I'm a designer who learned Django and launched her first webapp in 6 weeks 15 years ago
Yeah, I think a lot of it might be to target the areas you're uncomfortable with first to make sure you can get them right, and then end with what you're comfortable with and what you're good at.
I think doing the reverse might sometimes end up being a subtle form of procrastination where you might be afraid of doing the part you're not as familiar with.