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Working for Yourself: Pros and Cons of Being Your Own Boss

Living Well

November 28, 2023

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Courtesy of Kathy Reagan
Courtesy of Kathy Reagan/Delmaine Donson/Getty Images

Courtesy of Kathy Reagan Courtesy of Kathy Reagan/Delmaine Donson/Getty Images

by Kathy Reagan Young

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Fact Checked by:

Jennifer Chesak, MSJ

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by Kathy Reagan Young

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Fact Checked by:

Jennifer Chesak, MSJ

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It takes self-discipline to work long hours with no paid time off. But there are many benefits to self-employment, too.

When I left my job, I needed to generate an income while taking care of myself. But I wasn’t sure that was even possible.

Then I found out people living with conditions could be paid to write about their experiences. I reached out to online health outlets and was hired as a freelance writer.

I started working from my bed, recliner, hospital infusion center — wherever. At some point, I realized I was making more money as a freelance writer than I was at my previous full-time job. Next, I registered myself as a business.

It’s flexible, remote work I can do when I’m best able. I’m so grateful for the patient advocacy industry, and I’ve enjoyed it for over a decade.

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Challenges of working for yourself

When you’re self-employed, also known as a contractor, freelancer, gig worker, or 1099 contractor, you’re responsible for everything. You have to find and secure the work. You have to invoice for the work.

You have to follow up and make sure you get paid (accounts receivable). You have to pay your business bills (accounts payable). You have to purchase your own equipment — think laptop, desk, filing cabinet, lamps, paper clips, staplers, software, and more.

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Registering yourself as a business

Depending on where you live and the type of business structure you’re creating, you may need to register your business according to the rules of your state and municipality.

You must estimate your federal and state income tax (if your state has an income tax) and pay those estimates quarterly.

You must also track your business expenses and fill out the Schedule C tax form so that you can write off relevant business expenses. I enlist an accountant to help, which is another cost.

Hiring yourself for everything

In addition to doing your own work, you are your own marketing, accounting, and office management departments. Oh, and don’t forget — you’ll have to supply (and pay for) your own health insurance (and it’s often not cheap). Though some people, depending on their circumstances, can get on a spouse/partner’s employer-sponsored health insurance.

You’ll also allocate money into your retirement account, which you’ll need to set up. I personally set up a SEP IRA (Simplified Employee Pension).

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Plus, it’s risky

Let’s say you lose your largest client and are unable to replace them, and your business goes belly-up. In most cases, with some exceptions, those who are self-employed cannot apply for unemployment benefits. So you need to save an emergency fund as well.

It takes a lot of self-discipline to work long hours with no paid time off. If you’re not working, you’re not earning. It can be incredibly isolating with an inconsistent workload and therefore inconsistent pay. You’ll likely have to hustle to keep new work coming while maintaining your ongoing workflow.

The benefits of working for yourself

So why would anybody do that? Well, there are a lot of benefits too.

  1. Flexible schedule: Self-employment allows for greater flexibility in managing your work hours. This can be beneficial for people with chronic illnesses who may need to adjust their workday to accommodate medical appointments, treatments, or periods of low energy.
  2. Control over work environment: You can create a space that’s comfortable and accommodating for your specific needs. I often work from my bed or my recliner.
  3. No commute: Working from home (or wherever you deem suitable) reduces the stress and physical demands of a daily commute, as well as costs for gas, repairs, and parking.
  4. Customizable workload: As a self-employed individual, you have the freedom to take on as much or as little work as your health allows. You can adjust your workload based on your condition.
  5. Income potential: Self-employment can provide opportunities for potentially higher income, especially if you’re able to leverage your skills and expertise effectively.
  6. Tax benefits: Depending on your business structure and expenses, there may be tax benefits available to self-employed individuals.

Flexible, remote work can come in several forms. Knowing which one is right for you can help you make good decisions upfront.

Other resources to check out

Books:

Organizations:

Being a “chronicpreneur” isn’t for everyone. If you think it’s something you’d like to explore, I hope this article can help guide you in your decision — and be sure to check out Patients Getting Paid for support.

Kathy Reagan, creator of the FUMS website and podcast, founded Patients Getting Paid in 2021. Her mission is to help people with chronic illness find and create work that accommodates their health and generates income. In this Patients Getting Paid column, she shares advice, resources, and stories to help others navigate the world of work while living with a chronic illness.

Fact checked on November 28, 2023


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About the author

Kathy Reagan Young

Kathy Reagan Young is a prominent patient advocate and the founder of two innovative organizations, FUMSnow.com and PatientsGettingPaid.com. She has become a leading voice in patient advocacy, driven by her personal experience with multiple sclerosis and having founded the Patients Getting Paid membership community to help people with chronic illness find and create work that both accommodates their health and generates an income. You can also find her on Facebook.

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