Tax season always arrives faster than expected. The most reliable way to avoid stress and capture every dollar you are entitled to is to start preparing now. Use this guide from LEAF to set up simple systems, make smart adjustments, and keep your future self calm when filing opens.
Why starting early matters
Early preparation gives you time to gather forms, correct mistakes, and make contributions that lower your tax bill. It also prevents the last‑minute scramble that can lead to missed deductions or filing extensions. Think of September through December as your runway. Use it well, and April becomes routine rather than a fire drill.
Create a simple document hub
Begin with organization. Set up a single home for tax items so nothing goes missing. Pick one of these approaches and stick with it:
- Digital folder: Create a folder on Drive, Dropbox, or iCloud named Taxes 2025. Inside, add subfolders for income, deductions, health, education, and receipts. Use your phone’s scanner app to drop items in as they arrive.
- Paper folder: Use an accordion file with the same labels. Keep it next to your mail drop so statements and forms go straight in.
Pro tip: Start a running checklist of the forms you expect (W‑2, 1099‑NEC, 1099‑INT, 1098 for mortgage interest, 5498 for IRA, and so on). When an item comes in, check it off. If February arrives and something is still missing, you will know exactly what to request.
Know the forms that apply to you
Most people will see a standard set of documents. Here are the common ones and what they represent:
- W‑2: Wages from employers. Verify name, Social Security number, and income before filing.
- 1099‑NEC or 1099‑K: Self‑employment or platform income. Expect one from each client or platform if thresholds are met.
- 1099‑INT / 1099‑DIV: Interest and dividends from bank or brokerage accounts.
- 1098‑E / 1098: Student loan interest or mortgage interest paid.
- HSA and IRA forms: 5498 and 1099‑SA confirm contributions and distributions.
Review withholdings and estimates
If you are an employee, review your year‑to‑date withholding on your latest pay stub. If you are self‑employed or have side income, compare your estimated payments against your projected tax. Your goal is simple: avoid a surprise bill and avoid an unnecessarily large refund.
- Estimate your full‑year income using year‑to‑date numbers.
- Account for bonuses, side work, investment income, and retirement contributions.
- If you are off track, adjust your W‑4 with your employer or make an additional estimated payment.
Track deductions the smart way
Many valuable deductions get lost because records are scattered. Set up lightweight tracking now so you do not need to reconstruct anything later:
- Charitable giving: Save receipts or donation confirmations. If you donate goods, keep a simple list of items and their estimated value.
- Medical costs: Keep statements for out‑of‑pocket expenses. If your costs are high relative to income, early tracking makes evaluation easy.
- Education: Save 1098‑T forms and records for qualified expenses.
- Property and state taxes: File statements as they arrive to evaluate whether itemizing makes sense.
Use contributions to lower taxable income
Retirement and health accounts can reduce taxes and build long‑term savings. Map out what you can contribute between now and filing day:
- Traditional IRA: Contributions may be deductible if you meet income limits. Even if they are not, you still gain tax‑deferred growth.
- Roth IRA: No deduction today, but tax‑free growth and withdrawals later. Consider backdoor Roth strategies if appropriate.
- HSA: Triple benefit — contributions reduce income, growth is tax‑free, and qualified withdrawals are tax‑free.
- FSA: Spend flex accounts intentionally so dollars are not forfeited at year end.
Account for life changes
Certain milestones change how you file and what you can claim. If any of the following apply, note them now and gather proof:
- Marriage or divorce
- New child or adoption
- Buying or selling a home
- Switching jobs or moving states
Early awareness lets you choose the most favorable filing status, adjust withholding, and prepare the documents your preparer will need.
Build a five‑minute weekly routine
Small habits beat big sprints. Set a five‑minute weekly reminder to drop new documents into your folder, snap photos of receipts, and tick off items on your checklist. By January, your return will be mostly assembled.
When to bring in a professional
If you own a home, have investment or self‑employment income, changed jobs midyear, or experienced a major life event, professional guidance can more than pay for itself. LEAF looks beyond data entry to design a plan that supports your goals, flags risks early, and keeps your paperwork clean for next year.
Next steps
- Create your document hub today.
- Review withholding and estimates.
- Decide on IRA or HSA contributions.
- Book a planning session with LEAF to confirm your strategy.
