Tag: taxes

ESPP: Don't Leave Free Money on the Table

Your ESPP is a 15-32% guaranteed return hiding in your benefits portal. Here's the math, the tax rules, and why you should nearly always sell immediately.

Tax-Loss Harvesting: Free Money (Sort Of)

Tax-loss harvesting offsets capital gains and cuts your tax bill — if you follow the wash-sale rules. Here's the VTI→ITOT swap and the honest math on deferral.

401k Math: What You're Actually Saving

Maxing your 401k doesn't cost $23,500. At a 35% tax rate it costs $15,275. Here's the math, the 2026 limits, and how to stop leaving money on the table.

Side Income Taxes for Software Engineers

Side income hits harder than W-2: you pay SE tax plus income tax. Here's the Schedule C breakdown, the SE tax math, SEP-IRA limits, and quarterly estimates.

The Home Office Deduction, Demystified

W-2 remote workers can't claim the home office deduction post-2017 TCJA. Here's who can, how the simplified vs regular method math works, and when each wins.

Quarterly Taxes: Don't Get Wrecked in April

Owe $1k+ in taxes after withholding? You're supposed to pay quarterly. Here's the safe harbor rule, 2026 due dates, and the math on $30k freelance income.

The HSA Triple Tax Advantage

Your HSA is the only account with three tax advantages. Here's how to turn it into a stealth IRA — and the math that makes it worth maxing every single year.

RSU 101: Sell or Hold? The Math

RSUs are taxed as income at vest, not when you sell. Here's the math on concentration risk, your tax hit at vest, and why selling immediately usually wins.