In an attempt to get ahead in life financially I worked two full-time remote jobs at the same time.

I thought overemployment would get me closer to achieving my dream of financial freedom.

But after a year of being overemployed, I realized all that work was for nothing when I got an urgent bill in the mail from the IRS.

What is Overemployment?

Overemployment is the practice of someone that is working multiple full-time jobs at the same time.

This is different from traditional employment, where you would typically hold one full-time job and maybe supplement your income with part-time or freelance work.

Overemployment involves juggling the demands of two or more full-time positions, often in different industries or sectors.

How Did Overemployment Become Popular?

Several factors have contributed to the rise of overemployment in recent years:

Remote Work Opportunities:

The widespread adoption of remote work, sparked by the COVID-19 pandemic, has opened a door of new opportunities for people to work from anywhere in the world.

Remote work eliminates the typical office demand and allows employees to take on multiple jobs without being tied to a physical location.

Advancements in Technology:

New and improved technology has made it easier for people to work remotely and manage multiple jobs simultaneously.

Collaboration tools, project management software, and communication platforms enable seamless coordination and productivity across multiple roles.

My Journey Working Two Full-Time Remote Jobs

For me, it all began with the thought of financial freedom.

I was eager to escape the rate race, so I began looking for multiple remote jobs on sites like FlexJobs and LinkedIn.

Possibly doubling or tripling my income would speed up the process on my journey to financial peace, or so I thought.

The first job I got was a position as a technical recruiter for a renowned FAANG company, which I was hired as what’s known as a W-2 employee.

The second job I found was a freelance recruiting gig for a cyber security company, but this presented a different set of challenges.

Hired as a something called a 1099 contractor, left me to navigate the complications of self-employment taxes on my own.

The Difference Between W-2 and 1099 Taxes

Before diving into my personal journey, let’s clarify the difference between W-2 and 1099 taxes.

W-2 forms are standard for most employees, providing a straightforward overview of earnings and taxes withheld by employers.

On the other hand, 1099 forms are specific to independent contractors and freelancers, where taxes are not automatically withheld.

This places the responsibility of reporting earnings to the IRS on the individual.

Tax Consequences of Overemployment

As tax season began, I found myself presented with a harsh reality check.

The W-2 form from my first job revealed substantial tax withholdings, a bitter pill to swallow but a familiar one nonetheless.

The total that the IRS withheld from me from job #1 was $28,303.

However, it was the 1099 form from my second job that made me weak to my knees.

After speaking with multiple accountants, I discovered I was left with a massive tax bill of $56,854 from job #2.

When it was all said and done, I owed the IRS $85,157 for working two full-time remote jobs.

Lessons Learned Working Two Full-Time Remote Jobs

Looking back on my experience, there are several valuable lessons I’ve learned:

Understanding Tax Implications:

It’s crucial to understand the tax implications of working multiple jobs, especially when one of them is a 1099 position.

Seeking professional advice early on can save a lot of headaches down the road.

Budgeting and Financial Planning:

Proper budgeting and financial planning are essential when managing multiple streams of income.

Setting aside money for taxes and unexpected expenses is crucial to avoid financial stress.

Work-Life Balance:

Maintaining a healthy work-life balance is essential for overall well-being.

While the idea of multiple jobs may be tempting, it’s essential to prioritize self-care and avoid burnout.

The Upside of Overemployment

Despite the challenges, I was able to make some strides towards my goal of financial freedom.

Because of the major increase in my income, I purchased a home, invested in rental property, and started a small business that produces passive income.

By taking a leap of faith and hard work, I was able to turn the challenges of overemployment into opportunities for long-term financial success.

Conclusion

In conclusion, working two full-time remote jobs is not for the faint of heart.

Navigating the complexities of overemployment requires careful planning, resilience, and a willingness to confront unexpected challenges head-on.

While the idea of financial independence is worthwhile, it’s essential to fully understand the implications of taking on multiple roles.

With proper planning and budgeting, it’s possible to navigate the complications of overemployment and come out stronger on the other side.

For more tips and advice on remote jobs and taxes, feel free to visit our resource center!

FAQs: Working Two Full-Time Remote Jobs and Taxes

Q: What are the benefits of working two full-time remote jobs?

A: Working two full-time remote jobs can provide increased financial stability and flexibility.

It allows individuals to diversify their income streams and potentially earn a higher income compared to a single job.

Q: What are the potential pitfalls of working two full-time remote jobs?

A: One of the main pitfalls is the potential for burnout and exhaustion due to long hours and increased workload.

Additionally, managing taxes can be challenging, especially if one of the jobs is a 1099 contractor position where taxes are not automatically withheld.

Q: What is the difference between W-2 and 1099 taxes?

A: W-2 taxes are typically associated with traditional employment, where taxes are automatically withheld from each paycheck.

On the other hand, 1099 taxes are common for independent contractors or freelancers, where taxes are not withheld, and individuals are responsible for paying taxes on their own.

Q: How can I avoid tax issues when working two full-time remote jobs?

A: It’s essential to understand the tax implications of each job, especially if one of them is a 1099 position.

Seeking professional advice from a tax accountant or financial advisor can help navigate the complexities of managing taxes for multiple jobs.

Q: What are some tips for managing finances when working two full-time remote jobs?

A: Budgeting effectively is crucial for managing finances when working multiple jobs.

Setting aside money for taxes, savings, and emergency expenses can help alleviate financial stress.

It’s also essential to prioritize self-care and maintain a healthy work-life balance.

Q: What should I do if I find myself overwhelmed by working two full-time remote jobs?

A: If you’re feeling overwhelmed, it’s essential to take a step back and assess your priorities.

Consider whether it’s sustainable to continue working two full-time jobs or if adjustments need to be made.

Prioritizing self-care, setting boundaries, and seeking support from friends, family, or mental health professionals can help manage stress and prevent burnout.

Q: How can I learn more about managing finances and taxes when working multiple jobs?

A: There are numerous resources available online that provide valuable information on managing finances and taxes when working multiple jobs.