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Does he consciously know how to use fill, rather than the camera just doing it for him?
No he doesn't know how to. He figured out to pop up the flash and got fill light that to him improved the images.
Thank you for the comments.
Personally I'd rather be shooting and building a library of images rather than waiting to buy a camera that I could make use of. But then you probably already have a camera so don't really need anything other than that right now. I'm sure everything will be a different scene in 4 to 5 years.
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I will point out that my feeling is that the technical part of being a creative photographer, is the least important part and with todays gear may be of little importance just as Mason shows me and also my youngest 25 year old son has proven with his abilities to take impressively inspiring images (many paid commissions) without having any ability or interest in learning anything other than how to turn the camera on and use the Auto settings. Of course I have 30 years of experience with exposure and lighting and focusing - a majority of those years using medium and large format manual cameras and studio lighting, although I made good use of any automation I had with my RZ67 AE prism finder and 35mm Olympus film cameras and Metz and Vivitar flashes - - - and since moving to AF cameras 7 or 8 years ago and then DSLR's, I depend almost 100% on the automation that camera companies have poured millions of dollars into refining - that requires nothing more that setting the button properly and shooting. My cameras do almost everything for me on every job - except deal with the subject, compose, determine the best light and direction, organize crop clean up and post process the images, print the images.
What to me is impressive with these images and many others over the years that Mason has taken - is the way he is able to get great responses out of people, his being in tight with very good composition in so many, and the way he confidently handles the cameras and like with video games figures out what camera buttons get him what he needs in a very short period of time without any instruction. But then again, those are characteristics that I look for in photography while with others technical quality and ability are paramount. On the other hand, every day I see a ton of images on photography forums and photographers websites - even pro ones - that show poor to terrible results - - - all while shooting in Manual for purity sake or because they have been told that that is essential to being a successful photographer.