‘Ask yourself: what do I want my design to convey?’
Jason Santa Maria, On Web Typography (pp. 67–68):
Think of words that describe the feelings or moods you’d like to impart. Perhaps you’re designing a website for a day care. You may think of descriptive words like playful, innocent, colorful, handmade, and more. […] With these adjectives in hand, I can look for typefaces that suggest the same thing or help me portray those traits.