Calendars, checklists and a big to-do desk pad are part of my organizational toolkit. In terms of usefulness, I’d rank them right up there with spreadsheets. 

As a Type A financial planner, I’m always willing to give new strategies 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. 

JANUARY 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 includes your income, expenses, assets and liabilities.
  • Don’t forget: Check your credit report; update your financial goals.
  • Key dates: Jan. 1 to Feb. 14 (period for switching from Medicare Advantage to original Medicare)


FEBRUARY While you’re huddled up inside during this cold time of year, why not dig in?

  • Money must-do: I don’t suggest this for Valentine’s Day, but if you don’t already have a “money talk” routine, set one up with your spouse or partner. Dedicating a few minutes each month or week to talk about your financial objectives 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)


MARCH Here in San Antonio, we remember the Alamo. For the rest of the world, March is about St. Patrick’s Day, so 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 adviser.


APRIL April Fool’s Day, the start of 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. Years ago, an elderly client asked for advice on what to keep and what to throw away. She had hundreds of boxes of cancelled checks, receipts and other files. The IRS advises 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 adviser 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, or RMD), April 15 (tax-filing deadline)


MAY For many students, May marks the end of the school year. Summer vacation brings challenges and opportunities with respect to child care and camps. (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. If life’s circumstances have changed, update it. 
  • Don’t forget: Talk to your financial adviser about the pros and cons of a Coverdell education savings account or 529 college savings plan. Check your credit report.


JUNE Summer is here! Vacation time for many families, it’s also the start 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)


JULY Independence Day represents all we hope to accomplish from a financial standpoint – getting to a place where we’re financially secure, financially independent and free to pursue our dreams. 

  • Money must-do: 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 visit a a financial planner. 
  • Don’t forget: Start a savings account for next year’s vacation. 


AUGUST The kids are heading back to school, and the transition from laid-back summer to fast-paced fall is in full swing, so 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 toward $40,000. To help reduce this burden on your loved ones, consider a contribution to their college savings. If they don’t have an account, help them 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)


SEPTEMBER It’s Life Insurance Awareness Month, so add these tasks to your financial routine.

  • Money must-do: Perform a general insurance checkup. Lots of life events signal a need to update our insurance: kids getting their driver’s license, starting their first job, leaving the house. Confirm that your insurance reflects your current situation. 
  • Don’t forget: Use a life-insurance needs calculator like the one at or


OCTOBER The personal savings rate is just above 2 percent, 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 make changes if appropriate. 
  • Don’t forget: Get started on filing your FAFSA 
  • Key dates: Oct. 15 to Dec. 7 (window to change Medicare health and prescription drug coverage) 


NOVEMBER Typically, Thanksgiving is a time for families to come together, and that’s where our calendar events will focus this month.

  • Money must-do: While the new tax law makes estate taxes less of an issue for most Americans, family gatherings are still a great time to review your plans and wishes with respect to long-term care 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 to Dec. 7 (window to change Medicare health and prescription drug coverage)


DECEMBER It’s difficult to keep our focus on finances during the holidays. But if you stick to your budget, you’ll wrap up the year on a high note.

  • Money must-do: 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 1 the year after you turn 70½). A 50 percent 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) 


J.J. Montanaro is a certified financial planner with USAA’s Military Affairs Advocacy Group. USAA is The American Legion’s preferred provider of financial services.