DWYSYWD , or why I'm still working for Corporate America

As most of you know, I've been trying to quit my corporate job for over a month now. When I spoke to my boss at the end of February, I had 3 things that I wanted to complete to ensure that the role would transition nicely to the next person. There were 2 very involved projects that were late in the "work" stages of the process. The remaining component was just a pure job transfer piece - making sure that the new person had the files and the introductions needed to work well.

Now, since I'm planning to work on our business, and probably start our next business, write a book and do whatever else interests me, I don't have a hard end date for leaving my job. And since my boss knows that I know that he is in a tough position - understaffed and having trouble finding qualified folks - he is asking, very nicely, that I stay and cover a few things for him after I finish my current role.

And that is where we get into DWYSYWD. That acronym is familiar to most in my line of work - be they business/strategy consultants, process improvement people, or Six Sigma people - as well as just about anyone who has ever been involved in business compliance audits. It means Do What You Say You Will Do. And it is how I prefer to work. So, when I told my boss that I would help him out until "the end of June or until I can't manage it anymore", I intend to make it until the end of June.

Now, to complete the transition(s) that I would like to finish before I go at the end of June, my boss has to do several things: Craft and publish a few e-mails, interview a bunch of candidates (for 2 roles now, since I'll be covering a different role in the interim) and hire/transfer 2 employees. But, based on the fact that the first e-mail took 5 weeks to draft and still hasn't been sent out, I'm starting to wonder if we really will make the end of June deadline. In other words, unless something changes, there is a good chance that I WON'T by able to DWISIWD by the end of June.

So, here is my question to you: how have you handled this? I've done some managing of my manager - nothing fierce yet, though that is where I'm heading with him tomorrow - but he has, quite frankly, been far too overwhelmed to be responsive to even written requests. In my head, I'm drawing the line at June. But I do have some concerns about how to get the boss there from here....