Wouldn’t it be awesome if every time you hit the trails every thing went according to plan? You never got stuck, nothing breaks, all terrain is conquerable in all conditions….nice fantasy.
I always plan for the worst case scenario and hope for the best. Yes, this seems stupid. Just do it and be nice to your future self.
These articles should help you get started.
https://www.outsideonline.com/2135366/how-plan-road-adventure-your-4×4
https://www.outsideonline.com/2161106/10-essential-tools-roading
https://www.overlandjournal.com/the-basic-overland-gear-everyone-should-have/
https://www.popularmechanics.com/adventure/outdoor-gear/g2918/overlanding-essentials/
Other things that I consider indispensable to have on your overlanding rig:
Disclaimer: yes, these are affiliate links, but it’s the easiest way to link to the products I use, for you.