DIY Mid-Year Check-in Toolkit for Self-Employed

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Mid-Year Tax Check-In Toolkit  

Self-Employed & Small Business Edition

This toolkit is designed for self-employed individuals and small business owners who want to pause mid-year, review where they stand, and make informed decisions before tax season sneaks up.

It helps you review income, deductions, estimated taxes, and compliance items — while there’s still time to adjust, plan, and reduce surprises later.

This is not tax software.  

This is a practical, guided check-in to help you get organized and proactive.

✅ What’s Included

• Step-by-step checklists to review income, deductions, quarterly taxes, and compliance  

• Common business expense categories with real-world examples  

• Fillable notes sections to track questions, action items, and reminders  

• Planning prompts to help you think ahead to year-end  

• Live links to helpful tools and resources, including:  

 – IRS Withholding Estimator  

 – Secure document upload portal  

 – Optional tax planning and strategy session  

Why This Toolkit Is Helpful

Many business owners wait until tax season to look at the numbers — when options are limited.

This toolkit helps you:

• Reduce year-end surprises  

• Stay organized and IRS-ready  

• Identify potential tax issues early  

• Prepare smarter questions before meeting with a tax professional  

• Make tax season less stressful (and often more profitable)  

Who This Is For

✔ Self-employed individuals  

✔ Single-member LLCs  

✔ Independent contractors and gig workers  

✔ Freelancers and creatives  

✔ Business owners managing their own books  

No advanced tax knowledge required.

Important Notes

This toolkit is for educational and organizational purposes only.  

It does not provide personalized tax advice or replace professional guidance.

Format & Access

You will receive a fillable and printable PDF.  

You may complete it digitally or print it for handwritten notes.

Optional Next Step: Tax Planning Support

Many users complete this toolkit before scheduling a tax planning or strategy session.

If you want professional guidance after reviewing your information, you may choose to book a follow-up strategy session when you’re ready.

Using the toolkit first helps ensure your session is focused, efficient, and productive.