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Your equity is a plan, not a bonus

Vest dates arrive whether or not anyone has thought about them. The work is deciding, ahead of time, what you sell, what you hold, and what the tax bill will be.

In one paragraph

Equity compensation planning is the work of deciding what to do with company stock before it vests or expires. It covers withholding, sale timing, concentration limits, and which tax treatment applies to each grant type, so RSUs, options, and ESPP shares are handled on a schedule instead of a reaction.

The problem

The part nobody warned you about

Your grant letter explains what you were given. It says nothing about what to do next. So the default happens: shares vest, your employer withholds a flat 22% for federal tax, and the position sits in the same account it landed in.

Two problems compound from there. If your household income puts you in the 32% or 37% bracket, that 22% withholding is short, and the gap surfaces as a bill at filing or as an underpayment penalty. Meanwhile your net worth quietly concentrates in the same company that already pays your salary.

Options add a clock. Incentive stock options can trigger alternative minimum tax in the year you exercise, even with no shares sold. Non-qualified options create ordinary income at exercise. Both expire, and both are easy to leave until the notice arrives.

What we actually do

The work, item by item

  1. 01

    Map every grant on one page

    Grant type, grant date, vest schedule, strike price, expiration. Most people have this in three portals and one PDF. We put it in one view so decisions stop being guesses.

  2. 02

    Close the withholding gap before filing

    We estimate what each vest actually costs at your marginal rate, then decide whether to raise withholding, make an estimated payment, or sell shares to cover it.

  3. 03

    Set a concentration limit you can live with

    You pick the percentage of net worth you are willing to hold in employer stock. We build the sell schedule that keeps you there, so it stops being an emotional call each quarter.

  4. 04

    Sequence exercises around the tax year

    Which options to exercise, in what order, and in which year. For ISOs that means watching the AMT line; for NSOs it means managing the ordinary income you are adding on top of salary and bonus.

  5. 05

    Use the sale to fund something real

    Diversification is not the goal by itself. Proceeds go toward the things you told us matter: the tax bill, the house, the education fund, the point where work becomes optional.

  6. 06

    Loop in your CPA before the year closes

    Most equity mistakes are timing mistakes, and timing decisions belong to December, not April. We bring your accountant into the conversation while it can still change the outcome.

An example

What this looks like in practice

A director at a medical device company has 1,800 shares vesting over the next twelve months and about 40% of her net worth already in company stock. She has never sold a share because the stock has been good to her.

We start with the tax number, because it is the one with a deadline. Then we agree on a ceiling for employer stock and set a quarterly sale schedule that walks her down to it over two years rather than all at once. The proceeds have jobs assigned before they arrive.

Nothing here required a market call. It required a decision made on a calm Tuesday instead of the week of a vest.

A composite illustration, not a specific client. Your situation and results will differ.

Free tool

Vesting this year? Find the tax bill nobody warned you about.

Employers commonly withhold federal tax on vesting RSUs at 22%. Plenty of the people we work with sit in the 32% or 37% bracket, and that difference shows up as a bill at filing. Five inputs and about twenty seconds gives you the number.

Illustration only
Shares vesting
1,200
Value at vest
$180,000
Withheld at 22%
$39,600
Owed at 35%
$63,000
Gap to cover
$23,400

Straight answers

Equity compensation: common questions

Related

This material is for general educational purposes only and is not intended as tax, legal, or investment advice. Neither GGM Wealth Advisors nor Cambridge provides tax or legal advice. Please consult a qualified professional about your specific situation. Estimates are illustrative, based solely on the figures you enter and simplified assumptions. Your actual results will differ.

Let's start with a conversation

Bring whatever is on your mind: a vest date you are unsure about, an offer you are weighing, a business you might sell in three years. Nothing to prepare, no cost, and you will leave with something useful whether or not we end up working together.