Self Employed

A new SMB Readiness Report from G&A Partners, released July 29, finds that economic pressure, new legislation, and tougher federal enforcement are stacking up on small and midsize businesses. The survey reports that 87% of owners have changed how they run their business as a result. For self-employed owners and microbusiness operators, the report puts numbers to a strain many already feel. It also shows a gap between how owners describe the climate and the confident bets some are still making.

Every, a back-office platform for startups, has launched Every Benefits, a health benefits model that pairs fully insured plans with employer-funded reimbursements. The company says the setup lowers employer costs without cutting the experience workers receive. For a self-employed founder who has incorporated or is about to add a first employee, the launch speaks to one of the hardest parts of growing past a team of one.

Nearly every working creator now uses AI, but a large share worry that the rules around it could cost them, according to Epidemic Sound’s Future of the Creator Economy Report 2026. The study surveyed 3,000 professional creators across the US and UK. For self-employed creators, the findings capture a real tension. AI has become standard equipment, yet the legal ground under it feels shaky enough to threaten the brand deals that pay the bills.

The side hustles growing fastest in 2026 have one thing in common, and it is artificial intelligence, according to a recent Inc. roundup of the year’s breakout independent gigs. Interest in freelance writing alone jumped 5,546% over the past year. For anyone weighing a second income stream, the data points to where demand is actually pooling. The opportunities clustering at the top all reward people who can pair a skill with AI tools rather than compete against them.

Etsy is tightening how its sellers describe what they make, including whether artificial intelligence played a role, while several fees creep higher this year, according to a 2026 rundown of Etsy’s policy changes. The shifts matter because the marketplace runs largely on one-person shops. For a self-employed maker, these are not background details. New disclosure rules and rising fees hit both the storefront and the margin on every sale.

The US Department of Labor has proposed a rule that would make it easier to classify workers as independent contractors rather than employees, and it is now moving through the final stages of review. The proposal, announced February 26, 2026, would rescind a 2024 standard and revive the framework the department used in 2021. For people who work for themselves, the stakes are practical.

The U.S. Small Business Administration published a final rule on August 11, 2026, that changes how individually owned firms qualify as socially disadvantaged for the 8(a) Business Development Program. The rule removes a long-standing presumption tied to race and ethnicity and replaces it with an evidence-based standard that takes effect September 10, 2026. The 8(a) program helps small firms win set-aside federal contracts, and many participants are solo owners and micro businesses.

Thryv has launched an AI-native growth platform aimed at local service businesses, bundling marketing, customer records, and payments into one system, according to the company’s product announcement. The rollout marks the firm’s shift from a directory and marketing-services company into a software platform built around artificial intelligence. For a solo owner juggling a dozen tools, an all-in-one pitch is tempting.

Americans are still filing new business applications at close to a record pace, according to the U.S. Census Bureau’s July 2026 Business Formation Statistics, released August 12. The monthly report tracks how many people are taking the first formal step toward starting a business. For anyone weighing a jump into self-employment, this data is a useful barometer of the crowd around them. A high level of applications signals both opportunity and competition for the same customers and contracts.

The threshold for issuing a Form 1099-NEC or 1099-MISC is climbing from $600 to $2,000 for payments made in 2026, a change built into the One Big Beautiful Bill Act and summarized in a tax compliance breakdown from Avalara. It is the first meaningful update to that reporting floor in decades, and it takes effect for payments made on or after January 1, 2026.