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.

10 articles in this topic.

Featured posts

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.

25 Jul, 2026
9 min read
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.

23 Jul, 2026
10 min read
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.

9 Jul, 2026
8 min read
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.

3 Jul, 2026
8 min read
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.

1 Jul, 2026
8 min read
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.

27 Jun, 2026
10 min read

All Tax Strategy articles