Being fearless isn't about the absence of fear. It's about doing something despite your fears (and perhaps better judgement).
As a writer, this concept can be difficult to practice in daily life. After all, how fearless do you really have to be when you are mostly locked away from everyone else, writing nonsense? (well, maybe the nonsense part is just me)
The answer is VERY fearless! Writing is hard, even though you are doing it in relative seclusion (alcohol does help....I'm just saying. And did you notice I said "doing it" tehehe!) it takes a certain amount of courage to get those first, most likely awful, words out on the page.
But another important part of writing is getting out of the locked room, and experiencing life! Observing human behavior, getting silly and watching people's reactions.
For example, last weekend was my six year wedding anniversary. I know, I know, I'm old. My husband and decided to spring for a babysitter and go out and pretend like we were young again. We ended up in downtown Reno, where there was a SUPERHERO pub crawl in action. No, I didn't dress up, and if anyone asked, I told them I was a single mother.
At the Tap House (bar on the river), we ran into someone dressed as Jesus Christ. After giving a requisite "Amen brother!" and "Hallelujah!" to the Jesus man, my husband went to buy me a drink (Newcastle), and I waited, watching other people take pictures with Jesus.
So, I was standing there, and Jesus and his friends, er apostles, had their backs to me during their photoshoot. I don't know what came over me, I just couldn't resist. During one of the pictures, (to the amusement of my husband and anyone else watching) I snuck up behind Jesus and gave him bunny ears.
The moral of the story, my friends, is don't be afraid to be silly, stupid, crazy, or random. Be fearless in life, and in writing. Or be afraid, but do it anyways.