I've been on a quest for digital independence for almost five years now, and only recently achieved my goal thanks in part to paying off my debts in a debt avalanche.
The idea at the time was that we'd build up our websites to the point that we could sustain them as a full-time business. And while I was able to do that for myself in the time-frame, we're still on our way to working to that point for her.
Since that fateful conversation, the Financial Independence Retire Early (or FIRE) movement has taken off. Although it sounds like our story would be a case study for this philosophy, I really have to say the idea of it is, to put it bluntly, absurd.