Sometimes the Hows are necessary, particularly when you want to make leaps within a field of study or of practice; other times, the Whos, Whats, Whens, and Wheres are sufficiently clear for practice on their own. Knowing the Hows can be interesting, and will never leave you worse-off, but they're not the goal or the means behind every journey.
In a vacuum, knowing How is always better, but outside the vacuum, knowing How thing X works is an opportunity cost -- knowing means learning, and learning takes time, energy, and perhaps money. Learning X is time away from Learning Y, or practicing Z. In the end, we only have so much time, so much energry, and so much money, and you need to choose what things you will invest those resources in.