What Paid Courses Fail to Tell You About Freelance Writing

And my unconventional solution to these oversights.

I’m a freelance writer. It’s how I sustain myself financially and creatively.

But I wasn’t born a freelance writer. I didn’t aspire to leverage the written word to make a living. I didn’t journal as a teenager. My heroes weren’t authors and writing has never been a passion of mine.

I bumped into freelance writing serendipitously. But it was the “freelance” aspect that sold me.

I loved the idea of running my own business.

That said, the writing element was sort of new. It’s not like I couldn’t write — I’ve always considered myself to be a decent writer — but I hadn’t written in a professional capacity.

So, like many others, I relied on paid courses to learn how to improve a skill and leverage it to make money. The courses I took were instrumental to my development as not only a writer but also a freelancer. (Yes, those are two distinct roles.) They showed me how to set up a website, pick a niche, write samples, pitch potential clients, and run a business.

However, something was missing. There was a disconnect I couldn’t quite put my finger on.

Fortunately, it didn’t take too long to figure it out.

But, before we dive into those missing pieces, I want to highlight why paid freelance writing courses are still beneficial.

Paid Courses: the Good

Generally speaking, the framework behind educational content is pretty cookie cutter. A person learns a skill, “masters” it, and then re-engineers their process to help others. From a freelancing perspective, here’s what that looks like:

1. Learn about freelancing.

2. Build a sustainable business.

3. Make enough money to be able to compile a viable product.

4. Launch a course to help others follow the blueprint.

You can find dozens of freelance writing courses that mirror this four-step process. And, for the record, there’s nothing wrong with that. Hell, it’s how I learned to be a freelance writer! I took Elna Cain’s Writeto1k course many moons ago, and I attribute much of my success to it.

That’s because this approach has a few distinct benefits.

Convenience

You can learn how to become a freelance writer without paying a cent. There are countless articles, videos, forums, Reddit threads, etc. that explain everything you could possibly need to know about freelance writing. The problem is that this information is impossibly fragmented. Putting all of the pieces together would take an inordinate amount of time.

Courses address that pain point. They offer filtered lessons consolidated into a single resource.

Perspective

When we first start to learn about something new, it can seem like there’s an infinite universe of information to explore. We’re standing at the bottom of the learning curve with our necks craned upward, just trying to wrap our minds around the mountainous climb ahead.

Paid courses help set parameters for a new concept. Their organized format allows us to digest information in chunks and at our own pace.

A blueprint to success*

The creators behind paid courses typically have succeeded at their craft — and now they’re passing their knowledge forward for a one-time payment of $297. (Just kidding, sort of.)

By learning from someone who’s been there and done that, we can accelerate our development and growth process. They bulldozed a path already, we just have to get our bearings and follow in their footsteps.

The Problems With Most Paid Courses

Paid courses are framed logically. They explain things in straightforward, step-by-step sequences. This helps viewers wrap their brains around concepts and follow clear-cut processes.

However, I think this logic actually spurs two key problems. First, they overlook a major aspect of freelance writing and entrepreneurship: emotions.

From what I’ve seen, there isn’t a paid course out there that adequately captures the emotions you experience on a day-to-day basis as a freelance writer. Sure, it’s not uncommon for courses to outline cold pitching and the likelihood of rejection (FYI, it’s high).

But what does it really feel like to be ignored for weeks at a time?

What emotions surface when you send dozens of personalized pitches to no avail?

What are you supposed to do when you play the comparison game with a better, more successful writer who makes a lot more money and has a way bigger audience?

How do you bounce back from a bout of spiraling self-doubt? I haven’t seen a writing course outline how to bolster emotional fortitude.

Second, remember that asterisk in the previous section? Well, here’s the disclaimer:

*Not everyone’s blueprint is universally applicable or repeatable.

Paid courses are typically blueprints to success — but that can also be a problem. We automatically think if we follow in their exact footsteps, we’ll succeed too. However, you’ll be hardpressed to find a course creator that keeps a tally of everyone who completed the course but failed to achieve the intended results.

That’s because they’re blueprints to someone else’s success, not necessarily yours. Freelancing is not a clearcut, linear path — it’s a complex maze with more deadends than doors to unimaginable riches.

That’s why I tried to do something different.

My Unconventional Solution

I didn’t need years of full-time freelancing under my belt to notice the disparity between taking a course and experiencing the real thing.

It’s sort of like the contrast between studying for your driver’s permit and actually getting behind the wheel of a car. Knowing traffic laws helps you understand the rules of the road, but it doesn’t necessarily prepare you for road rage, six-lane highways, and poorly lit roads. You have to experience those things firsthand to truly know how to handle them.

How can a written test prepare you for the distracting adrenaline rush of getting cut off by some asshat in an oversized pickup truck?

Frankly speaking, it can’t. The same goes for all other walks of life. So, here’s what I did:

1. Learned about freelancing.

2. Captured my experience in real time and compiled a viable product.

2a. Built a sustainable business.

3. Published a book to give writers a transparent lens into freelance writing.

I took an unconventional approach to compile my freelance writing “course.” A few months into my career as a self-employed business owner, I started documenting the process. (Think of it as a “diary” of a freelance writer.) I shared lessons, emotions, challenges, successes, resources, and whatever else I thought could help aspiring writers — and then compiled it all into a book.

Instead of building a sustainable business and then creating a guide, I learned and recorded my journey simultaneously.

In a way, this was a risk. Who knew if I’d succeed? I sure didn’t. Fortunately, my freelancing strategy started to pay off a few months ago, but I certainly didn’t know that while I was writing my book.

And I think this helped address some of the problems I mentioned earlier. For starters, when I experienced something, I wrote about it — so there wasn’t an emotional disconnect. I dealt with frustration, doubt, anxiety, and everything else that comes with building a business from scratch.

Additionally, survivorship bias wasn’t really in play either since readers essentially co-pilot my writing journey. I didn’t sift out bad ideas and failures because I think there’s value in seeing the full learning process.

Paid courses still serve a purpose, and I highly recommend ones like Elna’s and Jorden Makelle’s. That said, if you want direct insight into the day-to-day lifestyle, the obstacles, the benefits, the stresses, and the overall growth process — I can show you.

See what it’s like to be a freelance writer.