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Starting a 1099 Contractor Job at the End of the Year: Pros and Cons


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The transition from traditional W-2 employment to self-employment as a 1099 contractor can be a significant financial and lifestyle decision. It's essential to consider the timing of this transition, as it can have various implications for your taxes and financial planning. In this blog post, we'll explore the advantages and disadvantages of starting a 1099 contractor job at the end of the year and provide guidance on making the best decision for your unique situation. Please note that while we provide general insights, it's crucial to consult with a tax advisor to ensure you make the right choice for your specific circumstances.

The Pros and Cons of Self-Employment Taxes

Before delving into the timing aspect, let's briefly recap the pros and cons of self-employment taxes:


  1. Independence: As a 1099 contractor, you have more control over your work, clients, and projects.
  2. Tax Deductions: Self-employed individuals can claim deductions for business-related expenses, potentially reducing their taxable income.
  3. Flexibility: You can set your own schedule and work from various locations, which can lead to a better work-life balance.


  1. Self-Employment Tax: Self-employed individuals are responsible for both the employer and employee portions of Social Security and Medicare taxes, which can be a significant financial burden.
  2. Irregular Income: Self-employment income can be irregular, making it challenging to budget and plan for expenses.
  3. No Employer Benefits: You won't have access to employee benefits like health insurance, retirement plans, or paid time off.

Now, let's address the question of timing and whether starting a 1099 job at the end of the year carries a significant disadvantage.

The Timing Dilemma

Starting a 1099 job at the end of the year, as opposed to any other time during the year, does have some unique implications. Here are some key factors to consider:

1. Income and Tax Liability:

  • Starting a 1099 job at the end of the year means you'll only have a few months of self-employment income in that tax year. This may result in lower total income for the year, which can have a positive impact on your overall tax liability.
  • Your tax liability as a self-employed individual depends on your total annual income. If your self-employment income for the year is relatively low due to a late start, your self-employment tax liability will be lower than if you had been self-employed for the entire year.

2. Quarterly Estimated Taxes:

  • When you earn self-employment income, you are generally required to make quarterly estimated tax payments to the IRS to cover your income and self-employment taxes. These payments are due in April, June, September, and January.
  • Starting your 1099 job at the end of the year may mean that you won't have to make estimated tax payments for the first three quarters, as you had no self-employment income during that time. However, you will need to make a larger payment in January to cover your income and self-employment taxes for the fourth quarter.

3. Deductions and Record-Keeping:

  • If you start self-employment at the end of the year, you'll need to quickly learn how to keep accurate records of your income and expenses. Proper record-keeping is essential for claiming deductions and accurately reporting your income at tax time.

4. Business Expenses:

  • You can only deduct expenses that are directly related to your self-employment. If you incur legitimate business expenses after starting your 1099 job, you can include them on your tax return. Keep in mind that the expenses must be incurred in the same tax year.

5. Penalties for Late Filing:

  • If you fail to report your self-employment income or pay your taxes on time, you may incur penalties and interest. It's crucial to familiarize yourself with the tax deadlines and requirements for self-employed individuals.

Making the Right Decision

The decision of whether to start a 1099 job at the end of the year or wait until January should be based on careful consideration of your unique circumstances. Here are some tips to help you make an informed choice:

1. Consult with a Tax Advisor:

  • It cannot be emphasized enough how important it is to consult with a tax advisor or professional. They can provide personalized guidance based on your financial situation, including your total income, potential deductions, and any applicable tax credits.

2. Estimate Your Income:

  • Try to estimate your total self-employment income for the year, including the months you plan to work as a 1099 contractor. This estimate will help you assess your potential tax liability.

3. Record-Keeping:

  • If you decide to start your 1099 job at the end of the year, be diligent about tracking your income and expenses. Consider using accounting software or hiring a bookkeeper to maintain accurate records.

4. Tax Planning:

  • Work with your tax advisor to create a tax plan that minimizes your liability and maximizes your deductions. This may involve strategic timing of expenses and income recognition.

5. Budgeting:

  • Be prepared for fluctuations in your income, especially if your 1099 work is seasonal or project-based. Develop a budget that accounts for irregular income and sets aside money for taxes.

In conclusion, while starting a 1099 contractor job at the end of the year presents certain challenges and advantages, it's not necessarily a huge disadvantage. Your decision should be informed by your specific financial circumstances and tax planning needs. Remember, the key to a successful transition into self-employment lies in seeking expert advice from a tax advisor who can help you navigate the complexities of self-employment taxes and make the best choices for your financial well-being.