In this post, I’m going to talk about the best book I read in 2021.

This book is called Winning, by Tim Grover.

Unlike most of the other book summaries/reviews, this post won’t just summarize the book and review it.

This is my 100TH POST (YAY!) so I thought I’d try something different.This post will be a compilation of quotes on the subject of winning with some of my comments interjected.

Since this is the best book I’ve read this year, you should just buy it. Unless you like losing. Yes, it’s an affiliate link – I get a cutback if you purchase through my link which’ll help run this site, at no cost to you.

The Brutal Truth About Winning

The race to greatness has no rules to protect you. Nothing says you’re not going to lose, you’re not going to get hurt, you’re not going to do all this work for nothing. There’s no guarantee it will be “fair.”

Winning is about results only, and winning isn’t fair.

Because winners all understand one thing: There’s a price to pay, and you must pay it.

Winning requires massive sacrifice. If winning was easy, everyone would win.

The Mental Headspace Requirements For Winning

Are you asking questions? Do you allow your mind to wander into new possibilities and scenarios, no matter how far-fetched and unattainable they might seem, like you did when you were a kid? Kids understand curiosity. They see something interesting and they have to play with it, eat it, throw it… they can’t leave it alone. For a few minutes, it’s the greatest thing they’ve ever known, until an adult comes along and takes it away. They’ll ask question after question after question… until the adult can’t take it anymore and tells them to stop asking so many questions.

That was MJ and me in the beginning of our relationship. There was so much I wanted to know, so much I knew I could learn from him. I’d ask about everything, until he finally said, “Man, you ask so many questions.” I kept on asking. I already knew what I was supposed to think about him, and I knew what everyone else thought about him. I needed to know more than that.

Curiosity is required to win in life. Ask question relentlessly, so you can learn endlessly. Curiosity’s the foundation for creative thinking and problem solving. Curiosity is not conformism nor contrarianism. It’s just looking at the world creatively. There’s social pressure to just “accept” that Michael Jordan is good, but the author’s job is to improve MJ’s skills. For you: there might be social pressure for you not to ask questions (i.e. for the fear of looking dumb), ask anyway if you want to get better, and ultimately, win.

You may be getting a lot of great guidance and knowledge, but it’s always going to be someone else’s knowledge, until you question it, adapt it, and find out for yourself if it works for you.

Learn how to think, not what to think.

When I was training MJ, the Bulls’ strength coach asked why I had him doing bicep curls. The theory was that biceps were just for show and didn’t really make someone a better basketball player. And that was probably true. But we were going for that .0001 percent, which included the intimidation factor of his bigger, stronger, more dominant physique. What’s the first thing you see on a basketball player when he takes off his warm-ups? Those arms.

Details matter. A lot. Because when you want to win, your competitors will be ruthless. You must be more ruthless.

In the early days of Michael’s career, a reporter asked his coach Doug Collins about his strategy for coaching the greatest player in the game.
“It’s pretty simple,” said Collins. “Give him the ball and get the fuck out of the way.”
The greats don’t need to be told what to do. They already know, and they always find a way to make the gamble pay off.
Very few people are able—or willing—to bet on themselves. They become the assistant manager of their own lives, waiting for directions and approval from some higher authority because they don’t feel confident enough to make decisions and take action on their own.

Confidence is the ultimate drug, and Winning is the dealer. It’s the cure for doubt and insecurity and panic and low self-esteem…

Trust and bet on yourself, and don’t wait for approval. Example: while interviewing and getting a higher paying job is great, if they reject you, fuck ’em. Take the feedback and start your own company if you have to. That’s how Elon Musk got started. He couldn’t land a job due terrible social skills so he started a business instead.

So if you “failed” an interview or couldn’t get a job, consider this: maybe you can’t get a job because you weren’t born to follow. Maybe you were born to lead.

Confident people are their own special breed of killers; you can’t break them because they’ve already been broken, over and over. That’s how they became so confident in the first place: not from others telling them how good they are and throwing confetti and parades, but by being pushed down and kicked and laughed at, and by learning for themselves how strong and powerful they really are. By being in the worst possible situation, and having the confidence to believe: We’re getting out of this mess.

Acquire confidence through adversity, not from approval. “Confidence” through approval is no confidence at all; it’s insecurity.

Do you want to see joy in the middle of the game while you’re losing? Sadness? Fear? Confusion? Hurt? Embarrassment? You really want any of those in your game? Those are all emotions. None are going to help you win.
You want energy. Focus. Intensity. You want to be alert and aggressive and strong. None of those are emotions, they are a state of mental power. You want your mind locked in, so you don’t even feel the nerves and pressure that come with competition. Emotional screaming and yelling doesn’t make you a winner. It just makes you loud and distracting.
I’m not saying you shouldn’t laugh or have fun or get excited about a big moment, go ahead. But only for the moment; you must be able to restore calm and clarity in an instant, because you don’t know what the next moment is going to bring…

You want the formula for this? I’ll make it easy for you:

Control your thoughts, and you control your emotions.

Control your emotions, and you control your actions.

Control your actions, and you control the outcome.

Emotions cloud clarity, and thus creates massive drag if you’d like to win. Control your thoughts and you’ll be able to win.

Most people worry about how long something will take. Winners just keep going until it gets done.

Persist until you hit your targets.

How To Keep Winning After You’ve Done It The First Time

Then there are the “winners” who finally reached their goals, got the big house, four cars, splashy vacations… and thought it would last forever. It doesn’t. Someone else watched what they did, and did it better. Winning loves to watch someone else kill your dream.
You had a great month? Good for you. See you in thirty days. Someone will be there winning. It might not be you.

This is why I think this is the best book I’ve read in 2021. This quote hits me hard. The journey to winning is pure hell. And despite all of your relentless efforts, you can lose your hard-earned throne at any time. Winning just paints a bigger target on your back for competitors to fuck. you. up.

Competition isn’t just about the grind, it’s about grinding for results. It’s about doing work that actually works. Everyone talks about the grind, grinding it out, keep grinding. Well, you can grind and grind and grind, and what’s left at the end? Dust. Grinding deforms, it obliterates. Excellence is about sculpting, creating something magnificent that wasn’t there before by artfully changing its shape and form. When you sculpt, you strategically remove the parts you don’t need, the elements that get in the way.

Work smart. And work hard. Add things that help you win. Reject and eliminate all distractions getting in your way of winning.

Everyone has this one muscle that’s essential to focusing, prioritizing, and ultimately winning. You can’t see it, you can’t show it off under your clothes. It’s internal: the IDGAF muscle. The medically correct term is the I Don’t Give a Fuck muscle. It’s stronger in some people than in others, and it gets stronger the more you use it. This is the muscle you flex when you need to make critical decisions about your life and your priorities, when others are telling you what to do, judging your decisions, and distracting you from your mission. You can also use it on yourself, when your fears and doubts are whispering—or screaming—that you’re not good enough and you don’t know what you’re doing.
I hear you. Flex. And I don’t give a fuck.

But you can’t just say it, you have to take real action based on a real decision.

Eliminate mental friction by not giving a fuck. And mean it.

It takes a strong and confident person to stand with you while you chase your dreams, and put everything else in your life on hold. Someone who believes in you and what you’re doing, and understands that a win for you is a win for everyone in your circle.
It takes someone as fucked up as you are.
Great partners share your obsession and commitment. They don’t think you’re crazy, they know you’re crazy, and that’s what they love about you. You tell them your plans, and even if they don’t completely understand where you’re headed, they know you know exactly where you’re headed. They only question they’ll ask is: You want me to drive?
If you can find that person, consider yourself fortunate. Your greatest partnerships, relationships, marriages, friendships, will be with people who share your craziness for the end result. That’s why I work so well with my clients. I’m as obsessed and fucked up as they are about Winning.

A great partner (whether in business, or in life) can accept that you’re willing to dedicate every last ounce of energy to winning.

Players like MJ and Kobe didn’t just work, they constantly and consistently elevated the work, because to get out of hell [of mediocrity], you have to elevate everything. They never stayed with what got them there, they were always adding pieces that would take them higher. They understood that if you keep doing the same thing, you’re going to get the same results. So to get better, they had to put in new work, different work.
If you don’t evolve, if you don’t find new ways to challenge yourself, you’re a BlackBerry in a world of iPhones. Everyone else keeps improving, and you’re still running the old tired software.

Don’t just work hard. Elevate your work, or be obsolete.

I can’t guarantee my athletes aren’t going to get injured, but I can’t live in fear of it. So everything I do is to minimize the risk of that happening. There’s no way to prevent every injury, but I can take every precaution to protect against it.
That helps me fight the mental urge to doubt myself, to create problems that haven’t happened and overthink everything that could go wrong.

Do all you can to prevent bad outcomes. After that, things might still go wrong, but you’ve done your part. If you’ve done absolutely everything you possibly can, there’s nothing you could worry about; by definition, you couldn’t have done any more.

Winning makes you an expert on Losing. You don’t ever get used to it, but you learn to control your reaction, until you have no reaction at all. You become less emotional about it, because the energy it takes to lose your mind over a loss is energy you need to redirect into Winning. And the more you hang on to that emotion, the harder it will be for you to move past it and the harder you’ll make it for everyone else to move past it. You understand it’s part of the process. You don’t have to like it, but you have to face it. It’s a necessary evil, and a reality of competition.

Move past your loss and redirect all that energy into your next win.

Why You Must Pursue Winning, At All Costs

One problem: His performance was mediocre at best, his team was losing, and people were starting to use the B word about him. Bust.
I guess that’s three problems, with more to come. When you’re not winning, those problems start to pile up quickly.

Life is very unkind to those who don’t win.

We have so many ways of lying to ourselves. The score was closer than it looked. The game was closer than the score. The team isn’t as bad as its record. We saw some good things. We’re headed in the right direction. This is our year.
No. The score is the score. The number on the balance sheet is the number. Your grade is your grade. The scale is accurate. You took that vacation or you stayed home talking about it.

Winning is binary. You either won, or you didn’t. The result is the result. Excuses on why you didn’t win can’t be deposited to your bank account. Excuses don’t win trophies. And excuses don’t put food on the table.

Showing up is in your control, in every way. It means being present—physically and mentally—when you’d rather be doing something else. Putting your long-term goals ahead of short-term pleasures, and controlling those pleasures for the long run. Staying in the race when you’re hurting and struggling. Because one day you won’t be able to show up, and it won’t be your choice.
Showing up is knowing that the life we’ve been given is temporary. Tomorrow is here permanently. So is Winning. We are not.

Every second that passes by is a second less that you have to win. So show up, don’t get distracted, and focus on winning. You’re going to die someday, and life isn’t fun if you’re just going to stay mediocre.

“It’s a marathon, not a sprint!”
Stop it…
…To me, it’s about procrastination, uncertainty, and a total lack of focus.
Folks: You don’t have that much time.
If you want to win, a marathon is a sprint.

You want to debate this with me? First do this: Get on a treadmill and try to run a mile in under five minutes. That’s a slower pace than the top marathoners would run, but close enough to make a point. They do it for 26.2 miles. I’m asking you for one.
Then come back and tell me whether it felt like a marathon or a sprint, if you can still stand up and breathe.
You get my point? Competitive marathoners push the entire distance. At no point do they say, “Eh, it’s a marathon, I can take my time here.” They may change speeds along the way, but to win a marathon, to even finish near the top, they’re going hard for 26.2 miles.

Life isn’t as long as you think. Stop using the assumed longevity of your life as an excuse to procrastinate. Work hard and smart. Everyday. Forever. And reap the benefits of winning.

You’re going to die. LIVE and WIN URGENTLY.

It’s not about how much time you have left, it’s about how much you can still do in the minutes, hours, weeks, and months that remain. Instead of counting down to the end of the calendar—and blowing off December because of holidays and parties and year-end fatigue—count each and every day that you can still accomplish something before the end of the year, as everyone else checks out. When you count up, you never get to zero, so you never lose momentum; you can start the new year at full strength, while everyone else tries to remember where they left off.
Time tells you what you didn’t accomplish. Focus turns off the clock and directs all your energy to the result.
If you’re focusing on a time limit, you can’t focus on the moment.

On the flip side, it doesn’t help you win when you just focus on how little time you have left. Just focus on what you can do, and do it.

Should You Quit?

Contrary to popular belief, quitting isn’t a bad thing. Quitting allows you to shift your focus onto something you’re more well-positioned to excel at. The book provides a brief guide on whether you should quit / pivot (bold is my own emphasis):

And if the answer to all three isn’t yes, Winning would like you to move on to something else:
Do you want to do it? Is this your idea, or someone else’s? Is it your dream, or are you doing it to please others? Because you can’t just want it, you have to crave it enough to make it your obsession.
Can you do it? If you’re not able, if you don’t have the skill or means to make it happen, all the focus in the world isn’t going to deliver the results. You must be realistic about what you’re capable of achieving, so that you’re focusing on something that has at least a chance of working.
Is it worth your time? I mean, really, really worth your time? Will it be worth the sacrifice and commitment and relentless grind? Because Winning wants all of your attention, not just spare moments when you have nothing else to do.

In other words, you don’t want to just do things, nilly willy. Pick something you can commit to and sacrifice a lot for. And pick something that’ll really reward you in life so it’s worth every waking second.

Not finishing. Most people accept that they won’t get to do everything in their lifetime. Winners can’t accept that. They need to finish. Everything.

On the other hand, once you pick something to ‘win’ at — it’s hard to stop. If you’re ultra-competitive and must win at everything: you’ll know the stubborn feeling of ‘I must finish this’, regardless of outcomes, setbacks, and how much it’s consuming you. And that’s fine; there’s not supposed to be a balance.

Everyone who has finished something has one thing in common: the urge to quit. There’s not a winner out there who hasn’t thought about quitting at some point. You can’t make the commitment to win until you’ve tasted the urge to quit.

You’re not ‘winning’ if you didn’t want to quit really badly at some point. If the thing isn’t even hard enough to make you want to think about quitting — a lot — and then re-conquering that urge, then what have you won if you do accomplish what you set out to do anyway?

Winning Is Hell. But You Must Enjoy It.

Winning is hell.

It demands everything of you, and then asks for more.

If you want to win, prepare to have whatever your obsession is consume most of your waking hours.

Prepare to lose frequently and learn frequently. And understand that wins will be very small, and far in between.

The road to winning is perhaps the most unpleasant mental anguish one can experience, and it’s all self-imposed. But when you get there, will it be all worth it?

Who knows?

But one quote I want to end this post with, should you embark on this journey paved with pain.

I began this book by talking about the hardship and endurance and sacrifice that go into Winning. Uncivilized. Hard. Nasty. Unpolished. Dirty. Rough. Unforgiving. Unapologetic. Uninhibited.
That’s the reality of racing toward a destination that will do everything possible to make sure you never arrive. It’s tough and unforgiving, and it’s supposed to be.
But at the end, and even along the way, there is joy.
There must always be joy.
No matter how intense and competitive and driven you may be, don’t shut out the opportunity to be in the moment, to embrace what you have, and hold on to it for as long as you can. Take time in your life for true fun and happiness and joy and laughter, wherever you can find it. It doesn’t make you weak to enjoy your life and appreciate the things that give you satisfaction and a sense of accomplishment.

There’s no guarantee you’ll win, even if you try your best, day in and day out. That much I know.

Thus, you must choose to be happy, even when you’re marching in hell. Take a little bit of time and savor the moment and find true happiness from within, as corny as that sounds.

Because that’s all the happiness you’ll get.