Win Today

#219 | Boring Is Sexy: How The Best Use "Boringness" As Secret Weapons To Win

• Season 5

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What if the real secret to extraordinary success isn’t in grand gestures or viral moments—but in embracing what most people consider boring?

In this episode, I break down how the best in the world use routine and repetition to their advantage. Mark Zuckerberg wears the same gray t-shirt every day. Steve Jobs stuck to his black turtleneck. Kobe Bryant spent hours shooting the same free throws. Tiger Woods drilled three-foot putts over and over again. These habits weren’t random—they were intentional ways to save energy for what really mattered and build consistency that compounds into mastery.

The truth is simple: consistency beats intensity every time. Yet, we’re wired to chase dopamine hits and quick wins. Social media can fool us at times.

As Naval Ravikant says, true wealth (and success) comes from the “boring” path—like steady index funds instead of risky meme stocks. The same principle applies across life: the unsexy, repeatable actions compound into greatness.

Cheers to embracing boring!

Thank you for tuning in! If you feel led, please subscribe & share the show to others who you believe would benefit from it.
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Speaker 1:

what if I told you that boredom not boredom, but the art of boring is a good thing? What if I told you that it's a good thing to embrace boringness, that being boring is sexy? Now, now, that might be the reason why you clicked on this episode. How the hell is someone going to say that boring equals sexy? What does that mean? Do hard things, help one person, be good and do good, live a life of discipline, and you will always win. You have all the tools that you need to succeed. Welcome to win today in what matters most to them in their lives. Every week, you're going to learn from either myself or renowned expert in their field, and we're going to unveil pieces of our playbook to help you win today. Please, if you love this show, subscribe and share it with somebody that will benefit from it. Let's dig in.

Speaker 1:

Diving into playbooks of people that you've often talked about or heard about whether it's Warren Buffett, michael Jordan, tim Cook, steve Jobs there's many themes that emerge on this podcast is that they all embrace this notion of practicing boring things and doing boring things over and over and over again, meaning they're known for the big, sexy things, whether it's Warren Buffett with Berkshire Hathaway and being a multi, multi hundred billion dollar conglomerate, or Kobe Bryant, with being trusted to take the game winning shots and hit the game winning shots and bring championships home to the LA Lakers, whether it's Steve Jobs and innovating the newest Apple products that are still the paramount in technological devices today. Those were the sexy things that they got to do, but what enabled them to do that, what helped get them there, was embracing all of the boring things and finding peace and joy and strength through that. Have you ever known somebody and perhaps this could be personal experience as well but maybe they lost a lot of weight and looked different and then shortly thereafter gained most, some, most, if not all of it back? And then you scratch your head how did that happen? The reason why these things happen and that's just one example is because people do not build a system around the very thing that they want to have or want to become. Rather so in this case, the sexy thing would be I lost a bunch of weight, I've got a six-pack now and I get a lot more attention. And I can do that if I go and drink a lot of water, work out a ton, don't eat a bunch of food, go and sweat, I can make my body change its form and lose a bunch of pounds and look a lot more cut. But if I never really built a system around it, meaning I just did whatever I needed to do for the number to hit whatever I wanted it to say, if I never really built a system and embedded it into my DNA, all I really did was achieved a short-term outcome and didn't change any of the underlying factors or variables. That's why you see a lot of people that they'll lose weight and then they gain it right back because they didn't transform their being.

Speaker 1:

This is all a process of becoming so what we're going to talk about is how boring is sexy, why boring matters. Look at a few people that are masters of the boring figure and then, by the time we finish this up, you're going to think, huh. I believe you'll think that, man, boring is in fact, sexy and there's a powerful reframe for the things that I don't want to do. Well, if they get me closer to things I do want to do and perhaps they're on autopilot, then, yeah, boring is actually sexy. So why does boring matter? Because by doing the same thing, the mundane thing, over and over and over again. Kobe taking thousands of shots over and over and over and over and over again. Kobe taking thousands of shots over and over and over and over and over again versus. I'm going to go take 5,000 shots today and go as hard as I can, and then now I'm good for the whole season. You might make some shots in the games, but all of that's going to wear off and eventually that skill level is going to fade because it is not backed by repetitive action. So in this case, consistency really beats intensity.

Speaker 1:

We'll often think at times that success may come from these big, flashy moments, these one-time things, whether it's the viral video, the record-breaking game, the massive deal. But it's really the small, repeatable actions that don't seem like they're a whole lot of fun at the time that compound in the greatness. So, as boring as it can sound quote to eat the same meals every week, to wake up at the same time, to follow your training schedule, to have your early evening routine. Though it may not appear to be the most exciting thing, those are the things that allow you to move closer to doing the sexy things and allowing those things to actually stick, because the more that we choose to embrace, boring is a decision to further embed into our DNA that, hey, this is who I am, and by doing this, this is what allows me to do the big things that I've always dreamed of. So a few examples of people that embrace boringness and are we'll call it champions of boringness Mark Zuckerberg, founder of Facebook, now Meta.

Speaker 1:

If you ever look at Mark, you'll see that he's wearing the same clothes. He's wearing a pair of jeans and usually a gray t-shirt. And you think a pair of jeans and usually a gray t-shirt. And you think why are you doing that? You have all the money in the world. Why don't you wear some cooler clothes or hire a fashion stylist or go buy some nice leather shoes? A few hundred dollar pair of shoes is like pennies for you. Why would you do that? And the reason why, in an interview, that Mark decides to do that every day, while it may seem extreme to the outside, is that he wants to reduce his decision fatigue, meaning that one of the richest men in the world doesn't want to spend a substantial amount of time in his closet looking at thousands of different options that he can wear, because that's what he has the opportunity to easily afford. And then now getting dressed becomes one of the most important things of the day, versus building Facebook and meta to what they are now. So by embracing boring, now we get to experience the sexy meaning that we have a thriving company. All of you are on Facebook. You likely are now with where AI is going. Use Facebook or Instagram to buy a bunch of things some of what you need and some of what you don't need. You can thank Mark for that, and Mark is embracing boring while we are sometimes funding his dream. So I could stop right there and you say, okay, I get it, but let's keep going. Look at Steve Jobs, apple. If you look at Steve, anytime Apple is doing a product launch, what was Steve wearing? Black pants, black turtleneck and similar to what Mark does. And perhaps Steve is who inspired Mark that he's reducing decision fatigue and, in his words, protecting mental bandwidth for what really matters.

Speaker 1:

Looking at Kobe, the legend he was known for countless hours of boring practice, shooting free throws to the thousands, showing up to the gym before everybody, staying until after normal practice ended, going back to the gym after normal practice ended and doing another workout. Thousands of shots, thousands of layups, thousands of the short shots. Of course we all want to hit the step back three pointer from deep and three point land, maybe even close to half court, like you see Steph Curry doing. And why did? Those guys will even bring Steph Curry into the mix now. Why do they get to hit those shots in the game? Why do they get trusted to take those shots? Because they take thousands of the boring shots, tens of thousands of shots, but also focusing on tens of thousands of three to five foot putts, so that he could then end up draining the clutch. 20 and 30 and 40 and 50 foot putts that everybody Boring is sexy.

Speaker 1:

Two more Usain Bolt, who is the fastest man in the world. A lot of people thought that Usain Bolt lived this very flashy lifestyle. Obviously, on the track he has quite a personality that he has carried, quite a personality that he has carried and he is somebody that clearly backs up his flashiness. But his coach had him do the exact same running sprint drills, same starts, same form corrections, endlessly, over and over and over and over again, just so he could run 100 meters, which is less than 10 seconds of actual racing effort. Just so he could run 10 seconds across the track faster than anybody else. Jocko Willink, who many people know, posts a picture of his watch every day around the hours of 4.30 to 4.45 every single day, with the tagline discipline equals freedom, discipline equals freedom, and the whole premise of that is that the beauty of repetition gets you what you really want in this life.

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To bring in the final example, and this is with Naval Ravikant, many people are often interested in what's the next hot meme stock going to be, what's the next trend, how can I get on top of the next Bitcoin? And while all of that is great and I certainly have those thoughts too man, how do I get those insights? Naval Ravikant, who is a big angel investor and philosopher author, author, has a great book, the almanac of naval ravikant, talks about wealth building being this boring practice. Boring wealth building. Focus on boring wealth building versus sexy wealth building. So, instead of chasing the meme stocks or what's the next Bitcoin going to be, by simply choosing to invest in index funds or the S&P 500, which are the top 500 stocks in the United States, all culminated into one stock. So basically, you're investing in the country. By doing that over a multiple decade period, you will amass just as much, if not more, wealth than you would by hitting the lucky meme stock or the lucky sexy Bitcoin once.

Speaker 1:

I should drop the mic here because I believe you get the point now that boring is sexy, but here's why it feels hard at times, or why it can. Because wearing the same gray shirt every single day, wearing the same black shirt, choosing to putt the same three to five foot putt 10,000 times a day, choosing to invest in the boring stocks that don't get all the headlines, versus finding the meme stocks, doesn't give us this dopamine rush. There's nothing exciting that follows those things. You don't jump up in the air after you put on your boring gray shirt in the morning. Why? Because it's a boring gray shirt but you're going to be jumping in the air later, knowing that by not spending eight minutes in your closet every single day times seven days a week, which is now we're looking at an hour of your week figuring out what the heck you're going to wear Now, we get more time to pour into our dream, which is pretty freaking sexy. I would imagine if you told me that you're living your dream right now, or moving closer to it or have touched a piece of it. It's pretty damn sexy. That gets you excited.

Speaker 1:

So embracing this boringness gives us resiliency. By embracing the minute, not-so-fun day-to-day things, and building that consistency, it allows us to experience results. It's not about it's not always about excitement in the moment. It's about stacking small wins that really become unstoppable momentum. So what can we do to apply this to our lives?

Speaker 1:

A few things. One is audit your decisions, think about your life and ask yourself what's one area where I can simplify and repeat, or really what's one area that I can make boring? Maybe it's meal prep. Maybe you are spending too much time getting dressed every day and would benefit from a simple five pack of neutral colored t-shirts. Maybe they don't need to be the same color, maybe that's a little extreme, but you get what I'm saying here. Maybe you're spending way too much time thinking about what you're going to have every single day of the week, versus, hey, let's just spend one hour, make five steaks, some rice, chop it up, throw it in a bowl, boom. We're done so that we can focus on the things that matter most to us and align to our goals, to our dream, to our vision. So that's the first thing. Next it's automate the basics, so piggybacking on what we were just saying. But are there, things that are complex in your life, that should be simple and that you can either automate or just create some more mental capacity. Because, hey, I'm not going to allow myself to think about this all day long. I'm going to go do this really boring thing and that's it. So we're going to continue moving forward.

Speaker 1:

The next thing is I keep bringing up boring and without this context, when we say the word boring, we think, oh yawn, don't bring up that word. Rather, let's reframe boring as I like to call it sexy, but figure out what you can call it other than boring itself, because that may be the very thing that moves you forward. Remember that language is the creator of all things. The words we speak matter, as we mentioned a few episodes prior about the importance of using the word outstanding even when you're feeling tired, because we can trick our minds. So by reframing boring into something more meaningful to you for me it's sexy, for you it could be something else that can keep you moving forward.

Speaker 1:

The other thing I like to call it is something that's quote, boring to me are weekly mobility sessions for my body. I love to run. I'm an ultra endurance athlete, what allows me to do more of the long, fun, fast, sexy runs is, embracing the quote, boring, or what I like to call just getting a lot of fuel and oil changes so that my body is ready to go. So a stretching or a mobility session, that's just an oil change for the body. You're not going to wait until your car's broken and change the oil, right. Don't wait until your body's broken to start taking care of it. Do the boring things, do the sexy things, get the oil changes. Fill up your gas.

Speaker 1:

The last thing is trust in the compound effect of all this. That's why I brought up these people as examples that, hey, even though you might feel in the moment that by doing the same thing all the time doesn't seem so fun and it looks like the people on the internet perhaps some of them that all they do are the fun things, that is highly likely not the case, and behind the one-minute clip that we get to see from a lot of people is countless hours of doing the same thing over and over and over again. So I want this to be a shift for y'all that boring is sexy. Boring creates freedom. Just as Jocko says, discipline equals freedom. Boring creates focus and rather than creates focus, boring is focus, and boring creates the life that you actually want. So if you want to win, stop chasing the big flashy moments and start building upon the boring ones. So be bored and win today. Thank you so much.

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Ryan Cass

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