I spend a lot of time teaching people, and also giving directions (which I seem to have to send out repeatedly) only to be faced with a remark that doing all these things to manage a website is hard and time consuming and complicated and painful. It takes a lot of effort for me not to reply like this:
Of course it’s hard. Malcom Gladwell, in his book “Outliers: The Story of Success,” posits that it takes 10,000 hours of work to become an expert at something. Anything. Now, believe that or not (and yes, some people are naturally gifted so maybe they can do these things faster or achieve an even better expert level than you), the fact remains that we all had to learn skills.
What’s interesting is this is nothing new. We know this. We’ve known it for years that we have to put in the sweat equity. But people look at a website as being “easier” and think it’s really all a ‘set it and forget it.’ But it’s not. It’s never been that way. Making a website and walking away is dangerous not because you might get hacked (which you might), but because people will walk away when there’s nothing new.
At WordCamp Chicago, I talked about this. There’s a difference between how someone like Ron Popeil sells things and how Julia Child did. No one can argue she wasn’t successful, but she, like Chris Lema sell you on yourself, rather than ‘You need this one thing to be a success.’ If I stick to my food analogy, Emeril sells things but Alton Brown sells you skills.
This just comes back to the basic understanding of needing skills, some skills, to keep your website up and running. We’re not all going to be hard core coders, nor should we be, but we do need a modicum of technical savvy to use the tools. Our technology gets more complicated, and while I know WordPress is concerned with that, even plain HTML is complicated to figure out that first time. The bar is there, and you have to master jumping it, or even peeking over it, to get through your day.
A website is work. The health of your website is directly proportional to the work you put in, and as we all know…

I would like to propose we all, for 2014, be shamelessly honest (to steal a phrase from my company). Be upfront, direct, and truthful. When people say “Is WordPress easy?” we say “It can be, but remember, no matter how easy a tool is, your website is still going to be work.” I would like us to stop selling our tools because they’re so easy a caveman can do it, and start selling truth about how it’s being used. “Everything gets easier the more you use it.” and “The more familiar you get with this, the easier everything becomes.”
This is not to say that our tools can’t be easy and shouldn’t be easier, but we have to face the facts that no matter how easy we make WordPress, or Drupal, or any tool, our presence on the Internet will remain work. And work means that sometimes you’re going to have to learn new, harder-for-you, skills to keep up with everything, or spend money to hire someone to do things.
No one can tell you how easy something will be for you, and I think we need to stop telling people “Don’t worry, it’ll be easy.” When I tell someone they can fix a hacked site, I tell them they can without losing their content, and while it can be overwhelming and scary, if they can copy files between folders, they can do this. By being honest about the work that goes into your website, the more prepared they will be for the inevitable moments of pain and difficulty, and the easier it will be for them to solve those problems.