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John Malone, JD, CTC
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July 12, 2024

Avoiding These 10 Tax Mistakes: A Guide for Small Business Owners

Whether a fledgling startup or an established enterprise, small business owners face a lot of challenges, not the least of which is the intricate realm of taxation. Missteps in this domain can prove costly, hampering growth and jeopardizing hard-earned profits. This comprehensive guide aims to illuminate the most common tax blunders, empowering entrepreneurs to sidestep these pitfalls and chart a course towards financial success.

Choosing the Improper Business Structure

The foundation of any small business is its legal structure, and selecting the wrong one can have far-reaching implications for taxation. Sole proprietorships, partnerships, limited liability companies (LLCs), and corporations each carry distinct tax obligations and liabilities. Failing to carefully evaluate the nuances of each option can lead to unnecessary financial burdens or inadequate legal protections.

To circumvent this pitfall, entrepreneurs must conduct thorough research or seek professional guidance to determine the optimal business structure. The simplest form that meets their needs is often the wisest choice, as complexity breeds opportunity for error.

Sole Proprietorships: Simplicity with Risks

Sole proprietorships offer the utmost simplicity, with business income and expenses reported directly on the owner's individual tax return. However, this structure provides no legal separation between the owner and the business, exposing personal assets to potential liabilities.

Partnerships: Shared Responsibility

Partnerships distribute profits and losses among the partners, who report their respective shares on individual tax returns. While offering greater financial resources than sole proprietorships, partnerships still lack the liability protection of more formal structures.

Limited Liability Companies (LLCs): Balanced Approach

LLCs combine the tax benefits of partnerships with the liability protection of corporations. Profits and losses pass through to the owners' individual tax returns, but personal assets are shielded from business debts and legal claims.


Neglecting Recordkeeping Until Tax Season

Bookkeeping may seem like a tedious task, but disorganized or incomplete records can hinder a small business's ability to claim legitimate tax deductions and credits. Waiting until the last minute to gather and organize financial documentation not only prolongs the process but also increases the risk of overlooking crucial details.

Diligent recordkeeping throughout the year not only streamlines tax preparation but also provides valuable insights for strategic planning and decision-making. Leveraging digital tools and applications can automate and simplify this process, ensuring accuracy and saving valuable time.

Commingling Personal and Business Finances

Maintaining separate bank accounts and credit cards for personal and business expenses is a critical practice for small business owners. Commingling these funds not only complicates recordkeeping and tax preparation but also jeopardizes personal liability protection.

Segregating finances not only facilitates accurate expense tracking and deduction claims but also helps establish business credit history and safeguard personal assets from potential legal claims.

Falling Behind on Tax Deposits and Estimated Payments

Cash flow challenges are a common hurdle for small businesses, particularly in the early stages. However, neglecting to set aside funds for self-employment tax, income tax, and payroll tax deposits can quickly spiral into a financial quagmire.

Establishing a dedicated account solely for tax obligations and promptly transferring the appropriate funds upon receiving income can help small business owners stay ahead of this curve. Consistently meeting these obligations not only avoids penalties and interest but also fosters a positive relationship with tax authorities.

Misclassifying Employees as Independent Contractors

While engaging independent contractors or freelancers can provide flexibility and cost savings, misclassifying employees as such can have severe consequences. Tax authorities closely scrutinize these arrangements, and violations can result in hefty back taxes, penalties, and legal repercussions.

Small business owners must carefully adhere to the established guidelines for employee classification, considering factors such as the degree of control exercised over the worker and the nature of the working relationship. Seeking professional guidance can help navigate this complex area and mitigate risks.

Paying Workers "Under the Table"

The temptation to pay employees or contractors in cash "under the table" may seem appealing as a means to circumvent payroll taxes and paperwork. However, this practice not only encourages tax evasion but also deprives the business of valuable deductions and contributes to a negative ripple effect throughout the economy.

Maintaining transparency and adhering to legal requirements for employee compensation not only protects the business from potential penalties but also fosters a culture of integrity and ethical conduct.

Overlooking Deductions and Tax Incentives

Small businesses often leave money on the table by failing to claim all eligible deductions and tax incentives. From overlooked vehicle mileage logs to missed opportunities for energy credits or job-related education expenses, these oversights can significantly impact a business's tax liability.

Thorough recordkeeping and meticulous attention to detail during tax preparation can help uncover these potential savings. Additionally, leveraging tax preparation software or seeking professional guidance can ensure that no stone is left unturned in the pursuit of legitimate deductions and credits.

Itemizing Deductions Incorrectly

Certain expenses, such as property taxes on business property, should be claimed as business deductions rather than itemized deductions on individual tax returns. Mishandling these deductions not only results in missed tax benefits but also potentially impacts eligibility for other tax advantages tied to adjusted gross income (AGI) thresholds.

Small business owners must carefully categorize and report expenses according to their nature and purpose, ensuring that deductions are claimed in the most advantageous manner possible.

Neglecting Tax Planning and Strategy

Tax compliance is undoubtedly crucial, but proactive tax planning and strategy can yield significant long-term benefits for small businesses. Failing to explore available tax credits, incentives, or restructuring opportunities can result in missed opportunities for legitimate tax savings.

Collaborating with a skilled tax strategist or certified public accountant (CPA) can provide valuable insights and guidance tailored to the specific needs and goals of a small business. These professionals can identify areas for optimization, recommend tax-efficient strategies, and ensure compliance with ever-evolving regulations.

Procrastinating on Tax Obligations

Procrastination is a common pitfall for small business owners juggling myriad responsibilities. However, delaying tax filings, payments, or deposits can quickly escalate into costly penalties, interest charges, and potential legal consequences.

Establishing a disciplined approach to tax obligations, setting reminders, and seeking professional assistance when needed can help small businesses stay ahead of deadlines and maintain a positive standing with tax authorities.


Putting it together 

By navigating these common tax pitfalls with diligence and foresight, small business owners can pave the way for long-term success. Embracing sound tax practices not only mitigates financial risks but also fosters a culture of compliance and strategic decision-making, positioning the business for sustained growth and profitability.

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