By the time a return is being prepared, nearly every decision that shapes it has already been made. Planning is the part of the work where the decisions are still open — and it happens in the months when nobody is thinking about tax.
Why April is the wrong month for this
A tax return is a record of a year that has finished. Very few things can still be changed once the calendar turns: some retirement contributions, an HSA contribution, an accounting method election here and there. Everything else — when income arrived, how it was characterised, what was bought and when — was settled months earlier. Planning is simply making those choices deliberately rather than by default.
A year, in four conversations
Spring: check the withholding
Once your return is filed, you know exactly what your tax picture looks like. If you owed a large balance, or received a very large refund, the withholding is wrong and there are still nine months to fix it. A large refund is not a win — it is a loan you made at no interest.
Summer: look at the shape of the year
Half the year is visible by June. Is income running ahead or behind? Has anything structural changed — a new business, a property, a job in another state, an inheritance? This is the moment when adjustments are still cheap, and when a projection is worth building.
Autumn: make the moves
September through November is when most planning actions are actually taken, because the numbers are nearly certain and the year is not yet closed. Common levers:
- Maximising retirement contributions, or setting up a plan if the business does not have one.
- Timing equipment purchases into this year or the next, depending on which year’s income they help more.
- Harvesting investment losses against realised gains — carefully, and with the wash-sale rules in mind.
- Bunching charitable giving into a year where it will actually be itemised.
- Considering a Roth conversion in a year when income is unusually low.
- Deferring or accelerating invoicing, for cash-basis businesses.
December: the last window
Payments made and actions taken by 31 December count for the year. After that, the list of available moves is very short. A single conversation in the second week of December is often the highest-value hour of the tax year.
Life events worth a phone call
Some events change a return enough that the call should not wait for the next scheduled conversation:
- Marriage, divorce, or the death of a spouse.
- A new child, or a dependant becoming independent.
- Starting a business, or changing its entity structure.
- Buying, selling or converting a property to a rental.
- A move between states, or remote work across a state line.
- An equity vest, an exercise of options, or a large one-off gain.
- An inheritance, a settlement, or an early retirement account withdrawal.
What planning is not
Planning is not a scheme, and it is not aggressive positions taken on a return. It is applying rules that already exist to a set of facts you still control — the timing, the structure, the account something sits in. Anything that depends on the position not being examined is not planning; it is risk with a nicer name.
Where to start
If you have never had a planning conversation, start with a projection: what this year looks like if nothing changes. Everything else follows from seeing that number while there is still time to act on it. Our clients get this as part of the relationship, not as a separate engagement.
This article is general information about how the tax rules work, not tax advice for your situation, and the rules change. Speak with a qualified preparer — we are happy to be that preparer — before acting on anything you read here.