Imagine turning financial planning into a manageable process with tasks divided throughout the year. This guide provides a month-by-month breakdown of key deadlines and practical steps to help you stay organized in 2025. We believe your future self will be grateful!
Financial management may consist of handling numerous components, which can be daunting. Instead of tackling everything simultaneously, try dividing it into smaller parts and addressing a few at a time. This month-by-month Financial Planning Guide is crafted to assist you in completing tasks with potentially reduced stress.
January
Define your financial goals
The beginning of a new calendar year can be an excellent time to pause, take stock, and decide what financial goals you’d like to achieve in the next 12 months. Maybe you want to pay down debt, develop a comprehensive legacy plan, or take concrete steps towards an early retirement.
No matter your goals for this year, we invite you to use two strategies we believe can increase your likelihood of success. First, write them down somewhere you’ll see them regularly. Second, make a plan for how you’ll achieve them. The more you can break your goals down into easy action steps, the more likely we think you’ll be to reach December with achievements you can be proud of.
Pay the first set of your estimated taxes
If your payroll withholdings aren’t sufficient to cover your tax payments, send your estimated payment to the IRS for money earned between September 1 and December 31 of last year. Note that this covers four months, not three! This is your last payment for the tax year, so it can also be your last chance to catch up before filing your tax return in April.
February
Organize your tax documents
The IRS requires most tax forms to be delivered to you by January 31, so it may be a perfect time to pull together all of the documents you need to do your taxes, including W-2s, 1099s, and receipts for any deductions (such as charitable donations or medical expenses).
If you’re hiring a CPA to file your taxes, get your documents to them sooner than later—it could make them more likely to be able to file by the April 15 deadline.
Get romantic with a spousal IRA
When your spouse says they want something special for Valentine’s Day, ditch the chocolates and consider a gift of a retirement contribution. If one spouse is working and the other is not, the non-working spouse may still be eligible to contribute to a spousal IRA. This is a special rule, since normally a taxpayer is required to have earned income to contribute to an IRA. And, it can help non-working spouses accumulate retirement savings that are otherwise reserved for income-earners.
March
Check yourself on "lifestyle creep"
According to LinkedIn, March is the most popular month for employers to pay out bonuses. Many people spend that money before even receiving it, but you’re no (lowercase f) fool. Rather than incorporating your bonus into your ongoing spending, consider saving a portion before splurging on the fun stuff. This can help get you closer to retirement in two ways: First, you’re adding to that all-important nest egg, and second, you’re limiting the upward creep on what it takes to maintain your lifestyle.
Review your 401(k) and other employer plan contributions
In 2025, employees can contribute up to $23,500 to 401(k) plans and 403(b) plans if you’re under 50, and $31,000 if you’re 50 or better. There’s now an additional catch-up contribution opportunity if you’re between 60 and 63—you can contribute up to $11,250. Review your contributions so you’re confident you’re setting aside enough to meet your retirement goals. If your employer offers a retirement contribution match, double-check that you’re taking advantage of as much of it as you reasonably can.
Since it’s Women’s History Month, we thought it would be worth mentioning that the catch-up contribution to retirement plans was originally conceived as part of The Economic Growth and Tax Relief Reconciliation Act as a way to help women in particular save for retirement!
April
Celebrate Tax Freedom Day
Tax Freedom Day, not to be confused with the tax deadline in the U.S., usually falls around mid-April. This is the date the Tax Foundation estimates the average U.S. taxpayer would pay their tax burden (state, local, and federal) if everything they earned was paid in taxes starting January 1. Getting to keep some dollars in your pocket after this date is certainly worth a celebration.
Catch up on last year's retirement contributions
If you haven’t maxed out your contributions to your Roth or your traditional IRA for 2024, you have until tax day to add more funds. Since every tax year has limits on how much you can contribute, putting 2025 dollars into 2024 contributions may help you sock away a bonus, a tax refund, or any other unexpected income for your future. Not sure if this is the right strategy for you? Our catch-up contributions guide can walk you through it.
Complete prior year FSA claim reimbursements
Don’t forget to get that money! Flexible spending accounts (FSAs) have a grace period that allows you to submit claims from the prior year’s expenses into the new calendar year. For your 2024 FSA, the deadline to submit claims on 2024 expenses is April 30.
Pay the second set of your estimated taxes and file annual tax returns
If your payroll withholdings aren’t sufficient to cover your tax payments, send your estimated payment to the IRS for money earned between January 1 and March 31.
It’s also time to file your annual tax return—or an extension. If you’re not filing an extension, the IRS expects you to pay anything you owe for the 2024 tax year by the April 15th deadline.
May
Confirm 529 plan deduction eligibility
If you contribute to a college savings plan, check whether your state allows you to deduct those contributions.
With the latest tax change, known as SECURE Act 2.0, excess savings in 529 plans may be eligible for conversion to a Roth IRA. Along with previous changes expanding the use of 529 plans for secondary tuition and student loan payments, these plans have become more flexible and potentially useful for parents and grandparents.
Review your financial goals
You’re a third of the way through the year, making this a good time to assess your progress toward the financial goals identified in January. Evaluate whether your plan is effective, if your approach needs adjustment, or if your goals themselves need refining.
Goals are tools to help create the life you want, and updating them to reflect current circumstances can ensure they remain relevant.
June
Pay the third set of estimated taxes
If payroll withholdings don’t cover your tax payments, send your estimated payment to the IRS for income earned between April 1 and May 31. Note that this payment covers two months, not three.
Open or add deposits to an IRA
Consider opening an IRA if you don’t already have one—especially if you anticipate being in a lower tax bracket later in life. Contributing to an IRA may lower your current tax bill, and the funds can grow tax-free until withdrawal.
If you already have an IRA, review the 2025 contribution limits: $7,000 for those under 50 and $8,000 for those 50 or older. Adding funds can help you move closer to your retirement goals.
Plan your required minimum distributions
For those required to take minimum distributions (RMDs) from retirement accounts, such as 401(k)s or traditional IRAs, begin planning now. Decide on the amount to withdraw, whether to take it as a lump sum or in increments, and the timing based on market conditions. You can reinvest withdrawn funds, which can provide additional flexibility.
July
Add transfer-on-death designations to taxable accounts
While you’ve likely named beneficiaries for accounts like your 401(k), IRA, and life insurance, you can do the same for brokerage accounts using transfer-on-death (TOD) designations. This step helps to simplify the process for heirs, bypassing probate for these accounts, though they’ll still be part of your estate for debt settlement.
August
Check beneficiary designations
After life changes, it’s essential to update your beneficiary designations. Ensure they’re accurate for life insurance, 401(k) accounts, and IRAs. Remember, these designations override what’s written in your will.
Review your estate plan
Assess existing estate planning documents, such as wills, trusts, and powers of attorney, to ensure they’re current. Changes in circumstances may necessitate updates.
If you don’t have these documents, consider consulting a lawyer. Having them in place can ease potential crises for you and your loved ones.
September
Pay the fourth set of estimated taxes
If payroll withholdings are insufficient to cover taxes, send the IRS your estimated payment for income earned between June 1 and August 31.
Evaluate your financial preparedness
National Preparedness Month offers an opportunity to review your financial resilience:
- Ensure your emergency fund covers 3–6 months of expenses. These funds should be fully liquid and accessible immediately.
- Check your insurance coverage for death and disability, ensuring that any disability coverage is paid with after-tax dollars for potential tax-free benefits if needed.
- Update retirement account beneficiaries and add TOD designations to bank and brokerage accounts. A Trusted Contact for brokerage accounts can address issues if you’re unreachable.
Review your financial goals
Two-thirds of the year has passed, which can make it an ideal time to reassess the goals set in January. Adjust your plan or goals as needed to align with current circumstances.
October
Plan for Medicare open enrollment
Open enrollment season allows changes to Medicare benefits, such as joining or modifying Medicare Advantage or drug plans. Confirm your current plan meets your needs.
Address required minimum distributions
If you’re 73 or older, you must take RMDs from pre-tax retirement accounts like 401(k)s and traditional IRAs. Begin planning early to reduce the chance of penalties and to help eliminate year-end stress.
November
Prepare for employer open enrollment
Employer open enrollment is your chance to adjust benefits, such as health insurance, FSAs, and HSAs. Review options to maximize savings and long-term benefits. HSAs, for instance, offer triple tax benefits: tax-deductible contributions, tax-free growth, and tax-free qualified distributions.
Consider tax-loss harvesting
If you’ve realized significant capital gains, you might offset them by selling investments at a loss. Be mindful of the wash-sale rule, which disallows losses if you buy back the same or similar securities within 30 days.
December
Plan for IRMAA premiums
Income-related monthly adjustment amounts (IRMAA) for Medicare Parts B and D update in January, based on income reported two years prior. High earners should review their Social Security Benefit Rate Change Notice to understand potential cost increases.
Estimate investment income
Prepare for tax season by estimating realized gains, losses, and year-to-date earnings from interest and dividends. Early preparation can help ensure fewer surprises when filing.
Here’s to a successful 2025!
Sources:
1 Walker, Kate Eberle. “Quitting before your bonus is paid: what to know before you go,” Linkedin. March 9, 2018. Accessed November 27, 2024.
2 IRS.gov. 401(k) limit increases to $23,500 for 2025, IRA limit remains $7,000. Accessed November 27, 2024.
3 Congress.gov. “H. Rept. 107-84 - Economic Growth and Tax Relief Reconciliation Act OF 2001.” Accessed November 27, 2024.
4 FSAFEDS.gov. “FAQs: Key Dates and Deadlines.” Accessed October 21, 2024.
5 Fidelity. “HSA contribution limits and eligibility rules for 2024 and 2025.” Accessed November 27, 202
The information in this material is not intended as tax or legal advice. Stratos Wealth Advisors or Flagship Financial Advisors does not provide tax or legal services. Please consult legal or tax professionals for specific information regarding your individual situation."