Topic
Tax Strategy
Taxes are the single largest expense most people never optimize. For tech workers — especially those with side income, consulting gigs, or a homelab that crosses into business use — there's real money being left on the table. These posts cover quarterly estimated taxes (so you don't get surprised in April), the home office deduction, deducting equipment and subscriptions, and the basics of self-employment tax when your side project starts earning. Not tax advice. But the stuff worth knowing before you talk to someone who gives actual tax advice.
21 articles in this topic.
Featured posts
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QSBS: The $10M Tax Break
QSBS lets qualifying startup stock skip federal capital gains tax on millions in profit, but exercise late or structure a buyout wrong and you lose it entirely.
11 min read -
529 Plans and the Roth Rollover
The old objection to 529s, what if my kid skips college, just got a lot weaker. The SECURE 2.0 Roth IRA rollover changes the entire funding calculation.
11 min read -
Should Your Side Gig Be an S-Corp?
Below about $50,000 in net profit, an S-corp election costs more than it saves. Here's the salary-split math, the real costs, and the breakeven number.
10 min read -
RSU Taxes When You Move States
Move from California to Texas, vest RSUs a year later, and you can still owe California tax on part of that vest. How state sourcing for equity works.
9 min read -
Solo 401k vs SEP IRA
For most tech workers with 1099 side income, the solo 401k beats a SEP IRA. The math, the shared deferral limit, and the backdoor Roth trap that decides it.
11 min read -
The 83(b) Election: Your 30-Day Window
The 83(b) election has a strict 30-day deadline with no extensions. File it and a future tax bill shrinks to pocket change. Miss it and it can cost six figures.
11 min read
All Tax Strategy articles
- QSBS: The $10M Tax Break
- 529 Plans and the Roth Rollover
- Should Your Side Gig Be an S-Corp?
- RSU Taxes When You Move States
- Solo 401k vs SEP IRA
- The 83(b) Election: Your 30-Day Window
- A Roth IRA for Your Kid
- ISO vs NSO: Options and the AMT Trap
- The 0% Capital Gains Bracket
- The Roth Conversion Ladder
- Roth vs Traditional: Which One?
- Rolling Over Your Old 401k: A Checklist
- Backdoor Roth IRA: A Step-by-Step Guide
- ESPP: Don't Leave Free Money on the Table
- Tax-Loss Harvesting: Free Money (Sort Of)
- 401k Math: What You're Actually Saving
- Side Income Taxes for Software Engineers
- The Home Office Deduction, Demystified
- Quarterly Taxes: Don't Get Wrecked in April
- The HSA Triple Tax Advantage
- RSU 101: Sell or Hold? The Math