🎉 Your 2025 tax playbook: planning for the end of the TCJA party

☕ Good morning!

If you’re earning $400K–$2M+ and dealing with RSUs, bonuses, or stock options, your tax picture is a complex live organism, and what you do between now and December could define your wealth trajectory for the next decade.

The TCJA party’s almost over. By Q1 2026, if Congress snoozes, and let’s be honest, they might, top marginal tax rates will go from 37% back to 39.6%, the standard deduction will be halved, AMT thresholds will be slammed down, and the estate exclusion is going to shrink like a wet wool suit.

In other words, the tax landscape that’s defined planning since 2017 collapses on Jan 1, 2026, and if you’re not using 2025 as your optimization lab, you’re burning money. 

Today, we’re talking about core restructuring for high-income execs sitting on complex comp packages, pre-exit equity, and estate-hinging net worth.

🔥 Income Acceleration Isn’t Optional, It’s Infrastructure

So, with a whole bunch of favorable tax perks on the chopping block, what can you do today? 

Most execs will think, “pull some comp forward.” That’s JV. You’re threading income cliffs, NIIT exposure, state taxes, and overlapping option exercises. Stack it wrong, and you could nail a $200K 2025 tax bill and still be worse off when 2026 hits harder. Ouch. 

To execute it right, you need to thread the needle. Max out deferred comp at lower rates, knowing you'll draw it when rates are higher. Also, realize the ISO spread in AMT territory, meaning you can capture credits you can use later.

You can start by reducing your W-2 taxable income through pre-tax contributions to your 401(k), HSA (if eligible), and Roth strategies, and even layering in the mega backdoor Roth (if available) can help 2–3x retirement savings beyond the standard limits.

🔄 By May 1: Log into your 401(k) and check your deferral pace. You should be on track to hit the $23,000 max for 2025 (plus $7,500 if you’re 50+). Adjust now so you don’t come up short in Q4.

🏥 By May 15: Confirm you’re HSA-eligible through your health plan. If so, automate contributions toward the $4,300 individual / $8,550 family limit (+$1,000 catch-up if 55+). Triple-tax-advantaged = no-brainer.

🧠 By June 1: Ask HR if your 401(k) supports after-tax contributions. If yes, calculate your unused space under the $69,000 total cap and kick off your mega backdoor Roth. This is how high earners unlock Roth access at scale.

You can also layer RSU liquidation to avoid phaseouts: 199A, IRMAA, child tax credits— yes, even at $1M+ AGI, every layer matters.

🎓 By May 30: Funnel cash into your state’s 529 plan (if it qualifies) → States like NY might hand you a $10K deduction just for showing up.

🔋 This summer: Upgrade your life (think solar, EV chargers, or insulation). This could unlock 30% back in federal tax credits.

📉 By September 1: Scan your taxable accounts and harvest losses to cancel out gains from RSUs or any fire-sale stock dumps.

Most execs (or even financial advisors) won't model 2025 income stacking across play types, but the sharp ones that do will bag the delta. 

This is especially useful when planning for RSU vesting and option exercises. 

🔁 By September 15: Take inventory of any chunky income (bonuses, severance, equity sales). If you can, punt it to 2025 and clear the deck for smoother stacking.

📆 Q4 2025: Expecting a bracket bump in 2026? Lock in income now and kick big deductions (donations, property taxes) into next year when they’ll do more damage.

📊 2025–2026 game plan: Break up ISO exercises, stock sales, and other big-ticket events. Avoid bracket blowups and AMT landmines.

🎯 DAF Stacking as an Estate Play, Not Just a Deduction

If stacking appreciated stock into donor-advised funds is your only move, you’re a decade late. DAFs have been used to drain embedded capital gains and slide around estate inclusion strategically.

The power play is to bundle RSU liquidation and DAF transfer in your lowest-rate year. This will help you capture full FMV deduction and bypass capital gains. Paired with a CLAT (charitable lead annuity trust), your estate could lose a chunk of tax exposure permanently.

One CFO we modeled cut $320K in gains and kept AGI under critical cliff levels in a single gift cycle.

The advanced play is to convert appreciated RSUs to common post-vest, 83(b) it into a DAF pre-exit. You didn’t just save tax; you erased gain recognition entirely. 

It's aggressive. It's not for the basic tax dude with TurboTax. But done right, it’s incredible.

By the way, if none of that made sense to you, that’s OK — that’s literally what I’m here for. Most CPAs just file returns. Most financial advisors don’t do in-depth tax planning. But if you’re a high-income earner, reducing your tax bill is essential. Having a comprehensive planner who does both isn’t a luxury. It’s a game-changer.

📈 By June 15: Scan your portfolio for appreciated stock or RSUs that are sitting on big, unrealized gains. It’s better to plan the exit than get surprised by the taxman.

🏛️ By August 1: Fire up a Donor-Advised Fund. Offload appreciated shares (not cash) to double-dip the deduction and dodge capital gains.

🎯 Plan ahead for 2025: Stack 3–5 years of giving into one tax year. “Bunch” donations to blow past the standard deduction and unlock a bigger itemized write-off.

📉 Deconcentration Tactics: Avoiding a Stock Implosion With a Tax-Savvy Playbook

If there’s one lesson markets whispered (or screamed) for everyone to remember lately, it’s that macroeconomic forces are unpredictable. 

So, let’s kill the “buy and hold till it crashes” strategy, at least with your nest egg. 

If 2025 is your exit year or the year you get fully liquid, don’t sit on a $5M single-stock cliff waiting for a diversification “later.”

Here are a few things you can do:

1. Harvest tax losses and pair them with RSU sales to clip your gains 

2. Use exchange funds to defer taxation and rebalance risk without touching your wallet.

Our 2025 Executive Tax Reduction Checklist goes deeper into what you can apply to your own  financial picture. No fluff, just smart planning that fits your comp structure and cash flow.

👉Get the Guide Here.

🧠 Making Sense of Your Final Offensive Year

2025 isn’t business as usual. 

It’s your last fully optimized tax year before rates, deductions, and estate rules reset, and the smart money is already playing like it.

They’re not just forecasting income; they’re modeling withholding schedules, Roth conversions, and option exercises by calendar quarter. They’re locking in gains and deductions with precise timing. 

By Q4, they won’t be planning; they’ll be adding the finishing execution touches. 

Key dates to own now:

🗓️ By May 15: Audit your advisor. Do they know equity comp and tax stacking inside out? If not, time to upgrade.

📞 By June 15: Interview one specialist. Ask for case studies with execs like you.

🔁 By September: Run a full Q3 planning session. Stack income. Flag gains. Realign your strategy with the actual calendar.

📤 In Q4: Accelerate income if your 2026 bracket is climbing. Delay deductions to next year where they’ll do more damage.

Let’s start NOW and make next year’s tax season something you actually look forward to.

Stay savvy, stay proactive, and keep your financial future bright.

Until next week!

This information is not intended to be a substitute for specific individualized tax advice. We suggest that you discuss your specific tax issues with a qualified tax advisor.

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