My experience running an annual financial review — what I check, in what order, and what I've found over 8 years of doing it.

January 1st: update net worth spreadsheet with all account balances. Calculate year-over-year change.

January (tax preparation):

• Gather all 1099s and W-2s
• Verify 401k and HSA contribution amounts match intended levels
• Check if backdoor Roth conversion was completed and Form 8606 is needed
• Review prior year tax return for planning opportunities

Open enrollment (October):

• Compare health plan options and costs
• Adjust HSA or FSA elections based on expected expenses
• Review life and disability insurance adequacy

Beneficiary review: every 2-3 years or after major life events, confirm beneficiaries on all retirement accounts and life insurance policies match current intentions.

Credit report review: pull from AnnualCreditReport.com. Check for errors and unfamiliar accounts.

The whole annual review takes about 3-4 hours spread over the year. It's the most high-leverage time investment in my financial management.