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The Daily Reckoning

I've spent years in organizations where people talked about what they "deserved" – the promotion they were owed, the recognition they had coming, the success that was rightfully theirs. But here's what I learned in clubhouses, boardrooms, and everything in between: the scoreboard doesn't care about your resume. The market doesn't care about your tenure. And your competition sure as hell doesn't care about what you think you're entitled to.

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The Journeyman: The Curious Case of Jesse Chavez

I've had to tell players that they've been traded. It's hard…I've also welcomed newly-acquired players into an organization…The disappointment and subtle sense of failure that colors the first conversation is contrasted by the excitement and optimism of welcoming the newly-acquired teammate. Goodbyes can be hard. But more often than not, they lead to Hellos.

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Leadership Fitness: Why Your Brain Needs a Gym Membership

When you skip the gym for six months, your pants get tight. When you skip leadership development for six months, your decision-making gets sloppy, but you might not notice until it's too late. Your team notices, though. Trust me on that.

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Are Leaders Born or Built?

When we’re young, we’re told who the “leaders” are. Usually, they’re the loudest kid on the team. The one who can rally the group with a speech or a stare. That’s who we follow—partly because we don’t know better, partly because we’re drawn to confidence, even if it’s unearned. But the problem is, we carry that logic with us into adulthood.

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We Would Have Taken This on Monday Morning

Great athletes are able to stay in the moment and focus on present execution, knowing what happened in the past--whether that was 10 years ago or 10 seconds ago--has little to no bearing on what they're doing right now. But this was more than that. This was understanding, embracing, and appreciating that everything McIlroy did to prepare for the Masters actually worked.

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Early Work

It's like watching a brilliant musician rehearse or being in a comedy club when a headliner shows up unannounced to workshop some new material. You're not just watching greatness. You're watching the act of greatness becoming great.

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Underwriting Your Greatest Investment

The best business plan can fail. The best hitter can strike out. How does that person process that setback, and ultimately respond to it? What drives them? Is it a quick pay day or building something that lasts? How has their background shaped their foreground? These aren't things that you can decipher from a balance sheet or a CV. You have to really get to know that individual as a human being.

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The Humble, Hall of Fame Leadership of Pat Gillick

Pat Gillick is a Hall of Fame baseball executive with a history of working with what he was given in an industry where the expectation is to clean house. This style and its effectiveness deserves a closer look.

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What Can Business Leaders Learn from a Hitting Coach?

Leading in business is hard. So is hitting a baseball. In fact, some say it's the hardest thing to do in all of sports. How would you like to make your living being responsible for how a dozen different hitters fare against the best pitchers on the planet? Being a hitting coach is a tough gig. Here are some lessons that business leaders can draw from the good ones...

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Nobody Cares About Your Culture

Like with most things, it's about balance. Culture will rarely be enough to put you over the top. You need talent, strategy, and execution. Similarly, relying solely on skill often won't cut it either. There are a lot of talented people and organizations out there. What's going to separate you?

Whether it's now or later, there's a symbiotic relationship between winning and culture. Without enough of one, you won't have enough of either.

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Don’t Call it a Comeback

Resiliency is relatable because it's tied to adversity, which is universal. We appreciate how hard it can be to rebound from failure, and that sometimes, we simply can't (or don't). But what is often underappreciated is the fact that the very act of getting back up is a win. I love the Japanese proverb "Nana korobi, ya oki", which translates to "fall seven times, stand up eight". Stay in the fight. Get back at it tomorrow. The ability to show up every day, rain or shine, is an incredible asset. It's more powerful than we give it credit for. It's more than grit or perseverance. It can portend remarkable success.

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Tribes of Five

I do believe in the "Five People" philosophy. I just think it's more nuanced and fragmented, which is a good thing. It gives us freedom. It allows us to diversify. I can embrace something similar to language immersion and surround myself with cutthroat corporate lawyers if I want to sharpen my negotiation skills, then hit the gym after work for a high intensity class workout with a bunch of fitness nuts, before meeting up with a group of dads to volunteer at my local church. Three different peer groups, three different areas of my life where I want to grow.

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Is Asperger’s Syndrome a Superpower?

When most of us can be dissuaded by peer pressure, self-doubt, or social norms, those with Asperger's (or at least traits consistent with the syndrome), aren't phased and soldier on. It's like wearing an invisible cloak that insulates you from societal pressures.

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Tolerance is For Losers

Tolerance. The notion that we need to be accepting of other people and their perspective. Tolerance says "come as you are" and "all are welcome here". I say no. I say put up the velvet rope, close the door and require a password to get in. I say tolerance is for losers.

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What Business Leaders Can Learn From Pitchers

Just like a pitcher's pace and strike-throwing can help his defense perform better, a pitcher needs help to maximize his performance, too. His catcher needs to be in sync with him and call a good game. His defense needs to make plays behind him. Sometimes even the weather needs to cooperate. Ultimately, though, no one can execute for you. No one can come out on that mound and help you throw the next pitch. You have to do that yourself.

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Efficiency Isn’t Always the Answer

In a world obsessed with productivity hacks, streamlined processes, and multi-tasking, we've developed a dangerous obsession with efficiency. Constantly hearing that we need to "do more with less" and "work on the margins", we're in a never-ending sprint toward optimization. But is this relentless pursuit of efficiency is actually stifling our creativity and hindering innovation?

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Building Unicorns & World Series Championships

I spent 15 years in Major League Baseball evaluating talent, negotiating contracts, and building teams on & off the field; all toward one goal: winning the World Series. When I pivoted away from sports, I entered the dynamic and frenzied world of startups, joining an early-stage company that two years later earned a $1B valuation and officially became a Unicorn. Both environments were fast, furious, competitive, and fun. Here are some of the parallels of, and lessons learned from those two experiences:

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Is Ego the Enemy?

If left unchecked, ego can spell the demise of careers, relationships, even entire empires. It's been the driving force behind scandal, war, treason, and murder, to name a few.

Then again...ever meet a really successful person who has no ego at all? …anyone who's ever been really good at something definitely has an ego. In some sense, they have to in order to be driven to do great things.

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The Compounding Effect of a Self-Policing Culture

Everyone wants passive income, right? Mailbox money. You put in some work up front, lay the foundation to create cash flow, then kick back and reap the rewards.

In the world of leadership, there is a similar opportunity to build a self-sustaining, perpetual cycle of value: the self-policing culture.

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