The Year-End Money Checklist: One Evening, Seven Moves

December is the only month with real financial deadlines attached to it: money that expires, contribution windows that close at midnight on the 31st, and penalties that arrive for the mail you ignored. The whole sweep takes one evening, and the same seven moves work every year, which is why this checklist contains no year numbers at all. Do the deadline items first; the rest is housekeeping you will be glad you did in January.

First, the items with hard December deadlines

1. Spend the FSA money that expires

A healthcare flexible spending account is use-or-lose by design: dollars you elected but did not spend are forfeited, subject to whatever softening your specific plan offers (some allow a small carryover into the new year, some a grace period of a couple of months, some neither, and your plan documents say which). Check the balance now, not on the 30th. Unspent dollars have honest uses: the dental visit you postponed, new glasses or contacts, and a long list of FSA-eligible items from first-aid supplies to sunscreen. Forfeiting $400 you already earned is the most avoidable loss in personal finance.

2. Top up workplace retirement contributions

401(k) contributions only count for the year if they run through payroll by the final paycheck, so December is your last chance to close the gap between what you have contributed and the annual limit (or, more modestly, between what you have contributed and what you meant to). If the year went better than planned, a raised deferral percentage on the last one or two paychecks is how you capture it; the 401(k) calculator shows what those extra dollars become over the decades. Two useful asymmetries: employer-match rules sometimes reward spreading contributions across the year (worth knowing for next year), and IRAs, unlike workplace plans, stay open for prior-year contributions until the tax filing deadline in spring, so an IRA shortfall is not a December emergency.

3. Check for harvestable losses

In a taxable brokerage account, positions sitting below what you paid can be sold to realize the loss, and realized losses offset realized gains on your tax return (plus a limited amount of ordinary income, with the remainder carrying forward). This is tax-loss harvesting, and the trade must happen by the final trading day of the year to count for it. The one rule that trips people: buying the same or a substantially identical investment within 30 days before or after the sale triggers the wash-sale rule and disallows the loss, so harvesters typically swap into a similar-but-different fund instead of repurchasing. Retirement accounts are exempt from all of this; there is nothing to harvest inside a 401(k) or IRA.

4. Take the RMD if you owe one

Past a certain age, and for many inherited retirement accounts at any age, the IRS requires a minimum withdrawal by December 31, and the penalty for missing it is severe by tax standards. If required minimum distributions apply to you or a parent you help, confirm the withdrawal has actually happened, not just been scheduled; the RMD calculator has the current age rules and shows how the required amount is computed from the year-end balance and your age. First-timers get a one-time extension into the spring, but using it means taking two distributions in the same tax year, which is its own trap.

Then, the money-savers with no deadline

5. Re-shop the insurance stack

Auto and home or renters premiums drift upward for loyal customers, and the fix is a once-a-year hour of quotes. Pull your current coverage amounts and deductibles, get two or three comparison quotes at identical coverage, and either switch or call your current insurer with the competing number. Households that do this annually routinely find savings in the hundreds per year, and December works only because you are already in the folder; any month works.

6. Audit the subscriptions

A year of free trials, price increases, and forgotten annual renewals has accumulated since you last looked. Scan twelve months of statements for recurring charges, sort them into keep, cancel, and downgrade, and be ruthless about the ones you had forgotten existed (forgetting is the strongest cancel signal there is). The full method lives in the subscription audit guide, and the subscription cost calculator will convert the survivors into an annual figure that motivates the second pass.

7. Reset next year's targets

Finish with ten minutes of forward-looking arithmetic. What did you actually save this year, as a percentage of what you earned? What should the number be next year, and what has to change on the first payday of January (not in February, not eventually) to make it automatic: a raised 401(k) deferral, a bigger automatic transfer on payday, one canceled subscription redirected to a goal. Deadlines made you do the first six items; this one is the only move on the list that changes the shape of the next twelve months.

What not to bother with

December is a poor month for grand reinventions: a portfolio overhaul, a new budgeting philosophy, a spreadsheet with 40 tabs. The holidays will eat the follow-through. The seven moves above are valuable precisely because they are bounded: an evening of clicking, a few hundred dollars defended here, a few thousand captured there.

Most of this checklist is really one question asked seven ways: what changed this year while you were not looking? A picture of every account that stays current on its own, the way Stoia keeps one, makes next December's sweep less of an archaeology dig and more of a confirmation.