It /does/ go away if I add the headline. So I think you're saying:

1. Plain list checkbox items cannot have a time-estimate associated them.
2. Plain list checkbox items cannot track time.
3. Only headlines/TODO headlines can have these features.

I suppose that a TODO headline is effectively a checkbox; it would be nice, though, to be able to time separate checkboxes (though I suspect that responsibility would lay upon me to edit the appropriate org-mode file <grin>).

Thanks for the clarification Nick.

Avery 

On Thursday, June 7, 2012 at 10:14 AM, Nick Dokos wrote:

> Avery Chan <avery+gmane@ootbdev.com (mailto:avery+gmane@ootbdev.com)> wrote:
> 
> > I have a plain list with checkboxes. I am trying to set a clock in time using
> > `C-c C-x C-i`. This emits this type of an error:
> > 
> > byte-code: Before first headline at position 30 in buffer TODO.org (http://TODO.org)
> > 
> > Here is the text of my org file:
> > 
> > ---START FILE---
> > - [ ] Clean upstairs windows
> > - [ ] Lunch with Taylor
> > ---END FILE---
> > 
> > How do I get the clock to start timing?
> > 
> > I get a similar error when I use `C-c C-x e` to set a time estimate.
> > 
> > org-mode version: 7.8.09
> > emacs version: 24.0.92.1
> > MacOS X 10.7.4
> > 
> 
> 
> Does it go away if you add a headline?
> 
> ---START FILE---
> * Tasks for clocking
> - [ ] Clean upstairs windows
> - [ ] Lunch with Taylor
> ---END FILE---
> 
> Nick