"Master Dayton" might be humorous, (I mean if Ph.Ds are called "Doctors," shouldn't MFAs be called "Masters?") but in all seriousness I have made a living freelance writing and after several years I have tons of information I want to share to help out my fellow writers, regardless of age, experience, goals, situation, or background. This blog isn't pretty-but it will help if real freelance writing information is what you want.

Monday, April 5, 2010

How I Became A Freelance Writer

How I Became A Freelance Writer

Update: I'll be addressing the eHow/Demand Studios situation shortly, but since I already started this post, this is the one I want to finish out while gathering more information on the new eHow situation before making a post or updating my review pages.

The only major regret I have with starting this freelance writing blog post is that I don't have a picture of the maladjusted Frankenstein of a computer I started my online writing career with. Because no matter how I describe that thing, it would never compare to a photo of it, and that single picture might encourage more people reading this blog to get writing than anything I could ever say. Because if Master Dayton could get started on that piece-mail p.o.s. with a dial up connection, everyone who saw that picture would suddenly believe (and rightly so) that they could do it, too.

But alas, that horror remains a memory with no photographic evidence, so we'll just have to move on and deal with the mental description later. For a while now I've hinted here and there that eventually I would get around to telling my story of how I became a freelance writer, including the embarrassingly low amounts I used to write for, the "lucky" breaks that pushed me to the next level, the "so close but not quite" moments, and all the ebb and flow that led me to this point.

This story starts out around late 2004 heading into 2005. At this point I was attending my second year of graduate school at the University of Fairbanks, Alaska (UAF) ((several of my friends up there who saw my situation joked that it should have been FUA for F**k U, A-hole based on "truth in advertising")). Even before the spring semester it was becoming pretty apparent that not only were my efforts to graduate early going to be blocked, but that a series of odd situations and "slightly" imbalanced individuals were not only going to keep me from having any chance of getting my degree, but were escalating things to the point where I feared for my physical safety, and after flunking the spring comps exams by a 3-2 vote and not having my space renewed in the program, I was done.

No degree, no job, no place to live, and no major prospects. At this point I knew nothing about freelance writing, and didn't even know where to look. Keep in mind that this was in 2004, and the Internet as a widespread thing was still kind of "new" to most people. Many of the writing sites I use today either didn't exist back then, or have their roots in those days.

I left Alaska and went to Iowa, deciding ahead of time to do the only thing that made sense in my position was to take the money I had saved from working, and to go Kerouac. At that point I was a creative writer, and although a couple of independent work study writing jobs at the University gave me the beginnings of a pretty impressive freelance writer and editor's resume, at that point I had no idea how to convert those experiences and skills into something better.

Besides, I was 24 going on 25, had some money, and some buddies who were willing to road trip with me that fall. Turning down an offer of a job doing maintenance at a camp outside of New Orleans that no longer exists (and if you did your math, yes, that would have been the year Katrina ripped through) in 2005 we went to the Northeast living from campsite to campsite and failing to find any work to allow us to stay more than a month and change. I did get a lot of creative writing done on the road, but came back and within a couple months was broke with student bills coming due, and sleeping on my friend's living room floor while living out of a suitcase.

On December 7, 2005, on my 25th birthday, Gabe and I lost control of the car on an icy road and flipped over a bridge, the undercarriage of the car catching, and flipping us so we hit roof first.

That entire night and the miracle of getting out with "as little" damage as we did could take up pages by itself, but the long story short: I had severe deep bone bruises from my ankles all the way up to my hips. The way the doctor explained it to me was to clasp your hands together with fingers intertwined. That's your bone with the marrow inside. Now move your hands an inch and a half apart while untwining your fingers. That's in simple terms what a severe bone bruise is - dozens or hundreds of "micro fractures" that take a long time to heal. In fact, it was over 3 years before the purple and black bruises on my legs disappeared completely.

So now I was broke, injured, and couldn't work anywhere. We had a computer that had a dial up connection, and there were only two skills I had that could make money online: playing poker and freelance writing. So that's what I did. On a dial up connection on a computer that looked like this: both sides were completely open, as the tower system was a 2000 PC that had been specially built to only function properly when running Windows Millennium (remember that piece of crap?) and that was attached to a partially burned out motherboards (as in at one point the old computer started smoking and there was black soot all over it) from a Gateway computer working as the brain. A CD disc drive was held in place with bubble wrap, folded cardboard, and duck tape and several of the wires from the original motherboard that ran Windows ME were literally cut and spliced to work with the gateway. The monitor's cord had to be run in through a hole in the side because there were no plug-in spaces in the back where they were supposed to be.

It was that ridiculous of an abomination a computer, and yet it started my freelance writing career. To this day I have no idea how Tim managed to get it to work.

So I started looking around and found Constant-Content, a website I still happily write for to this day and can still whole heartedly recommend to beginning online writers. I wrote a few articles, and within a week had two accepted for $40. In retrospect, I should have made $100 of of those two, but I was just getting started and two Andrew Jacksons are a lot of money when you're broke, injured, sleeping on a living room floor, and in need of food. The other site I found was Guru.com. I had enough left on one credit card for a one year subscription, and about $10 of room after that, so I did my research and decided jump jump in. I bought the 1 year subscription to Guru, knowing I had to make it work.

One long term positive that came from working with Guru was that with 100 bids a month, I had to write a lot of query letters. While you could save templates, learning to form a good query letter and how to adjust every template towards each bid is a skill that has paid off huge and is necessary for the success of any writer. The first month was hard, as I was accepted for only one job and received $200 as a kill fee - only to have the job fold in the first week. The second month on Guru I only managed one job, $45 to re-design and re-write a brochure that required 3 revisions - but this did lead to my first positive feedback.

I kept working on my query letters, and I could tell they were getting better as I was getting more and more communication with questions from potential employers, but the lack of feedback made it hard to get more work. But what happens to most really good writers who work hard happened to me as well: I worked hard enough to "get" my "lucky" break.

In March I was offered a job to work on some overflow work that a couple of writers were doing for a friend before they were overflowed. Unfortunately, since I was the second overflow, the 30 page e-book on poker was going to pay a measly $60. Still, I needed the work and took the job, especially because my gut told me I liked the tone of the guys. Thomas, from Journey Beyond Travel, was actually the one who gave me a lot of this work and more that followed, way back before they got such a nice website and really took off. After that poker book I wrote a koi pond e-book for the same price, and received a lot of apologies from them for having so little to pay.

But after they caught up, they liked my writing enough to hire me to provide Morocco travel articles and content, at $12-$15 per 400 words in batches of 10 and 20. That boost got the snow ball rolling, and after a few more jobs adding positive feedback, it snowballed. By the end of March I had over $700 of work not including CC sales, and in April I broke $1,300, not including CC. In May I was just short of two grand - and I still hadn't figured out how much I was worth and that I was under charging for my services.

Life happened in an odd way that summer, and as my friends who had put me up were both moving across the country, I received word that several of the professors and administration who had made my life a living hell up in Fairbanks were gone, and some of the very few professors who had supported me were in more powerful positions to help me not get screwed over. With a little encouragement, I did go back and finish, and by May of 2007, barely a year after starting my freelance career from virtually scratch, I accepted a job offer in Austin, Texas, for solid salary and amazing work at home benefits because of my skills as a poker and e-book writer.

Obviously anyone who knows my story knows that job disappeared a year and a half later, but I still get some of my best freelancing work from them, and I continued to develop my skills as a writer, learned about the opportunities available online, and began my quest for passive income.

There are some major points I want any beginning freelance writers to get out of this post:
  • I didn't start of with any experience freelance writing
  • I didn't start out with a strong support structure to support me as a writer
  • I could not write a good query letter when I started freelancing online
  • I didn't have any connections at all when I started my freelance career
  • I had terrible equipment when I started writing
  • I started off in a huge financial and life "hole" that worked against me at every turn.
Despite all these, in a year and a half I had an office job that would pay $38,000 a year and still allow me to work at home instead of the office while freelancing on the side. In retrospect, I did not take advantage of this nearly as much as I should have, but you live and you learn.

The main point I want to make is: Basic writing talent and a RIDICULOUS work ethic is MORE than enough to create a freelance writing career from scratch.

I want everyone to realize this. Basic writing talent, work ethic, and stubbornness is enough to get you from nothing to a full fledged career. I think that's really important for people to understand because too many people are being held back wanting to be perfect or not being sure if they can do it at all. Work. Then work some more. Then work even more. If you do that, you will succeed. There is always more space for a good hard working freelance writer.

I hope this was encouraging. This wasn't meant to be bragging or bravado or a "look at me and how great I am" blog post, but it underlines the fact that good solid writers who have an incredible work ethic and are willing to be stubborn and pursue that goal of a freelance writing career against all odds and hardships, will make it to the Promised Land.


  1. That is one hell of a story - I think some people who haven't worked in Academia would doubt how rough it can get - I have though and yup some of the craziest people I have worked with have tenure!

  2. Hi Lissie,

    Yeah, I was there for years and I'm still shake my head and find it hard to believe. It is crazy, and while there were plenty of troublemakers, the one who caused me the most grief was so out there that pretty much all the other tenures wanted her removed, too. Fortunately I came through in relatively decent shape, though to this day I feel a little antsy when I'm not carrying at least a knife around with me. Love the state, but that university is one place that's never seeing another dime from me, and I've long since done away with even the remotest shred of desire for an academic job! Thanks for the comment, Lissie, always a pleasure!

  3. Cheese and rice, that is one heck of a story! You are a testament to the value of hard work and reaping what you sow.

    Do you keep any of your creative writing online? I know that's where you passion lies and I'd love to read some.


  4. Dear Master Dayton: Thanks for sharing your story! Truly inspirational! You had been promising you would share it, and it did not disappoint. Cordially, Robin Elizabeth Margolis

  5. Thanks to everyone for the kind words. I don't have any creative writing still online, as most went past archives or most of my publications were print. I am working on a project with some friends I'm hoping to unveil in the fall that will have a lot of creative writing online, some independent films, a lot of stuff like that. I'll definitely make an announcement when the time draws near and that takes off. Thanks Robin, for the kind words, as well.

    I appreciate all my readers on this freelance writing blog, and find it pretty cool that "Master Dayton" and "Shayne Dayton writing blog" (that one's really funny since it misspells my name) actually get searched for via Google on a weekly basis now. Thank you for the kind words, and I'll be posting again soon.