I reviewed whether my income changed materially this year.

Salary adjustments, equity vesting changes, severance, or other shifts affecting your top-line taxable income.

I reviewed whether I changed jobs this year.

Transitioning employers often creates multi-W-2 scenarios, duplicated 401(k) limits to monitor, or benefits resets.

I reviewed whether I started or stopped freelance, contract, or business income.

1099-NEC, 1099-K, or Schedule C activities with separate self-employment tax obligations.

I reviewed whether I received bonuses, commissions, or other variable compensation.

Supplemental wage withholding at standard flat rates may differ from your effective marginal bracket.

I reviewed whether I received significant investment income.

Realized capital gains, non-qualified dividends, or interest distributions from taxable accounts.

I reviewed whether I received employer equity compensation.

Vested RSUs, exercised stock options, or ESPP purchase tranches during the calendar year.

I reviewed whether I experienced a major life or financial change that could affect my taxes.

Filing status changes, dependent arrivals, property sales, or relocations across state tax jurisdictions.

I know whether my tax situation is materially different from last year.

Knowing whether you can rely on prior-year filing patterns or need updated withholding and professional planning.

I reviewed my year-to-date workplace retirement contributions.

Confirming total employee salary deferrals across 401(k), 403(b), or governmental 457(b) accounts.

I know how much I have contributed so far this year.

Checking paystubs or benefits portals for cumulative traditional and Roth deferral amounts.

I checked whether my employer offers matching contributions.

Ensuring you contributed enough per pay period or throughout the year to capture the full company match.

I reviewed whether I am on track for the contribution level I intended.

Calculating remaining paychecks if adjusting contribution percentages before the final payroll cutoff.

I checked whether my employer has any year-end contribution rules or deadlines.

Company payroll processing cutoffs often occur several weeks prior to December 31.

I reviewed relevant IRA contribution activity, if applicable.

Tracking traditional or Roth IRA contributions, noting the tax filing deadline window.

I checked whether any retirement contribution deadlines differ depending on account type.

Workplace 401(k) payroll deferrals close December 31, while IRA contributions generally extend to the April tax filing deadline.

I know which retirement contribution records I need to keep.

Form 5498, year-end custodian statements, and Form 8606 documentation for non-deductible basis.

I reviewed realized capital gains for the year.

Net short-term and long-term gains locked in across all taxable brokerage accounts.

I reviewed realized capital losses for the year.

Realized losses available to offset realized capital gains plus up to statutory ordinary income limits.

I reviewed my brokerage tax-lot information.

Verifying specific identification accounting (SpecID, HIFO, FIFO) rather than default average cost.

I checked whether I have investments with unrealized gains or losses that may warrant review.

Assessing positions where current market value diverges substantially from purchase cost basis.

I reviewed whether any recent security sales could have tax implications.

Evaluating short-term gains taxed at ordinary rates versus preferential long-term treatment.

I reviewed my brokerage's year-to-date gain/loss information.

Reviewing realized gain/loss reports provided in custodian tax centers prior to year-end.

I understand that tax treatment can depend on the type and timing of a transaction.

Holding periods of more than one year determine long-term status with distinct rate schedules.

I have identified investment-related tax questions that may require professional advice.

Flagging complex assets such as crypto, private placements, options, or foreign holdings.

I reviewed recent security sales for potential wash-sale considerations.

Disallowing a loss deduction when acquiring substantially identical securities within 30 days before or after the sale.

I understand that substantially identical securities and transaction timing can affect wash-sale treatment.

Trading identical ticker symbols, options contracts, or near-identical funds across the 61-day window.

I reviewed my brokerage's wash-sale reporting.

Checking 1099-B preview or realized gain reports for disallowed loss flags.

I considered whether transactions across different accounts could matter.

IRS rules apply across all accounts you control, including spousal accounts and IRAs, which brokerages cannot automatically track.

I have identified wash-sale questions I may need to discuss with a tax professional.

Clarifying replacement share purchases, dividend reinvestment plans, or automatic recurring buys.

I reviewed dividend income received during the year.

Distinguishing between qualified dividends (lower capital gains rate) and ordinary non-qualified dividends.

I reviewed interest income.

Taxable yields from high-yield savings accounts, CDs, Treasury debt, or money market funds.

I reviewed income from taxable investment accounts.

Mutual fund capital gain distributions, REIT dividends, or foreign withholding taxes.

I reviewed income from CDs, money-market products, bonds, or other interest-producing assets where applicable.

State-tax exemption status for US Treasury obligations versus fully taxable commercial paper.

I reviewed relevant brokerage and bank tax-document expectations.

Anticipating 1099-INT, 1099-DIV, and consolidated 1099 forms arriving in late January through mid-February.

I identified any investment income that may require additional tax documentation.

Schedule K-1s from partnerships, master limited partnerships, or syndicated investments.

I reviewed my RSU vesting activity for the year.

Dates, share quantities, and fair market values at vest reported on employer share platform.

I reviewed the income reported from vested RSUs.

Ensuring the gross value of vested shares appears correctly in Box 1 and Box 14 of your W-2.

I reviewed taxes withheld at vesting.

Evaluating whether standard 22% statutory supplemental withholding caused underwithholding for your bracket.

I reviewed my current employer-stock holdings.

Tracking overall portfolio concentration, holding periods, and unrealized positions.

I reviewed my ESPP activity, if applicable.

Enrollment discount, purchase dates, offering periods, and qualifying versus disqualifying dispositions.

I reviewed shares sold during the year.

Identifying the exact grant lot, sale price, and capital gain or loss realized upon secondary sale.

I reviewed the cost basis reported by my brokerage.

Crucial check: Broker 1099-B forms often show $0 or unadjusted basis, risking double-taxation if uncorrected.

I compared relevant employer equity records with brokerage records.

Reconciling confirmation releases from Shareworks/E*TRADE/Carta against payroll compensation stubs.

I saved my equity compensation statements.

Retaining release confirmations, Form 3921 (for ISOs), Form 3922 (for ESPP), and supplemental cost-basis reports.

I identified equity-compensation questions that may require professional tax advice.

Complex items including 83(b) elections, ISO alternative minimum tax (AMT), or international equity transfers.

I reviewed my HSA contributions for the year, if applicable.

Verifying total payroll deductions and direct deposits align with qualified High Deductible Health Plan coverage.

I checked employer HSA contributions.

Employer contributions count toward the statutory annual maximum limit.

I reviewed my FSA activity, if applicable.

Healthcare FSA and Dependent Care FSA contributions, noting use-it-or-lose-it rules and grace periods.

I checked relevant year-end deadlines or balance rules for my plan.

Confirming employer plan specifics on carryover amounts (e.g. up to statutory limit) or grace period windows.

I saved relevant HSA/FSA records.

Retaining medical receipts, explanation of benefits (EOBs), and distribution logs for Form 8889.

I reviewed whether any contribution or distribution records need attention.

Confirming all HSA withdrawals during the year were for qualified medical expenses to avoid penalties.

I reviewed charitable contributions made during the year.

Tallying monetary gifts, donor-advised fund contributions, or payroll donation programs.

I collected receipts and acknowledgment records.

Obtaining formal written acknowledgments from 501(c)(3) charities for gifts of $250 or more.

I checked that documentation is available for relevant donations.

Bank records, canceled checks, or electronic credit receipts for donations under $250.

I reviewed non-cash charitable contributions, if applicable.

Documenting gifted appreciated securities (avoiding capital gains) or donated goods requiring Form 8283.

I identified any charitable-giving questions that may require professional advice.

Evaluating bunching strategies, donor-advised funds (DAFs), or standard deduction comparison.

I reviewed federal tax withholding from my paychecks.

Comparing year-to-date federal income tax withheld on latest paystub against expected annual obligation.

I reviewed state tax withholding where applicable.

Checking state income tax withholdings, especially if working remotely or across multiple jurisdictions.

I reviewed withholding related to bonuses or equity compensation.

Checking if lump-sum bonuses or RSU vestings created a tax gap due to standard 22% flat rates.

I reviewed estimated tax payments, if applicable.

Verifying record of Q1–Q3 estimated payments made via IRS Direct Pay or EFTPS, plus upcoming Q4 deadline.

I considered whether major income changes could affect my tax position.

Understanding IRS safe harbor rules (e.g. 100% or 110% of prior-year liability) to prevent underpayment penalties.

I identified questions about withholding or estimated taxes that may need professional review.

Formulating questions on adjusting Form W-4 allowances for next tax year or calculating safe harbor payments.

I know where my W-2 will be available.

Employer payroll portals (ADP, Workday, Gusto) and paper mailing preferences.

I know where my 1099 forms will be available.

1099-NEC (contracting), 1099-MISC, 1099-INT (banks), and 1099-DIV.

I know where my brokerage tax documents will be available.

Consolidated 1099 forms from custodians (Schwab, Fidelity, Vanguard, Robinhood) usually posted in February.

I have retained relevant retirement contribution records.

Roth IRA contribution logs, conversion receipts, and non-deductible contribution tracking records.

I have retained relevant charitable contribution records.

501(c)(3) gift receipts, DAF contribution letters, and property valuation records.

I have retained relevant HSA/FSA records.

Form 1099-SA (distributions), Form 5498-SA, and unreimbursed medical expense logs.

I have retained employer equity documentation.

Form 3921, Form 3922, RSU vesting release confirmations, and supplemental cost-basis reports.

I have access to my prior-year tax return.

Federal Form 1040 and state returns from prior year to cross-check carryforwards and income baselines.

I have a secure place to store tax documents.

Encrypted local or zero-knowledge cloud folder backed up securely for multi-year retention.

I have written down tax questions I don't understand.

Listing confusing terms, complex deductions, or disputed line items in advance of consultation.

I have identified transactions that may need professional review.

Stock sales, property transactions, equity vesting events, or business structure changes.

I have identified changes from last year that I want to discuss.

Relocations, marriage, dependents, substantial salary changes, or severance packages.

I have gathered relevant documents before contacting my tax professional.

Assembling W-2s, 1099s, prior tax returns, and statements so billable consultation time is efficient.

I know where to find authoritative tax information if I need to verify a rule.

Referencing official IRS publications, state department of revenue portals, or certified tax advisors.