June 30, 2026
The halfway point of the calendar year is a natural moment to take stock of where things stand. Many executives are occupied with other priorities at the year’s midpoint, and equity compensation planning doesn’t always make its way onto the agenda. A mid-year equity compensation review is a healthy practice for any executive to adopt, and something that many experienced advisors initiate.
What follows is a checklist of five areas worth examining now, while there is ample time to act before year-end windows close.
Five Areas to Cover in a Mid-Year Equity Compensation Review
1. Are withholding and estimated taxes tracking your actual liability?
RSU vesting generates ordinary income at the time of vesting, and default withholding often applies a flat supplemental tax rate that does not account for total household income or marginal bracket. If multiple grants have vested this year, or if bonus income has come in above expectations, there may already be a gap between what has been withheld and what will ultimately be owed.
The IRS requires estimated tax payments on a quarterly schedule when withholding is insufficient, with the third-quarter deadline falling in September. Missing that deadline can result in an underpayment penalty, on top of a larger-than-expected tax bill in April. Reviewing year-to-date vesting income and coordinating with your CPA now, rather than in December, leaves a meaningful runway to adjust. In RSU Withholding vs. What You May Owe, we covered the mechanics of this withholding gap in more detail.
2. Where does your concentrated position stand relative to target allocation?
Share prices move, grants continue vesting, and Employee Stock Purchase Plan (ESPP) purchases accumulate. What looked like an acceptable concentration level in January may look different today if the stock has run up or if additional shares have hit the account.
A mid-year check-in should give you a current picture of how much of your net worth is tied to one company, and whether that exposure still fits within the range you and your advisor have defined. If concentration has grown beyond the target, the question becomes whether any of the upcoming trading windows provide an opportunity to take action. A simple framework we use at Spectrum Asset Management is covered in detail in How Do Executives Diversify Concentrated Stock?
3. Are upcoming trading windows mapped to your plans?
For many executives, the trading windows that follow quarterly earnings are among the few chances each year to transact in company stock. Missing a window can push decisions out by three months. A mid-year review should include a look at when the next open window is likely to open, what liquidity needs or diversification moves are on the list, and whether a Rule 10b5-1 plan would help systematize future sales outside of those windows. As we noted in What To Do Before a Stock Trading Blackout Period, the goal is to build the plan before the window dictates it.
Here are common mid-year items to confirm before the next open window:
- What liquidity needs are on the horizon for the next 90 to 180 days?
- Have any planned sales become more or less compelling given current share price?
- Is there an existing 10b5-1 plan in place, and is it still aligned with current goals?
- Have vesting events this year increased concentration beyond the target?
- Are there any compliance, pre-clearance, or documentation requirements to handle?
4. Do any planned charitable gifts still make sense at current prices?
If appreciated employer stock was part of a charitable giving plan for the year, the current share price affects both the tax efficiency and the practical timing of that gift. Donating shares directly rather than cash is generally worth reviewing with a CPA before year-end, particularly when prices have moved meaningfully from where they were at the start of the year. Timing a gift into a high-income year can affect the benefit of the deduction. That coordination is part of the broader discussion we covered in Charitable Planning with Employer Stock.
5. Has anything changed that the rest of your plan doesn’t reflect yet?
Mid-year is also a reasonable time to flag any material changes that have occurred: a new grant, a role change, a company event that affects equity, or a shift in personal circumstances. Plans made in January with one set of assumptions may need to be revisited if the underlying facts have shifted.
This kind of review is part of what a coordinated wealth advisory relationship is designed to deliver. If your advisor is not initiating this conversation, that is worth noting.
Ready to run through these items for your own situation? Contact Spectrum Asset Management to address any of these items with our team.
Disclaimer: This material is for informational and educational purposes only and should not be construed as personalized investment, legal, or tax advice, or as a recommendation of any specific security or strategy. All investing involves risk, including the potential loss of principal. Tax rules and estimated payment requirements vary by individual situation; consult your CPA and financial advisors regarding your personal circumstances. Nothing herein constitutes an offer to enter into an advisory relationship. Spectrum Asset Management, Inc. (SAM) is an SEC-registered investment adviser headquartered in Newport Beach, California. SAM is not affiliated with any other firm using a similar name.
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