I'm a big proponent of the quantum leap approach. If you are at "A", and want to get to "D", you can either go through "B" and "C", or you can go directly to "D". Examples:

A. Group rides: You can gradually move up from slower to faster, or you can jump in with the big dogs, get dropped repeatedly, but progress quickly until you can hang with them.

B. Fit considerations: You can either gradually remove those spacers under your stem, avoiding any discomfort, or you can just slam it to the headset, and work through the discomfort until it feels fine.

I typically prefer the quantum approach. I start doing what it is I want to do, and keep trying until it works out.