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36 guides on taxes, deductions, credits, and more
Self-Employed·July 14, 2026Small Business Year-End Tax Planning: Equipment Purchases, Hiring, and Deduction Timing for Q3 and Q4 2026Picture this: It's mid-September 2026, and your small business has had a fantastic year. You're looking at your bank account, feeling proud of your success—unti...Self-Employed·June 29, 2026Mid-Year Estimated Tax Safe Harbor: Adjusting Your Q3 Payments to Avoid Underpayment PenaltiesPicture this: You're sitting at your kitchen table in mid-September, and you suddenly remember that third-quarter estimated tax payment is due in just a few day...Self-Employed·June 24, 2026How to Handle Quarterly Taxes When Your Income Fluctuates: Annualized Income Installment MethodPicture this: You're a freelance graphic designer who landed a massive $80,000 contract in November, but barely scraped by during the first six months of the ye...Self-Employed·June 22, 2026Quarterly Tax Payment Strategies for Airbnb and Short-Term Rental Hosts: Mid-Year Income Tracking and Deduction PlanningYou've been hosting your vacation rental on Airbnb for six months now, and the income has been fantastic—$18,000 already this year! Then your neighbor mentions ...Self-Employed·June 22, 2026How to Maximize Tax Deductions When Buying Business Equipment Mid-Year: Section 179 vs Bonus Depreciation TimingYou're scrolling through your business bank account in July, and you realize something: business is actually going well this year. Really well. So well, in fact...Self-Employed·June 17, 2026Summer 2026 Tax Moves for Small Business Owners: Equipment Purchases and Bonus Depreciation Before Year-EndPicture this: It's July 2026, your small business is thriving, and you've been eyeing that new delivery van, upgraded computer system, or piece of manufacturing...Self-Employed·June 16, 2026Estimated Tax Due Dates 2026: Q3 and Q4 Payment Deadlines and StrategiesPicture this: It's September 2026, and you're enjoying a long Labor Day weekend when suddenly you remember something about a tax payment due. You scramble to ch...Self-Employed·June 8, 2026Q2 Estimated Tax Payment Strategies: How to Catch Up If You Underpaid Q1You wake up in mid-June with a sinking feeling. That first quarterly tax payment you made in April? You're pretty sure you underpaid. Maybe you underestimated y...Self-Employed·June 3, 2026Hobby vs Business: IRS Rules for Claiming Losses and DeductionsYou've been selling handmade candles on Etsy for two years now. You've made about $1,200 total, but you've spent $5,000 on supplies, equipment, and that beautif...Self-Employed·June 2, 2026How to Pay Yourself from Your LLC or S-Corp: Salary vs Distribution Tax RulesYou've done it—you've formed your LLC or S-Corp, landed clients, and money is flowing into your business account. Now comes the exciting (and slightly confusing...Self-Employed·June 1, 2026Paying Quarterly Taxes Late: Penalty Calculation and How to Minimize Underpayment Fees for Q2 2026Picture this: You're a freelance graphic designer, juggling multiple clients and deadlines. Between invoicing, creating designs, and managing your business, you...Self-Employed·May 27, 2026Hobby Income vs Business Income Tax Rules: What Every Side Hustler Needs to KnowYou've been selling handmade jewelry on Etsy for the past year. Or maybe you've been mowing lawns on weekends for extra cash. Perhaps you're breeding French Bul...Self-Employed·May 25, 2026Summer Tax Planning for Self-Employed: Quarterly Tax Strategies and Year-End ProjectionsPicture this: It's a gorgeous July afternoon, and you're finally taking that beach day you promised yourself. You're scrolling through your phone when you sudde...Self-Employed·May 20, 2026Freelancer Tax Deductions Checklist for 2026 FilingPicture this: It's April 2027, and you're staring at your laptop, trying to remember whether that coffee shop meeting in March 2026 was tax-deductible. You've g...Self-Employed·May 19, 2026Form W-9 Guide for Independent Contractors: Everything You Need to KnowPicture this: You've just landed your first freelance gig, and your new client sends you an email asking you to "fill out a W-9." You stare at your screen, wond...Self-Employed·May 18, 2026What to Do If You Missed the Q1 Estimated Tax Deadline: Penalty Calculation and Catch-Up StrategiesPicture this: You're a freelance graphic designer who had a great start to the year. Projects rolled in, invoices got paid, and you were feeling on top of the w...Self-Employed·May 5, 2026Safe Harbor Rules: How to Avoid Estimated Tax Penalties in 2026Picture this: You're finally sitting down to complete your 2026 tax return, feeling pretty good about yourself. Then you see it—a penalty notice from the IRS fo...Self-Employed·May 4, 2026Q2 Estimated Tax Payment Due June 16, 2026: What You Need to KnowPicture this: You're sipping your morning coffee in mid-June, scrolling through your phone, when you stumble across a reminder that makes your stomach drop—"Q2 ...Self-Employed·April 27, 2026How to Report Cash App, Venmo, and PayPal Income on Your TaxesYou just got a notification from Venmo. But it's not a payment—it's a tax form called a 1099-K. Your heart sinks a little. "Do I really have to pay taxes on the...Self-Employed·April 7, 2026Tax Guide for Content Creators: YouTube, TikTok, and MoreIf you earn money from YouTube, TikTok, Twitch, or Instagram, you need to know about self-employment tax and deductions.Self-Employed·April 7, 2026S-Corp Reasonable Salary: How to Set It and Save on TaxesS-Corp owners must pay themselves a reasonable salary. Set it too low and the IRS will reclassify distributions.Self-Employed·April 7, 2026Small Business Tax Credits: The Complete Guide for 2026From the health care credit to the R&D credit, small businesses can claim credits that reduce their tax bill.Self-Employed·April 7, 2026How to File Taxes as a Sole ProprietorA sole proprietorship is the simplest business structure. Here is how to file taxes and claim deductions.Self-Employed·April 7, 2026Gig Worker Tax Guide: DoorDash, Uber, Etsy, and MoreEverything gig workers need to know about taxes, deductions, and quarterly payments.Self-Employed·April 7, 2026Self-Employment Tax 2026: How Much and How to Reduce ItSelf-employment tax is 15.3% on top of income tax. Here is how to calculate and lower it.Self-Employed·April 7, 20261099-NEC vs 1099-MISC: What Is the Difference?The IRS uses different 1099 forms for different types of non-employee income.Self-Employed·April 7, 2026Schedule C Explained: Report Self-Employment IncomeSchedule C is where freelancers and sole proprietors report business income and deductions.Self-Employed·April 7, 2026LLC vs S-Corp: Which Saves More on Taxes?Choosing between an LLC and an S-Corp can save or cost you thousands in taxes every year. Here's how each structure is taxed, when the S-Corp election makes sen...Self-Employed·April 7, 2026Quarterly Estimated Tax Payments: Complete Guide for Self-EmployedSelf-employed workers and business owners must pay estimated taxes four times a year. Here's who must pay, how to calculate payments, due dates, and how to avoi...Self-Employed·April 7, 2026Business Meals Deduction 2026: What's Deductible and What's NotThe business meals deduction is back to 50% for 2026. Here's exactly what qualifies, what documentation you need, and common mistakes to avoid.Self-Employed·April 7, 2026Section 179 Deduction 2026: Write Off Equipment and AssetsSection 179 lets business owners write off up to $1.16 million in equipment and assets in the year of purchase instead of depreciating them over time. Here's wh...Self-Employed·April 7, 20261099 Contractor vs W-2 Employee: Tax Rules for EmployersMisclassifying workers as independent contractors instead of employees can result in severe IRS penalties. Here's how to classify correctly and understand your ...Self-Employed·April 7, 2026Business Vehicle Deduction: Standard Mileage vs Actual ExpensesWhether you use the standard mileage rate or actual expenses, your business vehicle can be a significant tax deduction. Here's how both methods work and which o...Self-Employed·April 7, 2026How Good Bookkeeping Saves You Thousands at Tax Time (and What Happens Without It)The average freelancer misses $3,000 to $5,000 in deductions every year without proper bookkeeping. Here is exactly what that costs you, what the IRS expects, a...Self-Employed·April 7, 2026Side Hustle Tax Guide: What You Owe and How to Pay LessEarning money on the side? You probably owe more taxes than you think. Here is everything you need to know about self-employment tax, quarterly payments, deduct...Self-Employed·April 7, 20261099 Deductions: The Complete List for Self-Employed Workers (2026)Every deduction self-employed and 1099 workers can claim in 2026, organized by category. From home office to retirement contributions, here is the complete list...