What It’s REALLY Like to Break Into Freelance Writing – by James Leatherman

What It’s REALLY Like to Break Into Freelance Writing – by James Leatherman

So, you’ve decided to become a freelance writer. You’ve been told that you can work whenever and wherever you want. You’ve read tons of articles talking about making a writer’s website, pitching to clients, creating clips, and guest posting to boost your visibility. Now, it’s time to sit back and watch the clients come rolling in. Right?


Freelance writing isn’t for the faint of heart, and it’s certainly not easy money. It took me over a month to even get a response when I first started. That was because I had a lot to learn. So, here are some things you should know about what it’s really like to be a freelance writer (and how to survive the rough road ahead).

You won’t make money right away

Unless you have previous writing experience, and some already published work, you’re not going to land a paying gig right away. It took me two months to land my first paying assignment. And, four months after that before I made my first $500.

This is a great paying career for those who are patient. It’s going to take time for you to build a decent set of clips, and create the base necessary for landing your first gig.

The key to this game is to always be looking for opportunity. Will Smith once said: “If you stay ready, you don’t have to get ready.” Keep sending out queries. The money will come eventually.

Most of your queries will go completely ignored

This is, perhaps, the most frustrating element of freelance writing. In order to land writing assignments, you have to stand out among the utterly overwhelming amount of competition. In order to stand out, you have to deliver a personal touch to every query sent.

So, you spend all this time researching the person you are going to contact. You write up (what you think is) the perfect query, and you fire it off, assured in the fact that you are going to land the job.

And then…nothing happens.

So, you do it again. And nothing happens again…and again…and again. I sent out over 30 queries before I even got a response. When I got that response, they told me that they liked me, but that other people were willing to work for less money.

This is a numbers game. Sometimes your queries go completely ignored because of the overwhelming amount of responses a company gets. Persevere. Don’t take it personally. I’ve really only gotten one actual rejection based on my talent. Most of the time, it’s just your application not standing out enough to grab their attention.

You can’t do this part time

I hate to burst your bubble but if you think you’re going to do this for a couple hours a few evenings a week, then be prepared to eat ramen noodles. You may eventually get to a place where you aren’t working all of the time but, to build enough momentum to get to that place, you have to hustle.

I try to send out at least five queries per day. This can take several hours all by itself. When you start landing clients, then you throw in actually writing stuff on top of the long querying process. You will be at the grind for several months before you can build enough momentum to decide how much you want to work. But, if you work hard enough, and if you’re a good writer, it will eventually happen.

Expect to work hard in the beginning. Expect to go through a huge gamut of emotions including frustration, anger, and outright despair. You may want to pull your hair out, but go outside and take a deep breath. Center yourself and get back to it. If you truly have your heart set on being a full-time freelance writer, you CAN do it!


James Leatherman is a teacher, freelance writer, and owner of Leatherman Media. His passions are reading, writing, hiking, and traveling. You can find more articles like this on his website, Happy Mindsets.


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One Response to "What It’s REALLY Like to Break Into Freelance Writing – by James Leatherman"

  1. pamelaallegretto  July 12, 2018 at 2:19 pm

    Excellent article!