At a glance
- Tax prep
- March–April. Asks “What do I owe?” You get a bill.
- Tax planning
- All year. Asks “What can I change?” You get a strategy.
- Best fit
- Business owners who want fewer surprises.
- Main catch
- Most strategies can’t be added after the year ends, so planning has to start before December.
- Key date
- December 31, the deadline for most of the strategies in this series.
Key takeaways
- Tax prep looks back and asks what you owe; tax planning works all year and asks what you can change.
- Most of the tax strategies in this series have to be in place by December 31 to count for that tax year.
- Year-round planning fits business owners who want fewer surprises in April, especially when profit has grown faster than their tax planning.
- An extension gives more time to file, not to pay, and estimated payments are due during the year to avoid underpayment penalties.
Watch the story
A one-minute story about this strategy. Illustrative story; the people are fictional and are not clients. See all story videos.
Prep versus planning
For illustration purposes. Tax law may change, which may change these calculations slightly.
| Tax prep | Tax planning | |
|---|---|---|
| When | March–April | All year |
| The question | What do I owe? | What can I change? |
| What you get | A bill | A strategy |
The 2026 planning calendar
Here is how the key dates line up for the 2026 tax year, for a calendar-year business and its owners.
| Date | What has to happen |
|---|---|
| Now through December 31, 2026 | Most strategies: S corp salary and payroll, equipment placed in service, charitable gifts completed, Augusta Rule meetings held, children’s wages paid, rental hours logged, 401(k) deferrals run through payroll. |
| January 15, 2027 | Fourth-quarter 2026 federal and Oklahoma estimated tax payments. |
| March 15, 2027 | S corp and partnership returns for 2026 are due, or extended. Also the general deadline to elect S corp status for 2027. |
| April 15, 2027 | Federal individual returns are due, or extended. Last day for 2026 IRA and HSA contributions. First-quarter 2027 estimates are due. |
| September 15, 2027 | Extended S corp and partnership returns are due. SEP-IRA contributions can generally be made up to the business’s extended due date. |
| October 15, 2027 | Extended federal individual returns are due. |
Notice how little is left after December 31: a few retirement and HSA contributions, and elections for next year. Almost everything that lowers your 2026 tax has to happen in 2026.
Could this strategy work for your business?
In a free tax analysis, your tax strategist checks whether it fits and what it could save, using your real numbers.
How year-round planning works
- Start with a projection. Estimate this year’s profit and personal income early, then update it as the year goes.
- Pick the strategies that fit. Entity structure, salary, retirement, real estate, family, and giving strategies, chosen for your situation, not a generic list.
- Put them in motion during the year. Payroll changes, purchases, meetings, and gifts all need lead time.
- Check in before year-end. A fall review catches what’s changed while there’s still time to act.
- File what you planned. When tax season comes, the return reports a year you already shaped.
Who it fits
- Business owners who want fewer surprises in April.
- Owners whose profit has grown faster than their tax planning.
- Owners making big decisions, like buying equipment or property, hiring, or selling, who want the tax impact first.
When prep alone may be enough
- Simple W-2 returns with no business income.
- Very small or brand-new businesses with little profit yet.
The rules of the calendar
- The tax year closes December 31. For calendar-year taxpayers, most deductions, payments, and transactions have to happen by then to count for the year.
- Placed in service, paid, or completed. Each strategy has its own test, such as equipment in use, wages actually paid, or shares received by the charity. Starting isn’t enough.
- Extensions extend filing, not paying. An extension gives more time to file the return, not to pay the tax.
- Estimated payments are due during the year. Paying too little, too late, can bring underpayment penalties even if you pay in full in April.
Risks of waiting
- Missed strategies. If it wasn’t done by December 31, it usually can’t be done for that year.
- Rushed decisions. December purchases and gifts made in a hurry are where mistakes happen.
- Surprise bills. Without a projection, the first time you see your tax is when it’s due.
How we handle it for clients
With a Cannon & Brown tax plan, planning runs all year: we project your taxes, meet quarterly, put the right strategies in place before their deadlines, and prepare your returns from a year we planned together. You can call your advisor before big decisions, not after. Because our technology keeps your numbers current all year, we can test this strategy against your real numbers and adjust it as your business changes.
Educational overview. This page describes general deadlines for calendar-year businesses and individuals for the 2026 tax year; your dates may differ, and deadlines can shift when they fall on a weekend or holiday or when the IRS grants disaster relief. It is not a client example and not a promise of results. This page is educational and is not tax advice for your situation; tax rules and limits change.
Brooks leads Cannon & Brown Tax Advisors, a forward-thinking tax firm serving business owners in Oklahoma and beyond. He builds year-round tax strategies that help business owners keep more of what they earn and reach their goals. More about Brooks
Common questions about year-round tax planning
What can I still do to lower my 2026 taxes after December 31?
Not much: a few retirement and HSA contributions, such as 2026 IRA and HSA contributions until April 15, 2027, and elections for next year. Almost everything that lowers your 2026 tax has to happen in 2026.
Does filing an extension give me more time to pay my taxes?
No. An extension gives more time to file the return, not to pay the tax. Paying too little, too late, can bring underpayment penalties even if you pay in full in April.
When is the deadline to elect S corp status for 2027?
For a calendar-year business, March 15, 2027 is the general deadline to elect S corp status for 2027. It’s also the due date for 2026 S corp and partnership returns, unless extended.
Is tax planning worth it for a small business?
Simple W-2 returns, or very small and brand-new businesses with little profit yet, may be fine with prep alone. Owners whose profit has grown faster than their planning, or who face big decisions like buying property, hiring, or selling, are who year-round planning is built for.
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