It’s the Wild West out here, people

A decade ago when I started out as a full-time freelance writer, things looked a lot different. I certainly wasn’t alone out there, but competition was not exactly hot and heavy.

Here’s how it went pretty often:

Me: “Hello, I am responding to your job posting for a freelance writer. I have a very small amount of experience but I am good at writing!”

Client: “Great! Can you write this blog post by tomorrow? Actually, can you take over this entire section of my blog? Thanks!”

Within a few months of starting I was in charge of an entire vertical on a major website. In a few months more I was writing for a national magazine. Within two years I had a book contract with a Big 5 publishing house.

This was not so much because I’m inherently awesome (who, me?) as it was because I had intense hustle and the field was wide open.

That is not to say that there weren’t competitive corners of the industry, gigs that were more difficult to get, and more experienced people I would lose out to. For example, the world of print magazines has always been ruled by freelancers, many of whom had already had venerable, decades-long careers by the time I was born.

But ten years ago getting work as a freelancer outside of print glossies was just about as easy as firing up the craigslist “gigs” section. And moving from one thing to something bigger was mostly a matter of reaching out and asking.

Well, times have certainly changed since then. Some surveys predict that a majority of the U.S. workforce will be freelancing within a decade. While thankfully that doesn’t mean they’ll all be freelancing full-time and trying to support themselves that way, it does mean that a whole lot of people are starting to dip their toes in the freelance water, mostly as a side hustle.

Which means that this is more likely to be the conversation nowadays when responding to a job ad:

Freelancer: “Hello, I am responding to your job posting for a freelance writer. I have a very small amount of experience but I am good at writing!”


Freelancer: “Hello?”


Freelancer: [sad trombone]

Those of you just entering the fray may throw up your hands, thinking you missed the boat.

But I’m here to tell you: This is not a boat.

It’s a train!

And the destination is the Wild West of the work world. When I started out, the freelance world was in covered-wagon territory. The train track is now being laid, but make no mistake — it is still the Wild West out here.

The increased competition in the freelance landscape has made it more difficult to succeed, yes, but it has also created vast new opportunity.

There is so much dynamism and development in freelancing right now.

Employers are more and more familiar with the idea of employing freelance talent, and increasingly see how it benefits them. So they’re hiring like crazy. People who have struck out on their own in the past are offering advice, training programs, and resources (like this blog!) to help those who are starting out. Freelancers are joining together in unions and online groups and meetups and associations to discuss their industries, share best practices, get support, and generally professionalize the whole affair.

The field is developing, so that’s exciting, but it is still at an early stage, which is even more exciting.

Yeah, you can’t expect to get ahead by trolling craigslist anymore. We are past the era where you can get a whole lot of traction with job ads alone. You need to be much more proactive, putting yourself out there and learning how to network and market.

But the great news is that you can still shape your own career, figure out your own best way of doing things, and — if you have hustle and a little bit of strategery — make a whole lot of money.

So, gone might be the days when you could publish a book with a major publisher within two years of starting out. Or maybe not! That’s the joy of the Wild West. Anything can happen. It all depends on how you want your career to look and how ardently you’re willing to work to make it a success.

While it’s tempting to have someone tell you how freelancing is “supposed” to go, the more you learn to follow your own inner direction — to cultivate a CEO mindset instead of an employee mindset — the more amazing opportunities you’ll find.

Out here on the frontier, the field is still wide open.

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