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Plus what Upwork and Fiverr actually take, and the number to save instead of 15.3%.
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Happy Tuesday! September just showed up, and Labor Day weekend is still ahead of us instead of behind us this year. If the long weekend has you thinking about picking up extra income before the holidays sneak up, this week’s for you: where to start, how much to squirrel away before the IRS comes looking, and what counts as a “real” business versus a hobby that got a little out of hand. Let’s get to it.
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Let’s get to it.
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This week’s lineup:
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🖥️ Best freelance platforms for beginners — and what they actually cost you
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💰 The 25–30% rule that keeps freelance income from wrecking your April
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🧰 No “marketable skill” yet? Side hustles you can start this week anyway
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🚗 He told the Tax Court he drove 70,000 miles. Uber’s own logs said 9,438.
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Business & Gigs
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🖥️ Best freelance platforms for beginners — and what they actually cost you
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The Quick & Bristly: Upwork charges a variable 0–15% fee (most land around 10%), Fiverr takes a flat 20% no matter what, and Contra charges 0%. Whatever you use, the commission is a deductible business expense, and a missing 1099-K doesn’t mean the income isn’t taxable.
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Picking a freelance platform is less about which one is “best” and more about which one matches your personality. Upwork rewards people who don’t mind pitching themselves in a stack of competing proposals. Fiverr rewards people who’d rather build something once and let it find its own buyers. Neither approach is wrong, but the one that fights your instincts is the one you’ll stop logging into by March.
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👉 Compare your actual take-home across platforms
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Upwork: bid for the work. You browse job posts, spend “Connects” to submit proposals, and compete for contracts. As of May 2025, Upwork dropped its old tiered fee structure (20% on your first $500 with a client, down to 5% above $10,000) for a flat-ish variable fee between 0% and 15%, locked in at the proposal stage. Most freelancers report paying around 10%. It rewards persistence and a strong profile more than it rewards being cheap.
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Fiverr: let the work find you. You build “gigs” — pre-packaged services at fixed prices — and clients come to you. There’s no bidding, no proposals, no Connects. The tradeoff is the commission: a flat 20% off every order, including tips, with zero volume discount no matter how long you’ve sold on the platform.
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A couple of alternatives worth a look:
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Contra — 0% commission, portfolio-first, but a smaller pool of clients than Upwork or Fiverr
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Guru — 5–9% depending on membership tier, a reasonable middle ground for project-based work
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Freelancer.com — 10% or a $5 minimum per project, whichever is higher; heavy on price competition, which makes it a rougher start for beginners
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The tax facts don’t change no matter which one you pick. The commission the platform takes is a legitimate business expense — deduct it on Schedule C, don’t just treat it as money that vanished. And the platform sending you a 1099-K (or not) has nothing to do with whether the income is taxable. Federal law now requires a 1099-K only once you clear $20,000 and 200 transactions in a year, restored after several years of a much lower threshold nearly took effect. Fall under that number and you likely won’t get a form. You’ll still owe the tax.
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🧰 TAXSTACHE TOOLKIT
The Take-Home Calculator
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Punch in a project rate and watch each platform’s cut disappear right in front of you, ranked from best to worst before you ever submit a proposal.
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PRESENTED BY FIVERR
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Your skills could be making you money
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Good at writing, design, video editing, marketing, or something else people need? Turn those skills into extra income on Fiverr. Create your services, set your prices, and connect with customers looking for exactly what you do.
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👉 Start selling on Fiverr
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Tax Strategies
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💰 The 25–30% rule that keeps freelance income from wrecking your April
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The Quick & Bristly: Self-employment tax is 15.3% on top of your regular income tax, which is why you should set aside 25–30% of every payment, not 15.3%. Quarterly payments are due April 15, June 15, September 15, and January 15, and paying at least 100% of last year’s tax keeps you penalty-free, no matter what you actually owe this year.
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Nobody warns new freelancers about the two-tax problem. There’s self-employment tax, and then regular income tax is standing right behind it with its own hand out. Miss that second one and “I’ve been saving” quietly turns into “I owe how much?” every April, like clockwork.
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Why the number is 25–30%, not 15.3%. Take a chunk of freelance income, put 92.35% of it through the 15.3% self-employment tax, then add your income tax bracket on top. For most beginning freelancers, that lands the total somewhere between a quarter and a third of what hits their bank account. Save less than that and you’ll be short in April. Save more and you’ve got a cushion instead of a scramble.
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👉 See what 25–30% looks like on your own numbers
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The four deadlines that don’t wait for you. Once your net self-employment earnings pass $400, you’re on the hook for self-employment tax, and once you expect to owe $1,000 or more overall, the IRS wants its money in quarterly installments: April 15, June 15, September 15, and January 15 of the next year. Notice the second period only covers two months (April and May) while the third covers three (June through August) — the calendar isn’t evenly split, and neither should your assumptions be.
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Safe harbor: the escape hatch if you guess wrong. You don’t have to calculate your 2026 tax liability perfectly to avoid a penalty. Pay at least 100% of what you owed last year (110% if your prior-year adjusted gross income was over $150,000), split into four payments, and you’re penalty-proof regardless of how this year actually shakes out. It’s the easiest safety net available to anyone whose income moves around, which describes basically every freelancer.
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Open a separate savings account, move your percentage the day a payment lands, and pretend that money already belongs to the IRS. Because it does.
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🧰 TAXSTACHE TOOLKIT
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The Set-Aside Slider
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Drop in your next payment, slide the percentage, and calculate the exact dollar amount to move into savings before you’re tempted to spend it.
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Get paid to hang out with dogs
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Love dogs? Turn your daily walks into extra income with Rover. Set your own schedule, connect with pet parents in your area, and earn money doing something you actually enjoy.
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👉 Start today
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Every Thursday, we go to work.
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The TaxStache Business Edition is built for owners and operators. Quick hits on entity structure, quarterly deadlines, deduction strategy and the IRS rule changes that actually affect your bottom line. Plus a weekly download you can put to use the same afternoon.
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If you run a business (or you’re building one), Thursday is definitely your day.
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Would you like to receive our Thursday Business Edition?
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Wacky Tax Tales
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🚗 He told the Tax Court he drove 70,000 miles. Uber’s own logs said 9,438.
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Image by Andres M.
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The Quick and Bristly: In 2014, a Uber driver claimed $44,729 in vehicle expenses on his Schedule C, insisting he’d driven 70,000 miles that year. Uber’s own trip logs showed 9,438. The Tax Court allowed exactly what those logs supported and refused to guess at the rest.
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Everyone assumes their rideshare app is quietly keeping their records for them. One driver found out in Tax Court exactly how expensive that assumption can get.
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Semere Hagos drove for Uber in 2014 and filed a Schedule C claiming $44,729 in car and truck expenses, on top of $21,160 in “other expenses” and $5,345 in repairs and maintenance. When the IRS asked him to back up the driving figure, his answer amounted to, “It’s a lot, trust me.” He claimed 70,000 miles for the year. The number the court could actually verify, straight from Uber’s own trip data, was 9,438 miles — worth $5,286 at the applicable mileage rate.
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The IRS didn’t zero out his deduction. It allowed the $5,286 Uber’s records supported and disallowed the roughly $39,000 gap between that and what he’d claimed. Hagos took it to Tax Court, presumably hoping for a compromise somewhere in the middle.
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Why the judge couldn’t just split the difference. Tax law does have a mechanism for this exact situation — the Cohan rule, which lets a court estimate an expense even without perfect records, as long as the taxpayer gives it some credible basis to estimate from. Hagos gave the court nothing: no log, no calendar, no pattern of routes, not even a rough explanation for how he’d arrived at 70,000 miles. The opinion is almost sympathetic on this point — the judge notes the court “could make a guess” about additional mileage but that doing so without any foundation “is not appropriate.” Estimating in a vacuum isn’t generosity, it’s fabrication with extra steps, and courts won’t do it for you.
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The part every rideshare and delivery driver should sit with. Uber, Lyft, DoorDash, and Instacart all track your on-trip mileage automatically, and that number will always undercount your real business driving, because it doesn’t include the miles you drive to get into position for your first ride, between drop-offs while waiting for the next ping, or home at the end of a shift. Those miles are legitimately deductible. But the platform will never log them for you, which means the only record that will ever exist is the one you keep yourself.
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The IRS didn’t punish Hagos for driving for Uber. It punished him for assuming someone else’s paperwork was a substitute for his own.
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The quick (and slightly prickly) stories we didn’t have time to get to:
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If you made it this far, you’re our kind of nerd. Hit reply and tell us which story you want us to dive deeper into next week.
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Follow us for even more great tips, tricks, and deadline reminders.
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