Day 13: What to Know About 1099-NEC & Contractors: A Simple Guide for Businesses and Freelancers

🧾 Day 13: What to Know About 1099-NEC & Contractors: A Simple Guide for Businesses and Freelancers In today’s flexible work landscape, hiring independent contractors can be a smart move—offering agility without the long-term commitments of traditional employment. But with this freedom comes responsibility, especially when it’s time to tackle tax forms like the 1099-NEC . Let’s break down what you need to know about using this form and working with contractors, without the tax jargon overload. πŸ“Œ What Is the 1099-NEC? The 1099-NEC (Nonemployee Compensation) is an IRS form used to report payments made to nonemployees for services. It replaced the old use of Form 1099-MISC for service payments starting in 2020 . You’ll need to issue this form if you paid: $600 or more in the calendar year To an individual or business not classified as an employee For services (not products or rent) Who is not incorporated—i.e., a sole proprietor or LLC taxed as such It goes to both t...

πŸ“… Day 12: Quarterly Taxes – A Simple Payment Plan Guide

 πŸ“… Day 12: Quarterly Taxes – A Simple Payment Plan Guide

If you're self-employed or running a side business, quarterly taxes can feel like a ticking clock. Unlike traditional employees, you’re expected to pay taxes as you earn, four times a year. But what happens when cash flow is tight, deadlines sneak up, or life just gets in the way? That’s where a simple payment plan strategy can turn stress into structure.

🎯 Who Needs Quarterly Payments?

If you expect to owe $1,000 or more in federal income tax (after subtracting withholdings and credits), the IRS wants you to pay quarterly:

  • April 15
  • June 15
  • September 15
  • January 15 of the following year

This includes gig workers, freelancers, small business owners, and even side hustlers with no employer withholding.

πŸ’‘ Building a Simple Payment Plan (Not the IRS One—Your Own!)

Here’s a low-stress method to set aside taxes ahead of each deadline:

Step 1: Estimate Your Annual Tax Liability

  • Use last year’s return as a baseline
  • Or plug numbers into a tax calculator for self-employment income

Step 2: Break It into Quarters

Let’s say your estimated federal tax is $4,800
Divide by four = $1,200 per quarter

Step 3: Set Up Weekly Transfers

  • $1,200 ÷ 13 weeks = about $92/week
  • Set up an auto-transfer every Friday from your business account to a dedicated “Tax Savings” account
  • Optional: Save an additional 15% for state taxes if applicable

Step 4: Pay Online

Use the IRS’s Direct Pay or EFTPS system to submit your quarterly payment before the deadline. You'll avoid penalties and interest by paying consistently.

πŸ€” Behind or Can't Pay in Full?

If you're already behind:

  • File your estimated payment anyway
  • Use the IRS payment plan tool to request a monthly installment plan
  • Penalties may apply, but it’s better than ignoring the obligation

✅ Bonus Tips

  • Use a digital tracker (like your planner or spreadsheet) to log payments and reminders
  • Schedule quarterly check-ins to update projections as income shifts
  • Avoid the “January surprise” by saving more during high-income months

Quarterly taxes don’t have to be scary—they just need a rhythm. The moment you automate your plan, it becomes one less thing to worry about and one more step toward sustainable self-employment.

Want to download a printable tracker or plug this into your planner system? I’d love to help you build one that fits your workflow.

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