“December Is Too Late”
Every year around Christmas, my phone starts ringing off the hook. It's always the same conversation: "Hey, I just got my year-end bonus and my RSUs are vesting next week. What should I do about taxes?"
And honestly? By then, we are all playing defense. The good moves - the ones that actually save you real money - those happen months earlier.
The sharpest execs start year-end planning in July. They know their equity package isn’t just a reward - it can blow up in your face come April.
RSUs vest. ISOs expire. Bonuses drop. And without a strategy, April delivers a five-figure surprise.
Let’s make sure that’s not you.
Here are five strategic moves to make now - while there’s still time to act.
What Should I Do Before My RSUs Vest?
This is the one that gets everyone. You think RSUs are "free money" because you don't have to do anything. They just... vest. Like magic.
Except the IRS treats them like regular salary the moment they hit your account. So, if you're already making $200K and another $50K in RSUs vests in November, guess what? You're now in a higher tax bracket for the year.
I watched this happen to multiple people at tech companies. Roughly $200K base, $80K in RSUs vest in Q4, plus a $40K bonus. Total comp looked great on paper - $320K. Tax bill? Let's just say his December celebration was short-lived.
What to Do Now:
- Pull up your vesting schedule
- Forecast your Q3 and Q4 equity income
- Coordinate charitable deductions, deferrals, or other income around it
A little advance planning could save you thousands in surprise tax.
How Do I Avoid AMT on My ISOs?
I have a love-hate relationship with Incentive Stock Options. If you hold Incentive Stock Options (ISOs), you’re sitting on a double-edged sword.
Yes—they’re powerful.
But they're also the #1 way I see smart people accidentally trigger massive tax bills.
What to Do Now:
- Run an AMT projection before you exercise
- Consider a small test exercise in Q3 to generate AMT credits
- Keep your CPA looped in before you pull the trigger
ISOs can build wealth. But only if you use them strategically.
Are My RSU and Bonus Withholdings Too Low?
This one's sneaky. Most companies withhold 22% on RSUs and bonuses because that's what the IRS says to do for "supplemental income." Sounds reasonable, right?
But if you're in the 35% bracket (or higher), that 22% is nowhere near enough. You'll owe the difference, plus penalties if you really underpaid.
What to Do Now:
- Run a mid-year tax projection
- Increase W-2 withholding or make estimated payments
- Avoid a last-minute scramble (and a check to the IRS)
Waiting until April = damage control. Planning now = peace of mind.
Am I Too Concentrated in Company Stock?
I get it. You work for a great company. The stock's been good to you. You believe in the mission.
But here's the thing: having 60-70% of your net worth in one stock isn't diversification - it's gambling. And I've seen too many smart people get burned when their company hits a rough patch.
Remember Enron? WorldCom? Even good companies can stumble. Don't let your entire financial future depend on one stock ticker.
What to Do Now:
- Set up or revisit a 10b5-1 plan
- Schedule tax-efficient diversification across asset classes
- Build a more resilient portfolio before markets get volatile
You’ve earned the shares. But that doesn’t mean you should hold them all.
Get Ahead of 2026—The Tax Code Just Got a Makeover
With the passage of the One Big Beautiful Bill Act, we’re officially on the clock.
The bill made permanent some of the “Trump-era” tax cuts - but it also introduced new phaseouts, limitations, and planning cliffs that most executives haven’t seen coming.
Here’s what’s in motion:
- New deduction caps based on income and filing status
- Charitable strategies and Roth conversions that make even more sense now—but only for a limited time
Translation? The planning window is narrow, and the IRS is not waiting for you to catch up.
Final Thought: Don’t Let December Be Too Late
Look, I'm not trying to scare you. But I am trying to save you from making the same mistakes I see every year.
The biggest mistake we see executives make is assuming HR, payroll, or their CPA is tracking the big picture. We all know what happens when we “assume”.
The truth is, They’re not.
And by the time you realize it, the opportunity’s gone - and the IRS is already at the door.
This is the same framework we use with our top executive clients to stay ahead of taxes, risk, and deadlines - before the window closes.
You’ve earned the equity.
Let’s make sure it builds wealth - instead of triggering a tax bill.
Download our free Comprehensive Wealth Plan For Executives eBook and schedule a strategy session to make sure your next move is a smart one.
If you would like to discuss your current situation schedule a free 20-minute call with the link below.
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