Year-End Tax Planning for Stock Options, RSUs, and Deferred Compensation (2025 Guide)

If you have stock options, RSUs, or a deferred compensation plan, the weeks between now and December 31 aren’t just for holiday parties — they’re for decisions that can move your tax bill by tens of thousands of dollars.

Most executives wait until January, but the real savings window closes when the ball drops. Here’s what to look at now before you ring in the new year.

1. Stock Options: The AMT Game

If you hold Incentive Stock Options (ISOs) or Non-Qualified Stock Options (NSOs), timing is everything. Exercising ISOs before year-end could trigger the Alternative Minimum Tax (AMT), but done right, it can start your long-term capital-gain clock early.

• ISOs: Exercise strategically. Too much in one year can trigger an AMT surprise.

• NSOs: The spread between exercise and market price is ordinary income—check where it lands you in your 2025 bracket.

• Tip: Run an AMT projection with a tax advisor before December 15. The IRS doesn’t celebrate Christmas, but it loves a last-minute exercise.

2. RSUs and Performance Shares: Income You Didn’t Ask For

Restricted Stock Units (RSUs) and Performance Stock Units (PSUs) are a gift that keeps on taxing. When they vest, they create ordinary income whether you sell or not.

If you have shares vesting before year-end:

• Expect higher withholding, but don’t assume it’s enough. Many employers default to 22%, even if your marginal rate is 37%.

• You can sell some shares to cover taxes (“sell to cover”) or gift appreciated shares after they vest (see below).

• Review vesting schedules now—one December 31 vesting can push you into a higher tax bracket.

3. Deferred Compensation: The Hidden Lever

For executives with access to non-qualified deferred compensation (NQDC) plans:

• Consider deferring your 2025 bonus or other income into future years.

• This can offset RSU income or option exercises this year.

• It’s one of the few legal ways to smooth income spikes and stay under surtax thresholds.

If you haven’t made your elections yet, act before the plan’s cutoff date—most close in November.

4. Gifting Stock for the Holidays

Forget the sweater. Give stock.

• To family: Gift appreciated shares directly. You remove future appreciation from your estate and pass gains to someone likely in a lower tax bracket.

• To charity: Donate appreciated stock or use a Donor-Advised Fund (DAF). You’ll deduct the full market value and skip the capital gains tax entirely.

• Bonus move: If your RSUs vested at $200 per share and now trade at $300, that $100 of embedded gain disappears for good if you gift it to a qualified charity.

It’s one of the rare ways to beat both capital gains and the gift tax system in one move—and it makes a better story than a gift card.

5. Why Work with an Advisor Who Understands Stock Compensation

These strategies only work when the moving parts align—option exercise, RSU vesting, bonus deferral, and gifting strategy.

Most financial advisors don’t integrate tax modeling or understand how AMT, RSU withholding, and deferred comp elections interact. That’s where a specialized advisor—or a CFP® with tax experience—can make a measurable difference.

Because a “good problem to have” like too much taxable income still costs you 37% if you ignore it.

6. Your Year-End Game Plan

• Review vesting and exercise schedules.

• Check tax withholdings on RSUs and bonuses.

• Run a year-end AMT and income projection.

• Evaluate deferred-comp elections.

• Consider gifting appreciated stock before December 31.

• Schedule a strategy session—don’t wing it in April.

Final Thought

Year-end planning isn’t about beating the IRS. It’s about making sure you, not the calendar, controls when you pay taxes.

A few smart moves now can turn a stressful April into a calm one—and maybe even fund next year’s vacation with what you save.

The Big Beautiful Bill, Your Stock Options, and Why Your Uncle Sam Is Smiling

Every few years, Congress unveils a tax bill with a name so charming you already know someone’s about to pay for it.

This time it’s The Big Beautiful Bill — a sweeping reform promising “fairness,” “simplification,” and “support for working families.”

If history is any guide, those phrases are Washington-speak for:
“We mean the opposite.”

And if you earn much of your income through company stock, you’re probably in the someone category.

The Fine Print Behind the Smile

So what’s actually in this latest masterpiece of legislative optimism?

The headlines focus on “closing loopholes” and “asking the wealthy to pay their fair share.” But the details — always buried somewhere around page 1,200 — matter most to executives and professionals with complex equity compensation.

Here’s the short version:

• Higher top marginal rates. The bill nudges high-income brackets upward again, especially for earners above $400,000.

• Expanded Net Investment Income Tax (NIIT). The 3.8% surtax now covers more stock-based income, including certain option exercises and RSU vests that were previously exempt.

• A potential capital-gains surtax. Gains above certain thresholds may face an additional percentage point or two, depending on final reconciliation language.

• Increased IRS funding. The agency’s enforcement budget just got a raise large enough to make even Silicon Valley blush. Translation: more staff, more audits, more “friendly” letters.

In short, Uncle Sam is smiling because, for the first time in decades, he’s got both the data and the dollars to go hunting for uncollected tax revenue.

Where This Lands for Executives and Stockholders

For most high earners, tax season already feels like a slow-motion colonoscopy. This bill just adds another layer of paperwork.

RSUs

Every vesting event creates ordinary income — often right into the new, higher brackets. The company will withhold, sure, but not enough to cover your full liability if your total income crosses a threshold.

ISOs and NSOs

ISO exercises could re-ignite the Alternative Minimum Tax for many executives. And while the AMT thresholds are technically higher, the new surtax layers more liability back on top.

10b5-1 Sales

Your pre-scheduled sale plan still works — but the reporting requirements just tightened. That means more disclosures, shorter cooling-off periods, and less room to maneuver quietly.

Cost Basis

Brokers remain inconsistent with basis reporting. The IRS now has both the budget and the software to cross-check those numbers. Expect more questions when your Form 6251 doesn’t match your brokerage statement.

You Can’t Control Congress — But You Can Control Timing

No one can legislate their way into a lower bracket, but you can control how and when income hits your return.

A few quiet, practical habits go a long way:

• Coordinate vesting with bonuses. Bunching both in one year might push you into the new surtax territory.

• Double-check cost basis before filing — especially on partial option sales.

• Revisit your 10b5-1 plan. The SEC’s new reporting rules make transparency unavoidable; plan accordingly.

• Keep records of every option exercise and RSU vesting. Yes, every one. The new IRS matching algorithms don’t miss much.

You don’t need to outsmart Congress — just stay one spreadsheet ahead of your future self.

A Silver Lining (Kind Of)

The good news? None of this is catastrophic.
If anything, it reinforces what seasoned investors already know: tax planning beats tax reacting.

And for those who understand their equity, the Big Beautiful Bill doesn’t erase opportunity — it just penalizes procrastination.

“Every tax reform since 1986 has promised simplicity,” as one client once said.
“Yet I still have six different 1099s and a headache.”

Bottom Line

Uncle Sam’s smile may have gotten wider, but yours doesn’t have to fade.

You can’t change the rules, but you can learn them — and learning them is the whole point.

ExecStockTax.com — because every “tax simplification” somehow adds 47 new forms.

Disclaimer:
ExecStockTax.com is an educational blog. All content is for informational purposes only and should not be considered personalized financial, tax, or legal advice. For guidance specific to your situation, please consult a qualified advisor. We’re here to inform, not to file your 1040.

The EA Buyout: $55 Billion, One Giant Taxable Event

Every few years, a headline appears that makes investors cheer, employees squint, and tax advisors quietly refill their coffee.
This week, it was EA.

Electronic Arts will be acquired by a consortium led by the Public Investment Fund, Silver Lake, and Affinity Partners for $55 billion in cash — or $210 per share.
It’s the kind of number that looks better in a press release than on a 1099.

From Stock to Cash (and Then to the IRS)

If you’re an EA executive or longtime employee, your stock is about to become cash.
And cash, as it turns out, is much easier to tax than hope.

• RSUs? Ordinary income.

• Stock options? Either ordinary income or capital gains, depending on when you exercised.

• ESPP shares? A bit of both.

Each grant, vest, and exercise has its own basis, holding period, and tax treatment.
Think of it as a year-end bonus — only much larger, much more complicated, and arriving just in time for the IRS to notice.

The Real Game: Timing

In liquidity events like this, timing is everything — unless you’re late.
Once your shares convert to cash, most of the tax strategies people wish they’d used are off the table.

• A donor-advised fund can still soften the blow, but only if you fund it before the check clears.

• Trust structures (charitable remainder, Nevada, or Delaware) require time — not good intentions.

• Relocating from California might help, but the Franchise Tax Board has an excellent memory.

The difference between a smart liquidity plan and a painful one is rarely intelligence. It’s sequence.

After the Liquidity: What Usually Happens

Every major buyout produces two kinds of outcomes.

The first group treats their payout as freedom. They pay their taxes, diversify, and build the next phase of their lives with intention.

The second group treats it as victory. They buy homes, chase trades, and end up with the same worries — just in nicer zip codes.

If you’ve spent years building value inside EA, the hard part wasn’t getting the check. It’s deciding what that check now represents.

Optionality, Not Euphoria

A buyout is not an ending. It’s a forced reset — a chance to turn concentrated wealth into enduring capital.
Handled well, it’s liberating.
Handled poorly, it’s just expensive.

So take your time.
Get the math right.
And remember: the market may reward risk, but the tax code does not.

Timing Isn’t Everything — But It Might Save You 37% in Taxes (and Regret)

If you've ever watched your company stock soar 40%, only to sell a month later at a 15% loss because “the fundamentals still look good,” this post is for you.

Let’s talk about something most tax advisors won’t: technical analysis — yes, the charts and candles thing — as a way to make smarter decisions with your company stock.

Before you panic: no, you don’t need to become a day trader. You’re not buying NFTs.
But if you're holding a 7-figure position in Tenet stock (THC) and your retirement date is somewhere between “next year” and “please soon,” it pays to look at more than just your vesting schedule.

Meet THC: Tenet Healthcare, Wild at Heart

Take a quick peek at the last 3 years of THC's stock chart and it’s clear:
It doesn't move in straight lines.
It rips, it dips, and occasionally it moonwalks for no reason at all.

While you’re waiting for your options to mature, it might be worth noting that:

• THC dropped 40% in 2022, then doubled within 18 months

• The stock respects key support/resistance levels better than most executives respect their wellness stipends

• If you had sold on a technical breakdown below the 50-day moving average, you might have exited with more value (and less heartburn)

Why It Matters

When you own concentrated stock — especially something like THC — tax strategy is only half the battle.
The other half? Timing your exit with a little market awareness.

No, we don’t recommend trying to beat Wall Street. But pairing your tax plan with basic chart signals (think trendlines, moving averages, relative strength) can help you:

• Avoid selling at the bottom (always a crowd favorite)

• Lock in gains during market strength

• Diversify when your stock is cooperating, not capitulating

Bottom Line

You're not trading — you're managing risk.

Think of technical analysis as the weather radar for your equity position:
You still need to file your taxes… but maybe don’t schedule your entire financial future during a thunderstorm.

—

ExecStockTax.com — because “buy and hold” sounds noble… until it’s 52-week lows and tax bills.

ExecStockTax.com — because equity should feel like a reward, not an audit trigger.

There’s something deeply satisfying about earning company stock.

You’ve put in the hours, made the calls, survived performance reviews, and now you’re sitting on a generous pile of RSUs, stock options, or performance shares. It’s compensation with commas — the kind that shows up in your brokerage account, not your paycheck.

But if you’ve ever opened your tax return and muttered, “Wait, why do I owe that much?” — you already know the flip side.

Welcome to the "reward" that comes with fine print.

Equity Comp Is a Gift… With Strings Attached

Stock-based compensation is one of the most powerful wealth-building tools for corporate professionals — but it comes with a catch:
- It’s often taxable when you least expect it.
- It can become worthless if you leave the company too soon.
It can cause surprise AMT, Medicare surtaxes, and even get double-taxed if you report it wrong.

And here’s the kicker:
Many executives don’t know this until after they’ve already triggered the tax bomb.

You Deserve Better Than “Hope and Hold”

Let’s be honest — a lot of professionals take the “wait and see” approach with their equity:

• “I’ll just wait until I retire and sell everything.”

• “I’m sure HR set up the right withholding.”

• “It’s too complicated. I’ll deal with it later.”

Later becomes a spreadsheet from your CPA in April that reads:

Amount due: $128,449
Reason: You did… everything in one tax year.

Equity Should Build Wealth — Not Create Headaches

That’s why we created ExecStockTax.com — to help you take control of your equity compensation before it takes control of your tax bill.

This isn’t about beating the system. It’s about understanding how the system works so you can:

• Exercise stock options in a low-income year (not the year you cash your bonus)

• Sell RSUs with a plan (and enough tax withheld)

• Avoid Alternative Minimum Tax traps

• Diversify your holdings strategically — not in a panic the day you retire

This blog gives you practical insights, not financial jargon. Real strategies, not Reddit threads.

Because You’ve Earned This — After-Tax.

The truth is, you’ve already paid the price for this stock: in long nights, tough calls, and decades of commitment. You shouldn’t have to guess what it’s worth after taxes.

So consider this blog your unofficial stock compensation GPS — helping you navigate RSUs, ISOs, NSOs, AMT, and your eventual exit or retirement with more clarity and less cortisol.

Because equity should feel like a reward — not an audit trigger.

Stock Options, Taxes, and Tylenol: Welcome to ExecStockTax.com

If you’ve ever stared at your equity compensation statement like it was ancient Greek math, you’re in the right place.

Welcome to ExecStockTax.com, the blog where we unpack the wonderfully complex world of company stock compensation — and more importantly, how to avoid losing half of it to the IRS before you even book your retirement cruise.

We created this space for one simple reason:
You’ve worked hard, earned your equity, and now it’s time to make it count.
...But no one handed you a tax roadmap when those RSUs started vesting.

So here we are.

SNAP Stock: When Your Equity Plan Becomes a Check-Cashing Kiosk

Let’s talk about Snap Inc. — the social media company that may have invented disappearing messages, but whose stock charts suggest they also believe in disappearing shareholder value.

At Snap, executive stock behavior isn’t just a footnote in the 10-K — it’s a masterclass in how to treat your equity plan like it’s a paycheck from 1997 and you need to hit the check-cashing store on the corner.

SNAP: A Snapshot of Sell Now, Think Later

A quick look at insider activity shows a pattern that would make most wealth planners wince:

• Regular stock sales like clockwork, regardless of market conditions

• Exercise and sell combos, timed not with value or performance, but with the vesting calendar

• No pretense of “long-term holding” — just a straight-up liquidity event every month or two

It’s less “invested in the company’s future,” more “I’ve got property taxes due in Brentwood.”

The Problem with the Paycheck Mentality

For executives and directors with large stock compensation, this behavior can:

• Destroy the potential for long-term capital gains

• Trigger higher marginal tax rates (ordinary income + NIIT + AMT if ISOs are involved)

• Signal to markets (and employees) a lack of long-term alignment

More importantly, it turns what should be a wealth-building asset into just another cash flow tool — like you’re converting RSUs into DoorDash.

There’s a Better Way

We’re not saying you shouldn’t sell your stock — you absolutely should have a plan to diversify and create liquidity. But doing it without tax awareness, market sensitivity, or strategic pacing?

That’s not a plan. That’s deferred income with a side of regret.

Use your equity compensation like the strategic wealth lever it is — not like it’s the weekend and your vesting hit your account like a direct deposit.

ExecStockTax.com — because stock compensation should build wealth, not cover your HOA dues.

What We Cover (No Finance Degree Required)

Let’s be honest — there are only so many ways to make Incentive Stock Options, Restricted Stock Units, and Alternative Minimum Tax sound fun. But here at ExecStockTax, we try our best.

On this blog, we’ll help you:

• Decode the alphabet soup (RSUs, ISOs, NSOs… WTF?)

• Figure out when to sell, what to exercise, and how not to trigger AMT rage

• Learn why “just selling it all next April” might be the worst idea

• Understand your company’s equity plan rules before they bite you in Q4

• Plan for a smoother, smarter exit — whether that means retirement or just your next chapter

If you’re in your 50s or 60s and thinking, “I’ve got a lot of stock, and I have no idea what the tax bill will be if I touch it” — this blog is for you.

Who’s Behind the Keyboard?

I’m a tax and financial planning nerd who actually enjoys this stuff — and I’ve spent years helping executives and directors make better decisions with their stock. I'm not here to sell hype, predictions, or miracle strategies — just clear, experience-backed insights for people who want to keep more of what they've earned.

Think of this blog as the tax-savvy friend you wish you had at your last HR onboarding meeting. Except this friend won’t ask to borrow your Peloton.

What’s Next?

We’ll be posting regularly with:

• Real-world equity scenarios (and how they ended)

• Avoidable tax mistakes

• Tips to prep your equity for retirement

• And a few sarcastic headlines to keep it all readable

If you’re ready to stop guessing and start planning, stick around.
And if you're still not sure what the difference is between NSOs and ISOs, don't worry — neither does most of LinkedIn.