At the tail end of 2010, I entered WRKO's Next Great Political Blogger Contest and did surprisingly well, making it all the way to the finals. Armed with newfound confidence, I decided to put up this site to see what direction things take.

It seemed like a natural to me because I am a Web developer by day and I know how to maneuver the Internet. I also like to write, I am opinionated as all get out, and the barrier to entry has become incredibly low.

I am not somebody who normally jumps into a project without knowing exactly what my objectives are. I am a planner by nature. But in this case, I had no idea how to create a successful new media site, so I just dove right in and listened for explosions.

Frankly, it seems like the rules of the online media game are still being written. Everybody agrees that at least some of the content from newspapers and magazines is moving online, but as far as I can tell nobody is entirely sure what form it will take.

So I decided to slap up a site, start writing, and see what happens. I didn't even attempt to bring in revenue in my first year. The site has no ads. Its purpose is to entertain and inform the reader, and maybe more importantly to educate me on how to take this to the next level.

Struggling with labels: "Blogger"? "Digital Journalist"? "New Media Editorialist"?

I don't have a good label to describe what I do. I wish I did. I don't feel like I fit into the category of "blogger."

I networked for a while with a group called Boston Bloggers. Nice folks, but they are doing something different from what I do. Most of them are women with food or fashion blogs.

There's nothing wrong with that, but I see myself more as Andy Rooney with an IP address. I write about politics, sports, religion, and technology. It is a different audience and the topics I deal with are weightier than the ones that the typical blogger writes about.

While the term "blogger" seems understated, it would be a stretch to call me a "journalist." This is not a news site per se; it is more of an opinion site. "Online Editorialist" seems accurate, but I can't imagine that term catching on. It sounds awkward, like it is not really a thing.

I am different from the garden-variety blogger in that I do interviews and dig for interesting stories. I am not a reporter by trade, but when the Westboro Baptist Church came to Boston, I brought the video camera and got reaction from the enraged counter-protesters. I drove to Bath, Maine to interview a spunky radio station owner in his studio. I sat in a comedy club and groaned through an open mike night for a story. I called down to a church in Texas to get some information for a story.

Finding the right label is important to me because I would like to network with people who run other similar small sites. I can't really start a Meetup called "The Boston sort-of Blogger/New Media/Cranky Digital Guy/Online Op-Ed Dude Meetup".

I joined the Online News Association this year. The Online News Association is a "nonprofit membership organization for digital journalists, connecting journalism, technology and innovation."  I feel like I fit in with the ONA group better than the blogger group, but I don't quite fit in the ONA group either. There are a lot of big fish members of ONA like CNN and NPR. I met fewer people from startup sites through ONA.

Joining ONA was worthwhile to me because it allowed me to attend their yearly conference, ONA11, which luckily was held in Boston this year. It was tremendously interesting and I learned a ton.

Still, I would love to find a label for what I do, and it would be great if there were an Online Small News Association that could fill the gap between small blogger groups and the big boys at ONA.

Finding Your Focus

The conventional wisdom is that small niche sites are more successful than sites that cover a lot of different topics.

I often wonder if this site suffers from a lack of focus. The readers who are interested in my religion articles couldn't care less about my technology articles. The readers who are interested in my technology articles couldn't care less about my sports articles.

That probably makes this site less "sticky." When people come back to read more articles about the Methodist Church and are instead greeted with articles about Amy Winehouse, they are probably less likely to return.

The Huffington Post and Boston.com certainly deal with a wide variety of subjects, but they have the luxury of having a massive amount of content. For small sites with limited content, they say that a smaller, more focused site is better.

The trouble is that I am interested in a wide variety of topics. I love to write about people who do things their own way. That means that sometimes I write about comedians and sometimes I write about renegade radio station owners.

It is more fun for me to write about whatever topic intrigues me or pisses me off that day than it is to limit myself to a narrow niche. A focused niche probably makes for a more commercially successful site, but isn't as enjoyable to this writer.

Next year I plan to try a hybrid approach where I have one landing page for sports, one for religion, etc. The readers of thebostonobserver.com/sports will be happily oblivious to the content on thebostonobserver.com/religion. I'm not sure if that will solve the problem or not. I'll let you know a year from now.

If you happen to be intensely interested in one niche area like the Ivory-billed Woodpecker or Harley Davidsons, I envy you. You can build a committed following of readers who will return to your site over and over again. That makes advertising a breeze.

Choosing the right technology

The biggest mistake I made in my first year was my choice of technology. I built this site using Joomla. In hindsight, I wish I had selected WordPress right from the giddyup.

Joomla may be a good choice for building an e-commerce site, but using Joomla for this site was like using a flamethrower to kill a mosquito. I spent far too much time building and tweaking the site and far too little time writing for it.

The straw that broke the camel's back was that upgrading from Joomla 1.5 to 1.7 was frustrating and time-consuming. The third-party plugins weren't ready when I needed them and the new version was buggy and required me to implement work-arounds. Joomla's menuing system is also unnecessarily complex.

I toyed with the idea of using Méthode, the Content Management System that the Boston Globe uses. Since I need a CMS anyway I thought I could kill two birds with one stone and build my site and my resume at the same time. I thought if I became expert at Méthode, it might clear the way for me to get a day job at the Globe, which is a dream of mine. But it turned out that Méthode is not Open Source, so it didn't make sense.

My New Year's resolution for 2012 is to bite the bullet and migrate to WordPress. Unless you have some special requirements for your site, I recommend WordPress.

Some Useful Resources

I took several online courses at the Poynter Institute, a "school dedicated to teaching and inspiring journalists and media leaders." The courses were excellent.

If you plan to be anywhere near San Fransicko in September of 2012, you should join the Online News Association and attend the ONA12 conference.  I went last year in Boston and it was truly amazing. The ONA also has local chapters that have Meetups and they are often worth attending.

You can also take a peek at some of the 2011 ONA conference sessions.

Hacks/Hackers is a group whose mission is to "create a network of journalists ('hacks') and technologists ('hackers') who rethink the future of news and information." I have been to several of their local events and they have been excellent.

The best book on the subject, in my opinion, is Entrepreneurial Journalism: How to Build What's Next for News by Mark Briggs.

Mediabistro is a good site that has media news, online courses, and job postings.

And, finally, nothing beats Twitter for steering interested groups of people to your articles.

That is my brain dump for year one. I hope it was helpful to somebody. I'll do another one at the end of 2012. It's exciting to think of how much further along I could be by then.

I am very interested in your feedback. I would love it if you would leave a comment here or This e-mail address is being protected from spambots. You need JavaScript enabled to view it with your thoughts.