Beginner Knowing what’s ‘right’

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After some advice if possible. I’ve been photographing and editing for some time and am capable in photoshop and Lightroom from a practical standpoint. However, mostly that’s just been for touching up personal photos. Looking to improve now and find myself asking (a lot) ‘but how should it look?’.
Example, on a whim I took a quick b&w shot of my son in the garden. Out of camera I quite like it even though the shadows have limited detail. Shooting raw I can recover the detail but I lose something of the sense of the moment, I.e. the strength of the sun and brightness of the day.
 

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The bit that can't be taught is how YOU want it to look. Myself I would have binned it as I hate the shadows.. Other will Love it! .. You can't teach what looks right to someone :)
 
After five and a half decades of photography I still remember the advice of a German emigrant press photographer who told me"There's no right and wrong; only the picture which the customer likes".

If the customer is you, then you only have the problem of deciding what you like and carrying on from there.
 
Out of camera I quite like it even though the shadows have limited detail. Shooting raw I can recover the detail but I lose something of the sense of the moment, I.e. the strength of the sun and brightness of the day.
This kinda answers your question IMO. *You* quite like it even with its admitted faults.

Shooting in bright sun can be tricky because most people squint against the glare. Think less about the camera and more about the moment. A pair of crooked shades, or a cheeky grin, or moving under the shade of a tree to get less harsh shadows... But I can only tell you what I might do under those circumstances.

It's very easy to get into the "shadows and highlights are bad" frame of mind, but as said above - all that matters is what you like.
 
As has been said above, to some extent it depends on who or what it is for. I find it is helpful to come back to a photo after a few weeks or months and see what I think about it and given that Lightroom allows for virtual copies it is quite easy to start from scratch without loosing an earlier edit and then compare.
 
It’s fascinating isn’t it? I really like shadow in general, depending on what I’m shooting. That’s what I love about a ‘proper’ camera, you tend to be able to catch deeper shadows and higher contrast.
 
Keep both :D

I have multiple copies of pictures.
 
From my point of view on your photo of your son. It looks like you've globally lifted the shadows. I personally would have used the brush tool in lightroom set to 25% flow (this gives a bit more control, the more you brush over the same area, the more effect it has), set the shadows slider to something like +50-60 and just lifted the shadows on the face and shoulder. The dark Shadows in the background help to isolate the main subject, so I wouldn't want to lift those.
 
From my point of view on your photo of your son. It looks like you've globally lifted the shadows. I personally would have used the brush tool in lightroom set to 25% flow (this gives a bit more control, the more you brush over the same area, the more effect it has), set the shadows slider to something like +50-60 and just lifted the shadows on the face and shoulder. The dark Shadows in the background help to isolate the main subject, so I wouldn't want to lift those.

You’re right in this case it’s a global edit. This was just a phone edit and I thought it a suitable example, but I get to the point with almost every photo, where I’m wondering whether I’m improving the photo or not. I’ll try what you suggested on the picture as soon as I get a few minutes on the laptop.
 
Personally I don't like either but that is just my personal view.
I would try shooting your son with the sun behind him and expose for his face - then see if you like that kind of shot.
But as always when shooting anything but especially children, it's what the photo gives YOU - the remembrance of a particular moment in time.
I have many photos of children of my own family which technically are pretty rubbish and would be torn to pieces by quite a lot of people on here but I love them because they recall a particular moment in time which is special to me.
 
It's personal. Here, you've chosen contrasty lighting for a portrait!

And it's a delightful portrait. But as it stands, his eyes in particular - usually the focal point of a portrait - are shadowed. That's the catch.

There are various software-based remedies that help to address tonal distribution, but if you start to tweak it you have to be careful of over-egging it enough for it to look artificial in any way, since the hallmark of this kind of shot, and what contributes to its integrity, is its naturalness,

So play around by all means, but tread carefully. Use the radial filter and adjustment brush as well as global adjustments in LR, for instance. But don't spend over-long at it, life itself is more important.

There are judgements to be made about where shadows can be dark and detail lost within an overall scheme. The holy grail is not to reveal everything, but to reveal something important, whilst striking a balance.

Keep the light in mind, and take lots and lots of pictures - keep trucking!
 
Thanks for the replies guys. I’ve done another edit this morning, again only very quick but tried to just bring out the detail in the subject and leave the background in shadow.
Of course, I could just as easily in this example stage a portrait and get something much better straight out the camera. Just thought it was a good example of a shot that could be improved but where I struggle to know what is ‘best’.
 

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After some advice if possible. I’ve been photographing and editing for some time and am capable in photoshop and Lightroom from a practical standpoint. However, mostly that’s just been for touching up personal photos. Looking to improve now and find myself asking (a lot) ‘but how should it look?’.
Example, on a whim I took a quick b&w shot of my son in the garden. Out of camera I quite like it even though the shadows have limited detail. Shooting raw I can recover the detail but I lose something of the sense of the moment, I.e. the strength of the sun and brightness of the day.
What you are asking is the definiton of right, define right and you have the answer.
 
editing is the second half of the art of digital photography. There's no simple answer that can tell you how to create an appealing image. Taking black level as an example, some people lift their blacks to give a nostalgic 'filmic' look (a common instagram filter, but I've also seen wedding photographers do it) whereas other people prefer a more natural, richer look look with crushed blacks. It comes down to experience, and looking critically at lots of other people's work. part of experience though, is knowing that's it's quite hard to get good images in harsh sunlight!
 
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