Here's Which Money Rules Reset After Dec. 31 (& Which Don't)

Welcome back to another edition of "Rolling in Dough" Newsletter, where we serve up the simplest ways to save more, spend less, and build wealth with regular insights, behavioral science hacks, and tiny tips to do today. I hope to make your financial journey a little fun, simple, and totally doable, where ever you are on your wealth journey.

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What Resets on January 1

These are true resets. The clock fully starts over:

Health insurance deductibles and out-of-pocket maximums

Your deductible goes back to $0 on January 1.

Your out-of-pocket maximum also resets.

Any medical spending you already did this year no longer counts toward those totals.

Why this matters: Any medical spending from 2025 stops counting December 31st, and new costs starting January 1st will apply under the new deductible.

FSA balances (for most plans)

Many Flexible Spending Accounts are “use it or lose it” by December 31.

Some plans allow a small carryover or a short grace period, but many do not.

Why this matters: unused FSA dollars often disappear after the year ends. If you read this on December 31st before midnight, you still have time to spend this balance; you can try places like Amazon.com.

Annual contribution limits for retirement accounts

New annual limits take effect for:

• 401(k)s

• Traditional IRAs *

• Roth IRAs *

• HSAs

Any money added on or after January 1 automatically counts toward the new year’s limit, even though some accounts (like IRAs) still allow prior-year contributions until Tax Day (more on this in the section below).

Why this matters: Even though some accounts allow prior-year contributions into spring, the contribution limits themselves reset January 1, so timing and labeling deposits matters.

Dental and vision benefit allowances

Most dental and vision plans reset annually.

Coverage limits for cleanings, exams, glasses, contacts, and other services typically start fresh.

Why this matters: unused benefits from the prior year usually don’t carry over.

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What does NOT Reset on January 1

These follow a different clock, even though the year changes:

Roth IRA contribution deadline

You can still contribute to a Roth IRA for the prior tax year until Tax Day (usually April 15), as long as you’re eligible and within the income and contribution limits.

Why this matters: you don’t lose the chance to fund a Roth IRA for 2025 just because December ends.

Even though some accounts allow prior-year contributions into spring, the contribution limits themselves reset January 1, so timing and labeling deposits matters.

Choosing which year an IRA contribution applies to

If you’re contributing to an IRA between January 1 and Tax Day, your brokerage will usually ask whether the contribution should count toward the prior year or the new year.

Why this matters: the same deposit can apply to different years depending on how you label it, so select wisely.

Investment sales already made during the year

If you sold an investment during 2025 at a gain or a loss, that result is tied to that calendar year. Once December 31 passes, those outcomes are set.

Why this matters: you can’t retroactively change when an investment was sold after the year end.

👋  TO GO BITES: The Wrap Up

As the year turns, a few financial systems start fresh immediately, while others continue on their own timelines.

Knowing which is which helps you decide what needs attention now and what can wait into early spring.

If you check the items that reset on January 1 and note the ones that stay open past year-end, you’ll start the new year with fewer unknowns and clearer next steps.

Thank you for reading this year, and being such a valued member of the Rolling In Dough community! I wish you a Happy New Year! 🍾 

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