W-2 by Day, Wedding Photographer by Weekend? Don’t Let Your Side Hustle Become a Tax Nightmare

You launched your side hustle to gain flexibility.
 The additional income.
 responds, "hey, I'm good at this—why not get paid?"  a form of freedom.

Now that summer has arrived, reservations are starting to come in.
 marriages.  The brand shoots.  freelance design assignments.  additional coaching sessions.  While on vacation, you might even earn a little money from Airbnb.

But here's what nobody tells you about Instagram:
 What about the money?  It is taxed.
 And if you don't plan ahead, the IRS will be waiting at the end of your summer schedule.

The Side Hustle Tax Trap: Where W-2 Earners Get Caught

If your main employer already handles your taxes, you might believe your side hustle simply "fits in."
 Unfortunately, this isn't how it works.

Here is where side income catches up with you.

• Are you making more than $400?  You may owe self-employment tax (15.3%) in addition to your regular income taxes.
• Didn't receive a 1099?  Does not matter—you are still compelled to declare the income.
• Have you made money but not saved for it?  The IRS doesn't care that you reinvested everything in gear.
• Did you skip anticipated taxes?  That's a penalty waiting to happen next April.
  
  

Your W-2 salary may already place you in a higher tax rate.
 What about this "little extra" income?  It isn't being taxed softly.

You’re Not Alone. But You Do Need a Plan.

We frequently work with clients who:

• Excellent at their job
• Don't consider themselves as "business owners" (yet).
• Want to increase their side income without paying half of it to the IRS.
• have no notion that the IRS perceives them as a sole owner.

Whether you make a few hundred dollars a month or a few thousand dollars on weekends, you have options:

3 Easy Wins to Take Back Control of Your Taxes (Before It’s Too Late)

1. Start Tracking Like a Pro

No more Venmo screenshots or mental math.  Use an actual expenditure tracker or software (even a spreadsheet will suffice).
 Mileage, materials, website hosting, and subscriptions are all deductible.

2. Consider Estimated Taxes (Or Risk the Surprise)

Once your side income reaches $5,000 or more, you should consider whether quarterly expected payments are a good idea.
 Bonus: It prevents you from mistakenly underpaying and incurring fines.

3. Know When to “Go Legit” (and Why That’s a Good Thing)

Once your side hustle has gained traction, you may want to explore organizing an LLC, opening a company bank account, or even obtaining S Corp status.
 Not because it sounds fancy, but because it has the potential to save you thousands of dollars in taxes if properly designed.

Let’s Keep More of What You’re Earning

You do not have to do this alone.
 We work with a lot of clients that have W-2 employment and increasing side gigs, and we help them stay compliant, avoid surprises, and feel secure that they're doing things correctly.

Contact our officeif you want to go over your situation, speak about deductions, or just make sure you're not setting yourself up for a bad April.

Because your side hustle should help you achieve your goals, not your tax bill.