> I'll quit my CTO position in a few months to become a Freelancer
I'd suggest that you should consider a transition from FTE to freelancing over some (fixed?) amount of time vs. a quick change.
Depending on who your prospective buyer is, I would also reconsider using the "freelancer" title. I equate freelancer with the quick, sub-$1000 jobs that are advertised on various "gig" sites. That's not really a pool you want to swim in as it artificially constrains your rate ceiling.
Rightfully said, I transitioned from Upwork/Guru to solely Fiverr & get incoming requests on a daily basis around my niche, been earning twice of what I earned previously doing even less work. Went from service to product basically.
As unfortunate as it is my experience resonates with that advice. Move to the mindset and business practices of a consultant and you won't need sites like UpWork. It is a good source for temp work but it is a totally different market to consultancy. At least that was my experience.
I'd suggest that you should consider a transition from FTE to freelancing over some (fixed?) amount of time vs. a quick change.
Depending on who your prospective buyer is, I would also reconsider using the "freelancer" title. I equate freelancer with the quick, sub-$1000 jobs that are advertised on various "gig" sites. That's not really a pool you want to swim in as it artificially constrains your rate ceiling.