Fall Financial To-Dos: 5 Actions to Get Ahead for 2027

As the leaves change and the air turns crisp, life naturally slows down from summer’s hustle and bustle. Fall becomes a natural reset point, a chance to get organized and finally tackle those projects you’ve been putting off all year.

Why not make Fall a time to organize your financial life, and prepare for the year ahead?

In this blog, we will cover 5 actions that you can take right now to feel organized and confident going into the new year.

Key Takeaways:

• The last quarter of the year is a critical time to evaluate your contributions to retirement accounts, distributions from retirement accounts, and your overall financial outlook to ensure you are in the best position possible for the upcoming tax season.
• Use the time before open enrollment to determine the health care coverage that makes the most sense for you, your spouse or dependents, to avoid paying for coverage you might not need.
• Planning ahead and starting your holiday shopping before Black Friday can ease stress and potentially avoid over-consumption.

Make Your Benefits and Open Enrollment Selections

For many people, Fall is a time to consider your benefits elections for the next year. If your insurance is provided by an employer, your open enrollment period may be at a different time during the year. But if it does occur in the Fall, this is a good time to review your options and determine which choice makes the most sense for you, and your spouse or dependents.

If your employer offers it, you may also want to consider a plan that enables you to have a Health Savings Account (HSA). Not only can an HSA be used for qualifying medical expenses using tax-free money, but it can also be leveraged as a retirement account and benefit you long-term. Read our blog on How an HSA can be a Key Long-Term Asset.

For those 65 or older, one of the most important must-dos in the Fall is making your selections for Medicare coverage. This year, the Medicare open enrollment period runs from October 15 through December 7, 2026. Every year there can be changes in coverage or premiums, which is why it’s important to research the best coverage for you, and how your expected new premiums will work into your overall budget.

Evaluate Your Retirement Planning and Distributions

If you’re still working, this is the time you can look at your 401(k) contributions for the year to see if you will hit the maximum contribution limit. If you are below that limit, consider increasing your contributions for the last few pay periods of the year.

If you are retired and withdrawing funds from retirement accounts, consider how your distribution strategy has served you this year so far. Will you need more or less next year?

A financial adviser will be able to look at your age, your accounts, and your long-term goals to help determine the best distribution strategy for you while minimizing tax obligations or penalties.

Assess Your Tax Obligations

Speaking of taxes, the next action you can consider during this time is getting ready for tax season. Assessing your tax obligations in the Fall can potentially make the difference of thousands of dollars if you make the right moves before December 31.

For example, if you are not maxing out your possible contributions to tax-deferred accounts such as a 401(k) or traditional IRA, consider increasing your contributions for the remainder of the year. That little action can decrease your overall taxable income, moving less money out of the government’s hands and into your retirement pocket.

Check your withholdings from your paycheck to protect against having too little withheld and facing unexpected penalties. You can check to see if the right amount of tax is withheld from your paycheck using the IRS Tax Withholding Estimator.

Get a Head Start on Your Holiday Shopping

Do you ever say to yourself during the holiday season: “I just need one more thing and then I’m done.” That time between Thanksgiving and Christmas is the most frantic time of year in stores, which can lead to purchasing more than you budgeted or planned for.

While you are likely to find the biggest markdowns in the weeks leading up to and following Thanksgiving, getting started with some of your shopping in September or October also means you can spread your spending over a few months’ time, versus the last month of the year.

Planning ahead or spreading out your purchases can help keep you on track financially during the holidays.

Plan Your Charitable Gifting

As you get closer to the season of giving, it’s the best time to consider charitable gifting. This could be giving money to any tax-exempt organization such as a church, educational institution, public nonprofit, veteran’s organization, or fraternal society, just to name a few.

A qualified charitable distribution allows IRA owners who are 70 ½ or older to transfer up to $111,000 directly from their IRA to charity. That transfer is excluded from the IRA owner’s income and, if done correctly, counts toward the owner’s required minimum distribution upon reaching RMD age.

The key is that the distribution is directly transferred to charity. That means, if the IRA custodian makes a check payable to the IRA owner who then endorses the check to a charity, it is not qualified.

Bottom Line

There is never a wrong time to think about financial planning. But there are a few key deadlines in the last quarter of the year that require extra preparation and attention.

As you wind down from your summer travels and activities, take time to reflect on the year you’ve had and what you want for the year to come.

If you need support in taking any of these actions, meeting with a financial adviser is a great first step. They will be able to guide you into the future in a way that not only benefits you now but puts you in the best position for your retirement long-term. Schedule a complimentary consultation with one of our advisers.