Is it right to start with simple tasks?

Question

Work organization

Let's say you're working on a project.
There is a place where you come to a dead end and cannot move forward, while there are many more small and medium tasks that are not so difficult, but which take time.
Is it right to do simple tasks at first and gradually move on to complex ones? It seems to me that this is logical, since an attempt to break through the “wall” with your forehead can result in the fact that when the “wall” is broken, there will still be a lot of tasks left. On the other hand, somewhere I met that, on the contrary, it is necessary to start from the most difficult.
In what direction to think? Interested in your opinion.)

Answer 1

A couple of considerations
1. Switching to another in case of plugging, in principle, is useful.
Then there will be a fresh look at the problem, or the solution will come by itself (while eating , driving, in the shower, etc) will be broken, there will still be a lot of tasks. - I’m very disgusted at the conditional 20 pm after a difficult or dreary task to do a trifle instead of a well-deserved rest.

Answer 2

There is a place where you come to a dead end

Don't take orders that you can't afford.
Otherwise, the complexity of tasks just takes a certain amount of time + bureaucracy.