I Don't Know Where I Want To Be In 5 Years
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Hi Whoopidoo! Your name reminds me of a bird I had growing up named Poopidoo!
First of all, what do you mean when you say you hate the digital side of things? Digital art? Social media? Having to photograph or scan your own work? If it's just digital art you're referring to, then I don't think you have to worry too much. There are still a ton of illustrators who work traditionally.
Second of all, I'll offer some unqualified advice. lol Hopefully one of the instructors will jump in eventually though.
Personally, I don't think you need all the answers from the get go and you can just start with what you do know. You know you want to be a full time, self employed artist. You know you like to work in traditional mediums, you are drawn to art that explores darker themes, and you are interested in illustration. You know that there are certain things all professional artists need, regardless of their industry- they need a portfolio/body of work and they need exposure. I think that's probably enough to start with.
Instead of thinking of it as "This is exactly what I'll be doing in 5 years, and this is how my art will look like", it might be more helpful to think of it as a 5 year action plan to a main overarching goal. You can work backwards from your main goal (being a full time artist), with your 5 year timeline in mind, using your artistic tendencies as a guideline to make a plan.
What about the things that you don't know yet and still have to discover, like where you fit into the industry with your dark stuff? Well, you can put that research and discovery into your 5 year timeline. Make actionable steps that will get you the answers you need to your questions. Maybe you can devote a certain amount of your 5 year timeline to researching the industry. Maybe you can devote a certain amount of your timeline to studying a few different artists. Maybe you can devote a certain amount of your timeline to making an experimental portfolio. It's up to you and what will serve you best.
Luckily in the 3 Point Perspective podcast notes for episode 2, they have a good examples of what things to put into action. Notice that career and artist exploration are in the first 2 phases of their 3 phase plan, and that they say phase 1 could take 1-3 years.
Anyway, hope that helps! I'm in a similar place as you! I want to find my place and where I fit in. Right now I'm just trying to make some personal pieces, working on some skills, and seeing where it takes me. Wishing you the best of luck!
Website: www.tessawrathall.com
Instagram: www.instagram.com/tessawrathall_art/
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Thank you @tessaw some really good points there. I did start doing the 9 grid yesterday thinking that would be the easy place to start and it would take me half hour max. Wrong! I could only think of 4 modern illustrators close to the style I am hoping I am in or would like to be near and it took me all day to fill that grid! I couldn't believe it - I thought I knew loads of illustrators but turns out they are mostly the older ones from my childhood! So that was a really good exercise and I think it's going to be helpful to repeat it every few months to see how I progress.
Working backwards is a perfect way to think about this.
You made me laugh with the poopidoo! Wishing you the best of luck too
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@tessaw Oh I forgot to say - it's the digital art I'm struggling with. I was told by one of the young 'uns at uni that ALL students know photoshop. Um, no most of us older ones don't and we feel like we are holding that class back with our hands permanently in the air. I will definitely check out that Will Terry class before I go back to uni - thanks @Jason-Bowen Hopefully something will click. I just can't seem to keep it in my head. It frustrates me so much.
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@eli The pre-degree course ruined Fine Art for me. We did rotations and the FA rotation was all cardboard box sculptures and video installations. Trouble is I do feel like I have one foot in illustration and one foot in somewhere else - maybe fine art after all, or craft? Or all of them.
I'm loving that people are relating though - I'm glad I stopped lurking on here and started talking - it's been such a help already. And thank you. That's what I'm hoping. I was a weird dark kid, I don't believe they just disappeared.
Carmen Wing
https://www.instagram.com/whoopidoo.ings -
Phototshop is hard! I've had the benefit of working with it slowly through the years since I was 13 or so (now I'm almost 35) and I can't imagine if I had to start learning it from scratch today. I think even now, I probably know less than 10% of it's capabilities. Lol.
What are the 4 illustrators you included? If we made another post on here, asking for artist recommendations similar to what you're looking for, we may discover more modern illustrators that would work for you.
Website: www.tessawrathall.com
Instagram: www.instagram.com/tessawrathall_art/
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@whoopidoo "The pre-degree course ruined Fine Art for me. We did rotations and the FA rotation was all cardboard box sculptures and video installations." UGH! That would be a NO for me also, LOL. I didn't go to art school so I was spared that sort of thing. I just like the freedom of fine art. Illustration is a lot more challenging for me, but that isn't a bad thing. I feel like I've got feet all over the place (which seems like I've got an unnatural number of feet, haha)
Nowadays, it is cool to be weird, dark, nerdy, etc., but when I was a kid it wasn't. It was just lonely and frustrating. I think it's great, all the fun quirky stuff that is available now!
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@whoopidoo If your topics are dark don't force yourself to be all fluffy and cutie.
Be dark 
Photoshop is frightening at first. I hated it when I first used it and tried to avoid it for a while. But once you understand the dry foundation you will love it. It gets intuitive after a while. You don't need to know all the functions to work in it.
Also a good introduction to digital is an iPad with an apple pencil. The iPad drawing/painting apps are super simple to use and geared towards artist.
As for what you'd like to do, try simplifying your goals to one or two most important things. The others that are not that important will just take away time from your main goals. But I am struggling with the same thing of not knowing where to go.
Good luck -
Thanks @tessaw sorry for my slow replies - I don't seem to be getting the email notifications. The four that came to me straight away were Dave McKean, Chris Riddell, Amelie Flechais and Shaun Tan. By the end of the day I had added Oliver Jeffers, Emily Hughes, Man Arenas and Charles Vess. I also had Wolf Erlbruch but no space.
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Thanks @nasvikdraws I must admit it is helpful to know others are in the same situation, so often you see on social media that people seem to have it all sussed out. Is the only way to have Photoshop at home the monthly pay thing? It's so expensive.
I have to thank everyone on this post - you are right, I definitely need to break things down into bitesize chunks and hope that will make a bigger sense of the whole thing.
And thank you - I have tried to be cute and fluffy... it all went a bit sinister
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@eli I must admit I do sometimes wonder if I'm doing the right thing or if I would be better finding my way through doing courses like on here (I'm hoping to try and mage my time better this term and do both) But now that I've started I want my kids to see you are never to old and that I can see things through... plus I do get to use all their equipment and I do enjoy it but I am more confused than when I started. I know what you mean though - octopus feet
