Every so often, we get a message that stops us in our tracks—not because it’s unusual, but because it’s more common than people think.
A recent inquiry came from a small business owner who hadn’t filed taxes since 2019.
Their situation looked like this:
- No tax filings for multiple years
- Business disruption during COVID
- Income processed through platforms like Square
- Currently back in business and working a W-2 job
- Planning to buy a home in the next couple of years
Their message was simple:
“I need serious professional help.”
And honestly—that’s the right instinct.
The Real Problem: It’s Not Just Taxes
When someone falls behind for multiple years, the issue isn’t just tax filing. It’s two separate (but connected) problems:
- Tax compliance – multiple years of unfiled returns
- Bookkeeping gaps – no clear records of income, expenses, or financial position
You can’t fix one without the other.
Step 1: Rebuild the Financials
Before you can file taxes, you need accurate numbers. That means reconstructing the business’s financial history.
We typically start by gathering:
- IRS records (to see what’s already been reported, like 1099-K forms)
- Bank and credit card statements
- Payment platform data (Square, Stripe, etc.)
- Receipts and invoices
- Loan and financing documents
From there, we rebuild:
- Profit & Loss statements
- Balance sheets
- A complete transaction history
This step is critical. Without it, any tax filing is just a guess.
Step 2: File Back Taxes (The Right Way)
Once the books are clean, we move on to tax filings—year by year.
This is where many people feel overwhelmed, but the process is straightforward when handled properly:
- Start with the oldest unfiled year
- Work forward sequentially
- Ensure accuracy to avoid triggering further issues
If taxes are owed, the next step isn’t panic—it’s planning.
Step 3: Get Into Compliance (Even If You Owe Money)
One of the biggest misconceptions is that you need to pay everything immediately to fix the situation.
You don’t.
What matters most is getting into compliance.
That usually means:
- Filing all outstanding returns
- Setting up a payment plan with the IRS if needed
- Staying current moving forward
Once you’re in compliance, the pressure drops significantly—fewer notices, fewer risks, and more control over the situation.
Why This Matters More Than You Think
In this client’s case, they also wanted to buy a home in the next two years.
That’s where things get serious.
Lenders require:
- Filed tax returns
- Consistent income records
- Clean financials
Without those, major life goals—like buying a home—get delayed.
The Takeaway
If you’re behind on taxes, you’re not alone. And more importantly—you’re not stuck.
The path forward is clear:
- Fix the bookkeeping
- File the returns
- Get into compliance
It’s not about doing everything overnight. It’s about doing it correctly and completely.
Need Help Catching Up?
At Akif CPA, this is something we handle every day:
- Multi-year tax filings
- Bookkeeping cleanup and catch-up
- IRS compliance and payment plans
If you’re in a similar situation, reach out at info@akifcpa.com.