1099 Contractor IRS Tax Penalties: How to Avoid Underpayment Fees in 2026

For 1099 contractors and freelancers, managing tax liability is a year-round responsibility. Unlike W-2 employees, whose taxes are withheld from every paycheck, gig workers must proactively manage their payments to avoid potential 1099 contractor IRS tax penalties. In the 2026 tax year, staying ahead of these fees requires a clear understanding of the IRS “pay-as-you-go” … Read more

1099 Tax Basics: The Essential 8-Step Roadmap for 2026

Starting as an independent contractor in 2026 brings new financial responsibilities and opportunities. With the implementation of the One Big Beautiful Bill Act (OBBBA), the tax landscape has shifted significantly for freelancers, gig workers, and solopreneurs. To help you navigate this transition, we have built this comprehensive roadmap designed to help you understand your obligations, … Read more

Uber Drivers: Gas vs EV – How Vehicle Choice Could Impact Your 2026 Tax Strategy

For Uber and rideshare professionals, vehicle choice is no longer just about fuel efficiency—it directly affects how much of your earnings you actually keep. As we navigate the 2026 tax year, understanding how your real-world operating costs interact with IRS deduction frameworks is essential. For many drivers, a smart 1099 vehicle tax strategy in 2026 … Read more

2026 1099-K Rules for Venmo & PayPal: The $600 Fact-Check

For years, the phrase “$600 threshold” has caused significant confusion among gig workers. Specifically, the transition to a lower threshold has seen multiple administrative delays by the IRS. As a result, many drivers ask: “What are the actual 1099-K Rules for Venmo & PayPal for the 2026 tax year?” The 2026 Reality: The $20,000 Threshold … Read more

2026 IRS Audit Red Flags for 1099 Contractors: A Comprehensive Guide to Risk Mitigation

For the independent contractor, freelancer, and gig worker, the “Audit” is the ultimate tax-season nightmare. However, as we enter the 2026 tax year, the landscape has shifted. The IRS has significantly increased its budget for enforcement, specifically targeting Schedule C filings through advanced AI-driven data matching. Understanding these 2026 IRS Audit Red Flags is no … Read more

Can 1099 Gig Workers Deduct Phone & Internet Bills in 2026? (The Professional Guide)

If you are a 1099 contractor, your smartphone and home internet aren’t just for entertainment—they are the lifeblood of your business. Whether you’re managing clients through an app or searching for the next gig, these services are essential. However, a common question arises during tax season: “Can I deduct my entire phone bill?” The short … Read more

Can Uber or Lyft Drivers Claim a Home Office Deduction in 2026?

As a rideshare driver, your car is obviously your primary workplace. However, you also spend hours outside the car managing your business—tracking mileage, responding to support tickets, and balancing your books. This leads to a common question in 2026: Can Uber or Lyft drivers claim a home office deduction? The answer is yes, but only … Read more