I love what everyone has posted here so far! Here is my day 1 submission, I think I should have taken my time on the boat bit, it seems to draw the eye more than I anticipated. This was based off a character I had in mind a month or two ago, who inherited some bracers that allow him to take down monsters. Could today be the exception?!

Here is my day 2. It's weird how you think it looks great when you are doing it then after relooking at it this morning I was like 'AHHH' so many things I should have done different before I inked. Oh well, I guess there is always tomorrow. This is a continuation from yesterday's little drawing.

Day 4: My daughter and her balloon

Lessons learned: Don't put too much texture on a background item, detracts focus from what I wanted.
Learn composition
Figure out how to indicate reflectiveness on shiny objects
Get better on environments

Day 7 and 8 since I started yesterday but didn't get to finish. I have been wanting to draw this guy for a while. I hope I did him justice.

Thank you guys so much for the feedback. Here is the newest update with some of the revisions that I made. Fixed his hand and the angle his arm was and flipped the mouth to what it should have been. (Should have listened to my wife when she told me that the first time haha) I also tried to darken the shadows a bit.

You are definitely not alone, when starting something new I almost always feel that way like I forgot everything I've learned. Some of the things that help me are:

1. Watch some youtube videos of people I find inspiring
2. Study something I'm weak at so that I am at least bettering my craft
3. Copy another artists work to see how they identify forms and create character
4. What I find myself doing a lot is doodling in my sketchpad and creating faces of people, this usually helps me relax and unwind so that I can think about what I would like to work on or what project I could create next.

I wasn't planning on participating in the month's third Thursday, but I did use the prompt to help me practice something I had not drawn before and start designing a character based off it. I did these at work over my lunch period so I apologize for the shoddy lighting in the photos.

My day 3 drawing for Inktober

Day 5: Lessons learned- Need to work on 'Feathering'
Step away from drawing to see what is not adding up

Not terribly happy with this one but here it is. I used the Sketchbite App to come up with the idea since I was running low and the prompt was : A teen boy skateboarding but also bringing home an overloaded bag of groceries ( make it halloween themed if you would like)

Thanks @javier-diaz the draw over makes more sense. I was trying to go for a more dynamic pose like this but even with that I don't have that line of action correct. I definitely agree I need to make it more readable. The hand makes a lot more sense as well seeing it the way you did. I will keep reworking this and post the update when I get a chance.

One thing that helped me here in Omaha was to create a Meetup on meetup.com. It costs like 15 a month to create/host the group but once you get a steady group of people, like we did, we essentially moved it to a facebook group. I created one for digital artists (was thinking production pipeline type stuff) and we ended up having 110+ members with about 15-20 that show up on a consistent basis. Maybe that would help some.

Day 7 and 8 since I started yesterday but didn't get to finish. I have been wanting to draw this guy for a while. I hope I did him justice.

Day 5: Lessons learned- Need to work on 'Feathering'
Step away from drawing to see what is not adding up

Not terribly happy with this one but here it is. I used the Sketchbite App to come up with the idea since I was running low and the prompt was : A teen boy skateboarding but also bringing home an overloaded bag of groceries ( make it halloween themed if you would like)

Day 4: My daughter and her balloon

Lessons learned: Don't put too much texture on a background item, detracts focus from what I wanted.
Learn composition
Figure out how to indicate reflectiveness on shiny objects
Get better on environments

My day 3 drawing for Inktober

I just wanted to throw this out there and ask, since it is something I've been thinking about a lot lately and since there are many freelance illustrators working professionals on the the site I thought this would be a good place for it. The question I want to ask is how did you all know you were ready to take that chance and put yourself and artwork out there to attract clients/customers? I feel that there is so much that I need to work on to get 'good enough' and that I should put off showcasing my attempts until I get better. Did you all feel that way before taking the leap or do you, possibly, still feel that way after taking it? Just wanted to know peoples thoughts and stories on how or when they made that transition.

Here is my day 2. It's weird how you think it looks great when you are doing it then after relooking at it this morning I was like 'AHHH' so many things I should have done different before I inked. Oh well, I guess there is always tomorrow. This is a continuation from yesterday's little drawing.

Thank you @Ace-Connell . I'm hoping to work on some things that I've had floating in my head for a while, I wish I could come up with some cohesive story like Jake seems to do every year.

I love what everyone has posted here so far! Here is my day 1 submission, I think I should have taken my time on the boat bit, it seems to draw the eye more than I anticipated. This was based off a character I had in mind a month or two ago, who inherited some bracers that allow him to take down monsters. Could today be the exception?!

I wasn't planning on participating in the month's third Thursday, but I did use the prompt to help me practice something I had not drawn before and start designing a character based off it. I did these at work over my lunch period so I apologize for the shoddy lighting in the photos.