Chicago Entrepreneur Shares Tips for Side Hustle Taxes

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A Chicago-based entrepreneur who runs a small theater company called Dinner Cut shares her experience preparing her first tax return for her side business. She discusses the importance of tracking expenses throughout the year, categorizing them properly, and seeking help from a qualified tax professional, especially for independent artists and those with multiple income streams.

Why it matters

As more people take on side hustles and small businesses, navigating the tax process can be daunting. This first-hand account provides practical tips and insights that can help other entrepreneurs, especially those in creative fields, better prepare and file their taxes.

The details

The entrepreneur, who runs a single-member LLC for her theater company, explains how she uses a Google Sheet to meticulously track all of her business expenses, categorizing them in a way that makes sense for tax purposes. She emphasizes the value of working with a qualified tax professional, like her 'tax lady/jewelry artist' Janet, who specializes in independent artists' taxes. The entrepreneur also highlights the variety of expenses that can be written off, including a portion of rent/mortgage, cell phone/internet bills, mileage, and business travel.

• The entrepreneur started taking her theater company seriously as a business and officially formed an LLC in 2025.
• The entrepreneur's theater company, Dinner Cut, received a $10,100 grant from the state of Illinois in 2025.