Most tax “planning” happens in March, when the year is already over and every lever is bolted down. The version that actually saves money happens now — in June, when half the year is real data and the other half can still be steered.
Why June, specifically
By mid-year your books hold six months of actual revenue, actual payroll, and actual margins. That’s enough signal to project the full year credibly — and enough runway left to act on what the projection says. Wait until Q4 and you’re negotiating with a calendar instead of planning.
What we actually look at
1. The projection itself
Annualize the first six months, adjust for seasonality (restaurant summers and tax-season optometry visits don’t annualize cleanly), and land on a working estimate of taxable income. Every other decision hangs off this number — and it assumes books that are actually current; fix that first if needed.
2. Entity and owner pay
If you’re a sole proprietor clearing six figures, the S corporation question is worth re-asking annually. If you already have an S corp, mid-year is when we sanity-check that your salary is reasonable for the role and the remaining distribution split still makes sense — fixing that in December looks bad; fixing it in June looks like payroll.
3. Purchases you were going to make anyway
Equipment, vehicles, the POS upgrade — Section 179 and bonus depreciation reward timing. The question is never “buy something for the deduction” (spending $1 to save 30¢ is still losing 70¢). It’s whether a purchase you already planned should land this year or next.
4. Retirement contributions
Solo 401(k), SEP-IRA, or a full plan with employees — the right vehicle depends on profit and headcount, and some need to be established well before year-end. June is when there’s still time to set one up calmly.
5. Estimated payments, re-trued
The June 15 estimate lands right inside this review — convenient, because the projection from step one is exactly what the payment should be based on.
An April surprise is almost never a tax problem — it’s an information problem that sat unexamined for ten months. One mid-year session converts “I hope it works out” into a number you’ve already planned around.
Your mid-year checklist
- Get the books current through May — the review is only as good as the data
- Project full-year profit from six months of actuals
- Revisit entity choice and owner compensation
- List planned purchases and decide which year they belong in
- Pick (or fund) the retirement vehicle while there’s runway
- Recalculate the June and January estimates off the new projection
This article is general information, not tax advice for your specific situation. Rules change and details matter — talk to a CPA (we know one) before acting on anything here.