A Scandalous Story of Self-Assurance

And some keys to developing confidence

The Swing, Pierre-Auguste Renoir, 1876

Last month, my friend and I came up with a bold plan. “It’s going to be one hell of a story,” I told him, as I imagined its unlikely success. As we were on our way to try to execute it, I called another friend and asked him if he wanted to join. He laughed and said no, citing it was not a well-thought-out plan. I told him I didn’t blame him for thinking that, but that he was wrong to doubt us.

To stay out of potential trouble, I’m not going to share the details of the plan. What I will share is that we went to an extremely expensive event that we were not supposed to be at. We pulled it off with no tricks and no gimmicks, only slickness. We pulled it off by walking right in the main entrance. Right past crowds of people, right past security, right into the venue.

While we surely had luck on our side, I also think, or like to think at least, that we got in because of our confidence. You know, two well-dressed guys, shoulders back, moving with purpose. Anyone who saw us would not hesitate to believe we belonged. Whether it was really more luck or confidence, I don’t know. Regardless, carrying out this scheme made me reflect on the fundamental aspects of confidence. I thought, what are the basic elements of self-assurance?

The first that came to mind is style. It is easier than ever to excel in this regard. Timeless classics are timeless for a reason. I’m guilty of it, but I think the casual, athleisure era has gone too far. In a world of people working remotely in their pajamas, there is significant upside in developing a bit more formal of a style.

But style doesn’t mean much if you’re not proud of what’s beneath the clothes. The more fit you become, the more confident you become. It really is that simple. Not only because you look better, but because you feel better. And when you feel better, you have a clearer mind. And when you have a clearer mind, you make better decisions. Better decisions like committing to consistently going to the gym, for example.

Which can bring us to another element of confidence: self-trust. If you tell yourself, “I’m going to the gym today,” and then skip it, you lose a bit of self-respect. Your word loses weight. But each time you follow through, you win more self-respect. Your word gains weight. Self-assurance is a natural byproduct of your word being valuable, of you trusting yourself.

And the more self-trust you have, the easier it becomes to clarify your values. With genuine self-respect, you feel more “qualified” to be vocal about what you believe. I once read that the world steps aside for a man who knows where he’s going, and that idea stuck with me. When you trust yourself, you naturally become someone who knows where they’re headed, because your values are clear.

But then a new type of challenge arises: encountering people or ideas that are in direct opposition to your values. Which gives you a choice: to speak your mind, or to fold, and nod along. To respectfully disagree and learn through doing so, or to people-please, agreeing for the sake of agreeing. Bending the knee, of course, destroys your confidence. When you make a habit of saying what you actually think, especially to people who you anticipate will disagree with you, bold self-assurance becomes part of your character.

This self-assurance is not just about helping you stroll into amazing events like you own the place. Although—and I’m sure my friend would agree—that is a great perk. The real takeaway is knowing you can create that sense of calm belonging anywhere. This type of genuine confidence, built on style, strength, self-trust and clarity of values, lets you squeeze all the juice out of your experiences. And, dear reader, haven’t you heard? Squeezing all the juice out of an experience often makes for one hell of a story.