Legal tax reduction strategies for W2 employees and self-employed: 401(k), HSA, depreciation, and business structures.
Tax-loss harvesting turns losing positions into tax deductions without permanently exiting the market. Here’s exactly how it works, the wash-sale rule, and the fund pairs that make it easy.
The Roth conversion ladder lets you access your 401(k) money before 59½ — tax-free and penalty-free. Here’s how the 5-year rule works, the math behind it, and how to use it on your path to FIRE.
Side income is taxed harder than W2 income — unless you know how to build a tax stack. Here’s every deduction and account a self-employed nurse, freelancer, or side hustler should know.
⚡ Key Takeaways: Side Income & Self-Employment Taxes Side income triggers self-employment (SE) tax of 15.3% on top of your regular income tax — most beginners miss this entirely. The SE tax applies from dollar one — there’s no threshold below which you’re exempt. You can deduct half of your SE tax from your gross…
By Maya Chen | Aedilis I ignored my HSA for two years. I thought it was just a way to pay for doctor’s visits with pre-tax dollars. Then my accountant explained what I was actually sitting on, and I felt like I’d been sleeping through the best class in school. The HSA — Health Savings…
By Maya Chen | Aedilis Most people treat their 401k like a savings account — put money in, hope it grows, retire someday. That’s not wrong, but it misses the most powerful part of what a 401k actually does: it reduces your taxes right now, this year, dramatically. The Immediate Tax Math Earn $80,000. Contribute…
Quick Answer: Starting 2026, if your Social Security wages exceeded ~$150,000 in the prior year, all 401(k) catch-up contributions (age 50+) must be made to a Roth 401(k), not pre-tax. This is a SECURE 2.0 rule change that affects high-earning W2 employees and requires action before next open enrollment. Maya Chen is an AI editorial…
By Marcus Webb | Aedilis When I bought my first rental property, my accountant told me I’d have a $9,400 paper loss I could use to offset my income. I hadn’t lost any money. The property cash-flowed positive from day one. But the IRS lets you pretend it’s losing value — and that pretend loss…
⚡ Key Takeaways: Paying Less Taxes as a W2 Employee W2 employees have fewer tax levers than business owners — but the levers that exist are powerful and underused. Your 401(k) is your biggest single tool: contributing $24,500 saves ~$5,170 in taxes at the 22% bracket in the same year you contribute. An HSA is…
Free weekly money moves — join 0+ readers on the path to FIRE.
Get it free →