Tax Guides & Resources
Plain-language guides on self-employment taxes, quarterly payments, deductions, and more.
Gig Economy Tax Myths: 5 Things People Get Wrong
Five gig tax myths checked against IRS rules: the $600 rule, "my platform handles it," "I can deduct anything," no 1099 and low income. A worked example shows a $41,000 driver owing about $5,752.
October 15 Deadline: Extended Returns Are Due
If you filed Form 4868, your 2025 return is due October 15. What six months of waiting costs in penalties and interest (about $381 on a $5,800 balance, versus about $672 if you file one day late), two situations that stall people, and an 11-day plan.
What Is a 1099-K and What Do You Do With It?
A 1099-K reports gross payments, not profit. The current $20,000 and 200-transaction threshold, six mistakes that inflate or understate income, and how a $23,650 form reconciles to a $9,267 Schedule C profit.
Investing Inside Your Solo 401(k): What to Actually Put in There
The provider decides your paperwork. The fund choice decides your retirement. Why a 1% expense ratio costs a $100,000 balance about $109,765 over 25 years, brokerage window versus restricted menu, and a same-week checklist for building a low-cost lineup.
Home Office Deduction for Gig Workers and Freelancers
You do not have to earn money at home to claim a home office. Why a driver who does his paperwork at a spare-room desk qualifies while a virtual assistant at the dining table does not, the gross-income cap that catches small side businesses and how a $600 office turns 4,800 commuting miles into $3,568 of deductible driving.
Roth vs. Traditional Solo 401(k): Which Should Freelancers Choose?
The radio button on the setup screen is worth five figures over a decade. Why a traditional deferral at $96,000 of profit saves 14.1 cents on the dollar instead of the 22 the bracket implies, where the same $18,000 lands after 25 years, the 14.1% break-even rate that decides it, and why the 2026 Roth catch-up rule does not apply to sole proprietors.
Mileage Deduction Guide for Gig Workers: What Actually Counts
2026 has two business mileage rates, 72.5 cents through June 30 and 76 cents after, so one year needs two columns in your log. Which legs of a shift count and which are commuting, why platform mileage summaries come up short, one driver's 14,200 miles worth $10,554 and $2,313 in tax, and the depreciation choice that locks you out of the standard rate for good.
After Q3 Taxes: Projecting Your Full-Year Tax Bill
Eight months of real numbers beat any March forecast. Why straight-line annualizing overstated one freelancer's bill by $1,474, the full calculation on $82,800 of projected profit ($17,293, or 20.9%), a rate table from $40,000 to $140,000, and why a $12,000 solo 401(k) deferral saves 9.6 cents on the dollar while a $3,000 expense saves 23.
Multiple 1099s: How to Handle Income From Several Platforms
Four platforms do not mean four returns. What the raised 2026 thresholds ($2,000 for a 1099-NEC, $20,000 and more than 200 transactions for a 1099-K) mean for the forms you will actually receive, one freelancer's five income sources where the forms cover just 44% of $47,050 in receipts, and how to catch the duplicate that would cost $1,268 in tax on money never earned.
Q3 Estimated Taxes: What to Send by Sept. 15
The third 2026 installment is due Tuesday, Sept. 15, and it covers June through August. How to pick between paying 90% of this year and 100% of last year's tax, the same freelancer's year run both ways ($5,502 to be fully current versus $1,750 to sit in safe harbor), what a late $3,000 payment actually costs at the 7% underpayment rate, and the five-minute Direct Pay walkthrough.
Gig Worker Quarterly Tax Guide: All Platforms Covered
Three apps do not mean three tax bills. What Uber, DoorDash, Instacart, Upwork and Airbnb each send you for 2026 (many workers will get nothing, now that the 1099-K threshold is back to $20,000), the four-step calculation that turns combined profit into one payment, and what a multi-platform driver at $25,400 owes by Sept. 15.
The Freelancer's Guide to Business Entity Types
Sole prop, LLC or S corp is really two decisions: what you form with your state, and how the IRS then classifies it. The full mapping of entity to tax treatment, the four combinations freelancers use, what each layer costs to run and what an S election is worth at $130,000 of profit once payroll and the lost QBI deduction are counted.
LLC vs Sole Proprietor: Which One Saves You More in Taxes
A single-member LLC and a sole proprietorship file the same Schedule C and owe the same federal tax to the dollar. The $95,000 math run both ways, what an LLC really costs in year one (California charges $800 whether you profit or not) and where the S-corp election finally moves the number.
Contracts and Taxes: What Your Agreement Should Specify
Every clause in a freelance contract either produces a clean record or a loose end for next April. Contractor status and the W-9 that prevents 24% backup withholding, payment terms you can plan quarterly taxes around, why a kill fee clause is worth $4,171 on a canceled $12,000 project and the reimbursement wording that keeps a 1099 honest.
First Year Freelancing Taxes: What Nobody Tells You
Self-employment tax starts at $433 of profit, no one withholds a dime and the 1099 threshold more than tripled. The five surprises that catch first-year freelancers, what a $38,000 first year really costs and the 90-day setup that prevents an April shock.
Retirement Contributions Mid-Year Check: Are You On Track?
The 2026 limits went up to $24,500 for solo 401(k) deferrals and $7,500 for IRAs. How to tell whether you are pacing toward your target with 62% of the year gone, why the employer contribution is the half most freelancers forget, and why being behind in August is fixable when you are self-employed.
W-2 Job and Side Hustle: How to Calculate What You Owe
The same side hustle costs more or less depending on the salary underneath it. How your W-2 wages fill the $184,500 Social Security wage base first, what $14,000 of weekend income really costs at a $68,000 salary, and why a Form W-4 change beats a quarterly payment in August.
Bookkeeping Systems for Freelancers: Simple Options That Work
A spreadsheet, Wave or QuickBooks. What the IRS actually requires (less than you think), the free-tier limits both companies bury, current 2026 pricing, and the math on what a $19-a-month tool has to find before it pays for itself.
Consultant Taxes: How to Handle Variable 1099 Income
Retainers, project fees and quarters that look nothing like each other. Why the prior-year safe harbor is the most useful rule for lumpy income, the overpayment mistake that costs more than underpaying, which business development costs are deductible, and the QBI threshold consultants specifically lose.
Understanding Self-Employment Tax (And How to Reduce It)
The headline rate is 15.3%, but it applies to only 92.35% of your profit, so the real cost is about 14.1%. What that means at five income levels, the two levers that actually reduce it and the five popular strategies (including the solo 401(k)) that do nothing for it at all.
Freelance Musician Taxes: Gigs, Royalties and Instrument Deductions
Performance fees, private lessons, streaming royalties and merch mostly land on one Schedule C, and all of it carries self-employment tax. Where each stream goes, how instruments are written off, the 2026 mid-year mileage change, and a full year worked end to end at $59,000 of gross income.
When an S-Corp Election Is the Wrong Move: 5 Situations Where It Costs More Than It Saves
The S-Corp election cuts self-employment tax on distributions, but overhead, state entity taxes and a smaller QBI deduction eat the savings faster than most freelancers expect. Five situations where it backfires, plus a worked example at $95,000 of profit that nets about $406 a year.
Personal Trainer Taxes: A Self-Employment Income Guide
Studio rent, equipment, certifications, and mileage all lower the tax you owe. How independent trainers handle self-employment tax, what changes when you mix a W-2 gym job with 1099 clients, and what trainers owe at different income levels. Two worked examples plus a rate table.
The Emergency Fund for Freelancers (It's Different Than for Employees)
The standard 3 to 6 months of savings was written for salaried workers. Variable income needs 6 to 12. Why the target is bigger, how to size yours on a survival number, and why your tax reserve has to be a separate account. Worked example on a $3,700 monthly baseline.
Real Estate Agent Taxes: Commission Income and Deductions
Commission checks arrive with no tax withheld. How your 1099 split is taxed, five mistakes that trigger a surprise bill, why the mileage log is the deduction, and what agents leave on the table. Two worked examples on a $72,000 year.
Freelance Rate Setting: Are You Charging Enough to Actually Save?
Your rate is a financial plan, not a marketing number. Work backward from your take-home goal, taxes, expenses and real billable hours (about 1,200, not 2,080) to find your true floor. Two worked examples, including how to convert a $65,000 salary into an hourly rate.
Virtual Assistant Taxes: Working From Home as a 1099 VA
What remote VAs owe in self-employment tax, why the home office deduction usually favors renters who pick the regular method, and how to handle five 1099s, quarterly payments and the $600 myth. Full worked example on a $52,000 year.
Mid-Year Financial Review: 5 Numbers Every Freelancer Should Know
July is the halfway mark. Check your YTD net income, estimated tax paid, effective tax rate, savings rate and retirement pace, with worked examples and a 20-minute checklist to fix what's off.
Freelance Copywriter Taxes: A Practical Guide
What copywriters actually owe, the deductions they overlook, and how to handle lumpy project income. Follows one writer's $82,000 year with a full worked example and a quarterly rhythm that keeps April calm.
Health Insurance as a Freelancer: The Deduction Most People Overlook
If you pay your own health insurance, you can usually deduct 100% of the premiums above the line. Who qualifies, the employer-eligibility rule that trips people up, and worked examples showing the real saving.
Freelance Photographer Taxes: Gear, Travel, and 1099 Income
Seven costly mistakes photographers make at tax time, with worked dollar examples: how to write off a camera, log the miles, separate business from hobby, and tax event vs. stock income correctly.
Q2 Estimated Tax Check-In: What to Do After the June 15 Deadline
The June 15 quarterly deadline has passed. Whether you paid, underpaid, or missed it, here is how to confirm you are on track, what a late payment actually costs, and how to catch up before Q3.
Freelance Web Developer Taxes: What to Track and Deduct
A tracking checklist for developers plus one full year worked out: which SaaS, cloud, and hardware costs to deduct, and how to handle lumpy project income vs. steady retainers at tax time.
Home Office Deduction: Simplified vs. Regular Method
The IRS lets you deduct your home office two ways. The simplified method is easier but often leaves thousands on the table. A worked example shows where each method wins and costs you real money.
Freelance Graphic Designer Taxes: Deductions and Quarterly Guide
One designer's $78,000 year, worked end to end: software and equipment write-offs, the home office deduction, mileage to clients, and a full quarterly tax estimate showing what to set aside.
The Freelancer's Guide to Business Deductions
The write-offs freelancers miss most: phone, software, home office, mileage and more. A 12-item checklist plus worked numbers showing that each $1,000 deducted saves roughly $230 in combined federal tax at a typical freelance income.
Shipt Shopper Taxes: 1099 Income Explained
How Shipt reports your earnings on a 1099-NEC, how to claim the mileage deduction, a full SE tax worked example at $42,000, and how to calculate quarterly payments on variable delivery income.
Invoicing Best Practices That Also Help at Tax Time
Sequential numbering systems, net terms, late fee language and the eight fields every invoice needs to make your Schedule C self-proving at year-end.
Rover and Pet Sitter Taxes: A Simple Guide for 2026
How Rover classifies sitters, what the 1099-NEC shows versus what lands in your account, deductible supplies and mileage, and how to handle quarterly payments as your bookings grow.
Separating Business and Personal Finances: 7 Mistakes That Cost Freelancers at Tax Time
The seven commingling mistakes that quietly lose freelancers deductions, hours, and audit defense, plus a one-afternoon checklist to set up a business checking account, business credit card, and weekly bookkeeping habit.
Setting Up a Solo 401(k): A Step-by-Step Guide for Freelancers
How to actually open a Solo 401(k) in 2026: the six steps, where to do it (Fidelity and Schwab are the main options; Vanguard stopped new applications in 2023), the deadlines, and what to do once the account is open.
S-Corp Tax Advantages: The SE Tax Math Explained
How an S-Corp election reduces self-employment tax by splitting income into salary and distributions. Real numbers at $120k, $150k, and $200k, plus the overhead costs that determine whether it actually saves you money.
When to Elect S-Corp Status: A Self-Employed Person's Decision Guide
Income thresholds, consistency requirements, state-level fees, Form 2553 timing, and the signals that tell you when the S-Corp switch makes financial sense, and when to wait another year.
Upwork Freelancer Taxes: What the Platform Doesn't Tell You
Complete 2026 tax guide for Upwork freelancers: how the 1099-K reconciles with the platform fee, a full worked example on $68k gross revenue, what remote freelancers can deduct, and 6 things Upwork never tells you about taxes.
How a Solo 401(k) Lowers Your Tax Bill (With Real Numbers)
A before-and-after comparison: on $120,000 of net SE income, maxing a Solo 401(k) shelters $46,804 and saves about $7,100 in federal income tax once the QBI deduction is counted. The math at several income levels, and what the plan doesn't change.
Fiverr Seller Taxes: How to Handle 1099-K Income
Complete tax guide for Fiverr sellers: how the 1099-K works, a full worked example on $55k gross revenue, what platform fees and software costs you can deduct, quarterly payment rules, and 5 costly mistakes to avoid.
Solo 401(k) Deep Dive: How Employee and Employer Contributions Work Together
The two-bucket system explained: employee elective deferrals ($24,500 in 2026), employer profit-sharing (20% of net SE earnings for a sole proprietor), a full worked example on $95k net income, and the deadline rules that trip people up every year.
Airbnb Host Taxes: What You Owe and How to Reduce It
A complete 2026 guide for Airbnb hosts: the 14-day rule, Schedule C vs E, depreciation, and a case study following a host who earns $24,000 renting a spare bedroom, with the full tax breakdown.
The Self-Employed 401(k): The Most Powerful Retirement Account You Probably Aren't Using
2026 deep dive on the Solo 401(k): why it beats a SEP-IRA, the two-bucket structure, the $72,000 contribution cap, a worked example on $90k net SE income, and the December 31 target date and its first-year exception.
Instacart Shopper Taxes: What Every Batcher Needs to Know
Complete tax guide for Instacart shoppers: full-service vs. in-store classification, mileage deductions, worked example on $30k gross income, and 5 tax mistakes to avoid.
You Filed (or Extended). Now What? Setting Up for Q2
Post-tax-season reset: review what you owed, set your Q2 payment target with worked examples, organize your records, review your rate, and avoid 5 common post-filing mistakes.
Tax Week Checklist: What to Do Before April 15
Three tasks, three days: pay your Q1 2026 estimated taxes, file or extend your 2025 return, and consider a last-minute SEP-IRA contribution. A step-by-step action guide with worked examples.
Lyft Driver Taxes: 1099s, Mileage, and Quarterly Payments
Lyft-specific tax guide covering income reporting, deductible expenses (mileage, phone, car costs), quarterly estimated payments, and how to avoid underpayment penalties.
Last-Minute Tax Deductions You Might Be Missing
Home office, health insurance premiums, professional subscriptions, and the SE tax deduction itself. Deductions worth checking before you file on April 15.
DoorDash Taxes: The Complete Dasher Tax Guide
How DoorDash reports your income, what Dashers can deduct (mileage, hot bags, phone), how to calculate quarterly payments, and how to avoid an April tax surprise.
Tax Extension 101: Should You File for an Extension?
April 15 is two weeks away. Learn what a tax extension actually does, when it makes sense for freelancers, and why filing late and paying late carry different penalties.
Uber Driver Taxes: What You Owe and How to Reduce It
Complete tax guide for Uber drivers: 1099-K and 1099-NEC income, mileage deduction (standard vs. actual), quarterly payments, and the other main deductions.
How to Calculate Your Quarterly Estimated Tax Payment
Step-by-step formulas for calculating your Q1 payment before April 15. Covers the safe harbor rules, a worked example, and how to handle combined W-2 and 1099 income.
Quarterly Estimated Taxes: How They Work (and Why You'll Get Penalized If You Skip)
Q1 is due April 15. Learn how the quarterly system works, what triggers the underpayment penalty, and how the safe harbor rules protect you.
The Freelance Finance Mindset: Why Freelancers Need to Think Differently About Money
Nobody withholds tax from your pay or sets money aside for April once you work for yourself. How to rethink the way you handle money as a self-employed worker.
Why Quarterly Estimated Taxes Matter: How to Calculate Yours
Who needs to pay quarterly, how underpayment penalties work, and how to use the SE tax calculator as an ongoing planning tool throughout the year.