By the time most business owners sit down with their CPA in February or March, the year is over and the tax bill is essentially set. The CPA can compute it accurately, but they can't change what already happened. The decisions that actually move the tax bill — Roth conversions, retirement plan contributions, charitable bunching, deferred compensation elections, S-corp distribution timing — all need to be made inside the year, with enough runway for them to settle.
A four-meeting-a-year rhythm, coordinated between your CPA and your wealth manager, is what turns tax planning from a March emergency into a quiet, steady advantage.
Q1 (January–March): Last year's close, this year's setup
- Finalize prior-year retirement contributions (SEP-IRA, profit sharing, cash balance) before the extended return deadline.
- Confirm prior-year QCDs and DAF contributions are documented correctly.
- Set this year's quarterly estimated tax payments based on a realistic projection — not last year's safe-harbor copy.
- Identify which credits or deductions need a multi-year planning horizon.
Q2 (April–June): Project the year ahead
- Build a full-year income projection: wages, distributions, dividends, capital gains, and one-time events.
- Identify whether Roth conversions, deferred comp elections, or stock option exercises make sense this year.
- Confirm health savings account (HSA) and 401(k) contribution pace through year-end.
- Review charitable giving plan and decide whether to bunch this year.
Q3 (July–September): The decision quarter
- Most major decisions are made now, with enough runway for trade settlements, account openings, and document signings to clear by year-end.
- Execute planned Roth conversions in tranches — not in a single year-end rush.
- Confirm appreciated-share donations to charity or donor-advised fund.
- For S-corp owners: review reasonable-compensation analysis and final-quarter distribution plan.
- Revisit tax-loss harvesting opportunities in taxable accounts.
The most expensive tax mistakes we see are not aggressive ones — they're rushed ones. A Roth conversion executed on December 28th without modeling the IRMAA impact often costs the household more in Medicare premium surcharges two years later than the conversion saved on income tax.
Q4 (October–December): Confirm, document, finalize
- Final harvest of capital losses (or gains, if the 0% long-term-gain bracket is in play).
- Confirm RMDs taken in full (for clients 73+).
- Confirm year's charitable contributions complete with proper documentation.
- Set final estimated payment to match projected liability.
- Begin building the document package the CPA will need in January.
Where the savings actually live
Year-round planning rarely produces a dramatic one-time saving. It produces an annual saving of 0.5%–2% of after-tax wealth that quietly compounds. Over a 20-year window, the difference between "I file taxes in April" and "I plan taxes year-round" can equal one to two years of retirement spending — without any change in how you invest.
It is not glamorous work. It is the work that's done while everyone else is reacting in March.
