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.

27 articles in this topic.

Featured posts

NQDC Plans: Worth the Employer Risk?

Non-qualified deferred compensation can cut your tax bill, but the balance is an unsecured IOU from your employer. Here is when an NQDC plan is worth the risk.

5 Oct, 2026
13 min read
State Tax Residency When You Move

Moving from California or New York to Texas? Your old state may still tax you. Domicile, the 184-day test, the convenience rule and audits, with 2025 numbers.

2 Oct, 2026
13 min read
Direct Indexing: Worth the Fee?

Direct indexing costs 3 to 13 times more than an index ETF and only pays off through tax-loss harvesting. Here's the break-even math for tech-worker incomes.

28 Sep, 2026
13 min read
Concentrated Stock: Sell or Exchange Fund?

Exchange funds defer tax on a concentrated stock position for 7 years but cost 1%+ a year and require $500k+ minimums. Here's when they actually beat selling.

25 Sep, 2026
11 min read
Which Account to Drain First

Taxable, then traditional, then Roth is a fine default at 65 and a costly one at 45. The bracket-filling alternative, with the 2026 tax math worked out.

24 Sep, 2026
18 min read
Donate Stock, Not Cash

If you give to charity and hold appreciated stock, writing a check is the worst option. Donating shares skips capital gains tax and still deducts full value.

14 Sep, 2026
14 min read

All Tax Strategy articles