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The 10 Most Common Tax Mistakes Business Owners Make (and How to Avoid Them)

With S corporation tax returns due March 15 and personal returns due April 15, this time of year can sneak up on even the most organized business owners. And while most of us aren’t trying to outsmart the IRS, you’d be surprised how many smart people make the same avoidable mistakes year after year.

Here are 10 of the most common tax mistakes I’ve seen—and how to steer clear of them.

1. Mixing personal and business expenses
The mistake: Charging personal expenses to a business card or vice versa.
The fix: Keep clean books and use separate accounts. It’s a red flag for auditors and a mess for your CPA.

2. Missing S-corp deadlines
The mistake: Forgetting the March 15 S-corp filing date and assuming it’s the same as the personal return deadline.
The fix: Set calendar reminders in January and work with your accountant to prep early. If needed, file an extension—but don’t wait until the last minute.

3. Not paying yourself a “reasonable salary” as an S-corp owner
The mistake: Taking distributions only, without running payroll.
The fix: The IRS expects S-corp owners to pay themselves a fair wage before taking profits. It reduces your audit risk and keeps things compliant.

4. Overlooking estimated tax payments
The mistake: Failing to make quarterly payments—especially common for new business owners.
The fix: Ask your accountant to calculate your estimated payments and automate them if possible. The penalties for underpayment are annoying and avoidable.

5. Missing deductions
The mistake: Forgetting to deduct things like home office space, mileage, or business travel.
The fix: Track expenses all year (apps help), and ask your CPA what’s commonly missed. Don’t leave money on the table.

6. Taking too many deductions
The mistake: Getting overly aggressive—writing off your dog as a “security system” or claiming 100% of your vehicle use as business.
The fix: Be reasonable. If it feels like a stretch, it probably is. The IRS has a good nose for this.

7. Failing to issue 1099s
The mistake: Not sending 1099s to contractors by the January 31 deadline.
The fix: Keep track of vendors throughout the year. If you pay someone $600+ who’s not on payroll, chances are you owe them a 1099.

8. Not saving for the tax bill
The mistake: Spending everything you earn and then panicking in April.
The fix: Treat taxes like a recurring bill. Set aside a percentage of income each month so you’re not scrambling when the IRS knocks.

9. Relying on software instead of strategy
The mistake: Letting TurboTax do your thinking.
The fix: Tax software is great for simple returns. But as a business owner, strategy matters more. A good CPA pays for themselves by helping you plan—not just file.

10. Not asking questions
The mistake: Assuming your accountant has it all covered without any dialogue.
The fix: Don’t be afraid to ask. A 10-minute conversation can prevent a costly mistake. It’s your money—and your responsibility.

Final thought:
Most tax mistakes come down to one thing: waiting too long to think about taxes. A little planning and communication—now, not next month—can save you stress, penalties, and money.

What Wrestling and Karate Taught Me About Leadership

Long before I was running a company or mentoring teams, I was wearing a singlet and sparring in a gi. I wrestled in high school—captain senior year—and studied two styles of karate, earning belts in both. At the time, I thought I was just getting stronger. Turns out, I was also learning how to lead.

Here are a few things those sports drilled into me—literally and figuratively—that still shape how I lead today.

1. You’re on your own—but never alone
In wrestling, when you’re on the mat, it’s just you and your opponent. No one’s coming to save you. Same in karate. You can’t fake readiness—you either trained, or you didn’t.

Leadership is like that. At the end of the day, the decisions are yours. The accountability is yours. But behind the scenes? A team, mentors, training, and support make all the difference. You do the work alone—but you’re backed by others.

2. Pain is a great teacher (if you listen to it)
A bad takedown or lazy block in karate doesn’t go unnoticed. You learn—fast. The feedback is immediate and usually lands somewhere between “ouch” and “lesson learned.”

In business, mistakes hurt too—missed sales, bad hires, lost clients. Leaders who ignore those signals keep making the same mistakes. The best ones learn quickly, adapt, and come back stronger.

3. Discipline > motivation
There were plenty of mornings I didn’t feel like cutting weight, drilling techniques, or getting punched (lightly) in the face. But I showed up anyway.

That’s what leadership requires. You won’t always feel inspired. You won’t always have clarity. But if you’ve built discipline—habits, routines, and standards—you can push through.

4. Respect is earned, not assumed
In martial arts, you bow to your opponent. In wrestling, you shake hands before and after every match. You respect the work, the grind, and the person across from you.

Good leaders don’t demand respect—they earn it. Through consistency, fairness, and effort. And they give it, even when it’s not reciprocated.

5. Control what you can
Wrestling teaches you how to use leverage, not brute strength. Karate emphasizes control, not chaos. You don’t win by panicking—you win by staying focused, calm, and in control of your breathing and your mindset.

That’s leadership. You can’t control the market, the economy, or client decisions. But you can control how you respond. How you show up. How you lead.

I didn’t know it at the time, but wrestling and karate were less about fighting and more about focus. Less about toughness and more about resilience.

Turns out, those early lessons still apply—whether you’re on the mat or in the boardroom.

The Best Business Advice I Ever Ignored (Until It Was Almost Too Late)

When I was just starting out in business, I read a book by Michael Gerber. This was the core focus:

“Don’t just work in the business—work on the business.”

Too busy to think
Back then, I was coding during the day, handling proposals at night, managing clients somewhere in between, and generally trying to do everything myself. Growth meant more work, more chaos, more duct tape.

I wasn’t working on the business. I was sprinting in it—head down, inbox full, and calendar jammed. And I told myself that was what success looked like.

It took nearly burning out, missing some important family moments, and watching key people leave for me to finally listen to that advice.

Working on the business meant stepping back.
Not to disengage—but to lead. To think about where we were headed. To build systems. To delegate, hire better, and create a company that didn’t depend on me being everywhere all the time.

When I started carving out time to work on the business, things changed:

We hired stronger leaders
Our delivery process became repeatable
Client relationships deepened
Profitability improved
I slept better

Funny how that works.

What I’ve learned since
That advice wasn’t just good—it was essential. And the best leaders I know? They carve out regular time to work on their business like it’s a non-negotiable.

They treat strategy like a discipline, not a once-a-year retreat.

They document what works so others can repeat it.

They create a culture where growth doesn’t mean chaos—it means clarity.

So here it is again:

Don’t just work in the business. Work on the business.

You can thank me later. Or ignore it and learn the hard way. Either works—I’ve done both.

What I’ve Learned About Leadership From Watching Youth Hockey

I didn’t expect to learn anything about leadership sitting in freezing rinks at 6 a.m. on a Saturday. But after watching hundreds of youth hockey practices and games (and drinking gallons of burnt coffee), I’ve realized something:

Youth hockey is a masterclass in leadership—if you’re paying attention.

Here are a few things I’ve picked up between faceoffs:

1. You can’t coast on talent.
Every team has one or two kids with raw skill. They skate circles around everyone—until they don’t. As the season progresses, the grinders catch up. The lesson? Talent opens the door. Hustle keeps you in the game. Same in business. I’ll take a consistent B+ performer who shows up every day over a moody A+ who only plays hard when they feel like it.

2. Everyone has a role. Even the quiet kid.
In hockey, not everyone scores. Some win faceoffs. Some block shots. Some just skate hard and wear the other team down. It’s the same in a consulting firm. Flashy presentations might win work, but follow-through and behind-the-scenes execution keep clients coming back. Great leaders notice the quiet contributions—and reward them.

3. You’re only as good as your last shift.
In youth hockey, kids forget the scoreboard five minutes after the game. What sticks is how they played. Did they hustle? Did they support teammates? Did they give it their all? Business isn’t so different. Reputation isn’t what you say—it’s how you show up, over and over, especially when no one’s watching.

4. Coaching matters more than you think.
I’ve seen kids transform under the right coach—not just skill-wise, but in confidence, attitude, and self-belief. The best coaches teach, encourage, and hold kids accountable without yelling. Leaders in business would do well to take notes.

5. It’s supposed to be fun.
Yes, hockey is competitive. But when it stops being fun, kids burn out. The same goes for work. Culture, camaraderie, and a little levity keep people engaged. As a leader, your job isn’t just to drive performance. It’s to create an environment where people want to keep showing up.

I didn’t set out to write a leadership manual based on youth hockey. But it turns out you can learn a lot when you’re standing in the cold with your hands wrapped around a coffee cup, watching kids chase a puck and slowly figure things out.

Just like the rest of us.

Let’s Start Q2!

As we move from Q1 into Q2, businesses, managers, and leaders should take the opportunity to assess performance, refine objectives, and mitigate risks for the rest of the year. Here’s what should be on the radar:

1. Evaluate Performance & Adjust Goals

Q1 KPI Review: Are revenue, profitability, and other key metrics on track? If not, why?
Customer & Employee Feedback: Are there recurring pain points or emerging trends that need attention?
Budget vs. Actuals: Are expenses in line with projections? Are there areas to cut or invest more?
Sales Pipeline Health: Is there enough in the pipeline to hit annual targets, or does lead generation need a boost?

2. Identify Growth & Market Opportunities

Industry Trends & AI Adoption: Are competitors leveraging AI, automation, or new tech in ways you’re not?
Customer Needs: Has anything shifted in customer expectations or behavior that presents a new revenue opportunity?
Strategic Partnerships: Any new collaborations that could accelerate growth or provide a competitive advantage?
Expansion & Diversification: Are there adjacent markets or services that make sense to explore?

3. Address Risks & Operational Bottlenecks

Talent & Workforce Planning: Any high-performing employees at risk of leaving? Does hiring align with business goals?
Supply Chain & Vendor Risk: Any vulnerabilities in procurement, logistics, or dependencies that need mitigating?
Tech & Cybersecurity: Are systems secure and scalable? Are there process inefficiencies that tech upgrades could solve?
Regulatory & Compliance Risks: Any upcoming legal, tax, or compliance shifts that need preparation?

4. Reinforce Culture & Engagement

Employee Motivation Post-Q1: Are people feeling engaged and aligned with company goals, or is burnout creeping in?
Leadership Development: Are managers equipped to lead effectively and adapt to changing workplace dynamics?
Remote & Hybrid Work Adjustments: If hybrid/remote work is a factor, does the setup still support productivity and collaboration?

5. Plan for Q3-Q4 Success Now

Mid-Year Adjustments: If Q1 wasn’t strong, what immediate pivots can improve trajectory?
Summer Slowdowns: If Q2/Q3 is historically slow, what strategies can keep momentum going?
Big Projects & Initiatives: What needs to be set in motion now to hit year-end targets?

Bottom line: This is the perfect time to correct course, capitalize on early trends, and ensure the rest of the year unfolds with fewer surprises. What’s the biggest challenge or opportunity you’re seeing as Q2 approaches?