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Jess CatorcDecember 30, 2025
Who Needs to Pay Quarterly Estimated Taxes in 2025

A sudden boost in freelance income, a profitable stock sale, or even a large bonus might feel rewarding until the IRS expects its share. The U.S. tax system runs on a pay-as-you-go schedule, which means taxes must be paid throughout the year, not just at filing time. Anyone who expects to owe at least $1,000 in [...]

Justin GluskaDecember 29, 2025
Estimated Tax Guide for Irregular Earners Like Rideshare Drivers and Freelancers

Driving, delivering, or freelancing can give you flexibility and control over how you earn. But when income changes from week to week, keeping up with tax payments can feel confusing or unpredictable. Many independent workers are surprised to learn that taxes aren’t automatically withheld and that the IRS still expects payments throughout the year. Understanding how [...]

Justin GluskaDecember 25, 2025
What Is the Annualized Income Installment Method and How It Works

Freelancers, gig workers, and small-business owners often face uneven cash flow — and with it, the risk of IRS underpayment penalties. When income fluctuates throughout the year, dividing estimated taxes evenly across quarters can feel unfair. The Annualized Income Installment Method (AIIM) helps address that by aligning each payment with what you actually earned during [...]

Justin GluskaDecember 23, 2025
The Ultimate Guide to Qualified Business Income (QBI)

Here’s something worth exploring if you run a business. The Qualified Business Income (QBI) deduction under Internal Revenue Code Section 199A can allow certain business owners to reduce taxable income by up to 20% of qualified earnings. It may also apply to specific REIT dividends and income from publicly traded partnerships. Sole proprietors, partners, S corporation [...]

Jess CatorcSeptember 30, 2025
What Are Pretax Contributions to an IRA/401k?

Imagine reducing your next taxable income by as much as $7,000, simply by changing how a portion of your paycheck is allocated.  Pretax contributions allow you to direct part of your earnings into a traditional IRA or 401k before income taxes are applied. This may reduce your taxable income today, and your savings can potentially grow [...]

Jess CatorcAugust 12, 2025
Can I Trade Stocks Within My Solo 401k? Tax and Compliance Tips 

If you’re self-employed and using a Solo 401k to save for retirement, you may be wondering — can you actually trade stocks within the plan?  The short answer: Yes. But there are important tax rules and compliance issues to understand before placing your first trade.  This article is designed to help Solo 401k holders understand how stock [...]

Justin GluskaJuly 25, 2025
How State and Local Taxes Affect Your Investment Returns

When it comes to your investment returns, taxes can take a bigger bite than you might expect. Beyond federal taxes, state and local taxes (SALT) can also affect how much you actually keep. These extra layers of tax vary based on where you live and what types of investments you hold. That’s why understanding how [...]