Daniel Brooks 
The Section 179 deduction for freelancers lets you write off the full cost of business equipment in the year you start using it, instead of spreading it over several years. Software subscriptions are even simpler: they’re ordinary expenses you deduct as you pay them. And items up to $2,500 each can usually be deducted right … Read more
Unreported 1099 income almost never goes unnoticed. If you don’t report 1099 income, the IRS will very likely find out. Every 1099 your clients send also goes to the IRS, and its computers match those forms against your tax return. Usually, about a year or two later, you get a letter called a CP2000. It … Read more
Paying quarterly taxes with irregular income is easier than it looks. You don’t have to split your tax into four equal payments. Instead, you can pick one of three IRS-approved methods: pay a fixed amount based on last year, pay a share of whatever you earn each quarter, or use the annualized income method to … Read more
A SEP IRA for freelancers lets you save up to 20% of your net self-employment earnings for retirement, with a cap of $72,000 in 2026. Every dollar you put in lowers your income tax. It’s also one of the simplest accounts to run: no annual IRS filing, and you can open and fund it as … Read more
Use this underpayment penalty calculator to see what a late or missed estimated tax payment will cost you. The IRS penalty works like interest. For 2026, it runs at 6% to 7% a year on the amount you underpaid, for each day it was late. Missing a $3,000 payment in June and paying it with … Read more
The self-employed health insurance deduction lets you subtract the health insurance premiums you pay from your income. You take it on Schedule 1 of your Form 1040, so you get it even if you don’t itemize. It’s one of the most valuable freelancer tax deductions, because health coverage is often a freelancer’s biggest monthly bill. … Read more
For most freelancers, the best Solo 401(k) providers are the big brokerages: Fidelity, E*TRADE and Charles Schwab. All three charge no setup or annual fee, offer Roth contributions and let you trade stocks and ETFs commission-free. E*TRADE stands out because it also allows loans. If you earn a lot and want to save beyond the … Read more
The easiest way to pay estimated taxes online is IRS Direct Pay. It’s free, takes about five minutes and pulls the money straight from your bank account. You don’t need to create an account, and you can schedule a payment up to 365 days ahead. This guide shows the exact steps, the other online options … Read more
An HSA for self-employed people is a savings account for medical costs with a rare triple tax benefit. You can open one if you have a high-deductible health plan, even without an employer. In 2026, you can put in up to $4,400 with self-only coverage or $8,750 with family coverage. It pairs naturally with the … Read more
The Solo 401(k) contribution limits for 2026 let you save up to $72,000, or more if you’re 50 or older. That total has two parts. As the “employee,” you can put in up to $24,500. As the “employer,” your business can add up to 20% of your net self-employment earnings. Because you wear both hats, … Read more