Sometimes You Win Sometimes You Learn: Summary

Sometimes You Win Sometimes You Learn shows that to win in life, you have to remain teachable and learn from your mistakes.

Bullet Summary

  • To win tomorrow, you gotta become a learner (today)
  • Drop the search for “quick fixes” in your quest to become a better person
  • For the best and quickest growth stay inside your strength and get outside your comfort zone

Full Summary

Chapter 1 – Humility: The spirit of learning

Some people bounce back from losses. Others never recover. What’s the difference?
John Maxwell says it’s humility.

Humility as in the opposite of pride.
Prideful people respond to failure in ways that don’t help them move forward, like denying and blaming others. People with a spirit of humility instead learn from successes and losses (Ed note: this is what a fixed mindset does).

Here’s what humility does for you:

Gives you perspective: humility doesn’t mean you think less of yourself. It means you think of yourself less. And it will allow you to look at the bigger picture.

Enables you to admit a mistake: and thus to learn and grow.

Allows to let go of perfectionism: contrary to prideful people, those with a spirit of humility aren’t afraid of a mistake.

It’s not what we have that determines our success. It’s how we think

Chapter 2 – Reality: The Foundation of Learning

John Maxwell says that when we accept that life is hard, we begin to grow.

Successful people don’t shy away from difficulties, they learn to face them and move ahead in spite of them.
And here’s a new perspective for you: what if instead of fearing difficulties, you welcome them as a test of character and use them to rise to the occasion?

Roots author Alex Haley said: “Either you deal with what is the reality, or you can be sure that the reality is going to deal with you”.  Facing reality and accepting the problem will not conquer it, but it’s the very first step to overcoming it.

John Maxwell says you should realistically rate the performance independently of whether you win or lose.

And life is definitely harder for those who stop growing and learning. Some people become focused on a specific goal that when they achieve it they relax because they feel they made it. That mindset has the power to unmake them (arrival plateau).

What if you treated hardships as a welcome test of characters

Chapter 3 – Responsibility: The first step of learning

John Maxwell says that nothing happens to advance our potential until we step up and say, “I am responsible.”
If you don’t take responsibility, you give up control of your life (external locus of control). Taking responsibility for your life instead puts you in a place where you are always able to learn and often able to win (internal locus of control).

Lack of responsibility means:

  • Victim Mentality;
  • Blamestorming activity, which is what John Maxwell designs as the creative process to find a scapegoat
  • Giving away control of our lives: if you don’t take responsibility for what happens in your life you relinquish ownership of your life
  • No growth: and little chance of success-

Taking responsibility means:

  • First step in learning: taking responsibility for what you can control and letting go of what you cannot control will accelerate your learning process
  • Seeing Things in Proper Perspective: The best learners are people who don’t see their losses and failures as permanent (develop a growth mindset)
  • Backing Up Our Words With Behavior: Jeff O’Leary wrote “sign your work at the end of each day. If you can’t do that, find a new profession.” When you can take full responsibility for your work, you reach integrity.

Chapter 4 – Improvement: The Focus of Learning

The Stone Age didn’t end because people ran out of stones. It ended because people kept learning and improving.

1. Improving Yourself Is the First Step to Improving Everything Else. Whatever you want to improve in your life, you need to first start with yourself.

2. Improvement Requires Us to Move Out of Our Comfort Zone. Always doing the safe thing will not take you forward. You must surrender security to improve.

3. Improvement Is Not Satisfied with “Quick Fixes”. “Everyone is looking for a quick fix, but what they really need is fitness. People who look for fixes stop doing what’s right when pressure is relieved. People who pursue fitness do what they should no matter what.”

4. Improvement Is a Daily Commitment.  If you want to improve, you need to make it a habit. Motivation is nice but short-lived. It’s the positive habits you practice consistently that will get you far.

Chapter 5 – Hope: The motivation for learning

By reading this paragraph I had the impression John Maxwell was using the term “hope” for “optimism”, but he later says optimism is passive while hope is active.

It takes courage to have hope because it can be disappointing, but Maxwell is convinced it’s going to be rewarded.

Hope-filled people are energetic, they welcome life and all that comes with it -including challenges-.
And Maxwell believes it’s no coincidence depressed individuals often lack energy. Lack of hope and lack of energy usually go hand in hand.

Hope is your greatest asset against hardships: it looks for lessons rather than leaving us deflated. It sees what can be done rather than what can’t be done.

Doing the following three things will help you become hopeful:

1. Realize That Hope Is a Choice. And then choose hope

2. Change Your Thinking. We get what we expect in life. Have positive expectations

3. Win Some Small Victories. Success, even in the form of small wins, will encourage hope. And smaller victories show you that bigger ones are within grasp

Chapter 6 – Teachability: the pathway or learning

If you want to be successful tomorrow, then you must be teachable today.

Teachability is a choice and these are the traits of a Teachable Person:

1. Attitude Conducive to Learning People with a teachable spirit approach each day as an opportunity for learning. They know that success is less about natural talent and more about learning (Mindset by Carol Dweck).

2. Teachable People Possess a Beginner’s Mindset. It can be difficult, so you have to remind yourself.

3. Teachable People Take Long, Hard Looks in the Mirror. Always ask yourself “am I the cause?” If the answer is yes, then it’s time to make changes.

4. Teachable People Encourage Others to Speak into Their Lives. Surround yourself with people who know you well and will tell you the truth. This is even more important as you become more successful.

5. Teachable People Learn Something New Every Day. Any day will make you a little larger or a little smaller. Strung many days together and you will be a lot larger or a lot smaller

Daily Practices to Become More Teachable

1. Preparation. Every day ask yourself in advance what you’re going to learn. You will be amazed by how often you can improve from people and experiences in your daily life.

2. Contemplation. Observe and reflect on your experiences. Stopping and thinking allow us to gain perspective on both the successes and failures so that we can find the lessons within them. Only evaluated experiences teach us.

3. Application. The true value of teachability comes when we take something that we learn and apply it.

Recognizing your contribution in your failings, seeking solutions no matter how painful, and working hard to change for the best is teachability in action.

If you want to be successful tomorrow, then you must be teachable today

Chapter 7 – Adversity: The Catalyst for Learning

Difficulties can be a boost if you face them with the right mindset.

Adversity Brings Profit as Well as Pain If We Expect It and Plan for It Since adversity is going to be there anyway, we might as well plan for it. Gold medalist winners always expect pain.

Adversity Writes Our Story Adversity is unavoidable, and it’s your chance to be a hero: if you respond well, it will be a heroic poem. Will adversity be your tombstone or stepping stone?

You never win the gold without hurting

Chapter 8 – Problems: Opportunities for Learning

Problems get better or worse based on what you do or don’t do when you face them.

Sometimes You Win Sometimes You Learn delves a bit into problem-solving: interesting and useful, but less foundational when it comes to mindsets.

Chapter 9 – Bad Experiences: The Perspective for Learning

How we think when we lose determines how long it will be until we win.

If you are ambitious a danger for you is that you will quickly move past successes and focus on “what you should have done better”. Which way too often means you’re focusing on losses and building regret. But you can’t build on regrets. And the capacity to manage disappointment and loss is key to living a fulfilling life.

The next time you have a bad experience try this:

 1. Accept Your Humanness. We will fail sometimes no matter how hard we try. Why? Because we’re human. And that’s what makes you special.

2. Learn to Laugh at Yourself and Life. How much easier would your problem appear if you were able to laugh at them?

3. Keep the Right Perspective. Seeing difficulties as experience is a matter of perspective:
Don’t Base Your Self-Worth on a Bad Experience You are not your worst moment and you are not defined by your performance.
Don’t Feel Sorry for Yourself You are allowed a 24h grace period of feeling sorry for yourself, then pick yourself up (or you might get stuck)
Do Consider Your Failures as a Process to Learn and Improve Look at it like scientists: when it didn’t work, they tested a hypothesis.

4. Don’t Give Up If you want to succeed in life, you can’t give up. Og Mandino said “Your capacity for occasional blunders is inseparable from your capacity to reach your goals. No one wins them all, and your failures are just part of your growth. Shake off your blunders. How will you know your limits without an occasional failure”

Mistakes are painful when they happen, but years later a collection of mistakes is what is called experience

Chapter 10 – Change: The Price of Learning

Some people put the minimum effort to distance themselves from their problems without going to the roots, which of course can often be found in themselves.
And of course, they never grow and never solve those problems permanently.

Entrepreneur Alan Cohen said, “To grow, you must be willing to let your present and future be totally unlike your past. Your history is not your destiny.”

Here are a few ways to make positive change:

1. Change Yourself. Quit looking at the environment or people as the issue. In life, if you want more, you must become more.

2. Change Your Attitude Your attitude is fully within your control. Sometimes You Win Sometimes You Learn is all about giving the right attitude.

3. Change Your Non-growing Friends Wise is the person who fortifies his life with the right friendships. And of course, you have probably heard “you are the average of the five people you spend the most time with“.

4. Determine to Live Differently than Average People. The question “who am I” is important, but even more critical is “Who am I becoming?”. Keep an eye on where you are and an eye where you want to be.

5. Unlearn What You Know to Learn What You Don’t Know. Before you input new more empowering thoughts in your brain, you have to let go of the ballast you picked up along the way.

In life if you want more, you must become more

Chapter 11 – Maturity: The Value of Learning

Maturity doesn’t necessarily come with age.

Here’s what results in maturity for John Maxwell:

1. Finding the Benefit in the Loss.

2. Learning to Feed the Right Emotions. “Maturity is doing what you are supposed to do, when you’re supposed to do it, no matter how you feel.” Action is the key to success. Too often we want to feel our way into acting when instead we need to act our way into feeling. If you take the right actions, you will eventually feel the right feelings.

3. Learning to Develop Good Habits. By acting on our feelings with positive action over a sustained period of time, we will form positive habits. As poet John Dryden put it: “We first make our habits, and then our habits make us.” Comes hell or high water, you need to follow through.

4. Learning to Sacrifice Today to Succeed Tomorrow.  People are naturally inclined towards behavior that makes them feel good in the short term. Hence you have to cultivate the willingness to sacrifice.

5. Learning to Earn Respect for Yourself and Others. Brian Tracy says: “Self-esteem is the reputation you have with yourself.” If you want it to be solid and lasting, it must be earned and confirmed, day by day. Following through no matter what is a great way to earn that respect.

Too often we want to feel our way into acting, when instead we need to act our way into feeling

Chapter 12 – Winning Isn’t Everything, But Learning Is

Sometimes You Win Sometimes You Learn ends with another fabulous chapter on the advantages of a learners’ mindset:

1. Learning Too Often Decreases as Winning Increases Complacency. Winning may remove some of your hunger. Here’s the solution for John Maxwell: keep your hunger to learn instead. Then no matter whether you win or lose, you’ll keep getting better.

2. Learning Is Possible Only When Our Thinking Changes. Negative ideas and discouraging thoughts will try to creep in. But Maintaining a consistently positive mental attitude will be your greatest ally in growing and learning. So you stand guard at the gates of your mind. Think positively for long enough, and your positive thoughts will grow stronger and more natural.

3. Real Learning Is Defined as a Change in Behavior. The greatest gap in life is the one between knowing and doing. Remember to apply your learning and translate them into action.

4. Continual Success Is a Result of Continually Failing and Learning. Joseph Sugarman says, “(..) if you’re willing to consider failure as a blessing in disguise and bounce back, you’ve got (..) one of the most powerful success forces.” Progress requires risk, but there’s an art to managing that risk: be in your strength zone -the things you like and do well- but get out of your comfort zone. 

Sometimes you win sometimes you learn quote

How You Can Apply It

Sometimes You Win Sometimes You Learn is a condensed guide for a learner’s mindset. Here are a few distilled ideas on how to make it even more applicable:

Approach your challenges as an opportunity to learn
This will both prepare you to learn and grow and at the same time take some pressure off. “It’s just an opportunity to learn”, you tell yourself, and you will quiet your lizard brain which is so adamant about keeping you in your comfort zone.

Move past the mistake trap
If you are ambitious chances are you are very hard on yourself. The words of Hugh Prather in Sometimes You Win Sometimes You Learn will probably ring true to you: “I react to a mistake as if I betrayed myself. My fear of making a mistake seems to be based on the hidden assumption that I am potentially perfect and that if I can just be very careful I will not fall from heaven (…)“. Needless to say, this mindset is a straitjacket.
Solution: Realize you’re always a work in progress and your goal is not being perfect but getting better (learner mindset). Then fail quickly, forge ahead with a win-or-lose attitude, and base your self-esteem on doing it, rather than doing it perfectly.

Move past regret and losses
I put it here again because I know this is a sticky point for so many. Moving past losses and regret is key to a successful -and happy- life. But it’s not our default setting.
Solution: here’s what John Maxwell recommends to minimize the damage of losses:

  1. Let them go emotionally
  2. Remain positive -by feeding positive thoughts and interpretations to your mind-
  3. Watch out how you evaluate yourself: be constructive (start with a positive and end with a positive)
  4. Radically change the way you look at losses (as a learning opportunity, which is what the book is about)

We want success, but we should instead train for losses


Life is difficult. Really?
That life is difficult is a message repeated a bit too often in one of the chapters.
Well, life is not intrinsically difficult Mr. Maxwell. Life is what you think it is. And I don’t think it’s educational -or true- repeating on a loop “life is difficult”. So here it is for your benefit: no it’s not. Life is beautiful.

Some platitudes
A sub-chapter was “Life is More Difficult for Those Who Don’t Respond Correctly to Challenges” and then later on “Yet that is exactly what you need to be able to do—make good adjustments”. Not exactly earth-shattering, and lacking concrete steps on how to make those suggestions a reality.


Did you really make it thus far?
I applaud you (even if you just skimmed here).

Sometimes You Win Sometimes You Learn is an amazing book that I absolutely recommend you read.

Now for my review:

What I didn’t like:

Pride is not bad
I disagree with humility as opposed to pride. You can be humble and proud at the same time. As a matter of fact, you should be proud. You should just be proud of the right things, of course. Read here how to build a supportive and antifragile ego.

What I warn you about:

Cool VS Wise

John Maxwell says successful people in his circle had an attitude of “been there, done that, got it all figured out”. But as he grew older he realized that attitude only got them so far and they plateaued because they weren’t growing.
He had a continuous learner mindset instead, never getting to a place where it’s all figured out.

That makes sense.

Yet the attitude of ” been there, done that” is textbook charisma. Most people admire that attitude (when earned). Keep it in mind, and maybe keep it in your bag when you need to act up a bit.

What I loved:

All of it, but let’s pick a few key ones:

Take responsibility (for what you control)
I loved the idea of taking responsibility for all you can control and letting go of all you can’t. You can find it even more beautifully elaborated by Ryan Holiday and I find it a more empowering stance than feeling responsible for the final result no matter what (as preached, for example, by Extreme Ownership).

Sign your work (or don’t do it at all)
I loved the idea of signing whatever you do. Or not doing it at all.
You don’t like what you’re doing at work? Do yourself a pleasure and change.

If you want more, you must become more
Before you set out to change the conditions before you look at what others are doing wrong… Take a hard look at yourself. And the best way to improve your condition (the only?) is to improve yourself.
It’s not what you have, it’s not your past, it’s not your friends. It’s who you are. And who you’re becoming.

If you enjoyed this summary, check out my whole collection of book summaries.

And I will leave with a last quote from the book, which John Maxwell says will eventually make you successful:

I’m not where I’m supposed to be,
I’m not what I want to be,
But I’m not what I used to be.
I haven’t learned how to arrive;
I’ve just learned how to keep on going

9 thoughts on “Sometimes You Win Sometimes You Learn: Summary”

    1. Thank you, I am glad you enjoyed it, definitely do read the book if you got the chance.

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