16 guides published

Everything you need to know about running your own thing.

No jargon. No fluff. Real answers for freelancers, founders, and anyone who decided a W2 wasn't for them.

Starting Out
Getting Stable
Getting Stable7 min

Quarterly Estimated Taxes: The Complete Guide

How quarterly estimated tax payments work, when they're due, how much to pay, and how to avoid underpayment penalties. Everything in one place.

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Getting Stable8 min

Health Insurance for Freelancers: Your Actual Options

Leaving employer health insurance is one of the scariest parts of going solo. Here's every real option, what they cost, and how to choose.

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Getting Stable6 min

The Home Office Deduction: What Actually Qualifies

The home office deduction is one of the most valuable available to freelancers and one of the most misunderstood. Here's exactly what qualifies and how to calculate it.

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Getting Stable5 min

The Self-Employed Health Insurance Deduction

Self-employed people can deduct 100% of their health insurance premiums. Here's exactly how it works, what qualifies, and how to claim it correctly.

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Getting Stable5 min

How to Pay Yourself as a Freelancer or LLC Owner

Owner's draw, salary, distributions: what they mean, how they work, and the right way to move money from your business to your personal account without surprises.

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Getting Stable7 min

Freelance Contracts 101: What to Include Before You Start Any Project

You don't need a lawyer to have a good freelance contract. Here's what every agreement should cover and the clauses that will save you from the most common disasters.

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Getting Stable6 min

When to Hire a CPA (Signs You've Outgrown TurboTax)

TurboTax is fine until it isn't. Here's how to know when your taxes have gotten complicated enough to need a real professional, and how to find one.

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Building Wealth
Playing Offense