The way to climb a big mountain is to go up the foothills and then come back down, up another foothill, and then back down, up again and down again until you have more confidence in the route of your longer ascent. You learn ad much from a few steps in the wrong (or less than ideal) direction as anything else and certainly learn more that way than just peering at the peak.
And any embarrassingly small step is a step worth taking. Indeed, that is how you get moving.
Following your “shoulds” will almost always leave you dry. But contrast, a faster heart rate, shorter breath, and a little sweat on the skin are what happens physiologically when you're excited and when you are frightened. So . . . follow what excites you and follow your fear too.
It is our failure to become our perceived ideal that ultimately defines us and makes us unique. It’s not easy, but if you accept your misfortune and handle it right, your perceived failure can be a catalyst for profound re-invention.
—From Conan O’Brien speaking at Dartmouth. (Also the funniest commencement address ever. )