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// Tax planning

The transition tax picture is bigger than one paycheck.

A transition year can combine regular pay, severance, bonuses, equity, investment income, and a new salary. Withholding is money sent ahead. It is not the final tax calculation.

Reviewed July 24, 2026

01

Put the whole year on one page

Start with a calendar year view. List expected wages from each employer, severance, paid time off, bonuses, equity income, investment income, and any retirement account transactions.

The point is not to create a tax return. It is to see which events may stack into the same year and which choices still have timing flexibility.

02

Do not confuse withholding with the result

The IRS treats severance as supplemental wages for withholding purposes. The amount withheld from any payment may differ from the tax produced when every item on the return is combined.

Compare projected tax with year to date withholding and estimated payments. A CPA can confirm the calculation and whether an estimated payment or payroll adjustment is appropriate.

03

Coordinate the decisions

A rollover, Roth conversion, option exercise, stock sale, or large charitable gift can affect the same tax year in different ways. Model the interaction before treating any one move as isolated.

State taxes, residency changes, and equity earned across jurisdictions can require specialized advice. Bring those facts to a CPA early.

04

Where planning stops and tax advice begins

Jake provides tax smart financial planning. That means identifying interactions, building scenarios, and organizing the questions for the client and CPA.

Jake is not a CPA or EA and does not prepare tax returns. A qualified tax professional confirms tax treatment, filing positions, and the final numbers.

05

Questions for the transition year

A short list of open questions makes the CPA conversation more useful.

  • Which income items may arrive this calendar year?
  • What has already been withheld?
  • Which transactions are optional and which are fixed?
  • Did work or residency cross state or country lines?
  • Which assumptions need the CPA to confirm?

Primary sources

General education only. This page is not individualized investment, tax, legal, or insurance advice. Rules, plan terms, and personal facts can change the answer. Confirm your situation with the appropriate qualified professional.

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Start with the question

Most people don't need more information. They need clarity.

Bring the move, the offer, the package, or the question you can't get out of your head. We'll start there.

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