My Time Line – Rise and Fall of a Problogger

It seems like almost another life time ago that I was writing full time online for various blog networks, but I’m hoping that reflecting on this will help you understand my history, knowledge and motives.

I feel like I should start with something literary like, “It was a dark and stormy night…”


I’ve already worked as a web developer for over a year, and have started publishing content online. I am not really “blogging” yet, but it is the best I can do with my limited understanding of how the web works.


Early in the year, I create a Blogger account and use it to publish content on my personal website. Only my friends and family read it, but I’m figuring out how to manipulate the web, and while my skills in coding and design are weak, I’m enjoying tinkering and learning while publishing a dairy of my home and work life.

Later in the year, I get frustrated with Blogger and start experimenting with different PHP scripts that better integrate into my website. The one that I end up using is called Elite News. I haven’t yet heard of anyone blogging for money, and at this point, I’m actually turned off by the numerous sites plastered with advertising.


Sometime in 2004, I find WordPress. It is still pre-1.0 software, but I’m very interested in it because a blog I read, written by Michael Heilemann of Binary Bonsai is powered by it.

I begin following everything related to WordPress as well as blogging in general. While I can’t program as effectively as others, nor design beautiful websites, my ability to consume a great deal of content and my passion for the platform is quickly apparent.


This was the year than things really changed for me. I’ve found and I am hooked. Darren discusses how he makes money from his niche focused blogs, and my mind explodes. I had only been blogging to share my interests, and my personal life. The IT field still hasn’t recovered from the last great tech crash, but the web is alive and thriving again.

I also start reading and enjoy the various tips and tricks on this site, as well as the WordPress related news.

Darren Rowse decides he is going to take a vacation and asks his readership if anyone would help him by posting a few things on his content sites. I am one of the lucky few that receive one of the positions and am tasked with writing on his laptop blog.

I learn a great deal about researching, publishing and WordPress over the time he was off, and feel energized and excited about online publishing.

In the middle of the summer, Jacob Gower, a name I had never heard before comes out and buys some of the biggest sites that I visit, and with being one of those sites, I reach out to interview him on his intentions and ideas.

Interestingly enough, this brings him to my attention as well, and by the fall, I’m working full time for the Bloggy Network and writing on, one of my favourite sites.


Over the course of the year, I write thousands of posts on a variety of different sites. I help launch sites, code WordPress themes, and continue to help Jacob develop his network of blogs and websites.

I also begin to take over the administration of all the blogs, and get to flex my IT muscles a bit in writing scripts for upgrading hundreds of WordPress blogs, managing all the plugins, and dealing with spam and hacking attempts.


I am promoted to Director of Communications at Bloggy Network. I’m given a small share of one of their biggest network sites, and I’m given more responsibility. I am still writing, managing the IT needs of the network, but now I’m also helping sell advertising and train new employees.

I’m also helping with some external development work that Jacob has taken on and we help others with blogs redesign their sites thanks to Elena of Design Disease.

Late in the year, Jacob and his partner Ahmed, decide to sell off a piece of the network to a larger blog network, Splashpress Media. I transitioned with the blogs as I was writing on more than half of them.

This also meant that I was now the Head of Marketing of a company with more staff, more resources, and more sites. The learning curve is steep, and I don’t get to write much, but I find great enjoyment in working with an owner that has such a long view of success on the Internet.


Decidicing that I wasn’t really a good sales person or Head of Marketing, I move on from Splashpress to work with PicApp on their stock photography for bloggers web tool. The position was short lived for personal reasons, and I found myself without a platform, blog, network or job.

In the fall of 2008, a long time contact, Ryan Caldwell, asked me to be the Project Manager of a new venture he was undertaking, CollegeCrunch.


Over the course of ten months, I worked hard on promoting, developing and organizing CollegeCrunch into a viable business venture. Unfortunately, I didn’t really enjoy the niche, disliked chasing conversions, and found it very difficult to be passionate about writing. The wind really went out of my sails, and I felt it was the final nail in my descending career online.

Late in the year, I took a position with the government working as a Web Developer for the County of Bruce. I was able to go back to PHP web development, and focused on a variety of projects. I call this period my blogging detox period as I had very little to do with creating content online, and almost completely disappeared from the social web.

2010 – Spring 2012

Continuing to work for the County of Bruce, I helped redevelop half a dozen websites, built an Intranet site that became my personal responsibility to maintain, and worked with the tourism department on some basic social media marketing ideas and techniques.

Two weeks before my birthday, one of my freelance web development contacts asked me to work for them as their Online Marketing Manager. This is the position that I continue to work. My role includes working on web development, marketing various campaigns online and doing all of the network administration for two companies.

I started a personal blog again to get back into writing and publishing online. I’ve mostly avoided blogging for any kind of compensation because of the anxiety I feel over having to write things I don’t enjoy, or focusing on content solely as a way to generate revenue.


With everything in life, there are ebbs and flows that can change your path. The market changed, my personal life threw some monkey wrenches in the mix, and a lack of understanding of who I am and what I want to achieve also caused some interesting issues, but at the end of the day, I worked with some amazing people, and learned a great deal.

Only now, around ten years after I started, do I feel I have the understanding, maturity, and focus to do what I want and need. I have always wanted to teach, and blogging offers me that opportunity. The hard part is to focus on the enjoyment of creating and teaching and worry less about the monetization.

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