I recently spent a few days in New York, Philadelphia and New Jersey, and got to meet with great friends at consulting firms. One conversation in particular stuck with me regarding the hardest project they'd worked on in the last few years. It got me thinking that I should share a few of my most challenging SEO projects, and see if the community had stories they could share, too. I learned a lot in my short chat on the subject, and I'm hopeful that will translate here on the web, too.

Thus, my top 3 "toughest" SEO projects over the last decade were:

1. The "I Just Want PageRank 10"
   It's hard to believe in 2011, but in 2005, Moz really did have a client who's entire goal was increasing toolbar PageRank. He was a very wealthy individual who fretted over his PageRank score in comparison to a rival's organization in the same sphere. We were able to grow it from 6 to 8 with mostly white hat stuff (yes, even I used to dabble with link buying back in the day), but when he continued pressing for a PageRank 9, we gave up and sent him to a link broker. We provided very stern, very aggressive warnings that this could hurt his traffic or even make Google penalize the PageRank score, but he wanted all the options and did end up spending a small fortune on paid links. To my knowledge, the PageRank score never went above 8/10, and of course, since he wasn't doing any keyword targeting to speak of and didn't care about traffic, the value of those links was virtually nil.
   _
2. The "Breaking Out of the Sandbox"
   One of my first few SEO consulting clients, starting in 2003, was a commercial lender in Seattle. I did very old school SEO for them (not knowing any better, and really learning the practice as I went along), jamming anchor text and links wherever I could. Unfortunately, this was right around the time of Google's "sandbox effect," which a Googler explained to me once as "an artifact of something else we created." For nearly 18 months, I fought against the sandbox, earning #1 rankings for nearly every term in MSN search and Yahoo! (which, at the time, had much more significant market share), but page 10+ on Google. Then, suddenly, one morning, we were #1 across the board in Google, along with a number of other sites that also "popped out." One odd element of the sandbox was that Google seemed to release sites en masse, similar to the Panda updates this year. We celebrated heavily, the company started getting customers and over the next few years, we paid off a lot of nasty debt.
   
   But, I remember most that every day and every night, I did virtually nothing but crawl the web (manually - there weren't any tools like OSE or Link Intersect) and try to find link opportunities of any kind. I hadn't really discover the power of inbound marketing, and the social web was nearly non-existant outside of blogs + forums, which I used heavily. Walk to work. Build links. Walk home. Think about other places to get links. Eat dinner in a crappy, old 500 sq ft. apt. with Geraldine. Build links until 2am. Get up. Do it again. I sometimes wonder if we hadn't broken out whether I'd have career at all today.
    
3. The "Linkbait that Brings Customers"
   Later in my career - around 2007 - we had a client that wanted to invest heavily in linkbait, but wasn't quite sold on how the process worked. To be fair, neither were we. We'd seen plenty of examples of linkbait being very successful in driving links, which then drove great search rankings and more high quality traffic (vs. the typically more high-bounce-rate visits to linkbait pieces) and on occasion, we'd had success with a linkbait piece that did get email addresses or trials of a product. But, this was in the housing/real estate field, and those consumers are very research-heavy. It's hard to get a first-time visitor from any channel to fill out an application or leadgen form in that world, but this was the project, so we executed the best we could.
   
   Needless to say, it failed. Of 3 linkbait content attempts I recall, 2 generated some decent links and 1 was a real success, but only from a links perspective. The customers never appeared, and the client left, unsatisfied. If I recall properly, we refunded half of the cost and lost money on the deal overall (we hadn't charged enough in the first place, honestly), but wanted to preserve a positive relationship. Lesson learned - create realistic expectations and don't agree to a project that goes against the laws of marketing.

Of course, there have been (and still are, though I only provide consulting pro bono and through Q+A, now) plenty of other big challenges, but these ones stand out in my mind. I also asked some folks on Twitter and Google+ and received some terrific responses, highlighted below:

You can read the Google+ thread here and see Twitter replies here (at least for the next hour or two). I'd love to continue the conversation and the sharing in the comments. I'm flying back to Seattle tomorrow, but will try to be in the comments. I've also got a post coming tomorrow AM on a new Linkscape update.