How developing a Sense of Style is a lot like Gambling

Fashion & Gambling: Getting greedy makes you a broke dope.

HERE’S THE KEY: It’s about having the sense of self to know you’re good, or even better than good, yet having the willpower to resist getting greedy and going for great.

It’s often then, when you’re going for great, that you end up giving a ton, if not all of it back.

Think about it in terms of craps. How many hotels have been built in Las Vegas with the money that COULD have been taken off the table… but wasn’t?

Saw a friend go on a real hot streak recently at a casino. We had dinner reservations in a few minutes with some friends (including a couple of very attractive ladies). He was doing no wrong as the shooter at a craps table, and eventually after a prolonged streak, he rolled the point. Lots of high-fives around the table.

He picked up his chips and started to walk away. A portly dude in a tan golf polo was at one end, all alone smoking a cigarette, and gave him the business. “You can’t leave now! Are you serious? You’re leaving? You’ve got to be kidding” said portly smoking polo guy as he put his hands in the air. Y’know, the universal sign for “what gives?”

This guy was genuinely irritated that the shooter, who just made him a bunch of money, was taking his profits and walking away to go have dinner with friends.

Who would you rather be?

Over-pursuit often eliminates the return on your investment. And it’s no different in terms of developing a sense of style.

Having style isn’t just about the visuals of the clothing we wear. Most of having style is in our heads. Dressing better leads to dressing well. And there’s value in knowing when you’ve reached that destination. We all started dressing better for some reason. And that reason probably wasn’t because “I want to be viewed as a fashion expert on the internet!”

Style is a means to an end, not the end. Remember what your end is, and once you get there, take your winnings and walk.

The Vdara in Las Vegas. One of only a couple non-smoking hotels in Vegas. No casino inside either. It’s a 5 minute walk from Aria and the Bellagio. But that 5 minute walk makes a huge difference.