Fresh from a SkillShare high, and blessed with another quiet day at the office, what better time to think big! and imagine where we want this career to go. “Make money from writing” is a simple enough statement, but once you delve into all the varying avenues that make up freelance work, some larger and smaller decisions need to be made, about where exactly to start and where we want this project to take us.

Currently, I have two parallel trains of thought regarding a possible creative path:

Content and copy

One one hand: is the more practical, career driven idea of writing some form of Internet content. Options for this include website content, copywriting, blogs, articles and other type of freelance work one can find online.

Having never tried to write these types of things professionally, I’m unsure what suits my skill set or what I might enjoy, so I spent a few hours perusing UpWork, a freelance job board, to see what kind of work was out there.

There was a fair amount of underpaid, menial, uninteresting work, as well as some posts that appeared to be scams, but there were a few jobs that peaked my interest. There also appear to be real creative people who are making real money selling their services on Upwork. Definitely a good sign! Its a competitive market for sure, but most of the negative client feedback mentions people being hard to work with, late, or failing to respond, meaning it might be easy to stand out by being professional, on time, and easy to work with.

Getting the first job is going to be the tricky part, but once you get one client under your belt with a good review and good feedback, moving on from there should get easier each time.

So what do you need to get started with Upwork?

First, I need to understand how their platform works. A few hours in their ‘getting started‘ section should do the job.

Then, upload a CV. Which requires me to write a CV and make it appropriate to writing/creative work. (A children’s snowboard teaching certificate might not be so relevant for someone that needs me to proofread resumes)

Next, is to start creating a portfolio to showcase your skills.

My plan (thanks to Jesse Forrest) is to research each type of content, find an existing brief on Upwork for this type of work and then create that work as if I already had the job. Do this a few times, creating a collection of content with a cohesive theme, and then repeat. The idea is to create a number of small collections of work, covering varying topics based on my interests: Skiing/outdoor activities, fantasy nerd stuff, travel writing etc.

Research, write, upload, apply. Should be simple right?

No, I don’t expect this to be a walk in the park. Talking about doing work is always easier than actually sitting down to do it. And having never written travel content before, I am sure it will take me a while to really understand what people want/expect, how to make it good, and then take it a step further and understand how to make my work stand out from all the other people who are currently doing the same thing.

But I do now have enough of a plan to get things started. I know my step one and I know my end goal, which is further along than I was this morning, and gives me a tangible place from which to start working.

You might remember that I started this post by saying I have two ideas currently completing for space in my brain. So what is the second one, I hear you ask?…

The second, more creative but less financially stable, is the idea of getting into the world of TTRPGs.

TTRPGs, or ‘table top role playing games’, are a passion of mine. For anyone that doesn’t know what TTRPGs are, check out this post where I cover everything you need to know about the hobby, as well as some awesome ways to get started and get involved.

TTRPGs area an area I would love to get involved in creatively. They tick all the boxes for the kind of content I want to create: fantasy fiction tied with game systems and worldbuilding, and when I think of my ultimate creative goals, “Write for Wizards Of The Coast” is probably at the top of the list.

Now I understand that writing for WOTC is not the kind of thing that is going to happen over night. Like Andy J suggests, to be hired for a job, you need to show the client that you can do the job, which means making the thing which you want them to hire you for.

So, if I want to be hired to write D&D content… then I need to make some D&D content.

My plan of attack for this creative path is focused around The DMs Guild; a DnD 5E website where freelance writers upload their content for sale or ‘pay what you want’ download. This website is a well known starting point for creators within the D&D arena, and has been namedropped multiple times by creators answering that ever pressing question: “How did you get started in the industry?”. DMs guild is also a great place to find collaborations (or so I’m told) which will help slowly get a name for myself within the community

There are already countless creators publishing content on this website, which although makes for a tough market, I actually consider helpful at this stage. The type on content I want to create already exists, allowing me to so see how others are doing it, and “Copy like an artist”.

Copy Like An Artist

Now I know the word copy has very negative connotations in the creative world, especially in regards to writing and plagiarism, but let me explain.

YouTube creator Drawing Wiff Waffles introduced me to this idea. In a video about improving your art, she talks about how to analyze work you admire from other artists and incorporate the good into your own style, without compromising your creative integrity. This video was aimed at improving drawing technique, but I think the same can apply to writing: See what other people do well, see what they do poorly, and emulate the good stuff in your own style.

Stephen King actually talks about this same concept in On Writing: about how writers need first and foremost to read, how you learn more from a book you didn’t enjoy that a book you did, because you analyze what the writer did poorly and correct those mistakes in your own work.

More Cons that Pros?

The downside of this path is that I have never actually written content specifically with D&D publication in mind. I have hard-drives full of worldbuilding and campaign setting for my own D&D games, but none is written in the correct style, edited appropriately or set in the approved worlds.

My work to date is known as “homebrew” in the D&D scene; my own creations that borrow game mechanics from 5E but not the approved characters or settings, which, though intensely fun to make, doesn’t conform to the marketable IP allowed on DMs guild. This doesn’t mean that I can’t write approved DMs guild content, but it does mean that I don’t currently have any portfolio pieces to showcase, so will need to create a back catalog before I start trying to publish or find collaborations.

The other side to the D&D content coin, is that a lot of people are doing this work for free.

As I mentioned, many DMs guild pdf’s are ‘pay what you want’, which is a great way to have a lot of people see your work, but doesn’t convert well into actual income. One writer published their total earnings from DMs guild and although the numbers are slightly dated (2016), they earned only $3600 from a whole year of downloads. And this is a writer with a good variety of products (9 different works), large download numbers (one over 10’000), well known collaborations and a strong online presence. Even his officially WOTC licensed product only made him $1800.

– Caveat: I know this is only one person’s work, those numbers are old and D&D has become much more popular in recent years, but it does highlight an issue with the over saturated market. If so many people are doing this work for free, its going to be hard to get paid for it.

Now hard doesn’t mean impossible! This is not me giving up, nor is this me discounting the hundreds of people that do get paid for TTRPG content. DMs guild is not the be all and end all, nor is D&D 5E the only game system out there.

Anther avenue I would love to pursue creatively is TTRPG game design. I look at what the likes of Grant Howitt, Matt Mercer and Tim Hutchins are doing, and I can only dream of one day getting to create content with that level of magic and wonder. The idea of combining my love of fantasy, rulebooks, worldbuilding and all the things I love about TTRPGs, and putting that together with writing, is quite literally my dream creative goal right there. But that creative endeavor is going to take time.

did we come to a decision?

So, would I love to create TTRPG content? Yes. Is it one of my life goals to design my own game and play it around a table with my friends? Yes. Does that make me more excited than the idea of writing “how to” articles online? Yes. But am I in a position to actually earn money from game content today? No. How about this month? No. This year? Probably not.

This idea is going to take time and work; creating to learn the ropes, creating for free, collaborating for free to make a name for myself, learning the industry, finding a way in.

How does this differ from any other freelance work? It doesn’t, work is going to be needed no matter what I do, but starting from a place of little/no experience puts the destination of actually getting paid enough to do this full time further in the distance.

Do I still want to write for WOTC? Hell yes. Will I start writing content with the goal of DMs guild publication in mind? Definitely. But are other freelance avenues likely to yield financial results faster, allowing me to start writing full time sooner? I think the evidence is pointing to yes.

all writing work is work in the right direction

Writing this post has helped me come to the decision, that focusing on online content creation is the best direction for me to start.

Deciding to focus on travel/content writing initially will still give me transferable skills I can use to get better at all types of writing. Writing to a brief, working with clients, creating to a deadline, these are all things I learn no matter what path I choose, and any path that has me writing more, creating every day, working doing what I love- is the path we are going to follow.

That doesn’t mean I can’t keep writing gaming content. A rising tide raises all ships? is that the phrase? I am probably using that wrong, but what I mean is: getting into full time freelance work helps me in all areas of writing, and creating a marketable freelance business benefits all potential future projects.

So having come to that creative conclusion, what are our next steps?

First and foremost is getting this blog up and running. As I mentioned before, starting something, having a writing schedule, getting my words out there is the key next step I want to make happen. My 3 month action plan is full of topics such as portfolio research, practice projects and UBC course selection, but this week my focus is on one thing- starting this blog.

Goal defined.

Deadline set.

Lets make this happen.