Quick answer: Almost never. The IRS treats haircuts as a personal expense, not a business one — you’d need a haircut whether or not you worked, so it doesn’t count just because you’re a 1099 contractor. There’s one narrow, genuinely rare exception, and it’s easy to misread it as broader than it is. The general … Read more
Quick answer: Your Adjusted Gross Income (AGI) isn’t your Schedule C net profit — it’s that number after a few more subtractions, most notably half your self-employment tax, your self-employed health insurance premiums, and any retirement contributions. AGI is usually meaningfully lower than your net profit, and it’s the figure that determines a lot more … Read more
Quick answer: Schedule C is where every 1099 contractor and freelancer reports business income and expenses to the IRS. It has five parts — income, expenses, cost of goods sold, vehicle information, and other expenses — and the bottom line feeds directly into your self-employment tax and income tax. Part I: Income This is your … Read more
Quick answer: often, yes — because whoever paid you may have already told the IRS. If a client, platform, or payment app files a 1099 in your name and the income doesn’t show up on your return, an automated system is likely to flag it, sometimes a year or more later. How the mismatch actually … Read more
Quick answer: Yes — if you’re receiving business payments through Venmo, Cash App, PayPal, or Zelle, the IRS can see it, either through a 1099-K these platforms issue once you cross the reporting threshold, or through their own records even below that threshold. The 1099-K threshold, and why it’s not the whole story For 2026, … Read more
What a Stripe Express statement descriptor actually is, and why it should match your legal name or DBA for clean bookkeeping.
Why ‘independent contractor’ and ‘sole proprietorship’ answer two different questions, and why most gig workers are both at once.
Why there’s no single honest answer to ‘how much can you make’ driving for these platforms — and how to calculate your own real number.
Why self-employed borrowers in Essex County are underwritten differently than W-2 buyers, and how your own deduction strategy can work against you.
What documents MassHealth actually accepts as proof of self-employment income, and how to handle irregular or recently-changed income.
