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The 4 Biggest Accounting Challenges Business Owners Face (And How to Solve Them)

March 21st, 2025 | 5 min. read

By Kim Pope

Small business owner looking stressed with

Every day at Patrick Accounting, we talk with business owners who are at their wits’ end with their financial situation. They know something isn’t working, but without clear financial insight, they often struggle to pinpoint exactly what’s wrong or how to fix it.

After working with business owners for over 20 years, we’ve identified four core accounting pain points that hold businesses back and keep them from reaching their full potential.

If you’re feeling frustrated with your current financial setup, chances are you’re experiencing one of these four common challenges, too. So, let’s break them down and explain how to address each one so you can find a path forward that gives you the financial clarity and support your business deserves.

4 biggest accounting challenges

Challenge #1: “My Accountant Never Calls Me Back”

This might be the most common complaint we hear. You have questions about your finances, but your calls and emails go unanswered for days or even weeks. When you finally do connect, the conversation feels rushed as if you’re just another task on their to-do list.

Why Small Business Owners Struggle with Unresponsive Accountants

Sometimes, it’s a capacity issue. Your accountant is buried under work, especially during tax season. It may be that you originally chose them just because you needed someone to do your taxes. Other times, it’s a business model problem. They’re set up to handle transactions, not relationships.

The Reality Check

If you’re only paying for tax preparation once a year, your accountant may not be staffed to provide ongoing support throughout the year. They’ve been hired to complete a specific task—your tax return—not to serve as an ongoing advisor.

How to Solve It

Start by having an honest conversation with your current accounting firm about your expectations. What are you really looking for in an accountant relationship?

  • Do you want proactive advice throughout the year?
  • Do you need someone who can explain your numbers in plain English?
  • Are you looking for strategic planning rather than just tax preparation?

If you answered yes to any of these questions, it’s probably time for a new accounting partner. One that wants to build a relationship with you that is going to help you make decisions so your business will thrive.

Challenge #2: “I Got a Surprise Tax Bill (Again)”

Few things strike fear into a business owner’s heart like an unexpected tax bill. Whether it’s an unexpected tax bill or quarterly estimated payments, tax surprises can wreak havoc on your cash flow and peace of mind.

Why Small Business Owners Get Surprise Tax Bills

Tax surprises are almost always the result of poor visibility and planning. When you only connect with your tax preparer once a year, you’re essentially operating in the dark for the other 364 days.

Think of it like driving with your eyes closed and only opening them once you’ve reached your destination. You might get there, but the journey will be terrifying, and you’ll likely crash along the way.

The Reality Check

Annual tax preparation without year-round planning is a recipe for surprises. If your accountant is only seeing your numbers once a year, they can’t help you make adjustments throughout the year to optimize your tax position.

How to Solve It

The solution for avoiding tax surprises is proactive tax planning. You want to work with a provider who:

  • Reviews your financials regularly (monthly or quarterly).
  • Sets up tax projections early in the year and updates them as your situation changes.
  • Implements systems that give you real visibility into your tax obligations.
  • Creates a tax-saving strategy that lets you set aside the right amount throughout the year.

With proper planning, you should have a good idea of what you’ll owe well before the tax deadline. No more last-minute scrambles to cover unexpected bills. Just clarity and peace of mind.

Challenge #3: “I’m Drowning in My Own Bookkeeping (And I Need Help)”

Many business owners start out handling their own books. Maybe you have a spouse or administrative assistant managing the day-to-day financial tasks. But as your business grows, this DIY approach becomes increasingly unsustainable.

Why DIY Bookkeeping Becomes Overwhelming

This often emerges from one of several trigger events:

  • Your business has grown beyond what you can manage yourself.
  • The person handling your books has quit or threatened to quit (or maybe you know you need to let them go).
  • You’ve had a wake-up call (like a tax or cash flow issue) that showed you the importance of proper financial management

The Reality Check

Bookkeeping is more than recording transactions. It’s about creating a financial foundation that supports good business decisions. If you’re only doing the minimum to keep the IRS off your back, you’re missing out on valuable insights that could help your business thrive.

How to Solve It

Consider outsourcing your bookkeeping to the experts—accounting and tax advisors who do this work every day. They can help:

  • Implement systems that automate routine tasks and reduce manual entry.
  • Provide regular financial reports that show you exactly how your business is performing.
  • Interpret your numbers so you can make better decisions.

The right accounting and tax partner will give you back your time while providing better financial insights than you could’ve achieved alone.

Challenge #4: “My Business is Growing, and I Need Systems That Can Keep Up”

This is the most exciting challenge to have. Your business is thriving, and you’re ready to take things to the next level. Maybe you’re opening a second location, launching a new product line, or expanding into a new market.

But with growth comes complexity, and your current financial systems might not be equipped to handle it.

Why Growing Businesses Need Strong Accounting Systems

Growth creates new challenges that require more sophisticated financial management, such as:

  • Multiple locations or divisions that need separate tracking
  • More complex inventory management
  • Larger teams with payroll benefits to manage
  • Increased compliance requirements
  • Need for detailed, reporting and forecasting

The Reality Check

The financial systems and processes that worked when you were smaller, probably won’t scale with your growing business. Trying to force them to fit can lead to errors, inefficiencies, and missed opportunities.

How to Solve It

This is the perfect time to upgrade your financial infrastructure and find a trusted advisor with the expertise to guide you through the growth phases of your business. You’ll want an accounting partner who has the time, capacity, and wisdom to help you:

  • Implement more robust accounting systems that can handle your current and future needs.
  • Create standardized processes that can ensure consistency across your growing operation.
  • Develop more sophisticated reporting that gives you visibility into all aspects of your business.
  • Establish key performance indicators (KPIs) that help you chart progress toward your goals.

With the right accounting partner and systems in place, your finances can become a growth enabler rather than a growth limiter.

Finding the Right Solution for Your Business

If you recognize your business in any of these challenges, you’re not alone. These are common growth pains that nearly every successful business faces at some point.

The good news is that solutions exist for each of these challenges. The key is finding an accounting partner who understands your specific situation and offers services that meet your needs. And it ultimately comes down to trust.

At Patrick Accounting, we’ve spent over two decades helping small business owners overcome these exact challenges. We believe that financial clarity is about more than accurate numbers. It’s about using those numbers to make better decisions that drive profitability and growth.

Our approach combines bookkeeping, accounting, tax planning, and business advisory services into a comprehensive solution that addresses all four of the challenges we’ve discussed.

Accounting should go beyond compliance. It should help you build a better future for your business. If you’re tired of tax surprises, bookkeeping headaches, or accountants who never call back, let’s talk.

Check out Who Is a Good Fit for Patrick Accounting? or schedule a call to see how we can help you get one step better every day.