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TateLyman
TateLyman

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The Freelancer Tax Stack: Tools I Use to Not Get Destroyed by the IRS

April 15 is coming fast. Here's the exact stack I use to handle freelance taxes without losing my mind.

The Problem

As a freelancer, nobody withholds taxes for you. If you don't track everything yourself, April hits like a truck. Self-employment tax alone is 15.3% on top of income tax.

My Stack

1. Quarterly Tax Estimates

I use a simple calculator to estimate what I owe each quarter. Plug in your income, it handles SE tax, QBI deduction, and income tax brackets. Takes 30 seconds.

2. Invoice Tracking

Every invoice goes through a free generator that keeps things consistent and professional. I export and track everything in a spreadsheet.

3. Rate Calculation

Most freelancers undercharge because they don't account for taxes, insurance, and non-billable hours. A rate calculator shows your TRUE hourly rate after all expenses.

4. Deduction Categories I Track

  • Home office (simplified: $5/sq ft up to $1,500)
  • Software subscriptions
  • Internet/phone (business %)
  • Health insurance premiums (100% deductible)
  • Professional development
  • Mileage (70 cents/mile for 2025)
  • Equipment under $2,500 (Section 179)

5. SEP-IRA

You can contribute up to 25% of net SE income to a SEP-IRA. This reduces your taxable income AND builds retirement. Contributions are due by the filing deadline (including extensions).

The Move for April 15

If you haven't filed yet:

  1. Estimate what you owe → calculator
  2. File Form 4868 for an extension (free, 5 minutes)
  3. Pay your estimated amount by April 15 even with the extension
  4. Organize deductions and file by October 15

The extension reduces your penalty from 5%/month to 0.5%/month. Always file it.


All tools linked above are free, no signup required. I built them because I got tired of doing this math by hand.

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