Summary of What This Blog Covers
- Why tax software misses key deductions
- Common expenses often underclaimed
- Signs it’s time to hire a CPA
- How a CPA brings clarity and strategy
There’s a specific kind of tension that creeps in every spring.
It’s the tension of knowing your taxes are due, opening your laptop, launching your software, and telling yourself, “I’ve got this.” Because you’re resourceful. You’re smart. You’re capable. You’ve done hard things before. Filing taxes online can’t be that bad.
You start clicking through prompts. You upload your 1099-NEC. You enter your expenses. You nod along as your tax software tells you, “Nice work, you’re almost done!”
But deep down, that quiet doubt lingers:
“Is this actually maximizing my deductions?”
“Did I categorize that subscription correctly?”
“Is there something I’m missing that I don’t even know to look for?”
If you’ve ever walked away from TurboTax, H&R Block, or TaxAct feeling more uncertain than relieved, you’re not alone. We hear this all the time from entrepreneurs, freelancers, and self-employed professionals. People who work tirelessly to do the right thing but wonder if “doing it right” with tax software is really enough.
Let’s talk about that. Honestly. With empathy. And with answers.
Because you deserve clarity. And more importantly, you deserve to keep more of what you’ve earned.
The Real Problem with DIY Tax Software
Tax software isn’t the enemy. It’s accessible, affordable, and often convenient. For W-2 employees with a few deductions, it can work fine.
But when you’re self-employed—whether you’re a sole proprietor, LLC, or gig economy worker—things get more complex. You’re not just plugging in a W-2 and hitting submit. You’re navigating Schedule C, calculating self-employment tax, and trying to translate your business life into IRS forms.
And that’s where most tax software falls short.
Because it isn’t designed to think. It’s designed to process.
Software doesn’t ask follow-up questions. It doesn’t consider the story behind your expenses. It doesn’t look for patterns or push for better classification. It doesn’t know how your Zoom subscription, LinkedIn ads, and home internet bill relate to your client work.
It simply reacts to the data you enter.
And if you don’t know what to enter or how to phrase it, it quietly misses opportunities. Deductions disappear. Strategy is lost. And your tax return becomes a record of missed potential.
Let me say something that many people in your shoes need to hear:
If you don’t know what to look for, it’s not your fault.
You weren’t taught tax law. You weren’t trained to decode IRS deduction rules. You’re doing your best with what you know.
But at some point, best intentions and intuitive guesses are no match for expert strategy.
What Most Software Misses and Why That Matters
Let’s walk through some of the most common areas where tax software misses deductions or applies them in ways that aren’t optimized for your business.
Because the issue isn’t always that software gets it wrong. Sometimes, the real problem is that it doesn’t go deep enough.
1. Home Office Deductions
Most tax software defaults to the simplified home office method: $5 per square foot, up to 300 square feet. That might sound easy and efficient, but for many entrepreneurs, it’s the smaller option.
If you work from home and have higher rent, utilities, or property taxes—especially in places like Austin, Texas—the actual expense method could save you significantly more. But calculating that manually requires nuance, records, and guidance that software doesn’t always provide.
2. Phone, Internet, and Utilities
It’s one thing to list “internet expenses.” It’s another to know how much is deductible based on business use, and how to back that up with documentation. We often find that clients underreport these expenses or skip them altogether because software doesn’t prompt them to dig deeper.
A CPA knows to ask:
- What percentage of your home internet is used for business?
- Is your cell phone tied to client work?
- Are there shared services (like cloud storage or CRM tools) that should be allocated proportionally?
These are the small questions that unlock big savings.
3. Mileage vs. Actual Auto Expenses
If you drive for business whether to client meetings, site visits, deliveries, or even to pick up supplies, you may qualify for mileage deductions. Most software asks for total mileage and applies the standard deduction.
But what if your car expenses like insurance, repairs, gas, and depreciation actually exceed that value? If you qualify for actual expense method, you might save more. Tax software won’t know which method is best. It won’t run both scenarios and compare.
A CPA will.
4. Startup and Education Costs
This is a big one and it’s one that hurts when missed.
We meet so many entrepreneurs who invest in courses, certifications, books, coaching, and online training only to find out they claimed none of it. Why? Because they assumed it didn’t count.
In reality, education that maintains or improves your current business skills is often deductible. So is training related to software you use to serve clients, run operations, or grow your brand.
Tax software doesn’t make that distinction for you. It leaves you to decide.
We had one client who missed $4,000 in eligible education deductions not because she made a mistake, but because her software never asked the right questions.
The Emotional Toll of “Not Knowing”
Let’s step back for a moment.
This isn’t just about numbers on a form. It’s about the emotional burden you carry when you’re not sure if your return is accurate or fair.
It’s about wondering if the tax bill you just paid could have been smaller.
It’s about second-guessing your deductions.
It’s about opening that IRS envelope and holding your breath.
It’s about doing your best and still feeling like you’re winging it.
You deserve better than that.
You deserve to feel confident in your return. You deserve to know that someone who understands your business is watching out for you. You deserve a tax strategy that reflects the work, risk, and investment you’ve already made.
And most of all, you deserve to stop guessing.
When It’s Time to Bring in a CPA
Many entrepreneurs wait too long to switch from software to a CPA. They worry it’s too expensive, too formal, or too complex. They tell themselves, “Maybe next year, when I’m earning more.”
But here’s the truth:
The right CPA saves you money, time, and stress often far beyond the fee you pay.
So how do you know if you’ve outgrown software? Here are a few clear signs:
- You earn more than $50,000 annually as a self-employed person or business owner
- You track business expenses in tools like QuickBooks Self-Employed, but still feel unsure
- You issue or receive 1099 forms for contract work
- You use shared tools, utilities, and subscriptions for both personal and business use
- You’ve gotten letters or notices from the IRS and don’t know how to respond
- You want to grow your business and need a partner who sees the bigger picture
What Working With a CPA Looks Like at Insogna
If you’ve never worked with a CPA before, let me set your mind at ease.
At Insogna, we work with entrepreneurs, creatives, consultants, and small business owners across the country and especially right here in Austin, Texas.
We believe tax planning shouldn’t feel like punishment. It should feel like progress.
Here’s what you can expect:
- A discovery session where we listen first
We learn about your business. Not just your numbers, but your goals, your systems, your challenges. - A full review of your past returns
We look for missed deductions, reclassify expenses, and identify what’s working and what’s not. - A forward-looking strategy
This includes quarterly tax planning, retirement contribution analysis, and conversations about whether your current entity structure still fits where you’re headed. - A relationship not just a transaction
You’ll hear from us. You’ll be able to ask questions. You’ll have a partner in your financial corner not just during tax season, but all year long.
Because you deserve that kind of support.
The Deeper Purpose Behind All This
This isn’t just about filing taxes. It’s about honoring your effort.
You’ve taken the leap. You’ve risked comfort to pursue something bigger. You’ve worn every hat including one you never asked for: tax preparer.
But that doesn’t have to be your story anymore.
At a certain point, success means building a team around you. People who do what they do best so you can do what you do best. And your taxes? That’s where we come in.
Our goal at Insogna is simple:
To help you keep more of what you’ve earned.
To bring clarity where there’s confusion.
To replace anxiety with strategy.
And to make taxes something you feel confident about, not just relieved to survive.
Ready to Take the Next Step?
If you’re tired of wondering if your tax software is missing something, it probably is.
If you’re tired of doing this alone, you don’t have to anymore.
Stop settling for pennies on the dollar. Contact Insogna, and let’s maximize what you’re already paying for.
We’ll review your past return. Walk through your current strategy. And help you move forward, not just file what’s behind you.
Because your business deserves more than checkboxes and canned answers.
It deserves care, strategy, and clarity.
And so do you.