#independent-contractor

Independent Contractor

Contractor payments, 1099 tracking, and compliance

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July 16, 20268 min read

Professional Organizer Bookkeeping: Package Pricing, Client Property Liability, and Why the Donation Deduction Isn't Yours

A bookkeeping guide for professional organizers covering how to book package deposits and maintenance retainers as unearned revenue, the insurance clients expect (general liability, E&O, workers' comp — roughly $1,500–$3,000/year), why the Goodwill donation deduction belongs to the client rather than the organizer, and when a day helper must be classified W-2 instead of 1099.

Mike Thrift

bookkeepingsmall-businessself-employment

July 16, 202610 min read

Bookkeeping for Resume Writers and Career Coaches: Deferred Revenue, Package Pricing, and 1099 Writers

A $2,400 coaching package paid in April but delivered through July isn't April income. How resume writers and career coaches should split package payments into deferred revenue, recognize each resume, LinkedIn rewrite, and coaching call as delivered, track 1099 contract writers, and deduct CPRW and ICF certification costs.

Mike Thrift

bookkeepingcoachingrevenue-recognition

July 13, 20268 min read

Scuba Dive Shop Bookkeeping: Why Certification Training, Not Gear Sales, Keeps the Doors Open

Dive shops that book prepaid certification fees as revenue on receipt, lump training and retail into one sales account, or depreciate rental gear like retail inventory routinely understate their true profitability — this guide covers deferred revenue for course fees, tank-testing cost tracking, and instructor pay classification specific to dive centers.

Mike Thrift

dive-shopbookkeepingsmall-business

July 13, 20268 min read

Translation and Medical Transcription Bookkeeping: Per-Word Billing, 1099 Risk, and HIPAA Recordkeeping

How translation agencies and medical transcription services can cost freelance linguist payables against per-word client billing, avoid 1099 vs. W-2 misclassification risk, and meet HIPAA business associate recordkeeping requirements.

Mike Thrift

bookkeepingfreelanceindependent-contractor

July 11, 20268 min read

The DOL Wants to Rewrite Independent Contractor Rules Again: A 2026 Rule-Change Guide for Businesses That Hire Freelancers

The DOL's February 2026 proposed rule would rescind the 2024 six-factor independent contractor test and replace it with a two-core-factor economic reality test resembling the 2021 rule — here's what changes, what stays the same, and what businesses that hire freelancers should document now.

Mike Thrift

independent-contractorcompliancehiring

July 10, 20269 min read

Bookkeeping for Dog Boarding and Pet Sitting Businesses: Platform Income, Sub-Sitter 1099s, and Home-Office Rules

How dog boarding and pet sitting businesses should track revenue by service line, reconcile Rover and Wag payouts against the $20,000/200-transaction 1099-K threshold, file 1099-NECs for sub-sitters paid $600 or more, and apply the strict exclusive-use home-office rule — the childcare daycare exception does not extend to pet care.

Mike Thrift

bookkeepingsmall-businessself-employment

July 10, 20268 min read

NIL Income Taxes: What College Athletes Actually Owe the IRS in 2026

NIL income is self-employment income subject to a 15.3% self-employment tax on top of ordinary income tax, and college athletes owe tax on any net NIL earnings over $400 even without a 1099, a form now only required above the 2026 threshold of $2,000.

Mike Thrift

self-employment-taxtaxself-employment

July 10, 20269 min read

Fitness Studio and Personal Trainer Bookkeeping: Deferred Revenue, Instructor Pay, and the KPIs That Matter

Prepaid training packages are a liability, not income — how fitness studios should use deferred revenue accounting, classify instructors under the FLSA economic-reality test, and track the KPIs, like the 70–75% class utilization benchmark, that separate profitable studios from struggling ones.

Mike Thrift

bookkeepingsmall-businessrevenue-recognition

July 10, 20269 min read

Portable Benefits for Independent Contractors: A Guide to the New State Laws

Utah, Alabama, Tennessee, Georgia, and West Virginia now let businesses contribute to an independent contractor's portable benefit account without that contribution counting as evidence of employment. How the state safe harbors work, what Utah's 50% tax credit (up to $2,000 per contractor) covers, and how to track contributions in your books.

Mike Thrift

independent-contractoremployee-benefitsfreelance

July 9, 20268 min read

Driving School Bookkeeping: Deferred Revenue, Dual-Control Vehicles, and the 1099 Question

A $650 prepaid lesson package is a liability, not revenue, until the lessons are delivered. How driving schools handle deferred revenue, choose between Section 179 (up to $12,200 for light vehicles, $32,000 for 6,001–14,000 lb GVWR in 2026) and standard mileage on dual-control cars, classify instructors as 1099 or W-2 under the IRS three-factor test, budget for state surety bonds ($2,000–$50,000), and track the two KPIs — revenue per vehicle-hour ($70+ target) and instructor utilization (75–85%) — that predict margins.

Mike Thrift

bookkeepingsmall-businessrevenue-recognition

July 9, 202610 min read

Flight School Bookkeeping: Block-Time Deferred Revenue, Leasebacks, and CFI Classification

Flight schools should book prepaid block-time packages as deferred revenue, distinguish owned aircraft from leaseback and dry/wet-leased aircraft for depreciation purposes, classify CFIs correctly against IRS behavioral-control tests, and track revenue-per-aircraft-hour to know if the business is actually profitable.

Mike Thrift

bookkeepingsmall-businessrevenue-recognition

July 9, 20268 min read

Bookkeeping for Private Investigators: Retainers, Job Costing, and 1099 Compliance

Private investigation agencies should book client retainers as liabilities until earned, track costs per case with job costing, and classify subcontractors correctly to avoid misclassification penalties and licensing risk.

Mike Thrift

bookkeepingsmall-businessprivate-investigators

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