A Decade of Freelancing

Last November, I posted a pair of photos on Facebook. The photos took me about ten minutes, but actually took me about 30 hours, but really took me a decade to make happen. Here’s they are:

It took me ten minutes to arrange everything on that table and have my wife take the photo. 

It took me thirty hours or so to gather all the items for it, some of which I’d never received copies of and others of which are out of print. 

It took me ten years to write all these things, because that’s what this is. It’s a picture of (or in some cases of things representing) everything I’ve written in the first decade of my freelance writing career.

What’s On That Table?

This decade has resulted in a wide variety of types of assignment.

  • Most of the table’s left side is covered with tabletop role-playing game assignments, which is one of my most favorite hobbies. 
  • There’s a stack of books with a black book upright, with a picture of a monkey. That’s business manual writing.
  • The stack of papers in the middle represents online content writing, which has probably made me the most money of any kind of writing so far.
  • In among them are also other forms of business writing, which I will detail in their own section below.  
  • Around 2 o’cock there’s a line a stack of print magazines. I love working with them, though I don’t recommend it as a sole money-maker.
  • In the center of the table are several of my self-published books, ranging on multiple topics in fiction and nonfiction. 
  • Right in front of me there’s a book on the right. That and the books beneath it are my Kickstarter anthologies
  • The black books on the far right are ghostwriting projects. They can be fun and lucrative, but are really hard work.
  • The black books between the content pile and the magazines are my planners and calendars. More on that in a bit. 
  • You’ll see three books: Dark Tales From the Secret War, Sojourn, and Wrestling Demons. Those are my traditionally published titles so far. One book, and two anthologies.  

This BABA list is an attempt to share what I’ve learned about each type, especially information about how you can break in to that kind of writing if you are so inclined. 

Sound good? Let’s get Started!

Tabletop Role-Playing Games

Writing rules and content for my favorite hobby. It took me a while to break in, but it’s a lot of what I do now and a lot of fun, too.

  • Pros: really fun, fast and easy because of my knowledge base
  • Cons: pays less per word, many clients are less professional

Break in to any kind of hobby writing with three main points of entry. First, pitch the magazines you see on the rack at the hobby store. Do likewise for the major related websites you’re already visiting. Second, haunt the online forums and social media groups about the hobby. Get to know the people who are hiring. Third, go to at least one convention or conference a year. You’ll be in rooms with editors, and often the only writer in that room. 

Business Manual Writing

Companies need ops manuals for their people, and various pieces of copy for their clients. Somebody needs to write them.

  • Pros: usually templated and simple to produce, can be interesting, high referral quotient
  • Cons: can be extremely boring, they often try to get you to bill by the hour

Break in to this work by first approaching the small business owners you know personally, like the owner of your favorite restaurant or your buddy who runs a dive shop. Expand your reach by aggressively seeking referrals. Going to small business meetups in your area, and meetings of Rotary or your Chamber of Commerce can also be great sources of leads. 

Online Content

Blogs, ezines, and online journals produce acres of copy every day. The good ones pay professionals to do it. 

  • Pros: high potential rate of pay, unending demand
  • Cons: some sites try to lowball you, sometimes less prestigous


Break in to online content writing by haunting the job boards and brokerage sites. Once you have a half-dozen assignments on your resume, start approaching sites you like directly. You can also get a lot of traction by making friends at writing conferences, and asking them to refer you. 

Business Writing

Businesses need ad copy, white papers, blog posts, form letters, and all manner of things written. Few have in-house people for the job. 

  • Pros: deep well of work available, potentially high rates
  • Cons: hard to break in, often less fulfilling


Break in to business writing by putting together a really good resume, then hanging out on LinkedIn and Facebook, while nudging your corporate contacts. Ask everyone, all the time, until the dam breaks. This will take a while, but once you get in there it’s fairly easy to keep getting work. Corporations buy big into that whole thing about how much more it costs to train a new person instead of working with a contractor they know. 

Print Magazines

Potentially what you think of when you think “freelance writer”, this is writing articles for print magazines. 

  • Pros: physical stuff of yours in print, high rates per word
  • Cons: you spend a lot of time querying, slow payment and publication compared to most other models




Break in to magazine writing by querying all the magazines you can think of. Start with industry and hobby magazines. They need good writers, and you have the expertise. For the bigger publications, look at “front of book”: the shorter pieces in the first 1/3 of each issue. Editors are more likely to take a chance on an unknown with those, than with a full feature article. Once you’ve proven yourself there, go for the big pieces.

Self-Published Books

The overwhelming majority of self-published authors make very little, but if you do it right you can turn it into a full-time living.

  • Pros: complete creative control, you’re a published author
  • Cons: lots of competition, you have to learn marketing and act on what you learn




Breaking in is a matter of writing a book and putting it out there. That said, you should first learn everything you can about marketing self-published books. This is a whole other skill, and one you will not succeed here without. 

Kickstarter Projects

Kickstarter is a crowdfunding platform where you tell people about an idea, and they pay you to make it reality.

  • Pros: really fun, high potential earnings
  • Cons: takes a LOT of work


The first rule of a Kickstarter project is you promote the hell out of it before and during your campaign. It’s not for beginners, but once you have things in place it can do a lot of awesome things both in terms of building your community and making you a fair amount of money. I’ve had particular luck with Kickstarter anthologies, because a project with multiple authors by definition has more support. 


Writing words somebody else puts their name on, be it a book, a speech, a song, or a blog post. 

  • Pros: shockingly lucrative when done right, you meet interesting people
  • Cons: requires people management, can be high-risk

I’ve seen people advertise ghostwriting services, but in my experience the overwhelming majority of these gigs come through a contact. I’ve done five such books, and all but one of them were through a “guy who knew a guy.” Keep your contact network broad. Build a killer resume. Keep your ear to the ground, and when you see the opportunity make it reality. 

Planners and Calendars

Self-publishing planners and calendars combines an interest or hobby with self-publishing.

  • Pros: fast to produce, easy to make
  • Cons: needs solid marketing, low-profit

This is a niche self-publishing venue that also includes quote books, journals, coloring books, and anything else that has a lot of pages but not very many words. If you’re marketing savvy, and time poor, this can be a great place to start. Breaking in works like any other self-publishing venture. I’ve had very good luck with giving away a free .pdf version mid-year, then offering the print version for the next year in October. 

Traditional Publishing

This is what most of us thought of when we first wanted to be writers. Write the book. Get the deal. Become a “real” published author with your book in stores all over the place. 

  • Pros: highest prestige level, vast potential income
  • Cons: unbelievable competitive, low likely income




Breaking in here is an art unto itself. Stay tuned for looooong posts, and even an ebook, about the best way to break in.


You can learn what I know about a whole lot of other ways to make money at this gig from a talk I give at writers conferences called 50 Ways to Sell Your Writing. If you’re not in the Pacific Northwest, or can’t come to a conference for whatever reason, here’s a link to my slides for the talk