2025 Tax Filing Preparation Checklist
Organize your 2025 tax documents and uncover 2026 planning opportunities.
Whether you are still building wealth through your employment and investments, or managing retirement income streams, your income tax situation can be complex. Tax season should reveal planning opportunities, not create stress. This checklist is designed specifically for individuals and families like yours. It helps you organize the documents that matter most to your situation and positions your 2025 tax return as a strategic planning tool for 2026 and beyond.
Your Employment & Compensation Documents:
✅ W-2 from employer(s) – all locations and entities
✅ Year-end pay stubs (verify bonuses, commissions, RSU vesting)
✅ Stock compensation documentation:
- RSU vesting schedules and tax withholding
- Stock option exercises (NQSOs/ISOs)
- ESPP dispositions
✅ Deferred compensation plan statements (non-qualified deferred comp)
✅ Retention bonus agreements or special compensation
✅ Employment-related moving expenses or relocation benefits
✅ Executive benefits (club memberships, car allowances)
Your Investment & Real Estate Documents:
✅ Brokerage account 1099s
✅ Year-end statements for IRAs, 401(k)s, 403(b)s, HSAs
✅ K-1s from partnerships, S-corps, family LLCs, or trusts
✅ Private mortgage statements or real estate partnership income
✅ Kansas & Missouri property tax statements (primary + second homes)
✅ Records of capital improvements (for potential future sales)
✅ 1099-B for any concentrated stock positions sold
Your Business & Trust Income Documentation:
✅ Schedule K-1s from pass-through entities or family businesses
✅ Business depreciation schedules and Section 179 carryovers
✅ Family trust distributions (grantor, irrevocable, complex trusts)
✅ Business use of home calculations (if you have a home office)
✅ 1099-MISC/NEC for consulting or board positions
Your Charitable & Estate Planning Records:
✅ QCD documentation from IRA distributions to charity
✅ Donor-Advised Fund contribution records
✅ Itemized charitable receipts (cash + appreciated securities)
✅ Recent estate plan updates, trust amendments, or gifting
✅ Records of 529 contributions or direct payments to schools
Strategic Planning Questions:
❓ Did you exercise stock options or sell vested RSUs in 2025?
❓ Did you complete any Roth conversions in 2025?
❓ Are RMDs starting for you or a spouse in 2026?
❓ Have you reviewed beneficiary designations recently?
❓ Any concentrated stock positions or planned sales?
❓ Are you maxing out your 401(k), or other tax-deferred retirement plans?
❓ Changes in charitable giving?
❓ Second home or real estate transactions?
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