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Navigating Tax Challenges in the Multi-Hustle Era

Embracing the Multi-Hustle Phenomenon

Welcome to the new era where a single source of income is a thing of the past. Today’s multifaceted entrepreneurs, particularly those from Gen Z, are reaping the benefits of diversifying their income streams—from thriving on TikTok collaborations to selling handmade crafts on Etsy, and even taking up freelance gigs. This trend reflects a shift towards a more creative, financially rewarding lifestyle compared to the conventional 9-to-5 path.

But as tax season approaches, these diverse income streams can quickly complicate the financial landscape.

Each platform, whether it's Shopify, Venmo, Upwork, or TikTok, enforces distinct reporting requirements. Simultaneously, the IRS demands accurate documentation of every income and deductible expenditure. Overlooking a 1099-K form or missing a quarterly tax payment can swiftly turn a successful side hustle into a taxing ordeal.

Common Tax Pitfalls for Side Hustlers

These are the frequent stumbling blocks we encounter:

  • Skipping Estimated Tax Payments:
    As a self-employed individual, no one withholds taxes on your behalf. If you make more than $1,000 in untaxed income annually, you're expected to submit quarterly estimated tax payments. Missing these can result in significant penalties.

  • Combining Personal and Business Finances:
    While using your personal Venmo or debit card for business transactions seems convenient, it leads to a bookkeeping quandary. Should the IRS audit you, they expect a clear division of personal and business income and expenses.

  • Neglecting Entity Selection:
    As your earnings increase, staying a sole proprietor might not be the best choice. Opting for a more suitable business structure, such as an LLC or S corporation, can lower taxes and safeguard personal assets.

  • Forgetting Deductible Expenses:
    Entrepreneurs often overlook the tax-deductible nature of expenses like software, internet, phone bills, or part of their home office. Proper tracking of these expenses can significantly influence your tax obligations.

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Steps to Streamline Your Financial Management

Juggling multiple revenue sources doesn’t have to equate to financial chaos. Here’s how to maintain order and peace of mind:

  1. Establish a Dedicated Business Bank Account to clearly separate your personal and business incomes and costs.

  2. Invest in Accounting Software or Engage a Part-time Bookkeeper to manage your financial transactions efficiently.

  3. Allocate 25–30% of Your Income for Taxes to avoid unexpected tax bills.

  4. Seek Early Advice from a Tax Professional, especially if you're earning across various platforms. They can assist in planning, estimating quarterly taxes, and choosing the optimal business entity for your objectives.

The Final Word

Engaging in multiple side hustles presents numerous opportunities but also increases the likelihood of making tax mistakes. Equipped with the right strategies and professional advice, you can keep your finances orderly, comply with tax regulations, and truly benefit from your entrepreneurial ventures.

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Need assistance in organizing your side hustle income or planning your taxes? Reach out to ChesebroCPA today for expert, personalized guidance.

Schedule a Complimentary Meeting
Learn how we can help serve your business needs.
Schedule Here
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