When you roll out for vacation for couple of weeks – you can plan everything on your way. Stick to this plan, ride as it describes (though I don’t like planning actually).
When you preparing for overland journey – there is no sense in planning. Some drafts, key waypoints, approximate directions – that’s all. You can’t predict future.

You can disassemble your bike till the last bolt and nut, you can get all that fancy brand new quipment gear, you can surround yourself with gadgets, maps, routes – but all of this actions will lose it sense sooner or later. Sooner or later everything can happens. Broken motorcycle, worn out gear, failed gadget. It may happens in comfortable circumstances. Or it may not. No matter of your plans. Therefore the more you spent on preparations…the less you spend on preparations. Exceptions are only with paper works – sometime you need to sit tight and do some calculations\filling\formalizations etc.

But what is get some serious pressure – your nerves. A lot of bustle, dealings, thoughts, stresses. A step from your own comfortable world into total strangeness… It bothers. I can’t remember when I’ve had last deep sleep.