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Tax season is not April. It is now. Clients with businesses and stock comp ask how to keep April clean and the bill controlled. My stance is simple: Get the paperwork tight, automate the savings that move your rate, and tune withholding or estimates so you land on one small, beautiful bill instead of a surprise.
Key Takeaways
- Start tax season now by creating one organized folder for documents, deadlines, and contacts.
- Maximize the biggest tax levers first, like 401(k) contributions and HSAs.
- Plan proactively around equity events and align them with quarterly tax estimates.
- Choose a knowledgeable tax professional who can connect filing with long-term planning.
- Aim for a small, intentional balance due at filing rather than a surprise bill or oversized refund.
If you extended last year’s return, the final e-file deadline is in October, so your focus will shift to 2025 income that you will file in 2026. High earners and business owners often miss safe-harbor rules or rely on equity withholding that is too light, which triggers penalties. The fix? Planning. Set contributions and estimates on a calendar now so cash flow and taxes work together.
What I’m Telling My Clients
1. Create a Single, Shared Tax Folder
This consists of last year’s return, W-2s, 1099s, K-1s, brokerage 1099 composite, 1098s, charitable receipts, childcare and education statements, and HSA and FSA summaries.
Tip
If possible, go digital when organizing your annual tax folder.
2. Take the Easy Wins
Push 401(k) or Solo 401(k) deferrals toward the annual limit and add catch-up if you are 50+. For business owners, confirm plan type (Safe Harbor, Solo 401(k), SEP) and employer contribution timing with payroll and cash flow. Top off the HSA if eligible, set automatic contributions for the rest of the year, and review FSA balances to avoid forfeiture. Decide Roth vs pre-tax by comparing your current bracket to your likely future one, and coordinate any backdoor Roth steps with your preparer so you do not trigger pro-rata surprises.
3. Plan Around Equity
Put vesting, exercises, and planned sales on a calendar. Build a quick projection for each event so you can set aside cash or schedule an estimated payment near the date. For restricted stock units (RSUs), remember default withholding often undershoots for high earners. For nonstatutory stock options (NSOs) and incentive stock options (ISOs), model alternative minimum tax (AMT) exposure, bargain element, and holding-period choices before year-end. Consider a 10b5-1 plan for orderly selling, donate appreciated shares when it fits the plan, and mind wash-sale windows. Keep blackout dates and employer trading policies in view.
4. Decide the Filing Path Now
Choose who files. Make it your tax pro. A strong CPA or enrolled agent (EA) ties filing to planning, spots elections you would miss, and helps with time estimates and retirement contributions. Pick someone with small business and equity compensation experience, transparent fees, secure portals, and IRS representation rights. Do not shop for the biggest refund; instead, shop for judgment. Advisors will prep your organizer and stay available for their questions so they can file clean and on time.
The Bottom Line
Filing is a process, not a date. Get organized, raise the right contributions, and align withholding and estimates now so April is execution, not chaos.
