The thing that's been holding me back is fear: Is what I say relevant? Does an article I publish justify the time I'm expecting someone else to take to read it? Am I just adding more content (and noise) to a world that has too much of it already?
Once you've found/signed up the first (say) 100 subscribers to your list, it's much easier to grow that list (with new content and products), because you have a foundation from where at least some of those subscribers will help you out.
Most achievements are accomplished after applying a level of persistence and diligence that will seem alien to the majority of the people you know.
Exiting from WooThemes meant that I had achieved financial security for my family. The caveat to that is that we would still have to be smart about the way we use/invest our money and that we'd need to generate (new) income for the foreseeable future.
The two things that I've always associated with strong (and successful) individuals is their ability to be decisive and take action.