Another side of the coin is at $100/week that's $5k a year. What if you 'worked on your career' and got a $5k raise? Do that once and that $5k will be there every year from that point on.
I guess that was just a long winded way of saying: I understand where this is coming from, but in some situations the logical next step may actually be a side gig :-).
I'd recommend you try side gigs. Pick the one that offers you the best learning experience. Then consider trying consulting full time. If you want to break the wage ceiling, consulting is a great low-risk business.
A side benefit is that the more marketable skills you have, the easier/faster it is to get another job if you get laid off. My quickest time between looking for a job and getting an offer has been 4 days.