Summer Side Hustle Income Check-In: Stay Ahead on Taxes and Earnings

Summer can be the perfect time to pick up extra income. Whether you’re driving for rideshare services, delivering food, freelancing online, or selling handmade goods at local markets, the flexibility and added cash flow can make a big difference. But while side hustles can boost your bank account, they can also bring tax obligations you may not be prepared for if you don’t track your earnings and expenses throughout the year.

At Nacca & Capizzi, we work with many Rochester and Greece, NY residents who have side hustles, part-time gigs, or seasonal freelance work. The most common mistake we see? Waiting until tax season to figure out how much was earned — and how much needs to be paid to the IRS and New York State.

Why a Mid-Summer Income Check-In Matters

By the time summer is in full swing, you’ve likely earned a decent amount from your side hustle. Taking time now to review your numbers can help you:

• Avoid tax surprises: Self-employment income isn’t taxed automatically like a paycheck from a traditional employer.
• Plan for estimated tax payments: The next quarterly payment deadline is September 15, and being proactive can prevent penalties.
• Identify deductible expenses: Many gig workers miss out on deductions simply because they didn’t track them in real time.

Simply put, a mid-year review allows you to get organized while there’s still time to adjust your financial strategy.

Step 1: Total Up What You’ve Earned

Start by adding up all the income from your side hustle so far this year. This might include:

• Payments from online platforms like PayPal, Venmo, or Stripe
• Direct deposits from rideshare or delivery apps
• Cash payments from local clients or markets
• Checks or ACH transfers from freelance work

Keep in mind that the IRS expects you to report all income — even if you don’t receive a 1099 form. If you’ve been paid in cash or through nontraditional platforms, you’re still responsible for tracking and reporting it.

Step 2: Set Aside a Portion for Taxes

Unlike W-2 employees, gig workers and freelancers have no taxes withheld from their pay. That means you’ll need to set aside a percentage of your earnings for federal, state, and self-employment taxes.

As a general guideline:

• Set aside 25–30% of your side hustle income for taxes
• Consider making estimated payments each quarter to avoid penalties
• Use a separate savings account to make sure tax money isn’t accidentally spent

The team at Nacca & Capizzi can help you determine the exact percentage you should save based on your total income and deductions.

Step 3: Keep Receipts and Track Expenses

One of the biggest benefits of self-employment is the ability to deduct business-related expenses. Depending on your side hustle, you may be able to deduct:

• Mileage driven for business purposes
• Supplies and materials
• Marketing and advertising costs
• Home office expenses (if you meet IRS requirements)
• Equipment purchases

To claim these deductions, you need proof. Keep receipts, invoices, and mileage logs. Many gig workers find it helpful to use an app or software to track expenses automatically. The better your records, the easier tax season will be — and the more deductions you’ll be able to claim.

Plan for the September 15 Estimated Tax Deadline

If you’ve earned income from self-employment, there’s a good chance you need to make quarterly estimated tax payments. The upcoming deadline for Q3 is September 15.

Making these payments helps you avoid IRS penalties and keeps you from having a massive tax bill in April. If you’re not sure how much to pay, we can calculate it for you based on your income so far and your projected earnings for the rest of the year.

Benefits of Staying Organized Now

By doing a mid-summer income check-in, you’re setting yourself up for success. You’ll have a clear idea of where you stand financially, know exactly how much to save for taxes, and have organized records ready for tax season. Plus, you’ll reduce stress and eliminate the last-minute scramble in March and April.

Here’s what we recommend you do before the end of August:

• Review all income earned so far in 2025
• Calculate your estimated taxes for Q3
• Organize receipts and expense records
• Meet with a CPA to create a personalized tax plan

Work with a CPA Who Understands Side Hustles

Whether your side hustle is just a few hours a week or a full-time gig, the financial side can get complicated quickly. At Nacca & Capizzi, we understand the unique challenges freelancers, gig workers, and small business owners face. We’ll help you:

• Track and report all income accurately
• Maximize your deductions
• Plan for quarterly tax payments
• Stay compliant with IRS and New York State regulations

Request an Appointment Today

Don’t wait until September 15 is right around the corner — get ahead of your taxes now. Request an appointment with Nacca & Capizzi today, or call us at (585) 225-9290. We’ll make sure your side hustle income works for you, not against you.