year. Summer vacation brings challenges and opportunities with respect to childcare and camps for your kids and grandkids. (May is also the start of moving season!)

  • Money must-do: Revisit your financial plan.

I used to joke with clients that the only guarantee I could make is that their financial plan would be outdated before the ink dried. This is a great time to take a look at your financial plan, and if your life’s circumstances have changed, update it.

  • Don’t forget: Talk to your financial advisor about the pros and cons of a Coverdell Education savings account or 529 college savings plan. Check your credit report.


Summer is here! Vacation time for many, it’s also the beginning of hurricane season. So ….

  • Money must-do: Prepare for the unexpected.

Check the status of your emergency fund. With three to six months of your expenses in a savings account, you’re in good shape.

  • Don’t forget: Create an inventory of your personal property — video and written.
  • Key dates: June 30 (deadline for college-bound kids to submit their Free Application for Federal Student Aid, or FAFSA)


Independence Day. This holiday represents all that we are trying to accomplish from a financial standpoint — getting to a place where we’re financial secure, financially independent and free to pursue our dreams.

  • Money must-do: Determine your savings goal. How much do you need to achieve financial independence? If you don’t know what you’re shooting for, it’s hard to stay on track. To figure out how much you’ll need and what you should be saving, use online tools, such as USAA’s Retirement Planner, or make an appointment with a financial planner.
  • Don’t forget: Start a savings account for next year’s vacation.


The kids are heading back to school, the transition from laid-back summer to fast-paced fall is in full swing, and it’s time to take advantage of the opportunities that result from this annual ritual.

  • Money must-do: Take a look at your college savings plan.

In recent years, the amount of student loan debt college grads carry has inched towards $40,000. To help reduce this burden on your loved ones, consider a contribution to their college savings. If they don’t already have an account, help them to start one.   

  • Don’t forget: Give your teen some cash and use back-to-school shopping as an opportunity to teach basic budgeting.
  • Key dates: Tax-free shopping day or weekend (do a quick online search for your state’s dates)


With the kids back in school, you’re likely hitting your stride as you settle into a fall routine. September is Life Insurance Awareness month. As such, make these tasks part of your financial routine.

  • Money must-do: Perform a general insurance check-up.

Lots of life events signal a need for us to update our insurance — kids getting their driver’s license, starting their first job, leaving the house, etc. Confirm that your insurance reflects your current situation.


There’s a lot to be frightened about beyond Halloween’s ghost and goblins. Early in 2018, the personal savings rate plummeted to just above 2%; credit card debt is skyrocketing; and the ranks of the un- and underinsured is growing like a herd of zombies. This month, combat the scary.

  • Money must-do: If you’re enrolled in a Medicare Advantage or prescription drug coverage, take advantage of the Annual Election Period. Plans are constantly changing, and it could be an opportunity to reduce your premium or expand your benefits. Talk to your insurance agent or USAA to compare your coverage and costs, and make changes if appropriate.
  • Don’t forget: File your Free Application for Federal Student Aid (FAFSA)
  • Key dates: Oct. 15–Dec. 7 (window to change Medicare health and prescription drug coverage)


The holiday season moves into full swing this month. Typically, Thanksgiving is a time for families to come together, and that’s where our calendar events will focus this month.

  • Money must-do: Talk family finances.

While the new tax law makes estate taxes less of an issue for the vast majority of Americans, family gatherings are still a great time to review your plans and wishes with respect to long term care, potential incapacity and the management of day-to-day financial affairs.

  • Don’t forget: Get your affairs in order by updating your beneficiary arrangements, wills and other estate planning documents. Make your “on-budget” holiday shopping list.
  • Key dates: Oct. 15–Dec. 7 (window to change Medicare health and prescription drug coverage)


With all the joyful distractions of decked halls, boughs of holly and stacks of gifts, it’s hard to keep our focus on finances during all holidays. But if you stick to your budget and hit a couple of financial commitments, you’ll wrap up the year on a high note.

  • Take your Required Minimum Distribution.

If you’re 70½ or older, don’t miss the Dec. 31 deadline to take your minimum distribution from your retirement plan or IRA account (unless you just turned 70½ and it’s your first RMD, which you could delay until April 1st the year after your turn 70½). A 50% penalty is punitive for those who miss this deadline. And don’t forget the impact RMDs have on your budget — increased taxation of Social Security and increased Medicare premiums. Bah Humbug!

  • Don’t forget: Rebalance your portfolio; set up year-end doctor’s appointments/medical procedures.
  • Key dates: Dec. 31 (end of tax year)
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