Becoming An Independent Contractor

How to Find Freedom as an Independent Contractor

You might think the real question isn’t about freedom.

If you think money’s the answer, perhaps that question should be:

How do I make money as an independent contractor?

Or, perhaps, it’s about controlling time so you can do more of the things you love.

But, make no mistake. If these thoughts cross your mind, what you’re really thinking about?


And—the fact is—as an independent contractor, you can have more freedom than a full-time, W2 employee.

Think about it…Your time is yours, not the company’s.

YOU set your own hours.

YOU set your own rate

And YOU pick the jobs you want to do.

Of course, it’s not all unicorns and kittens. You have to find new clients and retain them. And, you’ll want to continually amaze them:

  • Demonstrating you’re a responsible business owner they can count on;
  • Effectively communicating how your skills will help them; and…
  • Showing—beyond the shadow of a doubt—why you’re deserving of your desired rate.

Sheesh. That sounds like it’s tough. Where do I even start?

Yeah…it can be tough. But it doesn’t have to be.

To help you get started, here’s an idea.

One way to get independent contractor experience? Become a transcriptionist!

Why? In a word, DEMAND.

Transcriptionists are in demand right now as more legal, law enforcement, and healthcare services need a reliable source to accurately document their files.

Plus, there are two ways to quickly gain experience.

  1. Look to websites like Upwork, Freeeup, and FlexJobs.

As Mark Twain once said, “The secret of getting ahead is getting started.” A great way to get started and build your portfolio—a necessary component to successfully land a position—is looking for independent contractor transcriptionist gigs on websites like Upwork, Freelancer, or FlexJobs.

Of course, like any job, when you’re just starting out, you may not earn a lot money, but the more experience you get, the faster you’ll see your earnings climb.

2. Get certified as a medical, or legal transcriptionist.

Medical transcriptionists must have an extensive knowledge of medical terminology, anatomy and physiology, medical procedures, pharmacology and other medical terms. Master the art of medical transcription to become an expert in this specialized field. Learn how to become a successful medical transcriptionist.

And, bonus! says, “Transcriptionists who graduate from a training program and those with experience in electronic health records (EHR) management, training and quality assessment are likely to find a job more easily.” Interested in learning more about the best type of transcription jobs? Click here.

The Important Skills to Have as a Transcriptionist

So, let’s say you’re ready.

You’ve built up your portfolio a bit, or perhaps you just got certified!

Now, it’s time to find a transcription company looking to hire an independent contractor.

The quickest way? A Google search! Search “transcription companies” and go directly to company websites.

Once you find the company that interests you most, you’ll likely be prompted to fill out a form.

If you want a job, be aggressive! Explain why you are the perfect candidate for the job. (If you do this, you’ll be ahead of the pack!)

To increase your odds and land a job faster, apply to a bunch of companies—at least five to ten each day—until you find the right client(s) for you.

How to Find Transcription Companies that Hire Independent Contractors

Get noticed with a well-crafted resume

Resumes are tricky.

Do it right? You’ve passed the first step.

Do it wrong? You miss out on the job.

In Selling Yourself Into A Job, Bill Swansen outlines the steps of getting a job.

The first one? Wow a potential client with a resume that “brags” about your past experiences.

Swansen writes, “What you should aim for is to have a well-structured, succinct and organized resume. It should clearly present your talents, skills, experience, and personality to a prospective employer.”

  • Pay careful attention to how you phrase sentences in your resume and cover letter.
  • Be unique with how you describe yourself as a legal transcriptionist and avoid clichés and common phrases.
  • Remember, you want to stand out!

Resume Clichés that Recruiters Hate

Give yourself credit and brag… the Right Way

When you think of a resume, what do you think of? Job experience.


But, what most people don’t consider is potential clients want to learn about not just your transcriptionist experience, but also the kind of person you are.


Consider adding things that can separate you from the pack. Include information about volunteer work and memberships in industry-related organizations, which helps show how well-rounded you are. Doing so makes you a more desirable candidate.


The key? Don’t overdo it. Don’t preach. And, never (ever) lie.

References Are a Must

Let’s face it. References can be a challenge…especially if most of your experience has been working on anonymous one-time gigs.

That said, if you want a gig, you need ‘em.

Businesses will usually ask for references or examples of work you’ve completed for other companies. Some independent contractors struggle with this.

What if I don’t have any references to give?

Ask previous clients for permission to show the work you performed for them. You can also ask if they’d be willing to be a reference. Make sure to get permission! You never want a reference to be blind-sided by a call or email they don’t expect.

Get Recommendations on LinkedIn

A fantastic way to stand out is to get recommendations on LinkedIn.

This has a different effect from reviews on a freelance website. Instead of a “screen name” vouching for you, potential employers see recommendations from real people on LinkedIn.

Remember, always be respectful of your references and show them your gratitude.

Jeff Shane, president of Allison & Taylor, recommends sending a thank you note: “Each time your reference supports you with a new, prospective employer, send them a personal thank-you note—or, at a minimum, an email.”

With only a little bit of effort, you can get the references needed to impress a potential client and stand out from the pack.

Always Respond to Client Inquiries Quickly

Perhaps the best way to stand out for good things? Respond FAST!!

As an independent contractor, you have competition! You want to stand out for good things, so be aggressive when bidding or applying for a job.

how to make money as an independent contractor

Fast response time shows a potential client you’re eager to work for them.

Just know it’s a fine line. Never worry if you don’t hear back right away!. And definitely avoid emailing or calling too frequently asking if you landed the project.

Comply with the client’s preferred communication channel, especially if asked to do so. For example, “no phone calls” means no phone calls!

Defying a client’s wishes makes you stand out…for the WRONG reasons. Trust me!! This happens almost once a week in our office.

It’s time-consuming and exhausting when an applicant wants to argue about how they didn’t get the gig. That ensures we’ll never hire that candidate again!

The Interview – how to get hired as an independent contractor

One of the most nerve-racking parts of landing any gig can be the interview.

Typically, a video or phone call to get to know you is a standard approach. But, don’t sweat it!

One of the best parts of being an independent contractor? You can do the interview remotely! That can be from your office space, your home, or really anywhere quiet.

No Matter What…Treat it Like an In-Person Interview

You might be asked to do a phone interview. It’s also not unusual to be asked to do a video conference.

In either scenario, dress up!

Dress like you are going to an in-house interview…even if only for a phone call. You might surprise yourself…wearing business attire sets up your mindset for a win. In fact, you can psychologically trick yourself into doing a better interview!

Remember…the potential client has the information they need from you from your resume, project portfolio, and references. The interview has more to do with getting to know you. It’s making sure you and your potential client can work well together.

The most important thing when it comes to your clients? A good relationship.

Always be respectful, even if you don’t agree with them, and never preach about your experience. Learn to share your expertise in a way that puts your clients at ease. You never want your clients to feel like you’re forcing them to do something “because I know what I’m doing!”

Competitive Pricing

Let’s face it. Pricing is hard.

And, especially starting out as an independent contractor, a HUGE mistake is believing being the cheapest gets you more work.

Freelance websites almost encourage you to have the lowest price to get the job. Just be warned…this tactic can come back to bite you!

Forbes shares three factors will affect how much you can or should charge:

  • Your budget
  • How good you are at what you do
  • How much time you have

Remember…Clients Know They Get What They Pay for

Instead of just charging the lowest price, do some research! Know what you’re worth.

When you ask for the right amount, it shows you have confidence in your skills. For example, we rarely hire the cheapest independent contractor when we need help with a project. You get what you pay for!

Stay True to Your Skills

Finally, always stay true to your skills as an independent contractor transcriptionist.

While it may seem counter-intuitive, calling yourself as a “jack of all trades” to get any gig is a mistake. Focus on a niche.

This serves two purposes:

  • It helps you hone your skills as an expert in that niche.
  • It makes you more desirable for any company looking for specifically what you do.

Your Path to Freedom – How to make money as an independent contractor

So, there you have it…your path to freedom and how to make money as an independent contractor!

If you take nothing else form this article, remember these three things you always want to do:

  • Demonstrate you’re a responsible business owner your clients can count on.
  • Effectively communicate exactly how your skills help your clients.
  • Show—beyond the shadow of a doubt—why you’re deserving of your desired rate.

Interested in independent contractor transcription work? Awesome! We’re always on the lookout for new transcriptionists!!

Check out Fill out an application…and of course…Follow the steps in this article!

Then go to 11 Tips for Independent Contractors to Hold on to Valuable Clients once you do start to get new work.

Freedom can be in your grasp.

How to find freedom as an independent contractor

Looking For A Transcription Service?

Ditto Transcripts is a U.S.-based HIPAA and CJIS compliant company with experienced U.S. transcriptionists. Learn how we can help with your next project!