Year-End Money Checklist

Taxes — Deadline December 31

Most of these can't be done retroactively. IRA contributions are the exception (you have until tax day).

• Harvest tax losses: sell losing positions in taxable accounts to offset gains, plus up to $3,000 of ordinary income
• Mind the wash-sale rule — don't rebuy the same (or substantially identical) investment within 30 days of a loss sale
• Max what you can into your 401(k) before year end — check the current IRS limit and adjust your final paychecks' deferral
• At minimum, contribute enough to your 401(k) to capture the full employer match — it's a 50–100% instant return
• Spend down your healthcare FSA — most plans are use-it-or-lose-it beyond a small carryover; glasses, dental work, and prescriptions all count
• Take Required Minimum Distributions if you're of RMD age or hold an inherited IRA — the penalty for missing one is up to 25% of the shortfall
• Make charitable donations by December 31 and keep receipts; consider donating appreciated stock instead of cash to skip capital gains
• If you're over 70½, consider a Qualified Charitable Distribution from your IRA — it counts toward RMDs and stays out of taxable income
• Consider a Roth conversion if this was a low-income year — you pay tax at today's lower bracket
• Estimate your total tax bill and make a Q4 estimated payment if you're under-withheld (avoids underpayment penalties)
• Contribute to a 529 by December 31 if your state gives a deduction or credit for contributions

Benefits & Open Enrollment

Usually a 2–4 week window in the fall. Autopiloting last year's elections is how people overpay.

• Actually compare your health plan options against what you spent this year instead of re-electing by default
• Max your HSA if you're on a high-deductible plan — it's triple tax-advantaged (deductible in, growth, and medical out)
• Set next year's FSA election based on what you actually spent this year, not a guess
• Elect a Dependent Care FSA if you pay for childcare — up to $5,000/year pre-tax
• Review employer life and disability elections — supplemental group coverage is often cheap
• Check for unused benefits expiring December 31: dental annual max, vision allowance, wellness stipends, and PTO that doesn't roll over

Planning & Housekeeping

• Rebalance your portfolio back to target allocation (do it inside tax-advantaged accounts to avoid triggering gains)
• Review beneficiaries on your 401(k), IRAs, and life insurance — they override your will, and divorces/births make them stale
• Run a subscription audit: cancel anything you haven't used in 90 days — the average household wastes $50–$100+/month
• Rate-shop auto and home insurance with 2–3 quotes — loyalty is routinely penalized $200–$500/year
• Move idle cash to a high-yield savings account if your bank pays under 1%
• Check your credit reports at AnnualCreditReport.com and dispute errors
• Calculate your year-end net worth and compare it to last year
• Check for unclaimed property in your name at your state's unclaimed funds site (missingmoney.com)

New Year Setup

• Set 2–3 specific money goals with dollar amounts and dates, not vibes
• Bump your 401(k) contribution by at least 1% effective January 1 — you won't feel it
• Update automatic transfers to reflect new limits and your new goals
• Schedule next year's money dates now: tax filing in February–March, a mid-year review in June, open enrollment in the fall
• Create or update your budget with this year's real spending as the baseline