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Working For Myself vs. Working For Someone Else

March 10, 2022 by Tamila McDonald

During my broader career, I’ve spent time in traditional roles, working for someone else, as well as working for myself. While each option has its own benefits and drawbacks, I know that self-employment is the absolute best fit for me. It was challenging at first, but what it offers in return is far more than I got from a traditional employer-employee arrangement. If you’re wondering why I believe that working for myself is best – as well as what I find most difficult about using the self-employed approach – here’s a look at my perspective.

Why I Love Working for Myself

First, it’s important to understand that I’m a writer. As a result, I’m able to handle all of my responsibilities online. I’m not meeting with clients in person or turning in work on paper. Instead, everything is digital, and that’s why it works so well for me.

As a writer, I’m able to work from anywhere and largely on my own terms. If I have a computer and an internet connection, I can tackle nearly any kind of project that comes my way. Since that’s the case, I’m not tied to a single office. Instead, I can travel the world as long as I find locations with reasonable wi-fi.

Additionally, I primarily get to work on my own terms. While I deal with deadlines, exactly when I handle assignments is entirely up to me. If I need to work incredibly early in the morning, I can. If I have something I need to do during the day, I can handle projects at night. Picking and choosing the days of the week I work is also possible. As long as everything is turned in on time, the rest is essentially in my hands.

The Hardest Part of Working for Myself

Working for myself does come with some challenges. While many would assume that finding projects is the hardest part – and it can be challenging when you first start out – I currently have a solid, reliable client base that mainly makes that a non-issue.

Instead, what I find difficult about self-employment is managing the financial recordkeeping side of the equation. Tracking income and expenses, ensuring I send in enough for quarterly tax payments, and similar steps are what’s the most difficult for me.

That’s especially true since – while I have a great client base – my income isn’t exactly the same year after year. Plus, my expenses fluctuate. As a result, what I need to pay in taxes varies. While there are calculators and programs that help do the math, I’m usually handling the math based on estimates, which can make it harder to get reliable figures.

Still, since that’s the main challenge I face and it is something I find ways to overcome, I feel that working for myself is the best option for me. While it would be nice to have someone else handle the complexities of the accounting and taxes, it’s something I’m willing to do because of the flexibility self-employment provides me.

Have you worked for yourself and someone else and want to tell others about your experience? Do you have any tips that can help someone make the most of their career, no matter which approach they use? Share your thoughts in the comments below.

Read More:

  • 23 Advantages of Self-Employment
  • Starting a Business While Being Employed – Pros and Cons
  • 23 Disadvantages of Self-Employment

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Tamila McDonald
Tamila McDonald

Tamila McDonald is a U.S. Army veteran with 20 years of service, including five years as a military financial advisor. After retiring from the Army, she spent eight years as an AFCPE-certified personal financial advisor for wounded warriors and their families. Now she writes about personal finance and benefits programs for numerous financial websites.

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