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Do I have to follow the Widow’s Guidebook in order?

Your goal is to address each and every checklist in the guidebook.  It is best to work through the guidebook as it was written, as there is a natural flow to the topics.  However, if it makes sense for you to jump ahead to address a “hot topic,” then do so.  Just make sure that you keep track of what you “jumped over” so you can go back and address those topics and checklists.
Remember, most widows don’t know what they don’t know.  They may think they only have one or two questions, but you will usually uncover many other issues they didn’t even know needed to be dealt with simply by working through each of the checklists.