Hi Sam! I love your site. We should definitely connect. I’m a school counselor and recently launched a site for parents to address pertinent teen topics. Like you, I struggle with the ultimate service I’d eventually offer on my site, but Ramsay’s idea is a great start. He’s absolutely right that people are looking for fresh content for their sites! Best of luck to you and I hope we can collaborate.
It’s dependent on traffic. Traffic goes up and down and you never know when it is going to do a major dip. Most advertisers pay based on the number of views their ad will get. This turns you into a traffic monster. You start to look for creative ways to get any kind of traffic, no matter if it’s good traffic or not. This can easily lead to your site becoming another junk site that you try to avoid.

My understanding is that you have to subscribe/pay for the business version of Word Press in order to use any of the monetizing functions. I think you should clearly state this in this article at the beginning. I think there is a degree of bait and switch here if people are just signing up for the free subscription and then finding out they have to pay for a subscription to make money. I am ok with that, it just needs to be stated up front everywhere.
Jaime, this is an excellent article. I’ve been blogging for fun for over four years, In the last year I’ve branched out and started a self-hosted blog about blogging for fun. I’m at the point think I have enough to offer on that subject and a few others. There are so many steps to get started, I think it overwhelms people, including those of us who are comfortable blogging. There are lots of courses available, but most of them that I’ve tried are pretty general. Do you recommend getting a coach?
Don’t get me wrong I have made many mistakes along the way but once I knew what I was doing it became a lot easier and more enjoyable. Many of my friends have emailed me or called me to find out more about “What Jamie Does”, but it can be a little hard to sink in at first as to how you can actually make a real income from running a successful blog(s). Therefore I have decided to create this guide for my friends, family, email subscribers and anyone else who wants to start doing “What Jamie Does”. 
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