ISO vs NSO: Options and the AMT Trap
ISOs and NSOs are taxed completely differently. Get it wrong and you owe a six-figure AMT bill on stock that's now worthless. Here's the full breakdown.
Tag: taxes
All the articles with the tag "taxes".
The 0% Capital Gains Bracket
The 0% long-term capital gains bracket lets early retirees harvest gains tax-free. Here's how it works, who qualifies, and the ACA subsidy tension you need to know.
The Roth Conversion Ladder
Access your 401k before 59.5 without the 10% penalty. The Roth conversion ladder is how early retirees bridge the gap, here's the full mechanics.
Roth vs Traditional: Which One?
Roth vs Traditional isn't a personality quiz. It's a math problem. Here's the break-even logic, the tax-diversification argument, and when each one wins.
Rolling Over Your Old 401k: A Checklist
Left a job with an old 401k sitting there? Here's exactly what to do, all four options, the direct vs indirect rollover trap, and a step-by-step checklist.
Backdoor Roth IRA: A Step-by-Step Guide
Earn too much for a Roth IRA? The backdoor conversion still gets you in. Step-by-step 2026 guide with pro-rata rule explained and full Fidelity walkthrough.
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.