Don’t get me wrong — I too dream of replacing my 9–5 job with a more flexible, rewarding and meaningful existence. However, short of living in a cheap developing company, it is incredibly hard to do so if you are not young, without student loans, family responsibilities etc. Building up your “hustle” to a reasonably lucrative and sustainable level can take many years — years during which the pace of technological and socio-economic change might render your strategy defunct.
The other issue is the cycle of of learning and relearning which as you correctly point out will be a “struggle.” There is tone of almost joyful fatalism that you and other freelance advocates share. Perhaps it is a necessary tactic to justify not taking the well-trodden path to a conventional day job. My issue with this tone is that when millions start subscribing to this, it deflates any serious conversation society needs to have on what we want the future to look like, to *feel* like for the working person. Will 100 million freelancers require a government provided minimum income? Is it reasonable to expect a 60 year old to learn new skills and be able to compete against a 25 year old in her cognitive prime?