There is certainly no "right" way to design. I think it's best for each person to find a workflow that works best for them individually. This said, I do find it useful to peek inside other designers minds and see their processes and techniques of how they work. A while back I wrote more detailed post about how I created There's More To Life, so rather than repeat those details, I thought I'd just show some of my original sketch studies for the new design It's About Time. This one was especially fun and challenging to create, and I'm really happy with how everything turned out.
In order to get the shadow effect for the overlapping letters, the shading had to be converted to halftones. While gradients can look great on-screen, they can't be screen printed as is and must be converted into tiny dot patterns to creates the same shading effect. If you want a more technical explanation of halftones you can read more here. You might be surprised with how many things you use everyday are printed with halftones. Just take a closer look at a cereal box or newspaper.