I’m going to be blunt here. 🙂
Every form of value that you offer to the general public for free should require an opt-in to your email list in exchange for that value or should point to a larger amount of value that’s behind an opt-in.
If someone ends up on for your email list for any reason (ex: they signed up to attend a webinar), you should email them regularly with valuable stuff combined with regular invitations to move up your “ladder of value”. You should do this forever or until they unsubscribe.
The first few weeks or months of doing this will make you feel like a spammer. That’s normal; get over that feeling by pushing through it as soon as possible.
You will underestimate the value of your expertise and chronically under-communicate with your list at first. That’s normal; get over that feeling by getting in the habit of telling your list about everything you do that has potential value. Ex: write a new blog post? Send an email about it to your list. Ex: release a new podcast episode? Send two emails about it to your list. Ex: have an interesting interaction with a client? Tell your list a story about it.
You will very likely fear angering, alienating, or offending members of your list. Remember that inert substances don’t repel other substances, but they don’t attract anything either! Allow yourself to incrementally become more bold in emailing your list. Set a goal of doing 1 thing that scares you a little bit each month with your list. The two things you actually should fear are neglecting your list and boring your list.
You will likely fear ever sending something even slightly redundant to your list. Don’t. You are at the apex of your “content panopticon” and can see every piece of content you create but your list members are very selectively scanning for signals that your content is valuable to them. That means that only a subset of your content gets noticed, even by people on your email list. Don’t be afraid to re-use content if it helps you regularly communicate with your list. Repetition is a signal of value, so don’t be afraid to be repetitive about the important things.