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Independent Contracting (for TypeWell Transcribers)

Are you an employee, freelancer, or independent contractor?

In both the U.S. and Canada, there are only two legal/tax classifications: employee and independent contractor (sometimes called self-employed in Canada). However, transcribers may experience these roles in different ways.

Employee

If you’re an employee, you are hired directly by a company, school, or agency as part of their staff. In this arrangement, your employer:

  • Determines your work schedule and location.Smiling woman with blonde hair and a black blazer, typing on a laptop
  • Provides your equipment and covers the cost of your TypeWell Transcriber license.
  • May offer benefits such as health insurance, retirement plans, or paid time off.
  • Pays employment taxes (U.S.) or contributions to CPP/EI (Canada) on your behalf:
    • U.S.-based employees complete a W-4 when hired and receive a W-2 each year.
    • Canadian employees receive a T4 slip each year.
Independent Contractor

You may contract directly with clients or through an agency that locates clients and offers jobs to you. In either case, you are not an employee of that agency or client. As an independent contractor:

  • You provide your own equipment and purchase your own TypeWell license.
  • You decide whether to accept or decline each assignment.
  • You handle your own business and self-employment taxes, and you do not receive employee benefits.
    • U.S.-based contractors complete a W-9 and receive a 1099-NEC each year.
    • Canadian contractors typically receive a T4A slip (or simply invoice clients directly and report business income/expenses on their tax return).

Independent contractors may work in two main ways:

  • Through agencies (sometimes referred to as “freelancing”): An agency finds and manages clients, and you choose whether to accept the jobs they offer. This can give you flexibility without having to market your own services.
  • Directly with clients:
    • You operate as your own business. Some transcribers work as sole proprietors, while others choose to establish a more formal entity such as an LLC (U.S.) or corporation (Canada). Forming a legal entity can provide liability protection and, in some cases, tax advantages.
    • Regardless of the structure, you’re responsible for much more than transcription: marketing, client outreach, scheduling, invoicing, bookkeeping, and maintaining relationships. This path may give you more independence and the potential for higher rates, but it also comes with more responsibility — including the risk of late or missed payments.

Whether you contract through agencies or directly with clients, you’re still considered an independent contractor. The next question is whether it’s worth setting up your own business and working directly with customers.

Is it worth it to contract directly with clients?

There are benefits to being a TypeWell transcriber who contracts directly with customers. You may enjoy more freedom and flexibility, and you may be able to charge higher rates for your work. But there are drawbacks as well.

This guide will help you decide if it’s right for you, and walk you through the essential steps to set up and succeed as an independent TypeWell service provider.


1. Decide if It’s Right for You

Are you…

  • Comfortable with managing your own schedule and work load?
  • Ready to market your services and handle client relations?
  • Willing to file and pay taxes, review contracts, and handle invoicing?

2. Set Up Your Business

How will you track your spending and income, manage risk, and pay taxes?


3. Get Your Equipment & Software

You will need to own or license:


4. Find Clients

  • Prepare a résumé, brochures, business cards, and a website.
  • Provide real-time demos upon request.
    • This is a common request from educational institutions when the service coordinator and/or reader are not yet familiar with TypeWell services.
    • Local colleges, schools, churches, senior living centers, and community programs are also promising places to find clients!
  • Include sample pricing on your website and provide formal, written quotes.

Helpful Resources for Further Reading


Tip: Protect your ergonomic health and set policies that ensure quality service. No job is worth long-term injury or poor service quality.

Sep 17, 2025

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