I teach a blogging class for mediabistro, and one of the unexpected bonuses of the gig is that the course forced me to realize that my site was achingly in need of a redesign. It's a little depressing to talk about categories and tags and social media icons and SEO headlines when you realize your site has none of those things. I felt out of it, especially when it was hinted to me, back in December, that my time with WBEZ might be limited. I felt like one of those ladies on What Not To Wear--in need of a pick-me-up but unsure where to start. So I became my own Clinton and Stacy.

I started by looking at the sites I like most for their design and emailing some of my blogger friends to get recommendations on designers. I know some HTML but unfortunately building a site isn't what I do. I thought about what changes I wanted: most sites I liked seemed to be on Wordpress so maybe a switch over from Movable Type would be good. I needed to incorporate the organization functions I outlined above. I would like it to be more image-friendly. I wanted a small facelift. I needed someone to also retrofit the ten-plus years of archives to fit the new look. I wasn't trying to re-invent the wheel because another thing I have learned through the years is that the Internet is an ever-changing blasted thing. I'd rather just make some subtler, manageable upgrades (at least according to the user) than to exhaust myself radically overhauling it only to have it become obsolete in four weeks.

The designers I reached out to came back to me with some estimates, ranging from about $600 to $1200. I asked my friend Fuzzy Gerdes, a designer I know, to take a look at the estimates and go give me his input. I took him out to lunch (at Noodles & Co.: I recommend the noodles) and he told me which designers he thought seemed the best. One company had typos in their proposal which he said turned him off a bit and I agreed. We're both weird that way.

"However," he said. "I would also like to submit myself as a possible designer." Fuzzy had been working for Time Out Chicago, happily, after going down with the ship at Playboy but unfortunately, the good ship TOC had also encountered an iceberg. Fuzzy would have some extra time and be open to some extra work. So, I hired my friend, after I made sure it wouldn't be weird to work together (I did this by asking "Do you think it will be weird to work together?")

I don't know how feasible it is to work with a designer who's familiar with you, but this worked out well for me. Fuzzy knows me and my site well enough to make some recommendations (which I had requested.) I don't know enough to know all of my options or what was really best for me. For instance, he recommended strongly that I stick with Movable Type, since not switching meant less work for the posts that were already in the system, plus there was a newly-available default theme that was mobile-friendly that we could use as the basis for the new design. (Not switching platforms also saved me a couple hundred bucks.) He presented me with a range of facelifts for the main pages and suggested that I eschew tags, which he thought would be a blog-clutterer, as well as SEO titles, which he thought were unsightly and unneccessary in my particular case due to my long internet presence as well as my own particular ambivalence about needing to jump to the top of search results for everything (really, it's OK if I don't pop up when you google "Paris Hilton" anymore.)

Fuzzy would check in with me periodically to ask for text that he needed, or how I felt about certain social media widgets, and what I wanted to name the categories. I asked for recommendations here and there and he made his suggestions based on his expertise (like using MailChimp, for instance, as my newsletter.) He'd pose these questions to me in digest form and was very patient when I asked him "What does that mean?" or "What do you think?"

Close to the relaunch date I bombarded Fuzzy with lots of questions about little tweaks and modifications, all of which he responded to helpfully--often saying something along the lines of "I have made this tweak and here's how I did it," so that I know how to fix things on my own in the future. I still do ask him some occasional questions although we agreed that if I embark upon another major project, I'll pay him more than he invoiced me for the general redesign/update. You can see what the the old site looked like here. A subtle change but exactly what I wanted.

So, if you're thinking about redesigning or designing your site, based on my experience, these are the things I'd say you should think about when looking for a designer:

• What's your budget? (And remember: you get what you pay for.)
• What do you definitely want done?
• How flexible are you? How much are you willing to tweak these desires based on a designer's recommendations?
• Does your designer seem familiar with your blog, or willing to become so? (It will be great if you can get the designer to tell you, in his/her own words, how he/she sees your site--that way you'll know whether or not your tone and themes are evident and to make sure that your designer gets you.)
• What is your communication style? Do you need prompt responses? Do you want to check in frequently or sporadically?
• Is this designer someone you like enough to speak to on a frequent basis? Not that you have to be best buddies but you'll need to find someone whose honest opinion and advice and communication style as at the very least tolerable for you, if not pleasant and fun like mine was.
• And ask yourself, why am I doing this? Blogging, I mean. Are you just crazy enough to keep doing this long enough to make it worth the time and money of a redesign?