Don't worry about segmenting the list at first, and don't worry about people being angry about email. They will either just delete it, or unsubscribe. If you ha

Don't worry about segmenting the list at first, and don't worry about people being angry about email. They will either just delete it, or unsubscribe. If you have ideas for three checkboxes, that means you have ideas for at least three email topics/categories! Don't waste these as filters; use them to send more email to keep your list interested. There may be some value to the checkboxes, in that they offer a preview of what's available to subscribers. For example the OP's checkbox "Mastering Your Finances/Cash Flow" is a nice teaser. But you could easily just make this a bulleted list for the same benefit.