Fortune favors the bold

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A close-up photograph of a clean, black-ink forearm tattoo in a serif font. The Latin phrase "FORTIS FORTUNA ADIUVAT" (Fortune favors the bold) is clearly visible and sharply in focus. The arm rests naturally, serving as a physical testament to the life philosophy discussed in the post.

Editor’s Note: I’ve always said if I were to ever get a tattoo, it would be this phrase. Here’s what that inspiration looks like

What’s a personal mantra or philosophy you live by?

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I’ve written about this one several times before, but if I had to choose only one mantra to live by, it would be:

“Fortune favors the bold.”

I firmly believe that. You have to take risks and be bold sometimes to succeed, and more often than not, boldness is rewarded. There is a certain level of brazenness that comes with it—almost a sense of unpredictability where people don’t know what to expect and you catch them totally by surprise. For that reason, yes, I believe that fortune does in fact favor the bold.

But if I had to choose a second guiding quote, it’s the one generally attributed to Robert F. Kennedy:

“Some people see things as they are and ask why; I see things that never were and ask why not.”

In a lot of ways, this expression goes hand-in-hand with the idea of fortune favoring the bold. Sometimes you have to be a visionary. You have to look at things in a way no one ever has before, challenge conventional wisdom, and ask why not.

To me, putting that philosophy into practice means refusing to settle. I think a lot of people settle for the way things are because they fear failure. In fact, many people fear failure more than they desire success; they would rather avoid the possibility of falling flat, even if it means sacrificing potential greatness. But you’re never going to know what’s possible if you never take a shot.

That applies to every aspect of life. Whether you’re asking for a promotion, applying for a brand-new job, or trying to build something you’ve never done before, you have to be willing to put yourself out there. You see it in dating, too—like when I finally asked Sierra out after knowing her for seven years, despite everything pointing to the fact that she wasn’t looking for a relationship. I had to know. When you make a move like that, you’re putting your heart on a limb and showing your cards, facing the very real fear of failure and people questioning why.

But whether it’s love, career, or personal growth, I would always rather know than not know. You can’t let the “what if” haunt you. Ultimately, part of being bold is simply having the courage to ask why not.

By the way—a new episode of Rebuilding Rob: The Podcast drops this Wednesday. It’s a heavy one. See you then


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 “fortune favors the bond“ first appeared on Rebuilding Rob.

Official Rebuilding Rob logo featuring a red clenched fist icon above the title "REBUILDING ROB" and the slogan "NO GLITZ. JUST THE WORK." in clean, bold typography.

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