I will say that I typed this from start to finish in one sitting though, so please forgive any typos in advance. This came from the heart and I never edit things like that.
When I first started writing online, it was nothing more than a hobby. I had recently sold a business and I got a cushy state job that I had planned on riding for 20 years into the state pension system, and the last thing I was looking for was a career change. I just wanted to relax, travel with my family and watch the kids grow up.
I had always loved writing though, so I'd look for small jobs writing content for $5-10 an article on Elance and similar sites. Then I started writing my own articles on the Yahoo Voices network and eventually they made me a feature writer for sports, home improvement and technology. These were 500 word articles that paid $15-20 each and they got syndicated out as well, so I was averaging 10-20k page views per post.
At that point, I was making around $300 a month just writing to write, but I had also surpassed 3 million page views on Yahoo and people were starting to contact me directly. In fact, one of the first ones was Caribbean Cruise Lines; they offered me $50 per Yahoo blog to talk about the cruising industry and some of their ships. And I thought that was great money until an affiliate marketing company offered me $150 per blog to talk about their various websites...and I think that's when I officially stopped being just another writer.
Now, at first I thought that they loved me as a writer...and I guess in some ways they did. All they really cared about was my link-juice from a PR10 site and my 1,000+ followers who seemed to comment on every article. (and this was back before we knew comments and on-page times were even a factor). So in a way I was being used for my resources but hey, at $50-100 a pop for 20 minutes of my time, I can live with that.
From that point forward, I kept writing about sports and technology for $10-20 a pop, but I also took on an extra $300-500 a week from select clients that were contacting me. And then I thought, "I make more money writing 5 hours a week than I do working 40 hours for the state," so I quit my job. Because even back then I understood that writing articles wasn't really about SEO or what Google wanted to see, it was about connecting businesses to people. And to do that, you don't focus on what the business says...you focus on what their customers would ultimately want to hear. Because Google has always said that the site with the best information should always rank #1 overall, and that's why the last 3-4 years of algorithms have focused so heavily on the social metrics of websites (time on site, pages viewed, comments, likes, etc.).
So here's the best piece of advice you'll ever hear- Google has never changed. Not one bit. They only got better at meeting their original objective of making the site with the best content appear in the #1 slot, and you can't do that by trying to optimize for Google. Instead, optimize your sites for the people you're trying to connect with...and then Google will see your value. If you do that, then no Penguin or Panda update in the world can touch you.
By 2007, I was ranked the #24 grossing copywriter on Elance simply because my copy converted ridiculously well. I was fortunate enough to get hired by a few awesome SEO companies early on that taught me a whole lot about websites, and because of them my rates steadily increased over time. First it was $15 an hour, then $25, then $40...and I went up in price with new clients every time I had more work than I had time in the week.
By 2008, I realized that I was working 80 hours a week and never coming up for air, so I completely changed my business model. Instead of doing all the writing myself, I posted ads online for people who wanted to learn online marketing and I asked them for a simple writing sample. I'd say something like, write me a paragraph about the best place on Earth...or the best food you ever eaten...and then I'd reply to those who genuinely impressed me. Even if the content was fantastic though, I'd pick it apart from an SEO and creative standpoint just to see how the writers would respond. If they said, "Thanks for the advice/critiques...it really helped!," I'd take them on as an apprentice. If they defended their work, then I blew them off since they didn't want to truly learn.
Within six months, I had four writers "in training" and I took every decent priced job on Elance for them to work on. I gave them 50-80% of the revenue (depending on how good they were), kept the rest for my editing/teaching and I promised to give them the clients they worked for directly once they got close to my level. I taught them everything they needed from a business standpoint though; time management, customer service, dealing with jerks, how to properly bid...I handed out complete blueprints.
By 2009, I was the #1 grossing writer on Elance BY FAR and I had probably cycled through at least 30 writers of my own. Surprisingly though, only 3 or 4 stuck it out...the rest would become lazy shortly after they received their first few big paychecks. Then they'd come back a week later with some super-lame excuse why they disappeared, and like an idiot I'd give them another shot. It taught me a lesson though, most people are not cut out for freelance writing because of the complete freedom. It's hard to stay focused and disciplined when nobody is watching ...maybe only 3 out of 100 aspiring writers have the work ethic. And I'm saying that because I've literally hired/trained a thousand people over the past 7 years, and only 30 stuck with it all the way through. And you know what? Out of those 30, almost all 30 make six figure salaries today...either running an SEO firm or doing their own thing. About a half dozen of them have surpassed me as well and I couldn't be happier for them.
On the other hand, about 800 of the thousand are still writing $10 articles on and off because they never understood the success they could have by truly committing. As soon as they had a little success, it went to their heads and they would forget that marketing is a business. You have to study, keep up with trends, talk to your customers, constantly market, build your network.....and post lots of content daily. The 800+ just couldn't do that without someone standing over them and telling them to.
In 2011, I was offered a job with one of the hottest internet marketing firms at the time...and I really struggled with what to do. I was clearing $80k a year doing my own thing and only working 40-50 hours a week, but it was also a massive opportunity to learn from other professionals. Because you have to realize that by this point, I still hadn't worked for any type of newspaper, marketing firm or magazine....I was as freelance as you can get. So I threw out a number that I didn't think they could even consider ($90k a year) and they said yes...if I'd sign a non-compete and drop all my clients.
Well, this was both the best and the worst decision of my life...because the company laid me off within six months because I didn't want to move to their city and take a big promotion. They did teach me the internet marketing side of the business though and showed me how they made tens of millions a year through affiliates, so I reinvented myself once again....but this time I was 100% broke because I had just bought a huge home.
From that point on, I went back to Elance (where my reputation had all but died since everything is based on your last 6 months of performance) and started searching for clients. I hit Craigslist, great job boards and everywhere else I could find as well. It was slow going though so I made my first affiliate site, which taught employers how to find freelance writers. Elance and oDesk paid me $50 each per new business sign-up (and $5 per new writer), and I spent about six weeks 100% focused on that site. The first month, it earned $450, and it took in $1650 in month two. I was at $1400 about halfway through month 3 when someone offered to buy the site for $15,000, and I countered with $28,000. We settled at $21,500 and I haven't done an affiliate site since. Because I reinvented myself yet again.
As a writer, I was worth $40-50 an hour and as a marketer I could bring in double that. But by teaching people to quickly rank their websites and writing their copy, I was coming out closer to the $150/hr range, and my phone was always ringing with new opportunities. It was about that time I started working with someone who was advertising online for local businesses and everything I was doing just clicked...how many industries out there needed more traffic but didn't know how to get it?
So I started working with a web developer and we built specialty sites for contractors, real estate agents, dentists and all the skilled trades...selling them qualified leads for $100 a pop. And we were getting tons of leads, so we slowly progressed to a percentage of the sale instead of flat rates...which turned out to be huge. Someone got a $30k swimming pool installed and I made 3k, someone bought a $150k home and I got $2k off of the commissions...and these leads were coming in daily. I OWNED the local search results because nobody else was doing this, and the biggest companies in my area would come to me for leads because I'd have the first five slots on Google and they'd be at #6.
Then I hit the exact same problem as I did with the writers though; the web developer made a quick $50,000 in two months and thought he was Donald Trump. So he became unreliable, stopped working but still demanded half...and I finally deleted all my content and gave the guy the entire business. Now, he works for a local company making $40k a year as a programmer in a dead end job...and I've been searching for a "web builder" version of me ever since.
So for now, I'm mainly writing video scripts, email marketing, blogs, eBooks and other marketing content for a few Fortune 500 companies, plus I have my SEO firm focusing solely on generating local leads as well. Almost completely by accident though, I think I learned just about every possible way to make money as a writer/entrepreneur and it has been an amazing journey. And honestly, I do not know what's next...but I will reinvent myself once again to raise the bar even higher. Because that's what a true entrepreneur does.
Anyway, I hope that helped...I just gave you at least a dozen ways to make the money you're looking for. And if you fall into that golden 2-3% of the writers/marketers out there that I worked so hard to find for years, then who knows...the sky is the limit.