do you cringe at your own legacy photos taken

I have just been looking through some of my old stuff, trying to see what I have got that's half decent..
Shadows, not even a tad of DOF, lighting cr4p, alsorts of things in the background.. Just all wrong !!

Any one else.. ( I know we all have to learn and we're beginners at some point!! but, still !!)........

You're not alone. I do it frequently. I start to get disheartened and then I look at how I would have approached the shot differently, used a different setting, recomposed. Then I start to feel good that I'm getting better and that I can at least see the mistakes I've made and this can only make me better. It would be far worse to look back and not see mistakes and keep on making them!

A timely thread as I have just been back through the last three years images. I found that the tip top images there were really good then are still really good, some that I did not rate (when looked at with a better developed eye and some judicious post processing) are far better than I thought and.....
...... some REALLY stink, because I did such stupid things. Ridiculous choice of shutter speed, ludicrous aperture etc etc. Just truly badly taken photographs.

We went to Germany and Austria in 2009 and I bought a Panasonic DMC-FZ18 rather than spring for a DSLR. Overall I'm pretty happy with the pics I got, but any nighttime shots have so much noise that I cringe when I see them. When I see what my 6D can do now in low light, I'm amazed. Of course, there was no 6D back in 2009.

fortunately, I didnt stick with point and shoots for very long, only a few months and I was a DSLR shooter.

Unfortunately, I really sucked at it back then, and my brother was much better than me. He has many shots of my kids that are very good, even by today's standards. Good light + any dslr = good combo. I started with fast glass after trying out the kit lens maybe once or twice...... no way the quality of my brother's shots... so I upgraded quick.

gear makes a difference.

Just deleted a couple of hundred images from my web site. I had a bad habit of when being stuck indoors, trying to salvage images that were poor...............mos​t of them salvaged via HDR. Back then (about 4 yrs ago) I thought they looked great, and -placed 'em on my site. Hadn't touched my site for some time due to being busy with flickr and on re-visiting it, I was quite embarassed by most of the HDR images there, so binned the lot. Now I must bin the original RAW's so that I don't get tempted again.

As the proverb goes, "you can't make a silk purse out of a sow's ear"

It's a good learning tool to go back through old shots. Really helps reinforce that (hopefully) the skills are improving and with a more experienced eye, you can recognize those short comings now before you push the button.

Heck, I cringe at the stuff I currently take, nevermind older stuff.

I've been taking snapshots for 50 years. It surprises me when one of them is actually good. Most are just snapshots. I guess the big question really is: So?

I was about to post similar sentiments as EOS5D.

I'll never be a great photographer. Heck, I'll probably never be more that a guy with a nice camera. But when I look at my snapshots, most of the time, I look at them for the memories they evoke.

Could I conjure the same memories with a PnS or even a cheap disposable? Probably, in some cases. However, since I can afford decent gear and enjoy using it, I choose to employ it to produce my crappy shots.

i just ran into some old photos of mine and while the quality isnt up to what I am doing now but I still enjoy looking at them.

I still suck.
Mine have got worse, but that could be the Red Wine.....

Just the opposite. I look at some of my old shots and think, "damn, did I shoot that? That's pretty good." The ones that were bad I just look at as a learning tool and don't associate negativity with them.

Absolutely. Heck, my current stuff is worth a cringe or two.

I'm my own worst critic. I cringe at the stuff I shot years ago. I still am very critical even today looking at photos I did yesterday wondering if the people I shot them for will like them.