11 Tax Moves High Earners Should Make After Filing | Dan Pascone | Ep #58

Written By: Dan PasconeMay 7, 2026

Answer Box (TL;DR)

TL;DR: If you just filed taxes and felt a “gut punch” (big bill or bigger-than-expected tax), your return is telling you exactly what broke, effective tax rate, withholding gaps, capital gains, and equity comp exposure. This solo episode lays out 11 post-filing moves to make in the next few weeks so you don’t repeat the same mistakes next year. The goal isn’t perfection; it’s fewer surprises, better coordination, and a system you run before Q4.

Key Takeaways

Your tax return is a diagnostic document: it’s a breakdown of what happened, your real tax rate, equity comp exposure, capital gains, and whether withholding was aligned.
The window is short: the “fresh motivation” after filing fades fast. Book time now so the numbers don’t go cold.
Lumpy income breaks withholding: bonuses, commissions, and equity events often withhold at rates that don’t match high-earner marginal rates.
Schedule D is underused: it shows realized gains/losses and whether last year’s results were intentional or accidental.
W-2 earners still have levers: retirement mix, asset location, tax-loss harvesting systems, charitable structure, equity comp playbooks, and mid-year projections.
Tax planning is a cadence: mid-year check-in + simple income forecast is how high earners prevent surprise bills.

Key Moments

00:01 — The “gut punch” after filing and why it keeps happening 01:43 — Why this solo episode exists: post-tax-return strategy for high earners
03:00 — Your return is diagnostic: effective rate, equity comp, withholding, gains
06:00 — The first 3 moves to do now: effective rate, withholding, Schedule D
12:00 — Retirement contribution opportunities (incl. mega backdoor if eligible)
15:00 — Asset location + tax drag (what you own vs where you hold it)
17:00 — Charitable strategies: DAFs and donating appreciated securities
20:00 — Equity comp: tax exposure + concentration risk and diversification
24:00 — Estate docs + beneficiary designations (avoid silent mistakes)
27:00 — System moves: mid-year check-in, income forecast, one commitment

Episode Summary

Most high earners treat tax filing as the finish line: they scramble to gather documents, file, pay (or receive) a refund, and then never look at the return again. Dan reframes the tax return as one of the most useful planning documents you’ll see all year because it reveals your effective tax rate, the true drivers of your tax bill (bonus, equity events, investment income), and whether your withholding was aligned or dangerously off.

This episode is a practical “next few weeks” playbook: 11 moves designed to keep you from repeating last year’s mistakes. First, read the return while it’s fresh: compare effective tax rate year-over-year, fix current-year withholding using what you now know about your income mix, and review Schedule D to understand whether capital gains/losses were intentional. Then upgrade the structure: optimize retirement contribution mix, improve asset location to reduce tax drag, build a charitable giving structure, and create a multi-year equity compensation playbook that also reduces concentration risk.

Finally, Dan turns the checklist into a system: schedule a mid-year tax check-in now (June/July), build a simple income forecast for the current year (salary, bonus, vest schedule, investment income, spouse changes), and make one clear commitment that next year’s return will reflect intentional decisions rather than reactive scrambling.

Transcript

Dan Pascone (00:01): …If you just filed your taxes and felt that gut punch moment… you’re not alone… this is built for high earners who want to use their tax return for what it actually is… a diagnostic document…

Dan Pascone (01:43): …this is all about post-tax return strategy… “Dan, I paid way more in taxes than I feel like I should have…” …your tax return is a diagnostic document… a breakdown of the financial decisions you made in the last 12 months…

Dan Pascone: …The document’s gonna show you your real tax rate, your equity comp exposure… whether your withholding is dangerously off… bonuses or equity events hit and the withholding on those was not in line with their real tax rate…

Dan Pascone: …First three: do them right now… Item one: review your effective tax rate… compare to last year… Item two: check your withholding for this year… bonuses and equity events typically withhold at a lower rate than your real rate… Item three: pull Schedule D and review capital gains and losses…

Dan Pascone: …Next: review retirement contribution opportunities… asset location… charitable giving timing and structure… review equity compensation events… check estate documents and beneficiary designations…

Dan Pascone: …System: schedule a mid-year check-in (June/July)… build a simple income forecast… and make one commitment around next year’s return…
Dan Pascone: …We created a checklist… available on yourtailoredwealth.com… You can get all of our content at makingsenseofyourmoney.com…

Resources & Citations

IRS Tax Withholding Estimator
IRS Topic: Capital Gains and Losses (Schedule D context)
Making Sense of Your Money (Content Hub)
Tailored Wealth Website
Podcast Archives

FAQ

What should I do right after filing taxes if I had a surprise bill?

Use your tax return as a diagnostic document while the numbers are still fresh. Start with your effective tax rate, then immediately check current-year withholding (especially if you have bonus/commission/equity income), and review Schedule D to see if gains/losses were intentional. The goal is to fix the inputs now so you don’t repeat the same outcome next April.

Why is withholding often wrong for executives with bonuses and equity comp?

Because “lumpy” income events (bonuses, commissions, equity vests) can be withheld at rates that don’t match your true marginal rate. That creates the illusion that taxes are being handled, until filing reveals the gap. A mid-year projection and a withholding update can prevent the bill from compounding all year.

What is the most valuable page in my tax return for planning?

Schedule D is one of the most underused pages because it summarizes realized capital gains and losses. It tells you whether you created gains on purpose, whether losses were harvested effectively, and whether gains stacked on top of high W-2 income in a way that increased your overall liability.

How do high earners reduce “tax drag” in taxable accounts?

Two big levers are asset location (holding tax-inefficient assets in tax-advantaged accounts when appropriate) and running tax-loss harvesting as a system rather than a one-off move. For some households, direct/custom indexing can create more frequent loss-harvesting opportunities, subject to suitability and execution quality.

What should I do about equity compensation after filing?

Review what triggered taxes last year (RSU vests, option exercises, ESPP sales) and build a forward-looking playbook. This typically includes both a tax strategy and a concentration-risk plan, because company stock often impacts both your net worth and your paycheck. The goal is multi-year coordination, not reacting to each event.

What is the one system step that prevents next year’s surprise?

Schedule a mid-year tax check-in now (June/July) and build a simple income forecast (salary, bonus, vest schedule, investment income, spouse changes). When you can see the year coming, you can make decisions ahead of it instead of scrambling after it’s too late.

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