Your Financial and Tax To-Do List: Steps to Take Now to Pay Less in 2025

Do you ever wake up in the middle of the night in a panic, because you just remembered something you had to do—a task that had slipped your mind—that is very important?

I hate to admit it, but that happens to me … especially every three months or so when I have to pay estimated quarterly taxes. You would think that as someone who has been self-employed for several decades, those dates would be hard-wired into my brain. But—like a lot of other people with their own businesses—daily to-do lists become so long that sometimes certain tasks do get missed.

And I don’t want to miss any deadlines—especially financial dates such as tax payment due dates, IRA contribution deadlines, etc.—that may come with unwanted costs or missed opportunities.

Consequently, I decided it was time to create a monthly financial checklist that I can mark on my calendar to keep me from worrying about missing important dates and to help me become more organized.

I found many resources for such checklists, including asset management, brokerage companies, and other advisory firms. After reviewing them and narrowing down the choices, I came up with the following list that should be fairly easy to implement for most investors. But feel free to add any additional ideas that will help you customize your list!

2025 Month-by-Month Financial/Tax To-Do List

January

If you are nearing (or already there) Medicare age, open enrollment for Medicare Advantage begins January 1. There are tons of Advantage plans and Supplement offerings, so find a great insurance agent to help you wade through this minefield to determine which plan is right for you.

If you have college students seeking financial aid, January 1 is also the deadline to complete the Free Application for Federal Student Aid (FAFSA).

Plan to save more. This would be a perfect time to assess your savings and investments and determine if you can put away a bit more money in 2025. If you are currently saving/investing 10%, why not plan to increase that to 12%-15%? As you can see in the following graphs, just a small difference in your contributions can turn into a whole lot of financial freedom over the long term!

Do a retirement goal checkup. Are you on track for your retirement goals? If not, it may be time to review your expenses and income to see where you can allocate additional funds for your golden years.

For 2024, you can contribute up to $23,000 in your 401(k) plan (for those under 50) and $30,500 for those 50 and older. Note that in 2025, the catchup contribution for folks aged 60-63 is $10,000. And if you have IRAs, you can contribute up to $7,000 (under 50) and $8,000 if you are over 50 this year (increasing to a $5,000 catch-up contribution for ages 60-63 in 2025).

If you’re not making the maximum allowable contributions to those accounts, I hope you’ll recalculate your budget so you can do so. After all—especially with your 401(k)—you will be leaving free money (your employer’s contributions) on the table if you don’t contribute the maximum!

And why not put your retirement savings on automatic? Most likely, your 401(k) contributions are automatically taken out of your paycheck. But did you know you can set up automatic contributions to your IRA also? Just contact the institution that holds your IRA funds. Easy-peasy.

Consider a Roth IRA conversion. If your income has not exceeded the Roth limit, you may want to consider doing a Roth conversion to convert your pre-tax retirement savings in a traditional IRA into a post-tax Roth IRA, which would exclude you from having to pay taxes on future earnings.

Make a plan to pay off high-interest debt. Forbes recently reported that the average interest rate on credit card debt in the U.S. is 28.46%—outrageous! For every dollar you spend on interest, that’s a dollar that doesn’t get invested (and also a dollar that is accumulating more interest)! And especially, if you are nearing retirement, you do not want to enter that life stage with a mountain of debt.

Quarterly estimated taxes for independent contractors and business owners are due January 16. You can also automate these payments; please check with your accountant.

February

Rebalance your investment portfolio. January is a great month to take “stock” of your holdings and see just how you are doing at meeting your long-term goals. Fortunately, most of you have probably greatly improved your portfolio with the healthy performance of the stock market in 2024.

Consequently, you may be overinvested in certain sectors and underinvested in others. I love setting aside some money for “fun,” more speculative investments, but I’m a great believer that—for the most part—investors should practice diversification—by sector, style, and market capitalization, and invest in mainstream (not too risky) companies.

Start gathering your tax documentation for your accountant. Your 1099s, W-2s (supposed to be completed by January 31), mortgage interest and home insurance statements, brokerage statements, payments made to local, state, and federal tax organizations, and any other deductions. In case you are not itemizing your deductions, here are the standard deductions for 2025:

Other financial aid applications for college-bound students are generally due from January to mid-February, so plan to submit applications to https://cssprofile.collegeboard.org before then.

March

If you haven’t yet made your 2024 IRA contribution, now would be a good time to do so.

Consider making your contribution to a health savings account (due by April 15). For 2024, if you have self-only HDHP coverage, you can contribute up to $4,150. If you have family HDHP coverage, you can contribute up to $8,300. In 2025, those contribution limits rise to $4,300 and $8,550 respectively. If you’re over the age of 55, there’s also an additional $1,000 catch-up provision.

The filing deadline for S corporation and partnership returns is March 16, or the next business day if March 16 is a Saturday, Sunday, or holiday unless you file for a six-month extension.

Medicare Advantage open enrollment period ends on March 31st.

April

If you turned 73 in 2024, you have until April 1, 2025, to take 2024’s required minimum distribution (RMD). After that, you will need to take your annual RMD by the end of each year.

April 15 is the tax filing deadline. E-file or postmark your individual federal and state tax returns by midnight or request an extension to push your deadline back to October 15. Also:

• File your federal gift tax return or extension by April 15th for gifts made between January 1st – December 31st in the prior year.
• File federal estate and trust income returns or extensions.
• File your partnership income tax returns or extensions.

Quarterly estimated tax payments are due by April 15.

Clean up your tax files. The IRS says you should keep records for three years from the date you filed your original return or two years from the date you paid the tax, whichever is later, if you file a claim for credit or refund after you file your return. And retain records for seven years if you file a claim for a loss from worthless securities or bad debt deduction. Don’t forget to make sure your investment documents regarding your cost basis are in your save file (although your brokerage firm probably has this information). Mutual fund companies and brokerage firms are now required to maintain cost-basis information, but that wasn’t the case until early last decade.

Don’t hesitate to shred all those documents that are cluttering up your file cabinets. When my mom passed, I kid you not—I found envelopes (not just the invoices) for utility bills dating back to 1949! Please don’t do this to your children! And by the way, when I moved last year, I found that I had accumulated an enormous amount of paper, and I found a very reasonable local company that came to my house and shredded the unneeded documents right in front of me. And even better, their bill was much less than the big chain office supply stores charge for shredding. Additionally, our local banks offer free shedding (up to so many bags/boxes) a couple of times a year, so check around.

Organize your documents—wills, trust documents, tax returns, living wills, and other important documents. Store very hard-to-replace documents (birth and wedding certificates, for example) in a safe deposit box or fireproof box.

And make a list of all your documents and where to find them as well as the location and account numbers for all your banking, brokerage, and insurance accounts, so your heirs won’t have to deal with paper confusion as well as grief. Give a copy to your attorney and/or accountant and retain your copy in a safe place.

Consider going paperless. No doubt, your financial providers (like mine) have been sending you numerous emails to do this. Perhaps it’s time to do this and get that never-shrinking pile of papers off your dining room table! Just make sure your computer security is up to snuff.

May

May is Social Security Education Month. If you are nearing retirement age, log in to your Social Security account and check for accuracy. You can also look at your estimated benefits based on the age you begin receiving them, which will help you decide when to apply for your benefits.

Is the money you have set aside for emergencies adequate? Experts recommend that everyone should have three-six months’ worth of expenses in easily accessible cash (not in the stock market).

According to the IRS, every organization exempt from federal income tax under Internal Revenue Code section 501(a) must file an annual information return by May 15. Exceptions exist for churches, interchurch organizations of local units of a church, and a convention or association of churches.

June

If you don’t already have one, June is a good time to review your investment goals by creating your investment policy statement (IPS). Your IPS will define your financial goals (e.g., retirement, vacations, education, etc.), completion and duration times, your asset allocation strategy, and establish how often you will monitor your portfolio (I recommend at least every three months).

Consider drafting a retirement policy statement. This is basically a budget—your expected retirement income and estimations of your monthly and yearly expenses. Financial advisors used to think that retired people would spend less money than when they were working. That isn’t necessarily true. You may spend it on different things (travel versus work clothing, medical outlays, or education for grandchildren) but you have to consider that your expenses may not decline much during your retirement years.

Quarterly estimated tax payments are due by June 16.

June 21st is End Alzheimer’s Day, so this may be a good time to consider long-term care coverage. According to the 2024 American Association for Long-Term Care Insurance (AALTCI) annual Price Index survey, the average annual premium for a $165,000-benefit policy with no inflation protection is $950 for a single male (age 55) and $1,500 for a single female (age 55). For a couple who are both age 55, the average combined annual premium is $2,080.

Premiums may be expensive, but they don’t look too bad compared to the cost of long-term care:

Monthly Median Costs: USA - National (2023)

Of course, the older you are when you buy long-term care insurance, the higher the premiums will be.

June 28th is National Insurance Awareness Day, a good time to review your insurance policies and perhaps compare rates. Also, make sure you are claiming all the discounts that may be available to you, such as multi-policy, employee, student, and safety and security discounts.

Conduct a cost audit of your investment plan. If you are invested in exchange-traded funds (ETFs) or mutual funds, review the associated expenses. You may find a fund that performs as well that will cost you less in expenses. Believe me, they exist.

Likewise, review your brokerage and/or asset management accounts to assess your trading and management fees. And don’t be afraid to negotiate!

Listen, these expenses and fees can add up significantly over time, and they cut into your investment dollars, so it’s worth your while to review them annually.

Assess your tax efficiency. Are you contributing the maximum to your 401(k) and IRA’s? How about your HSA? Is a Roth or Traditional IRA better for you? As a reminder…

* Age 70½ (if you were born before July 1, 1949), age 72 (if you were born after June 30, 1949, and before January 1, 1951), or age 73 (if you were born after December 31, 1950).

Source: Mission.org

August

Is your estate plan in order? Of course, you don’t want to think about it. Hardly anyone does. But I’ve been privy to plenty of estate planning conversations and discussions when there was no estate plan, and believe me, your demise will cause a lot less consternation (and fighting) if your wishes are known.

You’ll need to consider living wills, trusts, wills, guardianship for minor children or special-needs loved ones, what happens to your house or business (or pet), and who gets what (possessions as well as financial assets). Keep in mind blended families and the problems inheritances can cause.

August through December are prime months to search for college scholarships for the following school year’s fall semester.

August is usually the time of the year for back-to-school sales tax holidays that your state may offer. Taxadmin.org lists the holidays by state.

Review the IRS’s 529 Plan qualified education expenses to determine how/when you can use the funds. Savingforcollege.com may help.

Consider putting your utilities on a budget plan. That way, you will know exactly what you need to set aside for these monthly bills.

September

September is National College Savings Month. This is a perfect month to investigate 529 and other college savings contributions for the following school year. For more information, see the IRS page on qualified tuition programs. Don’t forget, the retirement legislation called Secure Act 2.0 allows you to roll over up to $35,000 in unused 529 assets into the same beneficiary’s Roth IRA, subject to annual IRA contribution limits.

Third-quarter estimated tax payments are due by September 15th.

Extended corporate, trust, estate, and partnership income tax returns are due by September 15, if you filed for an extension.

September 30th is the last day to determine beneficiaries after an IRA owner’s death. Visit this IRS retirement topics page for additional information.

Review your mobile phones, internet, home phone, television, and home security contracts for special offers, and don’t be afraid to renegotiate! Each year when I get my Sirius satellite renewal invoice, I call them up and have—so far—been able to reduce the new contract by at least 50%.

October

The CSS/Financial Aid Profile application is available beginning October 1 for early decision and early action applicants who are applying for nonfederal financial aid (most deadlines are early to mid-February). Search the CSS Profile website to see which institutions require you to submit the Profile form for financial aid consideration and research their priority filing dates.

For students entering college in the following September, the Free Application for Federal Student Aid (FAFSA) is available beginning October 1.

October 1 is also the deadline to establish a SIMPLE IRA.

Open enrollment season begins in October for certain employee benefit plans. Now’s the time to determine your contributions to a flexible spending account (FSA) or Health Savings Account (HSA).

If you received an extension on your tax return, you must have the return completed and postmarked by Oct. 15.

Original Medicare, Medicare Advantage, and Part D annual open enrollment begins October 15th and runs through December 7th.

October is Cybersecurity Awareness Month, so check your passwords and ensure your computer software has the latest security updates. Consider using a password manager to make your passwords more resilient to hackers.

November

Affordable Care Act (ACA) open enrollment begins November 1st.

Have you made any life changes (marriages, divorces, children) that may require you to rethink your financial plans?

Review your bank accounts—can you get a higher rate of interest and/or lower monthly expenses at a different institution? I’ve just completed this assessment and am moving both my business and personal accounts to a different bank, which should save me a couple of hundred dollars a year.

Review your credit cards—for interest rates, rewards, and balance transfer benefits. Depending on which rewards you prefer—travel, gift cards, cash rebates, etc.—I guarantee you that there is a credit card made especially for you!

Be on the alert for capital gains payouts. By November, mutual funds begin to publish estimates of their upcoming distributions and then they distribute those capital gains in December. Do not buy funds right before they make distributions, or you will pay for fun you haven’t had (or capital gains on returns you have not received).

December

The holidays often bring the reminder that there are many families in need, so take a moment to consider how to spread your generosity.

You may want to consider a charitable contribution (or two), which will make you feel good and also lower your taxes. Usually, the IRS allows you to deduct cash donations to qualified charities worth up to 60% of your adjusted gross income (AGI).

If you are 70 ½ or older, you can direct distributions from your IRA to charity via a qualified charitable distribution (QCD). You can donate up to $105,000 for tax year 2024. That has two benefits: reducing your taxable income and also reducing the amount of your portfolio that is subject to required minimum distributions in the future.

And if you are donating appreciated long-term investments, you won’t have to recognize the capital gains, and you can receive a tax deduction for the full fair-market value of the donation (up to 30% of your AGI).

And if you want to put something in your heirs’ stockings, in 2024, an individual can gift up to $18,000 per person per year without having to file a gift-tax return.

Consider tax-loss harvesting for losing investments. That can offset gains you have realized in your portfolio as well as up to $3,000 of your earned income. But one caveat: Investments can be repurchased only after 30 days; otherwise, you will trigger a tax.

Take your required minimum distributions from your retirement accounts.

Make your 401(k) contribution by December 31.

The deadline for ACA open enrollment is December 15th.

Consider prepayments to offset income, such as prepaying property taxes and/or an extra mortgage payment before December 31. If you own a business, you may want to pay your vendors before December 31 so you can deduct those expenses in this tax year.

Consider deferring income (such as a year-end bonus) into the new year to reduce your 2024 taxes.

Adjust your income tax withholdings, aiming to make your tax payment at the end of the year as close to zero as you can get. That way, you won’t owe the IRS, and they won’t be using your money for free!

Beware of the Alternative Minimum Tax (AMT). Consult your accountant about whether you will be subject to this tax that originated to make sure wealthy people didn’t “legally” reduce their taxes. One of the problems with the AMT is that these days, it affects not only the wealthy but an increasing portion of the middle class.

Avoid the kiddie tax, which came about to prevent mom and dad from transferring their investment taxes to their children’s lower tax brackets. For 2024, the amount of a child’s unearned income up to $1,300 is not taxed. From $1,300 to $2,600, it’s taxed at the child’s rate and amounts higher than $2,600 are taxed at the parents’ rate.

I hope this calendar helps you get better organized in your financial life. Of course, many of these monthly tasks can be switched to other months that may be more convenient for you.

Now, one last thing I want to discuss regarding financials is purely hypothetical—what the presidential candidates may do—after the election—that may affect your pocketbook!

How Harris and Trump Economic Policies May Cost—or Benefit—You

Oh, my goodness! I’m not taking sides here, but I’ll just say, historically, what the candidates proclaim now and what they actually do once they are elected are often radically different.

With that disclaimer in mind, here’s the latest economic proposals from both Kamala Harris and Donald Trump:

Harris

• Expanding the child tax credit, providing a credit of $6,000 for families with newborns in their first year and a credit of $3,600 per child after that for middle and lower-class families.
• Providing $25,000 in tax credits for first-time home buyers.
• Providing tax credits for developers building affordable housing.
• Increasing taxes on corporations and top earners.
• No tax on tips, although they would still be subject to payroll taxes.
• No tax increases on folks earning less than $400,000 annually.
• Increase health care subsidies under the Affordable Care Act, which the Harris campaign estimated would save Americans an average of $700 on their health insurance premiums.
• Levy a 25% capital gains tax on Americans whose net worth is $100 million or more, including taxing unrealized gains.
• Institute a combined 33% capital gains rate for Americans who earn more than $1 million, consisting of a 28% rate on long-term capital gains—profits from assets that are held for more than a year—and a 5% rate on the net investment income tax.
• Raise the corporate tax rate from 21% to 28% and increase the alternative minimum tax for corporations earning more than $1 billion from 15% to 21%.
• Increase the tax on stock buybacks from 1% to 4%.
• Offer a $50,000 tax credit for new small businesses—a tenfold increase from the current $5,000 credit.

Trump

• No taxes on tips.
• No taxes on overtime.
• No income tax on Social Security benefits.
• End double taxation on U.S. citizens who live abroad (would primarily benefit those earning more than $120,000 annually).
• Make auto loan payments deductible.
• Extend expiring provisions of the 2017 tax law (which expire next spring), such as a deduction for “pass-through” business entities and deductions for U.S.-based research and their investments in machinery and equipment, with provisions that would raise the marginal tax rate for top earners and lower the tax exemption for estate taxes if they expire.
• Eliminate a $10,000 cap on the state and local tax deduction.
• Lower the corporate tax rate from 21% to 15% for companies that manufacture their products in the U.S.
• Impose severe tariffs on imported goods into the U.S., up to 20%, with a higher 60% rate for goods imported from China.
• Raise the child tax credit to $5,000 from $2,000.
• Provide tax deduction for “major newborn expenses” (proposed as Trump floated providing free in vitro fertilization).
• Provide tax deduction for the total cost of home generators bought since September 1.

As I said, who knows which—if any—of these proposals would actually be put forth, and more importantly, make it through Congress.

But both candidates’ platforms would be very costly. The nonpartisan Committee for a Responsible Federal Budget reports that, “both their tax plans and other proposals—would increase the federal deficit. Harris’ agenda would add approximately $3.5 trillion to the deficit, the group estimated, with the impact ranging from not impacting the deficit at all to adding $8.1 trillion. Trump’s plan would be costlier, adding approximately $7.5 trillion to the deficit but potentially ranging anywhere from $1.5 trillion to $15.2 trillion.”

Who knows?

But let’s take this one step further, extending our speculation to which investment sectors may benefit under a Harris or Trump administration. Let’s take a look.

Investing Ideas for a Trump or Harris Win

Trump

Sectors that may benefit from a Trump win include:

1. Energy due to expected increased drilling.
2. Defense, as a result of rising spending.
3. Finance, due to deregulation.
4. Technology, maybe. The possibility of trade wars with China could harm our big tech companies, but firms with more domestic revenues may benefit.
5. Automotive, especially domestic manufacturers.

Harris

Sectors that may benefit from a Harris win include:

1. Clean energy and electric vehicles, which should see tax credits, deductions, and increased spending.
2. Healthcare, due to potential Medicare drug pricing reforms.
3. Infrastructure, as a result of rising federal spending, focusing on green industries, broadband expansion, and modernization policies.
4. Technology, especially artificial intelligence companies. Although there will be additional regulations, Harris’ connections to Silicon Valley may serve that area well.

Now, to hedge our bets, if you want to purchase investments based on a hypothetical election outcome, my recommendation would be to buy ETFs instead of individual stocks. That way, you are somewhat diversifying while reducing your overall risk.

Let’s look at some ETF ideas that are each highly recommended:

Energy: S&P 500 Energy Sector SPDR (XLE)
Defense: U.S. Aerospace & Defense iShares ETF (ITA)
Finance: S&P 500 Financials Sector SPDR (XLF)
Technology: GX Robotics & Artificial Intelligence ETF (BOTZ)
Clean Energy: Global Clean Energy iShares ETF (ICLN)
Healthcare: S&P 500 Healthcare Sector SPDR (XLV)
Infrastructure: GX U.S. Infrastructure Development ETF (PAVE)
Automotive: There is no common ETF that covers the domestic auto industry, but out of the American manufacturers, General Motors (GM) and Tesla (TSLA) rank the highest.

Now, I wouldn’t bet the bank on the election outcome, but chances are, you won’t go wrong by throwing some money in one or more of these funds. Happy investing!