There’s actually quite a few quotes that I like. In fact, a few years back I even started a page on this blog devoted to the quotes that I like. You can check out that quiet page here.
Now granted, most of them are from the novel Fight Club. But there is one quote for me that stands above all others. One that I try to live my life by as much as possible. In fact, it would probably be the one quote I would actually get tattooed on my body first:
Fortune favors the bold
-Virgil The Aneid
I’m a firm believer of the idea that good things happen to you in life when you take chances. Of course, taking chances on things doesn’t mean acting recklessly. There is a big difference. When something is reckless, it feels like there really is no chance of it succeeding. Being bold is when there is at least a decent chance of success—even if the path is difficult or unconventional.
The truth is, a lot of people who fail in life do so because they fail to try in the first place.
I think I’m a pretty lucky guy. I have had my share of failures in life, but so far I don’t think I’ve really had any either spectacular successes or spectacular failures. At the same time, I do like to think that when an opportunity presents itself, I go for it.
When people talk about boldness, they usually imagine some cinematic, high-stakes gamble—like picking up and moving across the country. And sure, I’ve taken those kinds of external leaps before, like when X1 and I moved to South Carolina in the early 2000s to teach. It was risky and bold, leaving our entire support network behind. It didn’t work out in the end, but I don’t regret it because it was an experience most people only romanticize.
But as I’ve gotten older, I’ve realized that true boldness isn’t always about grand gestures or big physical relocations. More often, it’s about those small, unglamorous choices to keep going—or to finally stop—when staying still and letting yourself be stagnant would be so much easier. Sometimes it’s just telling yourself fuck it, go for it, what the hell have you got to lose?
For me, the defining moment of boldness in my life didn’t happen on a highway or in a classroom. It happened when I finally learned how to walk away from a situation that completely compromised who I was.
A few years ago, I found myself in a relationship where, on paper, a lot of people probably would have just kept their mouths shut, gone along with the program, and stayed put. There was a lot of financial comfort and established security attached to it. But I wasn’t happy. I felt like I was just a “plus-one” walking into someone else’s world, and that we weren’t actually bringing our worlds together.
When things finally came to a head, it forced a realization that I had never faced before. In past relationships, I was always the one waiting to be left, or letting someone else pull the trigger so I wouldn’t have to be the heavy. But this time, I didn’t wait around. I stepped back, felt an immediate weight lift off my shoulders, and ended it completely on my own terms.
People might look at walking away from that kind of security and call it foolish. I don’t look at it as some grand anti-materialistic statement. I look at it as simply standing up for myself because I knew that what I was in the middle of wasn’t what I wanted.
That’s what the quote means to me now. It’s not just about chasing big wins or rolling the dice on a map. It’s about having the nerve to choose yourself when the easier path is to just stay quiet, keep the peace, and let your life shrink.
Rebuilding a life takes grit, consistency, and a lot of ‘Option C’ thinking. Having crossed the 1,000-day milestone, I’m now charting the territory beyond. The mission remains the same: No glitz. Just the work. New to the blog? Start your journey here to see the blueprint and the ‘Tricorder’ perspective behind the rebuild.
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The article “The Quiet Kind of Bold“ first appeared on Rebuilding Rob
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