Risks come in many forms, but genuine wisdom is difficult to acquire, unlike plain old knowledge. Wisdom is often obtained by questioning what we have always believed, and allowing those beliefs to stand--or fall--on their own merits. This is risky as once we have settled on a worldview, we find comfort in at least thinking that we understand and have answers we are satisfied with. To put that comfort at risk is courageous indeed, and absolutely essential in the pursuit of truth.
In my view, the acquiring of wisdom does involve taking risks. Consider the risk involved in learning something that might appear at first intimidating or overwhelming. Also, when you gain knowledge, and your view of life is broadened, it might be difficult for you to engage with people who do not have a broad view, or less knowledge. Wisdom can be isolating!
There is a risk involved in being smart, the risk of feeling alone, that no one understands what you are thinking. When I was in graduate school, each class was like a think tank. When it ws over, I felt sad at the loss of my classmates great discussions about literature and history.
Maybe not so much continually taking risks, but absolutely living and gaining experience. Wisdom is, after all, knowledge through experience and education--both hands-on education and through reading others' experiences.
Montag takes huge risks, but I'm thinking of other who are considered "wise" whose daily risks weren't as extensive. Mother Teresa, perhaps.
Faber makes this remark after Montag shows some fear of going forward with their plan. This occurs after Montag has read the poem to Mildred and her friends causing Mrs. Phelps to cry because she identified with the poem. Faber is talking to Montag through the two-way radio in Montag's ear. Montag says that it shook him up to see Mrs. Phelps cry and maybe they're right, it's better not to face things, to just have fun. Faber says that Montag is just afraid of making a mistake, but that it's OK to make mistakes because one learns from those mistakes and avoids making them again. He explains that this learning process isn't always easy and sometimes requires risk taking. He says that if people don't take a chance and risk making a mistake that could hurt them, then they won't learn. It's always possible that when one learns, the information acquired will not be pleasant. For example, a person experiencing a new and mysterious pain may do some research and find out that the pain is a symptom of a major illness. That newly learned information isn't pleasant. It's just as likely though that the newly learned information can alleviate any fear one has or can steer one in the right direction.