No, not that first time (well, not exclusively).
Think about the first time you did something that scared the hell out of you. For me, the best example is the first time I set out to ride a rollercoaster and actually enjoy it. Before, the tiny number of times I'd been on coasters were all profanity-laced panic-attack-like attempts to assert my masculinity. This time, however, I decided to seize my fear and enjoy the ride. It worked- that summer, and the two years thereafter, I bought a season pass to the local theme park and racked up literally hundreds of out-and-back trips, and I made a couple of special trips to other theme parks to hit THEIR coasters, too. Something that had been previously unimaginable became a source of tremendous enjoyment to me.
What about the first time you used a tool you'd never used before? I was terrified of the vertical milling machine until the first project I used it for; now I can't imagine NOT having access to it.
Or the first time you used a skill? What spurred this post was my maker's notebook project. I'd considered doing something like that for a very long time, but never did. Now that I've done it, a whole new world of possibilities is opened up. I used some hot glue to repair an engineering notepad that had lost its cardboard backing this morning, basically using the same process I used for the maker's notebook. I'm starting to collect scrap paper (all those orphan printouts from around the printer, for starters) to make future pads. It's too easy NOT to do that, now that the skill is in my stable.
My point is, never underestimate the power of doing something once. Whether you're scared to do it, or think it'll take too long, or think it'll be too hard, you have nothing to lose by giving it a shot. If you succeed, even partially, the second, third, and fiftieth times will come almost without thought.