Good analysis! I totally agree with you. The mental cost of saying "I'll do that first step and then decide whether to carry on" turns the inertial difference from a huge wall to a stairway which is easier to climb than the wall although you gain the same height in both cases.
Scott Adams, author of Dilbert, believes that trying to try is more effective than trying:
Regular Less Wrong readers will remember Eliezer Yudkowsky's warning about trying to try:
Adams says the danger of trying is that you will fail in trying, which will bruise your self-esteem and cripple your motivation to try again. Yudkowsky says the danger of trying to try is that you will succeed in trying to try, leaving you too easily satisfied and unmotivated to actually do the thing you were trying to try to do.
Have any readers had success in trying to try?