How I progressed as a photographer is I challenged myself as much as possible. Sometimes baby steps, sometimes giant steps, dependant on how comfortable I felt about the specific challenge. I took reproductive challenges, lighting challenges, both short term and long term goals/projects.
Specifically about reproductive challenges is I was inspired by a specific photo and I attempt to reproduce it as much as possible, sometimes they change slightly because I've added my own touch of style in all factors so its rarely ever exactly 100% reproduced just broadly reproduced. If I do get the exact photo reproduced its nice to have for yourself, but my goal is to learn how to reproduce it and add my own touch of style and personal changes to the photo.
Lighting Challenges... I started off in shooting strobes primarily, which I learned at my college. If I didn't take the course and was purely self-taught as most photographers today I would have done the strobes after learning using only natural/ambient lighting photography. But let me share my experience about lighting, I knew lighting after taking a course fairly well, and shot portraits for about a full year in my studio with strobes only until I was fully comfortable with shooting within a studio environment and strobes. After that year I decided I was ready to move into natural/ambient lighting portraiture and using the environment to add value to my portraits than detract it, more like environmental portraits.
After photographing portraits outdoors for about 9 months straight (to date as of this writing), I still feel its my weaker area of using light than using light in a controlled environment and strobes. As a photographer I personally prefer control as much as possible like up to 90% or more control of the shot (not so much on poses). So shooting outdoors using uncontrolled lighting and other obstacles, this can challenge myself even more in a good way because a great photographer is a great problem solver so being able to improvise on the fly is a huge plus. But, and a big one, chaos like so mentioned, isn't great to have on paid client productions, as I recommend to have everything possible ready such as pre-production and knowing the environment you will be photographing in, if possible. In many cases it's not possible unfortunately so having your improvising photography skills sharp and regularly sharpened (and challenged) will be required when a paying client puts you into a difficult technical situation to your workflow.
Today I intentionally shoot TF to challenge myself with different lighting in the studio and shooting outdoors, using the environments properly to add value, posing direction and themes assignments. As I challenge myself I grow as a photographer, not just my level of skills and talent, but as well my portfolio. Many photographers say, don't be a "stealer" or "copy cat" or etc... on theme assignments, as long as you're shooting you'll be fine. You may get a original and unique theme idea time to time but non-stop, not easy, unless your goal is to only be a fine art photographer then ok, that would make more sense to only be original but concentrate on growing when you're in the early stages as a photographer and still building first level stage portfolio plus finding yourself as photographer such as your style. As many photographers say, JUST KEEP SHOOTING! Don't just wait until you find an original theme idea, sharpen yourself, find yourself first...
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