What is
tax timing?
Most tax advice asks what you owe. Tax timing asks when — and plans the moves before the dates that decide it. It’s the core of what we do.
~30 minutes, free, no obligation.
What is tax timing?
Tax timing is proactive planning around the dates that decide your tax: when income is recognized, when gains are realized, when deductions are taken and when wealth is transferred.
The same vest, sale or gift can be taxed very differently depending on the year, the holding period and the steps taken beforehand. A tax-timing strategy maps those dates in advance — the vest, the exercise window, the QSBS clock, the 1031 deadlines, year-end, the years before a sale — models each move, and coordinates it with your CPA and attorney before the window closes. It complements tax preparation, which reports a year once it’s over.
“Our advantage isn’t just knowing the tax code.
It’s knowing when to act on it.”
Most of the tax is decided
before the return.
By the time a return is prepared, the year is closed. The vest happened, the shares were sold, the deadline passed. Preparation reports what happened; it can’t change it.
Planning works forward. The highest-value moves have long lead times — a plan established before December 31, a holding period that has to run, a trust that needs years to season before a sale. Miss the window and the option is simply gone.
And the cost of waiting is real but invisible: dollars overpaid never get the chance to be invested, compounded or passed on.
Three taxes, each
with its own clock.
Most people deal with income, capital gains and estate tax one at a time, and too late — at filing, after the year is over. We plan all three together, ahead of the dates that decide them.
Income tax
Time RSU vests, bonuses and ISO exercises around your bracket — and, for owners, put the right retirement plan in place before year-end.
Capital gains tax
Harvest losses, choose the year a gain lands in, and plan concentrated positions, property and startup stock — each with a window to act in.
Estate & legacy tax
Get beneficiaries, titling and the step-up right first; add gifting and trusts as the estate grows — and receive an inheritance on the timetable the rules allow.
Start with the date
that’s coming for you.
Each area has its own deadlines — and its own window where planning still changes the outcome.
Life planning
Buying a home, getting married or facing illness or injury changes more than one part of your finances. We connect cash flow, goals, protection and tax timing in one plan.
Asset protection (insurance)
Insurance is one part of a coordinated financial plan. We review the risks to your income, family and business, then consider coverage that fits your needs and existing protection.
Charitable strategies
Your charitable goals belong in your financial plan. We coordinate the assets you give, the year you give and the structure you use with your broader cash flow and tax strategy.
The dates that decide it.
A sample of the deadlines and clocks we track for clients. Which ones apply to you depends on what you hold and what’s ahead.
Within 30 days of a grant
The 83(b) election window after receiving restricted stock. Miss it and it’s gone.
Each vest date
RSUs are taxed as ordinary income at vest — check withholding and cash before the date, not at filing.
More than one year
Assets held longer than a year can qualify for long-term federal capital-gains rates.
45 and 180 days
After a property sale: generally the deadlines to identify and close a 1031 exchange.
3 to 5 years
QSBS holding periods for the partial and full federal exclusion, depending on when the stock was acquired.
December 31
The close of the tax year — for loss harvesting, annual-exclusion gifts and, ideally, establishing a defined benefit plan.
Your filing deadline
Defined benefit contributions are generally funded by the tax-filing deadline, often up to 8.5 months after year-end.
2–3 years before a sale
While entity, QSBS, trust and gifting moves still have time to work.
Within 10 years
Most non-spouse heirs must empty an inherited IRA — the timing of withdrawals drives the tax.
Age 73 or 75
Required minimum distributions begin, depending on your birth year. The low-bracket years before them are the ones to use.
Dates reflect current federal rules as of September 2026 and are subject to change. Whether and how each applies depends on your situation.
Common questions
Is tax timing the same as tax preparation?
No. Tax preparation reports the year that just happened; tax timing plans the moves in the year ahead, before the return is due. We plan it, your CPA prepares and files it, and we coordinate so nothing is missed.
Isn’t timing just deferring the tax?
Sometimes it defers, sometimes it moves income or gains into a lower-rate year, and sometimes it uses an exclusion or deduction that’s only available if a step is taken in time. Every strategy relies on rules in the tax code — holding periods, elections, exclusions and plan limits — and no result is guaranteed.
Who benefits most from tax timing?
People with a date coming that will change their wealth: equity-comp professionals facing a vest, an exercise or a lockup; founders with a QSBS decision or an exit; business owners with a company to run or sell; and families with an estate taking shape or an inheritance to receive.
When should I start?
Before the date, not after it: before you exercise options or a large vest lands, within 30 days of a restricted-stock grant if an 83(b) election is on the table, 2–3 years before selling a business, and before year-end if you’re considering a defined benefit plan.
This page is general education, not tax, legal or investment advice. Rules and figures reflect current law as of September 2026 and are subject to change; any examples are hypothetical and not a guarantee of any result.
Put your dates
on the calendar.
A free, no-obligation Tax X-Ray of the dates ahead — and two or three specific moves to consider before they arrive.
~30 minutes, free, no obligation.