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Justin GluskaJanuary 8, 2026
Tax Deductions and Retirement Tips for Software and Web Developers

Rising income from tech work can create just as many tax questions as financial opportunities. Whether you’re a salaried developer, independent contractor, or juggling both, the way you report income and choose deductions may have a meaningful impact on how much you actually keep in 2025. The right retirement plan can also turn tax savings [...]

Jess CatorcJanuary 6, 2026
Tax Deductions and Retirement Tips for Sole Proprietors

Running a business alone means every financial decision affects both today’s income and tomorrow’s security. Each deductible expense can reduce your current tax bill, but it can also shape how much you’re able to set aside for retirement. In 2025, sole proprietors will continue to report income and expenses through Schedule C, yet small updates, like [...]

Justin GluskaJanuary 5, 2026
Tax Deductions and Retirement Tips for Partnerships

Partnership income is not taxed at the entity level. Instead, it flows through to each partner and appears on their individual return, along with deductions and credits that affect self-employment tax and retirement contributions. This is why Schedule K-1 allocations, guaranteed payments, and how income is classified are more than bookkeeping items. They directly determine your [...]

Jess CatorcJanuary 2, 2026
How the IRS Calculates Underpayment Penalties

Many people don’t realize that paying too little in estimated taxes throughout the year can lead to an unexpected penalty from the IRS. This underpayment penalty is essentially a charge for not paying enough tax when it’s due, and it can catch you off guard if your income varies or comes in irregularly.  In this quick [...]

Justin GluskaJanuary 1, 2026
Tax Deductions and Retirement Tips for Independent Contractors

Independent contractors face a unique money challenge. They need to handle their own taxes and save for retirement without the help of an employer plan. Every payment they receive must cover both current needs and future goals.  Many freelancers and gig workers stay focused on finding clients or earning more income. But managing taxes wisely can [...]

Justin GluskaDecember 31, 2025
Quarterly Tax Deadlines Every Taxpayer Should Know in 2025

Do you ever get caught off guard by a year-end tax bill?  Many freelancers, investors, and small-business owners face that same frustration. The good news is there’s a simple, proactive way to avoid it: making estimated tax payments throughout the year. Paying in smaller portions can help steady your cash flow and prevent big surprises at [...]

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 [...]