Falling behind on taxes is way too easy. Maybe you transitioned from a W-2 job to freelancing and didn’t realize you needed to pay quarterly taxes. Maybe life got hectic, and before you knew it, one missed deadline turned into two… then three. Now, you’re staring at unfiled returns, IRS letters, and a growing sense of dread.
Sound familiar? You’re not alone. And more importantly: it’s fixable.
At Insogna CPA, a trusted CPA firm in Austin, Texas, we help self-employed professionals, freelancers, and small business owners catch up on unfiled taxes, minimize penalties, and stay IRS-compliant without the stress. Here’s how to get back on track, step by step.
Why Do So Many Self-Employed Professionals Fall Behind on Taxes?
If you’re an independent contractor, freelancer, or small business owner, your tax situation is way different than someone with a traditional 9-to-5.
Why It Happens:
✔ No automatic tax withholdings – When you’re self-employed, the IRS doesn’t automatically deduct taxes from your paycheck like they do for W-2 employees. You have to set aside and pay taxes yourself—but many don’t realize that until it’s too late.
✔ Estimated tax payments are confusing – The IRS expects you to pay taxes quarterly, not just in April. If you miss these payments, you could end up with penalties and a massive tax bill.
✔ No bookkeeping system in place – When your income is coming from multiple clients or platforms like Stripe, PayPal, and Venmo, it’s easy to lose track of what you owe.
✔ Fear leads to avoidance – The longer you wait to file, the more overwhelming it seems so you put it off even longer. (We see this all the time. No judgment here.)
Good news? No matter how many years you’ve fallen behind, there’s a way to fix it.
How to Catch Up on Unfiled Taxes (Without Losing Your Mind)
If you’re behind on your taxes, don’t panic. Here’s what to do, step by step.
Step 1: Gather Your Income Records
Before you can file, you need to figure out how much you earned.
What to Collect:
✔ 1099 forms from clients or gig platforms (if applicable).
✔ Invoices & bank statements to track payments received.
✔ Any W-2s (if you had a part-time job or side hustle).
✔ IRS transcripts (if you’re missing documents, a CPA in Austin, Texas can request them for you).
Pro Tip: If your income is scattered across multiple platforms, export transaction reports from PayPal, Stripe, Venmo, or Cash App to make tracking easier.
Step 2: Identify Deductible Expenses to Reduce Your Tax Bill
One of the biggest mistakes people make when catching up on taxes? Not claiming all the deductions they qualify for. Every legitimate business expense reduces your taxable income, meaning you pay less.
Common Deductions for Self-Employed Professionals:
✔ Home office expenses (if used exclusively for business).
✔ Internet & phone bills (business portion).
✔ Marketing & advertising (Facebook/Google ads, website costs).
✔ Business mileage, meals, and travel expenses.
✔ Software & subscriptions (QuickBooks, Canva, Zoom, etc.).
Pro Tip: If you didn’t track expenses properly, a small business CPA in Austin can help estimate and reconstruct deductions legally to lower your tax bill.
Step 3: Work with a CPA to File Past-Due Returns & Minimize Penalties
If you owe multiple years of back taxes, the thought of penalties and interest can feel paralyzing. But here’s what many people don’t realize: the IRS actually wants to work with you. A CPA can help you file strategically and minimize what you owe.
What a CPA Can Do for You:
✔ File past-due returns efficiently so you avoid further penalties.
✔ Request penalty relief if you qualify for IRS forgiveness programs.
✔ Set up an IRS payment plan if you owe a balance (so you’re not stuck with a lump sum).
✔ Ensure you’re claiming every possible deduction to reduce how much you owe.
Pro Tip: A tax advisor in Austin can help negotiate with the IRS on your behalf, so you’re not dealing with them alone.
Step 4: Set Up a Tax Strategy to Stay Ahead Next Year
Once you’re caught up, let’s make sure this never happens again.
How to Stay On Top of Taxes Going Forward:
✔ Make quarterly estimated tax payments (April 15, June 15, September 15, January 15).
✔ Open a separate business bank account to keep income & expenses organized.
✔ Use accounting software (QuickBooks, Xero) to track income and expenses in real-time.
✔ Work with a CPA firm in Austin Texas to get year-round tax planning support.
Pro Tip: Taxes don’t have to be a yearly source of stress. With the right plan, you’ll never fall behind again.
Final Thoughts: Let’s Get You Back on Track
Look, falling behind on taxes happens. The key is taking action now.
At Insogna CPA, we help self-employed professionals and small business owners catch up on taxes, minimize penalties, and set up tax strategies that actually work. Whether you’re one year behind or several, we’ve seen it all, and we’re here to help—judgment-free.
Let’s Tackle This Together!
Schedule a free consultation with Insogna CPA, the go-to CPA firm in Austin, Texas, and let’s get you back on track—stress-free.