I create highly technical videos about various topics of IT security. Many of my videos are walk-throughs of CTF challenges explaining my thought process. I think this playlist could be interesting: https://www.youtube.com/playlist?list=PLhixgUqwRTjywPzsTYz28...

I have also recently started a series on Pwn Adventure 3, where we are hacking a game and I explain my process: https://www.youtube.com/playlist?list=PLhixgUqwRTjzzBeFSHXrw...

Besides that, I can also really recommend livestreams/screenshares from the following creators. To me, seeing how somebody really does it and where they struggle, really really helped me break through a wall I was hitting:

+ ippsec: https://www.youtube.com/channel/UCa6eh7gCkpPo5XXUDfygQQA

+ John Hammond: https://www.youtube.com/user/RootOfTheNull

+ Gynvael EN: https://www.youtube.com/user/GynvaelEN

+ Derek Rook: https://www.youtube.com/channel/UCMACXuWd2w6_IEGog744UaA

+ ...