I feel like if you're technically savvy enough to have a good reason to be anonymous on the internet, you're hopefully technically savvy enough to not use incognito mode to do so.
There's plenty of reasons non-technically savvy may want to be anonymous:
* Don't want companies building a profile on them
* Writing under a pen name and don't want to accidentally link it to real name
* Researching a topic that might result in peers/society judging them badly
* Want to price shop without companies raising prices because of their browsing (I don't think this happens, but it's a common fear/accusation)
* Activists worried about being spied on
* Person with some suspicious looking connections who doesn't want that to reflect onto them (perhaps you have a cousin that joins a enemy of your country - you didn't do anything but just want to email your family about news without getting on a watch list)
* Doing illegal things and don't want to get caught
In fact I'm kind of struggling to think what reason for anonymity is unique to the technically savvy... pirating?
You should really look Matt Might up. He was an entrepreneur while working on his PhD. While he was a CS professor he had a child who had an extremely rare genetic disorder. He pivoted his entire life and focused all of his energy on learning about his son's condition. Since then he has become the Director of the Hugh Kaul Precision Medicine Institute at the University of Alabama. Hardly a career of "wasted years" of an "entire life in academia".
> In 2012, four-year-old Bertrand Might became the first-ever patient diagnosed with a rare genetic disorder called N-glycanase (NGLY1) deficiency. The discovery of this condition and Bertrand's diagnosis allowed doctors to look for other children with the same genetic defect. Since then, more than 60 additional patients have been found.
> The disease affects every system of the body and is characterized by low muscle tone, seizures, developmental delays, and an inability to produce tears.
> Sadly, Bertrand passed away in October at the age of 12. Although his life was cut short, his legacy will benefit children around the world. Through their website, NGLY1.org, Bertrand's parents collect and share a wealth of research and family stories to help educate and inform the community. As more patients have been identified, it's become apparent that even though the same gene is deactivated in all of them, their symptoms and severity of disease vary widely.