Mastering Taxes for Side Hustlers: A Weekend Wedding Photographer's Guide

You embarked on your side hustle journey to embrace flexibility.
The allure of additional income.
The sense of freedom that comes from turning a talent into profit. But as the summer season kicks off and bookings surge, a crucial aspect demands your attention: taxes.Image 1

Weddings, brand shoots, freelance design endeavors, and perhaps even some Airbnb earnings during your vacation—all these contribute to your income stream. But here’s a truth seldom shared on social media: that income? It’s taxable. Without proactive planning, the IRS may be a bigger presence in your life than anticipated by year-end.

The Freelance Tax Predicament: How W-2 Earners Miss the Mark

Your primary job may handle tax deductions seamlessly, but this doesn't mean your side venture naturally dovetails.

Here’s why unexpected tax surprises arise:

  • Generates over $400 in income? You’re liable for self-employment tax (15.3%) in addition to regular income taxes.

  • Missed receiving a 1099? It doesn’t exempt you from reporting earnings.

  • Reinvested all profits back into your business? The IRS expects you to account for taxable income nonetheless.

  • Skipped estimated tax payments? It can lead to penalties during tax filing season.

Your W-2 salary may already nudge you towards a higher tax bracket, and this “little extra” income? It won’t be subject to minimal tax rates.

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You're Not Alone, Yet Preparation is Key.

This is a common scenario we address—clients who:

  • Excel in their craft

  • Do not yet see themselves as “business owners”

  • Aim to expand their side income without succumbing to hefty IRS dues

  • Are unaware of being classified as sole proprietors by the IRS

Whether your side earnings are a few hundred dollars monthly or several thousand over weekends, you have strategic options:

Three Strategies to Manage Your Taxes Effectively (Before It’s Too Late)

1. Implement Professional Financial Tracking

Forego Venmo screenshots and mental calculations. Embrace expense tracking tools or apps—even spreadsheets can suffice. Mileage, supplies, website hosting, and subscriptions are deductible expenses.Image 3

2. Evaluate the Necessity of Estimated Taxes

Once side income surpasses $5,000, consider reviewing the viability of quarterly estimated payments. This proactive step prevents underpayment and subsequent penalties.

3. Transition to Formal Business Status

When your side hustle gains traction, explore the benefits of forming an LLC, opening a dedicated business bank account, or opting for S Corp status. These steps can provide substantial tax savings when structured optimally.

Secure More of Your Earnings

You don’t have to navigate this landscape solo. We collaborate with numerous clients juggling W-2 employment with expanding side ventures, ensuring compliance, minimizing unexpected scenarios, and instilling confidence in managing their financial operations smartly.

Reach out to our office for guidance on evaluating your circumstances, optimizing deductions, or ensuring you’re not setting yourself up for an unfavorable tax filing experience.

Your side hustle should amplify your aspirations—not inflate your tax bills.

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