For many business owners, January marks the official start of tax season and with it, a familiar mix of urgency, stress, and second-guessing. Maybe some things slipped through the cracks last year. Maybe a transaction made things more complicated than expected. Or maybe tax season just feels chaotic every year, no matter how prepared you are.
In the latest episode of Ask a DHJJ CPA, we take a step back from filing forms and deadlines to talk about what really drives tax season challenges and what business owners can still do now to make this season smoother while setting themselves up for a better 2026.
In this episode, host Emma Yurchik sits down with Mirella Hernandez, Principal at DHJJ and leader of the firm’s Tax Practice, to unpack lessons from the 2025 tax season, common pitfalls that cause delays and stress, and why proactive, year-round tax planning makes such a difference for growing businesses.
If you’d rather watch or listen, the full episode is below.
Why Tax Season Problems Usually Start Long Before Filing
One of the biggest takeaways from the conversation is that tax season challenges are rarely caused by taxes alone. According to Mirella, many of the delays and frustrations businesses experience stem from larger business events, especially transactions like acquisitions, mergers, or structural changes.
“These types of transactions don’t just affect the tax return,” Mirella explains. “They impact the financial close process, communication across teams, and ultimately the timing of everything.”
Smaller businesses often feel this strain more acutely because they may not have in-house expertise to handle purchase accounting, reconciliations, or complex integrations. On the other end of the spectrum, larger organizations face challenges simply because more people are involved, increasing the risk of misalignment and delayed decisions.
Across the board, one theme shows up again and again: communication gaps. When clients and CPAs aren’t in regular contact throughout the year, tax season becomes reactive, and that’s when stress and surprises tend to show up.
The Biggest Early Warning Sign a Business Is Unprepared
If there’s one red flag Mirella sees consistently, it’s this:
If you haven’t talked to your CPA in months, that’s a problem.
Tax season works best when it’s the continuation of ongoing conversations, not the moment everything gets addressed at once. Regular check-ins allow issues to surface earlier, planning opportunities to be identified, and expectations to stay aligned on both sides.
When communication goes dark until March, businesses often discover too late that something needs more time, documentation, or strategic discussion.
What Businesses Should Be Focusing on Right Now
January is still early enough to set the tone for a smoother tax season. Mirella emphasizes that this is when businesses should be closing out year-end financials, reviewing reconciliations and journal entries, and identifying anything out of the ordinary that occurred during the year.
Non-typical transactions such as acquisitions, ownership changes, or major financial events often require additional documentation and discussion. Gathering those agreements early gives both the business and the CPA time to understand the tax and accounting implications before deadlines loom.
For businesses undergoing a financial statement audit or review, coordination becomes even more important. When assurance work is underway, the tax team can often build on that progress, but only if documentation and timelines are clear.
Just as important, Mirella notes, is working with your CPA to prioritize requests. Not everything needs to be done immediately, especially if an extension is expected. A good CPA should help business owners focus on what truly matters first, rather than overwhelming them with long to-do lists.
It’s Not Too Late to Fix 2025 Records
A common concern business owners voice in January is whether it’s already too late to fix issues from the prior year. The short answer: no.
If 2025 just closed, there is still time to clean things up. The key is identifying the problem area, understanding the risk, and determining who should own each part of the fix. For many businesses, this is where outsourced accounting support, such as client accounting services or fractional controller/CFO support, can make a significant difference.
Accurate financials aren’t just about compliance. They’re the foundation for better tax planning, cash flow forecasting, and decision-making.
When Amended Returns Make Sense
Mirella also addresses when it may be appropriate to amend a tax return. Generally, amended returns are worth considering when a material error is discovered or when a credit, deduction, or incentive was missed.
She reminds listeners that the statute of limitations is typically three years from the original filing date, which creates a defined window for corrections.
The episode also touches on changes from the new tax bill, including opportunities related to Section 174 R&D expenses. For certain businesses, these changes may open the door to amending prior returns, a topic DHJJ has covered in depth through recent articles and webcasts.
Why Waiting Too Long Creates Risk
One of the most relatable moments in the episode is the acknowledgment that it’s human nature to avoid uncomfortable issues. When something doesn’t look clean or straightforward, it can feel easier to delay addressing it.
Unfortunately, that delay often increases risk. Waiting too long narrows planning opportunities, increases audit exposure, and makes solutions more limited. Mirella encourages business owners to trust their CPA and start the conversation early, even when the situation feels uncertain.
“The right answer isn’t always black and white,” she notes. “But having the conversation gives us the opportunity to arrive at a compliant, well-supported result.”
Tax Planning Is a Year-Round Strategy, Not a Year-End Task
A central theme throughout the episode is the difference between reactive and proactive tax planning. When tax is treated as an ongoing part of running the business, rather than a once-a-year event, businesses gain flexibility and clarity.
Early planning allows CPAs to model multiple scenarios, consider the timing of income and expenses, evaluate credits and incentives, and align tax strategy with broader business goals. This is especially important for growing companies and those preparing for future transactions.
As Mirella explains, when tax strategy becomes part of the overall business strategy, it supports smarter decisions in both the short and long term.
Three Actions to Take Away From This Episode
Before wrapping up, Mirella shares three actions she believes every business owner should focus on right now:
- Understand how the new tax bill affects your business and personal situation. New tax laws can be complex, and understanding their impact early creates better planning opportunities.
- Set clear, measurable goals and timelines with your CPA. Defined expectations reduce stress, allow flexibility, and help both sides stay on track.
- If a transaction is on the horizon, involve your CPA as early as possible. Early involvement leads to better due diligence, clearer tax implications, and fewer surprises.
Tax season doesn’t have to feel chaotic. With the right conversations, preparation, and planning approach, it can become a more manageable and even strategic part of running your business.
Watch or listen to the full episode of Ask a DHJJ CPA above, and if you have a question you’d like answered in a future episode, we’d love to hear from you.
