Ask HN: Freelance or product dev to transition to indie work?

As I and several friends I know look forward over the next five years, many of us see ourselves transitioning away from corporate track careers into independent and self-driven paths. What would HNers recommend as a (financially) wise way to transition into such a track: freelancing in spare time or working on a product in spare time?

For example, I have successfully freelanced in the past and enjoyed it, but there is always the limiting combo of time and hourly or project charges. If marketing and developing a new product the upside is potentially higher, but the build-up is slower and it may be less sure. Eventually I would like to be in the product space so that I'm not restricted by simply the hours I can bill.

Thoughts? I realize much of it may come down to opinion, but there are always unique and insightful opinions shared in the comments.