Amateur painter, hit a road block on my design

First off, I do have some painting knowledge, but mainly with making non-shaded/vector style paints. I decided to start a new paint a few hours ago, and here is what I am up to (Fullsize here).

WIP

The only issue is, here is the source photo I am using.

Source Photo

…I don’t even know where to start with this. Normally, I start with making the border of more complex objects, then fill it in from there. Should I do the same thing with this? I have also had issues with using gradients in the past, which I know I will have to use here, as they seem to look bad if they overlap anywhere. I also know that my text is slightly off, especially the C, but I did make it without the default text so I should be able to alter it. If you have any advice, please leave it here, I am open to any kind of criticism as long as it helps me with painting.

yes you should start really simple and do what you know. either it will work or you will figure out a way to make it work and that is how you grow and get better in the editor.
ive been working on a little tutorial for 3d type shading. just keep banging at it. to shade anything you have to understand light source and direction otherwise you may be fighting a losing battle. start simple start simple start simple.

another little tip and this goes out to the world. print you image of on a piece of paper, grab some tracing paper and trace the image. then tape that to the TV. and then use that to either outline or block in the shapes of his shirt,face ,etc. its just a lot easier to get your proportions close. some may say its cheating…and id be more than happy to let anyone use on of mine and then fill it in just to see how “cheating” it is.
or you can use the grid which also works well for some people. try and do it flat with zero gradients etc more of the cell shaded type look and see what that does for ya. and then just work from there.

Keep at it…it does get easier as you learn what little tricks work for you and what dont

“Cheating”, I just found this a little funny. Cheating in this case is extremely subjective at best. An old “trick” also used for countless times in industry before computers was the use of a simple overhead projector. This was pretty much standard for recreating quick media (time is money). I dont know how well an overhead would work against a tv though?

Another “trick” I discovered was to use the XB1 Snap with your subject matter from the internet while working. This works great as seeing as you can group everything, move, compare, even under/ overlap while Snap/ IE is open.

Why work hard when one can work smart.

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i find that “cheating” saves me so much time trying to shape things and get the proportions correct. saves me time i could be enjoying the paint instead of struggling to get the image right. not to mention i do this for fun…not a paycheck. so i need to prove nothing to anyone…just make paints people like

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Nicely said Mimic, and the tip from LostKauz is quite a good idea, I didn’t think of using xbox snap feature… As to the original question, mimic pretty much covered it, start small and you will learn new ways techniques, you will start to get frustrated and lose interest in painting if you try something too difficult. Keep practicing, we all started somewhere and always learning.