Tax Planning

Tax Planning & Mid-Year Advisory

By the time you hand me your W-2 in March, the year is closed and almost everything that could have changed your number already happened. Planning is the part you can still do something about.

The difference

Preparing a return is looking backward

Tax preparation is history. I take what happened last year, report it correctly, and file it. If you sold stock in July or took a distribution in November, my job in March is to record it accurately — not to change it, because it cannot be changed.

Planning is the other half, and it is the half most people never buy. It happens while the year is still open, when a decision can still go a different way. The client who calls me in June asking whether to exercise options is in a completely different position from the one who tells me about it the following March.

The most common one

The mid-year check-up

Most people come to me for the same question: am I actually covered for April, or am I heading for a bill? Between May and September, that is a question with a real answer instead of a guess.

You upload your year-to-date paystubs and anything new to the portal. I project where you land for the full year, and you get a written one-page projection showing the number and what to change — a W-4 adjustment, an estimated payment, or nothing at all if you are fine.

The point is timing. A withholding change made in June has seven months to work. The same change made in December has three weeks.

What we work on

The decisions worth a conversation first

Some of these are seasonal, some are once in a lifetime. All of them are cheaper to discuss before you act than to clean up after:

Income & withholding
Withholding check-ups — are you covered, or short?
Estimated-tax recalibration for 1099, K-1, and investment income
Equity compensation — RSU vesting, ISO and NSO exercises, ESPP
A new job, a raise, or a second income in the household
Retirement & later life
Roth conversions — how much fits before it costs more than it saves
Medicare IRMAA — this year’s income sets your premiums two years out
Inherited IRAs and the ten-year distribution clock
When to start Social Security, and how much of it gets taxed
Investments & property
Capital gains timing and loss harvesting before December
Selling a home — the exclusion rules and what documentation you need
Buying or selling a rental
New York residency if you are splitting the year with Florida
Family & giving
Marriage, divorce, a new baby, a child aging out
Charitable bunching, donor-advised funds, and giving appreciated stock
Qualified charitable distributions once you are taking RMDs
Education funding and how the credits interact

If your situation is not on this list, ask anyway. The list is what comes up most, not a menu.

Straight answer

Who this is not for

If your return is one W-2 and a standard deduction, you probably do not need planning. Your withholding is close enough, there is not much to time, and I would rather tell you that than sell you a session you do not need.

It earns its keep when there are moving parts — self-employment income, a rental, equity compensation, a retirement transition, a year where something big happened or is about to.

How it works

Three ways to do this

A mid-year check-up is the usual starting point — a projection and a written recommendation, May through September. A planning session is an hour on one specific decision, whenever the decision comes up. Year-round advisory bundles the check-up, a November projection, two sessions, and email access between filings for clients who would rather ask than wonder.

All three are separate from return preparation, and available whether or not I prepare your return. Current pricing is on the pricing page, and every engagement is quoted before any work starts.

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