What a tax strategist should do before tax season

A tax strategist should not appear after the year is over and call that planning. The real work happens before tax season, when there is still time to change wages, estimates, elections, entity decisions, documentation, and cash movement.

At Anomaly CPA, a Boston-based CPA firm serving clients nationwide, John Malone, JD, works with business owners who need more than tax preparation, especially when qualified business income, multi-state income, cost recovery, or owner compensation planning is in play. This article explains what a tax strategist should actually do before filing season begins, which limitations matter early, and how to tell whether you are buying proactive tax strategy or just a better explained return.

Bottom line: if the advice arrives after the year is locked, it is usually too late to create most of the value.

Key takeaways

• Pre-season tax strategy is about changing outcomes while the business can still act, not reviewing numbers after the fact.
• The biggest early limitations often involve estimated taxes, §199A rules, and whether the business falls into an SSTB or other restricted category.
• A strong tax strategist coordinates books, payroll, and owner-level tax planning instead of treating them as separate projects.
• The fastest way to test value is to ask what specific decisions should happen before year-end or before filing season starts.

If the plan starts after the year closes, most of the easy levers are already gone.

What pre-season strategy actually means

A tax strategist usually should help the client do four things before tax season:

1. model taxable income;
2. review owner compensation and distributions;
3. check elections, deductions, and documentation;
4. decide what still needs to happen before the year or filing cycle is finished.

Key takeaway: pre-season strategy is a decision process, not a prettier tax return.

Limitations to flag early, not later

IRC §199A, 26 U.S.C. §199A, allows many noncorporate taxpayers a deduction of up to 20 percent of qualified business income, but the deduction can be limited by W-2 wages, qualified property, taxable-income thresholds, and specified service trade or business rules (Source: 26 U.S.C. §199A, Cornell LII).

Definition — The §199A deduction is a federal tax deduction for certain pass-through business owners. In plain English, it can reduce taxable income materially, but only if the business structure, wages, and income profile line up with the statute's limits.

This is why SSTB status and taxable-income phaseouts should be flagged in the first planning conversation, not buried in a filing memo. If the client is above the threshold amount or operating in a specified service trade or business, the deduction may shrink or disappear (Source: 26 U.S.C. §199A, Cornell LII).

The second early flag is estimated tax. The IRS states that individuals generally must make estimated payments if they expect to owe $1,000 or more, and corporations generally must do so if they expect to owe $500 or more (Source: IRS Estimated Taxes page).

Key takeaway: the earlier you identify the limiting rules, the more planning room you still have.

Worked example: how a strategist changes a §199A outcome

Assumptions: an S corporation owner expects taxable income above the §199A threshold amount, the business is not an SSTB, qualified business income is $300,000, and there is no meaningful UBIA limitation support.

Under IRC §199A, the tentative deduction is 20 percent of QBI, or $60,000. But if W-2 wages are only $40,000, the 50 percent wage limit is $20,000, which can cap the deduction well below the tentative amount (Source: 26 U.S.C. §199A(b), Cornell LII).

If the owner reviews compensation and payroll structure before filing season and W-2 wages rise to $120,000, the 50 percent wage limit becomes $60,000. The full tentative deduction is now supported.

Why this matters for business owners: a tax strategist creates value by spotting wage, timing, and structure issues before the return turns them into fixed results.

Key takeaway: strategy often comes from aligning facts to the rule before the filing deadline, not arguing about the rule later.

How pricing usually relates to depth

On Anomaly's public pricing page, Assessment & Advisory starts at $4,000 and Advanced Tax Planning starts at $7,500. Ongoing strategy-focused tax support starts at $450 per month, while VIP tax support starts at $2,000 per month for more customized work (Source: Anomaly CPA Pricing page).

That range makes sense because a real strategist is not only preparing forms. The work may include modeling, implementation meetings, payroll coordination, and specialty follow-up through resources like Specialty solutions.

Key takeaway: the cost of tax strategy usually reflects how much implementation and decision support is included, not just how many forms get filed.

How to choose the right tax strategist

Ask these questions before hiring:

• Which decisions do you expect me to make before filing season?
• How do you coordinate with bookkeeping and payroll?
• What limitations could eliminate value in my case?
• What implementation work do you actually own?
• How often do we revisit the plan?

A strong answer should sound specific, current, and operational. That is why many business owners start with advanced tax strategy advisory only after they are sure the advisor can move from planning into execution.

Key takeaway: the best strategist is the one who can name the next decision, not just the next tax form.

FAQ

What is the difference between a CPA and a tax strategist?

A CPA may focus mainly on compliance, while a tax strategist is expected to change facts, timing, and implementation before the return is final. The distinction is mostly about timing, scope, and accountability.

Why does §199A matter before tax season?

Because the deduction can depend on wages, property, business type, and taxable income. If those issues are reviewed too late, the owner may lose planning options that were available earlier (Source: 26 U.S.C. §199A, Cornell LII).

When should a business owner start estimated-tax planning?

Before income is fully earned and before the next payment deadline. The IRS makes clear that taxes generally must be paid as income is earned, not only when the annual return is filed (Source: IRS Estimated Taxes page).

Action steps for business owners

• Identify the tax decisions that still can be changed before filing season or year-end.
• Review whether your books and payroll data are current enough to support planning.
• Ask whether §199A, SSTB status, or owner-compensation issues could limit strategy value.
• Compare one-time planning against ongoing support on Pricing.
• If your current provider only explains the return, evaluate whether Advanced tax strategy advisory is the missing layer.

The next logical question is which planning moves still remain open in your business before the return becomes history.

© 2026 Anomaly CPA. All rights reserved.

Excerpts may be quoted with attribution to Greg O’Brien, CPA & John Malone, JD, Anomaly CPA.

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