Making Money Writing Part One: The Level Up Method

Note: This post is primarily about marketing writing, copywriting, content writing, and other commercial stuff. You can apply the core tenets of this strategy to fiction, but I suspect it’ll stick better with commercial work.
That said, there’s still a ton of creativity involved in the kind of work that pays consistently, so if you’re interested in flexing your writing muscles and still making some cash, read on.
One thing I like about copywriting is it’s pretty easy to get a feel for if you’re good enough. If you are, and you have the discipline to build a name and some clips, it’s actually quite a bit easier to make money writing than you might think.
More to the point, it’s pretty easy to build a path where you get decent pay per piece if you’re willing to put that work in. There are outlets out there paying $1000-plus for blog posts not much longer than this one. The trick’s in working towards those kinds of roles.
I’ll break the process down with bullet points to make it a little easier to digest:
- Pay your dues. Perhaps the worst part of your early freelancing will be building those initial clips. For this, the best bet is to go to a platform like Mechanical Turk, Upwork, SolidGigs, etc. and get some newbie-friendly gigs, of which there are many. These gigs do tend to be a bit exploitative in terms of pay per output, but you’ll at least make some side cash, and — way more importantly — get your name on some work that you can show to your next round of clients.
- Get those first clients. This part can be easy or hard depending on the market you want to get into, the strength of your early portfolio, how good you are at selling yourself via resume, etc. In my case, this is the step where I went from five cents a word to pieces that paid $100 and up.
- Use the clips you generate to apply to higher-paying stuff. Build a portfolio of stuff you’re proud of and apply to jobs, even if you think you aren’t quite qualified. Good writing makes up for a lack of experience or formal education; in my instance (and I am not flexing here), most of my longest-standing clients are people who sought me out after catching my work on another client’s publication.
I will admit there are a lot of subskills required here. Most important — I’ll probably make a longer-form talk on this the next in my little series — is the ability to write resumes and cover letters that sell your skills and draw direct links to the qualifications in the posting.

That said, if you are willing to grind out some good work for what amounts to beer money, the market will tell you pretty quickly whether you have the skills to move up to the next level, in so many words. Don’t take failure as a sign that you aren’t cut out, however. One of the most brutal things about freelance is the application-to-jobs ratio; ten failures in a row might lead to an eleventh dream gig, which is something that happened to me frequently.
One final bit of advice: Always be looking for ways to sharpen your business sense. This will help you in terms of resume building and generating deliverables. LinkedIn professional groups are an amazing resource and a great way to network, for one example.