Whether you want to be a better father, get in shape, or build wealth for your family or support your community: winning is for everyone. Kobe Bryant and Michael Jordan explain what winning is all about and how you can win in life.
Tim Grover is a sports enhancement specialist who consults professional sports teams and high-level athletes such as Michael Jordan and Kobe Bryant on their mindset. He is very good at taking athletes at the highest level and making them better.
Business and sports are similar in that they both are highly competitive and require a winners mindset to succeed. The difference between sports and business is that players compete in typically one to three games a week, and they have a whole week to prepare their strategy and game plan. In the off-season they get time to recover and prepare some more for the next season. Entrepreneurs, on the other hand, play 24/7, 365 with the rules constantly changing, and thus the game plan also in constant development.
This constant change requires the ability to adapt and overcome. A lot of people can adapt. But do you have the ability to overcome? Adapting is surviving. Overcoming is adjusting and thriving with your given situation. Ask yourself: when things go south, do you adapt or do you overcome?

“Be careful what you want”
Identifying What You Want
When consulting, Tim notices a theme when he asks athletes and business people what they want; their answer tends to be pretty vague. “I want more success… I want more money” and to that Tim hands them a dollar and says there you go now you have more money, you’ve won. As expected they still aren’t satisfied. So he asks again, what do you want?
Athletes and businesspeople tell Tim all the time they will do anything for what they want until they find out what Tim’s definition of anything is.
First, define what you want. Then ask yourself, do you have the ability, know-how, and knowledge to hustle for it? Also understand that in the process of working for what you want, you will not go from average to great. You must first capture and master average, then do the same with good, then great.
During his career, Michael Jordan started every single practice with a chest pass—the most foundational move in the sport at the most average level. He continued to master the average even at his greatness in his prime.
“I Practice so hard that the games are easy.”
Do You Want It Or Would You Just Like To Have It?
Everyone would like to be wealthy, but few actually want to be wealthy. Everyone would like to own a successful business, but few actually want to.
True story: A high school basketball team had a rough practice where people were missing lots of shots, so the coach lines up the players and asks “who in here said at the beginning of the year that they wanted to be a better shooter?” all the players put their hands up. “Put your hands down if you left after practice yesterday” everyone except two players put their hands down. “How can you say you want to be a better shooter but won’t work on it?” And the coach made the players run sprints until they puked.
The moral of the story, only two people on the team wanted to be a better shooter. If the others wanted it, they would stay after practice and improve their shooting. But if a shooting ferry offered to give them the power to shoot better, then they would accept it.
If you’re not doing the necessary things to get what you want, then you don’t want it—you would just like to have it.
“The successful ones know that there is no finish line.”
Overcoming And Winning
“Be careful what you want” Tim points out another common hindrance of achieving success or winning. Many people are afraid of what success actually looks like and what it takes to get there and to live it. This is why many professional teams can’t win back to back. They might be able to win one year with that current situation and the game plan for that situation, but aren’t willing to win differently and hustle just as hard but in other ways the next year. In the business equivalent, this would be a successful businessperson winning during a booming market, but holding out and not adjusting their strategy when the competition rises, or when a recession hits.
Tim mentioned when things are tough, you don’t lower your expectations. Because when you overcome difficult situations, then when things go back to normal everything becomes easier to you. Michael Jordan would say “I practice so hard the games are easy. The harder I practice, the easier the games were.”
Winning makes you different, and different scares people. People start out learning what to think, how to close the deal, and get it done. But the people who are winning learn how to think. Winning ability is being able to do both. A lot of people are in the game and are competing. They know what to think. But few are in the game are actually winning with individuality, creativity, and trust in their instincts. These winners know what to think and how to think.
“Winning isn’t heartless. But you use your heart less”
Put Your Feelings In Check
Many ambitious people have a hard time getting along with people even when it’s not their intention. “Winning isn’t heartless. But you use your heart less.” Tim says your mind must be stronger than your feelings in order to win. Winning and leadership have a price. Every morning, your mind tells you to get out of bed. Your feelings tell you to stay in bed. Feelings also make you overthink and overanalyze. You think thinks like I don’t know if this is right, I don’t know if it will hurt this person, or if this is the right time to do this. Many business deals are fumbled due to overthinking.
Winners understand how quickly things can change in a moment. So that fear doesn’t paralyze them, but it keeps them going as part of their fuel. They may have fear, but they never have doubt. When you have doubt, then your confidence starts to affect your performance. Kobe would have games where he shot 2 for 20, and they would ask him why he kept shooting. He would say because if he stopped shooting, people would know that he lost his confidence. Even in his bad shooting games Kobe still wants to take the game-winning shot because he doesn’t overthink it.
Meanwhile, your mind makes decisions. The majority of the time, people don’t want to make decisions, they want to make suggestions. Your mind can handle disappointment and failure and learn from it, forget about it, and move on. Your feelings make you hold on to it. The most successful individuals in all fields have the shortest memories—they don’t forget, but they don’t constantly think about it. They use their short memory to move on from losses and to not get complacent when they win.
One day Tim’s daughter was watching him get ready for work and asked him “why do you have to go?” and he replies “well, daddy has to put food on the table” and she replies “daddy if I eat less can you stay home more?” Tim ended up still going to work because he committed to his clients and his mind told him that’s the right decision for himself, his family, and everyone’s future. Most fathers would break down emotionally and feel guilt by choosing to go to work.
Years later, Tim discussed this with his daughter. Now she says she’s glad he went. The example he set for her while in the moment she didn’t like it, it helped her become a better version of herself. When making decisions, choose the one that has wins for everybody down the road. Tim’s daughter said she now understood and she reaps the benefits today—not only financially, but seeing how happy he was, and what he taught her. Perform with energy and not emotions. Most emotional decisions don’t end as well as calculated ones.
“Learn from the things that guarantee a loss”
Use Your Losses To Your Advantage
“I never lost a game. I just ran out of time” – Michael Jordan. Winning has no loyalty, it doesn’t belong to you; it belongs to someone else. The majority of the time you are going to lose which is fine because you cannot win without losing.
When Michael got to the locker room after every game, Tim gave him a separate stat sheet. This one recorded things he wasn’t supposed to do. Michael knew he was supposed to make his teammates better, score, rebound, and get assists. But he wasn’t supposed to miss free throws, miss defensive assignments, turn the ball over, or make stupid fouls.
This stat sheet was important because sometimes doing the things you’re supposed to do still doesn’t guarantee a win. But if Michael could learn from the things that guarantee a loss, then the chances of him winning become greater. You must learn to lose in order to win on a consistent basis. This is why Tim doesn’t agree with participation trophies. He believes we’re not here just to participate. We’re here to win, make a better life for ourselves, and thrive.
“Anyone who says they’re not addicted to something, they’re addicted to lying.”
Winning And Happiness
Tim noticed a correlation between winning and happiness. He asks everyone he coaches to describe winning in one word. The best answer he got was from Kobe who said “winning is everything”. When he was asked to elaborate, Kobe said when he wins, he feels unbelievable. When his kids win, he feels unbelievable. When his family wins, he feels unbelievable. When his friends win, he feels unbelievable. Same with people he roots for or people he has helped.

It’s the best feeling in the world. And when you catch the winning bug, you want more of it and you’ll do whatever it takes to get that high again. That’s why when CEOs and athletes retire, they never stop competing. In Michael Jordan’s final seasons with the Wizards, his shoes outsold the top five Nike best-selling shoes combined. He still wants to win. When Kobe Bryant retired, he won an Oscar, wrote a best-selling children book, and was winning in the entertainment industry.
The competitive nature of wanting to win is in all of us. We’re just afraid to show it because we’re afraid of how others will perceive us. It’s easier to be perceived in the middle of the pack as normal/average/good than it is as an exceptional winner.
“Winning is everything”
We All Win In Different Ways
Winning is different for everybody. You don’t need to be a superstar or a boss. For some people, winning is a secure job, or owning a house, or living a healthy lifestyle, and some would say they could never do that. Wins can be large or small, but you can never judge others on their definition of winning. Michael would say, the only way he knows how to win is his way. You don’t have to like it, but you have to respect the end result.
Not everyone can have a relentless mindset, but winning is for everyone. In some form of your life, in some aspect of what you’re doing, there are wins available to you on a daily basis. The euphoria of winning is in all of us, and everyone should experience it.
Kobe Bryant was addicted to winning—probably more than anyone you or I will ever meet. Kobe won with his premature passing because it gave the rest of us the understanding that you don’t know how long we have. So play every game like it’s the 4th quarter, and win.
Now is the time to reflect on your goals and ask yourself again; do I actually want this or would I just like to have it? Am I willing to do what it takes to achieve it? Am I comfortable with being different, being a winner?
Tim Grover tells his story and his experiences with Kobe and Jordan on this podcast.
Read his book here.