How do you decide when to upgrade your gear?

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This question relates to the thought process, technical but also philosophical.

For example, does one start with the current gear they have (say body and lenses) to pursue the photography of interest (wildlife, nature, landscapes, portrait etc)? If you are unable to achieve what you are looking for how do you know its a technology issue and not a lack of skill? Some things are obvious- faster lenses, longer reach etc. For reference, I have no formal photography training, just learning as I go and I enjoy the hobby.

What about camera bodies?

It seems like most people here are shooting with pro level/top end bodies. I'm assuming many here are professionals. For those who are not pros or make money from your photography (a hobbyist) what criteria/reasoning do you use to upgrade? Do you buy the most advanced camera you can afford in hopes that the technology will last the longest? Do you let your wallet decide? Do you always buy the best?

How did you learn when your photography skills were holding you back and when your technology (say sensor resolution or autofocus speed for wildlife) were holding you back? Thanks for sharing.
 
It is mostly greed IMO. Wanting to take shortcuts to better pictures without the pain of failed attempts.
New gear brings instant improvements in technical quality, but the mastering of the scene skills remain same.

Simplified: If one's problem is technical quality it is a case for new equipment. If it is something different, it will not bring the effect.
Corollary: It never hurts to have new toys.

:) So said the Amateur.
 
I started out with Nikon with the D200. Then I moved up to the D7000, D800, D500, and D850. The only one I still have is the D850. Each time I bought a new camera my skill and knowledge regarding equipment and my needs for good wildlife pics improved. I learned that a faster frame per second rate could catch that strategic moment between animals that a slower frame rate might not catch, I learned that the buffer's ability to handle fast shooting on a camera for wildlife was very important, I learned that not all sensors were created equal and many other things along the way. Example: on the way to Africa 12 years ago I bought the D800. I knew it was not billed as a wildlife camera so I decided to take the best portrait shots I could and that worked out fine, but the shutter on that camera is very slow and not good for moving wildlife and eventually I moved on to wildlife in action. For me, it was a learning process all along the way with getting the best shot, the artistic part, and learning about cameras and lenses. I studied all the photography concepts as well as the gear and went to shoot with people much more skilled than me and I took a lot of shots. I moved up step-by-step and, fortunately, had the money to do so. Someone I used to shoot with, during this moving-up process, said to me, "why not buy the best right away because you'll save a lot of money doing that since you're going to buy it anyway." But the truth is the gear improved along the way as I improved and I benefitted from that. Start with what you have, learn about the equipment, learn what a good shot is and how to take it, and then move up as the need arises. Others may have a different opinion. All that really matters is what is your goal and how do you want to get there, for you, and each person is different.
 
I tend to keep gear until there’s something it’s not doing that I feel is holding me back.

If my gear isn’t limiting my photography and I’m happy with its performance I tend to keep it. For instance I’m still shooting a lot of F mount glass on mirrorless bodies. Sure if I had money to burn I’d probably replace some or all of that with native Z mount lenses but I don’t feel my current lenses are holding me back.

Before any new gear purchases I ask myself what problem I’m trying to solve and how I think the new gear will help solve that problem.
 
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