How To Make Your First $100 As a Freelance Creator

Why It's the Easiest and Hardest Thing You Will Ever Do

I seldom talk to freelance creators who made a few bucks doing what they loved, only to give up, discouraged, and quit their passion.

Instead, I most often find two types of creators: A) those who haven’t started working for others, and B) those who have pressed through the pain and now earn a decent income from their efforts. There is a reason for this. Getting your first client can be a massive mental hurdle to overcome, but when you do, everything changes. As Steve Jobs said,

Most people never pick up the phone, most people never ask. And that’s what separates, sometimes, the people that do things from the people that just dream about them. You gotta act. And you gotta be willing to fail.

This means that to earn your first $100 as a freelance creator, you’ve got to be willing to press through some critical mental barriers. While everyone is different, here were three that held me back.

1. I didn’t feel competent. Sure, I’d written a few books myself, but who was I to help others? I didn’t have a degree in English Literature or some amazing resume to share.

2. I wasn’t sure ghostwriting was for me. I’d once heard someone say that “ghostwriting is lying,” and that it’s essentially becoming a writing prostitute to do someone else’s homework. That didn’t sound like a good time to me.

3. I wasn’t sure this was a serious business. When I started, I was on my way to a PhD in Intercultural Studies. Didn’t this mean I should be doing something serious with my life, like teaching or working a traditional 9-5?

Recognizing these barriers, I realized I needed help with my mindset.

Competence and Confidence

I realized that to grow a business, I needed a boost in two traits: competence and confidence.

To address the competence angle, I signed up for a writing course by NYT bestselling author Jerry Jenkins. I also took courses like Writing With Flair by Shani Raja. These gave me added tips and showed me I was better than I thought.

To boost my confidence, I read entrepreneurial-style books like Think and Grow Rich, Rich Dad Poor Dad, and lots of biographies. Resources like these showed me I wasn’t crazy and that my original goals were actually quite small.

I continue these practices to this day. In an age of AI, I’m always trying to increase my edge as a writer so that I can offer a premium service that’s better than Chat GPT5. One book I picked up recently is Jane Friedman’s The Business of Being a Writer. It’s excellent, and in it she writes,

Many people want to stand on top of the mountain, but it’s the countless hours you spend on the mountainside that get you there. The secret to success, if any, is that you enjoy those hours of work—that the work breathes life into you, day after day.¹

Another book I’ve enjoyed recently is Noah Kagan’s Million Dollar Weekend. In it, Kagan notes, “Business is just a never-ending cycle of starting and trying new things, asking whether people will pay for those things, and then trying it again based on what you’ve learned. If you’re afraid to start or ask, you can’t experiment. And if you can’t experiment, you can’t do business.”²

Focus on Doing

If you're struggling to earn your first $100 as a freelance creator, it is a sign that you need to grow your competence and confidence. So take a writing course—this week—to increase your competence and stop making excuses. Read a book or watch a video on entrepreneurship that gives you confidence.

Some people (I think most) are the “ready, steady, aim” types and never get around to firing. They spend way too much time overthinking the process and not nearly enough time on getting their reps in. As someone who works out 4-5 times a week, I’ve realized that talk only gets me so far. I can buy a cool weight bench, download the coolest fitness app, and read fifteen books on how to get in shape in thirty days.

But if I don’t put the work in, all that knowledge is useless. If I don’t increase my protein intake, take creatine supplements, follow a workout plan, and eat nutritious food, I’m sunk.

The same is true in your business. At some point, you’ve got to stop talking and start doing. And here is what you’ll discover. When you do, this will bring new life to what you read and watch.

Only after you’ve gone through the messy process of pitching yourself to a client, only to be rejected, do some books make sense.

Where To Start?

If you’re looking for a place to start, be like my friend Elliot Huff. Several weeks ago, he moved out to Boise, Idaho (about twenty minutes from where I live) and went full-time into freelance video editing.

When he asked me where to start? I suggested he go on Upwork and pitch his services to fifty clients. To his credit, that’s exactly what he did, and a few days ago, he texted me that he already has five. The key was that he stopped talking about it and started doing the work.

You can do the same.

If you’re stuck and don’t know what to do, here are five basic steps you can take today:

Step 1: Write Your Why. Why are you doing what you do? What motivates you? Is it financial freedom? Is it a side income to help you travel? The stronger your why, the less likely you are to give up when times are hard.

Step 2: Write a strong cover letter and resume. Don’t go overboard, and if you don’t have all the credentials, that’s fine. Look for your unique angle that sets you apart from other creators. Maybe you have a degree of work experience that others don’t.

Step 3: Create an account on Upwork and pitch your services to fifty clients. Yes, I said fifty. Not ten, not two or three. Fifty. Make it a game. Carve out some time to go to a nice coffee shop and send out one proposal after the next. Pay attention to what people want, and if it gets you over the mental hump, offer your first service for free.

Step 4: Streamline and build. After you’ve pitched yourself to fifty clients and started to have some interactions, you will quickly discover what you need to adjust. Maybe your prices are too low, maybe there are some jobs you can’t take on, or maybe there are some types of personalities that don’t work for you.

Step 5: Sharpen your axe. Take writing courses, read books, and watch videos. Always strive to keep getting better at your craft.

If you are serious about building your business, you should be able to take these first four steps in one week. (Seriously, don’t extend it beyond this. Get focused and build some serious momentum.)

Building a freelance creation business isn’t rocket surgery. It’s just a whole lot of waking up each day and doing the next right thing. So get started on the right foot today. Stop talking, start doing!

As always, if you have a question, leave me a comment or set up a coaching call, and I’d love to help if I can.

1. Jane Friedman, The Business of Being a Writer, 2nd ed. (Chicago: University of Chicago Press, 2022), 7, Kindle.

2. Noah Kagan, Million Dollar Weekend: The Surprisingly Simple Way to Launch a 7-Figure Business in 48 Hours (New York: Harper Business, 2024), xvii, Kindle.