Empowering Healthy Business Podcast Episode 54 : Tax Season Preparation with Greg Reed

Tax season has a way of arriving quickly. One minute you’re wrapping up year-end work, and the next you’re staring at a list of tax documents you think you already sent to your CPA.

In this episode of the Empowering Healthy Business Podcast, Cal Wilder talks with Greg Reed about tax season preparation, what business owners should do in January to reduce stress, avoid surprises, and keep the filing process moving smoothly. They also discuss why many people feel anxious about their tax bill, what changes may impact 2025 returns, and how ongoing support (not just once-a-year filing) can make a big difference.

Why tax season preparation matters more than ever

A lot of business owners don’t fear taxes because they hate paperwork. They fear taxes because they don’t know what’s coming.

Greg shares that many new and existing clients feel anxious because they honestly can’t predict their tax bill. That uncertainty creates stress, and it often leads to a rushed tax season.

Cal also points out something important: this year isn’t “business as usual.” There are changes in the mix, and some people may need to engage with their CPA more actively than they did in prior years.

While no one can go back and change decisions after December 31, tax season preparation still matters. You can still make the process smoother, cleaner, and more accurate by getting organized early and staying in communication.

A simple way to think about tax support: filing vs planning vs coaching

One of the most useful parts of this conversation is how Greg breaks down the levels of tax support. Many business owners assume there are only two options: either you file your taxes, or you don’t. In reality, support can go much deeper.

Here’s the framework they discussed:

1) Tax filing

At the most basic level, you need your tax return filed correctly and on time. That’s the foundation.

2) Tax projections

The next level is getting a clearer idea of what you’ll owe before the year ends. Projections help reduce the shock factor.

Even one meeting a year (or one or two check-ins) can help you estimate what your tax bill may look like and prepare for it.

3) Tax planning

Planning is where a CPA helps identify tax-saving opportunities based on your situation. But there’s a catch.

A plan only helps if someone implements it.

4) Tax coaching (the proactive approach)

Greg explains SmartBooks’ newer approach: monthly tax coaching.

This is more hands-on. Instead of only telling you what you might owe—or pointing out strategies and hoping you follow through—tax coaching includes regular check-ins to help make sure strategies actually get put into place.

The goal is simple: fewer surprises and a smoother tax season for both the client and the CPA.

What to do in January to make tax season smoother

Once you hit January, you’re not really “tax planning” for the year that just ended. But you can make tax season far less painful.

Greg and Cal share several practical steps that fall under strong tax season preparation.

Pull your documents early (especially if itemizing might apply)

Greg recommends starting early with your tax documents, especially anything tied to deductions.

One key topic they mentioned is itemized deductions. Even if you’ve taken the standard deduction in the past, changes may make itemizing more relevant again—especially for people in high-tax states.

That makes it worth pulling:

• Medical expenses (if significant)
• Property taxes
• Mortgage interest
• Other documentation you normally ignore because you assume you “can’t use it”

The main point: don’t assume last year’s approach will apply forever. If rules shift, your best move is to gather the information and let your CPA advise you from there.

Close your books cleanly (business owners)

For business owners, Greg stresses a big one: clean books.

The sooner your year-end bookkeeping is closed and accurate, the sooner tax prep can begin. Waiting too long creates delays and increases the chances of errors.

If you work with a bookkeeping team, make sure:

• Year-end close is completed
  
• Final entries are recorded correctly
  
• Nothing important is missing or miscategorized

Prepare for 1099 season

January isn’t just tax prep season. It’s also 1099 season.

If you paid contractors, you’ll likely need to issue 1099s. That means gathering records early so deadlines don’t sneak up on you.

Organize estimated tax payments

Another common issue: people forget what estimated payments they made during the year.

When payments aren’t tracked properly, it can lead to confusion, notices from the IRS, or refund situations that could have been avoided.

Even if a refund sounds nice, Greg makes a simple point: you don’t want to loan money to the IRS. Good tax season preparation includes pulling together:

• Payment confirmations
  
• Dates and amounts
  
• Any state payments made separately

Review home office reimbursements

If you use part of your home for business and you haven’t been reimbursing yourself regularly, January is a good time to review.

Cal notes that you can:

• Add up home office-related costs (utilities, home expenses)
  
• Estimate the percentage of your home used for business (10% or 20%, for example)
  
• Submit an expense report to the business and reimburse yourself
  

This is one of those areas where documentation matters. Keep records clean and clear so the numbers make sense.

Don’t forget travel and other Schedule C items

Greg also mentions reviewing travel expenses, especially for small businesses and single-member LLCs reporting on Schedule C.

The message isn’t “hunt for deductions.” It’s “don’t miss what’s real.” If something is a legitimate business expense, ensure it’s documented and included.

Small but important “housekeeping” steps with your CPA

Not everything is a tax strategy. Some of the most valuable steps are basic—but easy to miss.

Greg recommends:

• Make sure you still have access to your CPA’s client portal (if they use one)
  
• Confirm your CPA is active and available this year
  
• Watch for tax organizers (often sent in the second or third week of January)
  
• Expect some communication soon, and follow up if you don’t receive it
  

He even mentions a real situation where clients found out their CPA “closed up shop” without warning. It’s rare, but it happens. A quick check-in can prevent a major headache.

A quick warning sign: anxiety usually means you need more support

Toward the end of the episode, Greg shares one of the clearest takeaways:

If you feel anxious about your tax bill, it’s usually a sign you should be meeting with your CPA throughout the year—at least for projections, and possibly for planning.

That proactive approach helps you:

• avoid surprise tax bills
  
• stay organized throughout the year
  
• make smarter decisions with better timing
  

Cal agrees and adds that avoiding unpleasant surprises is a big part of what SmartBooks aims to help with.

Conclusion: Make tax season preparation easier by starting now

Tax season doesn’t have to feel like a panic cycle every year.

The simplest way to improve your tax season preparation is to start early, get your documents organized, close your books cleanly, and stay in communication with your CPA, especially in years where rules and limits may shift.

If you only take one action after reading this, do this:

Set a short check-in with your CPA and ask what they need from you in the next two weeks.
That one step can prevent delays, confusion, and last-minute stress.

Want to go deeper? Listen to the full conversation on the Empowering Healthy Business Podcast