Playing to Win vs. Playing Not to Lose: Why Winners Win and Losers Lose

If you scour the internet looking for interviews with people who operate at the highest levels in their field, professional athletes, hit songwriters, politicians, famous actors, invariably they will mention a drive to succeed that sounds almost like an obsession.

“When I thought about the idea of losing I just couldn’t take it. I had to win or it would eat at me and eat at me.” – Tony Romo

“A leader, once convinced that a particular course of action is the right one, must be undaunted when the going gets tough.” – Ronald Reagan

“The spirit, the will to win, and the will to excel are the things that endure. These qualities are so much more important than the events that occur.” – Vince Lombardi

Nowhere in interviews with these leaders will you hear them talking about working very hard to avoid failure, they will always talk about working towards success. This framing is imperative, we must think of ourselves as winners with obstacles to overcome rather than a neutral party trying to avoid losing, or, at worst, an imposter trying to pass as competent.

The evolutionary turducken

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We tend to move towards pleasure or away from pain, these motivations have origins deep within the human brain. Rather than dive deep into the evolutionary structure of the human brain we’ll use a quick analogy: human brains are like an evolutionary turducken. (also called a Three Bird Roast, it is a chicken stuffed into a duck stuffed into a turkey). There are three areas of the brain that work seamlessly together but have different motives and functions and influence our decisions accordingly.

  • Nearest to the spine, the oldest parts of your brain have to do with basic nervous system operations, fear and anger response, drive for food and reproduction. This is often called the lizard brain.
  • Next is the mammalian brain, where we form bonded relationships with those around us. Family, team, tribe, whatever, those relationships neurologically rest in this second layer of the human mind. This is the ape brain.
  • Lastly is the thought-centers of the brain, the large complex systems which govern our rational thinking, the ability to consider things abstractly, etc. This is the “human” part of the human brain–what separates us from the rest of the animal kingdom.

The brain is wired so that the oldest parts which are closest to the spinal cord will tend to have powerful effects on us (this is why you can still be frightened in the midst of a movie that you understand is entirely fictional, sights and sounds can set off alarms that go far deeper than conscious thought), while the higher parts can influence the lowers parts only through practiced focus. As such we tend to automatically avoid pain and pursue pleasure unless we learn to do otherwise.

Beyond Natural Impulses: Choosing the Right Thing

Winners do not merely resign themselves to the automatic tendencies of their lizard brain, they choose to pursue the affirmative action rather than avoid pain. Consider two athletes who are identical in potential, opportunity, and physical prowess. One athlete sets her goal saying “I want to be the best runner in this team, no matter what.” While the other says “I want to maintain my scholarship at this university because losing it would be awful. I better practice.”

Both might do well in races, but the first athlete’s drive towards success rather than merely avoiding pain/failure (the loss of scholarship) is going to do considerably more to succeed. They’re going to push past any barriers that might be in front of them, while the second might be satisfied merely with performing well enough to not lose their scholarship.

Not only is this idea true in this scenario, most of the time people with more drive and less talent far outstrip the accomplishments of people with less drive but far more natural ability. These people can develop skills where their natural talent might be lacking, while the naturally gifted person is often lackadaisical and doesn’t put as much effort in, peaking early and failing to grow in the long run.

What does this mean for us? We look at the options before us in the pursuit of what we want, and we must always choose the thing which will make us more likely to win, rather than what avoids pain or is easy.

What is the right thing? If we want to become excellent track stars and we can run every day, once a week, or once a month, we know what the right choice is. If we truly want to achieve excellence, training as much as possible is 100% the right choice. It might not be as immediately satisfying, especially if there are social gatherings or other things we miss out on. But succeeding in what we set out to do will give much greater returns in the long run.

Explanatory Styles & Choosing the Right Thing

One thing that factors into how we might come to our options list in scenarios like the one mentioned above is our explanatory style. The most recently developed parts of our brain are constantly working to find patterns and assign meaning to the phenomena all around us, and over time we can collate these judgments and experiences into an outlook that colors how we view the world around us.

2078716This is grossly overcomplicating an important area of psychology, but there are a few different modes of explanatory styles that people tend to fall into optimism/pessimism, internal/external personalization, stable/unstable, global/specific.

If you’re an optimistic person, for example, it is likely that you will see positive experiences as personal, permanent causes and yet when negative ones arise, you’ll point to external temporary ones. “In a workplace environment, those with an optimistic explanatory style show greater productivity relative to those with a pessimistic style (Seligman & Schulman, 1986). Unlike pessimists in the learned helplessness model, those with an optimistic explanatory style assume that situations will work out for the best in the end.” – Positive Psychology Program

We’re going to explore this more in depth in future articles, but you should consider what your tendency in worldview is when looking at reframing yourself towards winning vs. trying not to lose. Pessimistic people might be less likely under normal circumstances to assume that trying something risky like reaching out to someone who is far advanced in your field for help will work, but if we give in to those impulses we lower our chances of success and we’re making decisions around avoiding pain (being ignored or snubbed by someone we admire) rather than pushing towards winning (receiving expertise and support from someone in a strong position to give it).

Reflection: What do you do?

If you’re faced with a difficult situation, be it in a game or in real life, what is your default position? Do you search for the easy route, the one which avoids the most pain? Do you aim for whatever is most difficult, do you stop and consider your options at all or do you rush in without thinking?

In truth, there are moments where each of these options might be the best choice. But the way to know which is correct is to know what you’re aiming for beyond that moment. We must value success more than the pain of losing. Sometimes that means avoiding injury now so that you can take another crack later, sometimes it means taking a big risk.

Playing Not to Lose. In other words: losing.

“If you let the other guy get in your head at the weigh-in, now when you get in the ring you’re fighting your doubts about yourself and you’re fighting him. You’re going to lose.” – Joe Rogan

Joe Rogan is a podcaster, comedian, and MMA aficionado. He’s been ringside between fights held by the greatest mixed martial arts competitors in the world, and he says that approach at the weigh-in can sometimes make or break the fight that comes later on. Confidence, belief in yourself and the amount of training you’ve done, that will carry you farther in the octagon than all the weights and sparring in the world can if you don’t have it.

If you approach whatever it is you’re working towards, but you’re full of doubts about whether or not it can be accomplished, if you’re afraid of the pain or the embarrassment of failure, and you choose to navigate the work that way, you’ve already set a massive roadblock in front of your own success. Human minds are terrible at multitasking, if you spend half your time working anxiously to avoid failure and the other half thinking “Oh no, what if I fail?” then you’re far more likely to fail than you would be if you committed yourself to the ask assuming you will win, even if the odds are not in your favor.

Our brains aren’t as subtle with wording in our self-talk, so if we approach a free throw, for example, and think to ourselves “I hope I don’t miss this free throw,” the brain will miss the double negative and you will be more likely to miss the shot. So when it comes to self-talk, thinking in terms of anxiety, in terms of hoping to avoid pain or failure, we actually increase the likelihood that we will fail.

If instead, we approach the line saying “Make this free throw. I’m going to nail it.” We have committed our whole selves to it and are more likely to succeed, especially if we’ve done the work ahead of time to hone our talents.

Side Note: Avoiding Failure is Bad for Another Reason

Why is it that we assume our own failure is only going to be harmful, that it cannot teach us something we might never learn otherwise? If we approach the idea of pain and failure the way designers approach a beta test, that is that we expect a certain amount of failure so that we can continue to improve, we are not only going to be less afraid of negative outcomes when they arrive, but it actually increases our confidence in pushing for the winning outcome.

With massively popular games that have large audiences, games like Fortnite, Call of Duty, or Fallout 76, beta testing (the term in development when a version of the game is released to the public or to a small section of the public in order to test how it functions under pressure) is designed for failure.

Beta testers who do not find any problems in a game’s design, some problem with the scenery or some mechanical malfunction, do nothing to improve the overall quality of the product being tested. Letting people who never designed the system run free in it is a great way to see where there might be gaps that need fixing.

If we think “Make this free throw” and then we miss it, we know we didn’t psych ourselves out, so there must be some other piece that needs fixing. We might watch a video of ourselves shooting throw after throw, especially in high-pressure scenarios, and catch a failure in technique we couldn’t have noticed without this reflective work. And if we hadn’t committed ourselves to the idea of winning in the first place, we might have made a hundred other mistakes by being non-committal in our shooting and then will have learned nothing from failing.

When failure comes, and it will if we are doing something worthwhile, we must welcome it as a teacher, rather than agonize in the pain of it. Yes, there is a pain in failure, but there is also a lesson, which can help us to succeed later on.

Expect (and prepare) for success

1930630So when you enter the risk scenario (shooting the free throw, tackling that big problem at work, etc.), enter it expecting to win. But how can we be confident in the midst of a risk scenario?

  1. Know that you’re prepared – If you’ve done your homework, if you’ve thoroughly studied what you needed to and can visualize everything that needs to be done to succeed at this moment, you can be confident in yourself.
  2. Know the stakes – anxiety is far more powerful if the consequences for a scenario are nebulous, even though we often think it is easier not knowing what is at stake. Think clearly about this moment, what happens if you fail? What happens if you succeed? Know what you stand to gain, and push for it.
  3. Know that you’re fully committed – You have clarity of vision about what you’re working towards and why this risk scenario is important in pushing towards the next step. You aren’t wondering about whether or not this is truly your passion or whether or not you might have been happier doing something else. This is your goal, you’re 100% in.
  4. Have Confidence – this ties in the other three points. You don’t just believe that you are capable of achieving success but that you deserve it and you’re hungry for it. You know that you’re a talented, capable, hardworking person with a drive to do what others want to succeed.

Never Default: Always Affirm a Choice

What matters most once you enter the risk scenario is that you fight all the way to the end, no matter how things might look in a moment. Never choose to play prevent defense (playing not to lose, trying not to embarrass yourself), always push aggressively for what you want. Don’t do what might come naturally (read: easily), do what you believe to be the best choice for success.

In sports, this means always fighting to score and push the game forward. Never merely defending what you’ve already achieved. In a career, this means always striving for the next right thing. Never merely performing your job duties to expectations. But In art, this means not relying on your past creations to try and coast to success. Always innovate, always push yourself.

Winners Win, Losers Lose

This isn’t 100% true since everything in humanity rests on a bell curve, but far more often than not those who win are going to continue winning. The same is true of those who lose.

In football, There are guys you can always seem to bet on (Guys like Tom Brady or Russell Wilson), and guys it always seemed to favor betting against when everything is on the line (guys like Peyton Manning, Philip Rivers, or even Andy Reid). Now here’s the thing, every once in a while that won’t pay out well. Peyton Manning has won from time to time, but those flashes in the pan pale in the face of the consistency of those who win regularly.

Does it make for a great movie to think this way? No, not really. But life isn’t a movie, so why bother trying to make it that way? Winners win, losers lose. Let’s look at why:

Winners Win

The successful are successful because they are successful, not because they stole it from someone else or somehow lucked into something they didn’t deserve. They deserve their success because they did the work to get in the place where luck could actually help them. Luck is earned.

winVSwinWinners get to where they are by taking massive action but recognizing what it is their competition is unwilling or afraid to do and doing it. They put in the extra hours, they make sacrifices in their personal lives, they push themselves far beyond what they thought was possible.

This is coupled with and fueled by the drive to succeed we’ve been talking about, the desperate wanting it that can put someone like Tony Romo in front of a screen watching play after play and analyzing what was missed and what was done well when other quarterbacks might be enjoying their six-figure salaries. Winners win because they want it that much more than those who don’t.

Because of these things, because of their willingness to do what others won’t and their drive to take a chance at it over and over again, winners develop luck in a way that losers just can’t. If you are trying to become a famous actor and the chances of success are 1 in 1,000 (they are in fact far worse), if you get 100 chances to audition for the right people you are much more likely to find success than if you only get to do it 10 times.

Working hard, taking massive action, having a drive to succeed so that you keep coming back over and over again in spite of failure means you’re more likely to find success. Repetition builds strength in muscles and luck in people who work hard for it.

Losers Lose

If winners have drive and willingness to take massive action, and therefore have better luck to succeed, losers will find a way to lose in spite of any opportunities or luck that might come their way.

If you walk through life expecting to fail, and then suddenly find yourself in your dream career, you’ll self-sabotage because you’ll believe that you haven’t earned it (you haven’t) and that you won’t be able to keep it up. As a result, you fulfill your own prophecy and then end up back where you started, explaining away all the things that caused you to fail.

Getting in your own head is the best way to lose, as mentioned before with the Joe Rogan quote. Self-doubt, because we cannot successfully doubt ourselves and try to win at the same time, will cause us to destroy our own chances of success. Even if you are handed resources, opportunity, mentorships, if you don’t believe that you have what it takes to succeed, you will not.

In baseball, a good closing pitcher has to throw every pitch as if it were the only pitch. Note that I didn’t say “the last pitch,” I said the only one. Focusing on sequence (this is my last chance to get this guy out before his buddy runs from third and we lose the game), on performance (I’ve only struck out one person this whole game), or anything else other than the present moment will ruin their ability to play effectively and they’ll lose the game.

They can’t focus on whether or not the last pitch was a hit or a miss or a ball, they have to focus on the present moment, on this one and only pitch. The best closing pitchers aren’t phased by their success or failure on the mound, they just keep throwing as if it was the one and only pitch they’ve thrown and that is how they win.

Making Sure You’re a Winner (and not a loser)

To close we’ll go through some helpful pieces for ensuring that you’re setting yourself up to win, not avoiding pain and trying not to lose.

  • Seek accountability – in order to rise to the challenge (and have those necessary teaching failures mentioned earlier), you need to find a source of accountability for the thing that you’re pursuing. Look for ways to regularly “walk the talk,” to prove that you’re actually doing what you say you want to do.
  • Know What You’re About – we cannot create the clarity and focus needed to achieve excellence in our work if we are distracted by a hundred other things. Know what your purpose is, what you really want.
  • Don’t Waste Time with Side Projects – this isn’t 100% true all of the time, but if any side venture is distracting you from your main goal, then you absolutely need to cut it out of your life. If doing that seems impossible, consider that you might have the wrong thing as your main focus.
  • Never Blame Others, Choices, or Circumstances in failure – this is important in order to avoid dwelling on failure and developing distracting anger or doubts. Recognize what happened and why, but don’t waste and energy casting judgment on those things, even if your choices caused you to fail in an individual moment. You now know, and the next time you won’t make the same mistake.
  • Don’t Attach Meaning – it is very easy with our pattern-seeking-meaning-assigning brains to cast meaning onto moments that don’t really deserve that much attention. If you fail (or succeed) in one moment, don’t revel or sulk in it, don’t cast judgment on it by calling it good or bad, especially when reflecting on the past. Everything is here to teach you, to make you better. Remember the closing pitcher, don’t focus on any hits or misses. Focus on the one and only moment you have, right now.

Choosing to Win

When it comes to reframing our thinking towards a winning-oriented approach, the key is to do make any choice, if it is the one that allows you to win. It might seem silly, risky, or outright stupid to other people, especially those locked into a pattern of avoiding pain or discomfort, but if you know that it is the right move to increase your chances of success, do it.

Making this hard moves, taking these actions that affirm our success rather than affirm our avoidance of failure, will create momentum in us to try harder and harder. We will find we have the capacity to do more, to take risks, to push ourselves. Our actions create feelings, not the other way around. We cannot wait around for the motivation to take massive action to succeed, we must know that taking massive action is what creates those positive feelings we so want.

This is why winners win and losers lose, winners seek the solution that creates the highest possible chance of success, losers try their best to avoid pain.



I’m trying to reframe my focus onto aiming for success instead of trying to avoid failure, but I find myself constantly worrying about how things could go wrong. How can I learn to be present in the moment?

For some, it seems that anxiety can flare up at the worst times. Learning to center yourself and doing all that you can do to present in the moment should be very helpful. There’s a tool you can use called grounding, where you go through each of your five senses and list one thing you can perceive with that sense in the moment. Go “what’s one thing I can hear? The wind, okay what’s one thing I can smell?” And go on down the line once or twice, and that should help in the heat of the moment to be less off in your head and more present with yourself. You could also try mindfulness meditation, exercises that focus on how you feel in your body can help you stop worrying so much about the future.

I’d also suggest trying a kind of exposure therapy on yourself, write out the possibilities:


  • If I fail this will happen:
  • If I succeed this will happen:
  • WhatIf scenario A happens, this will be my response:
  • If scenario B happens, this will be my response:

I’ve found that making peace with the reality of what can happen in a scenario is far better than letting the possibilities float endlessly around you.

How can I know that having a really intense drive to succeed isn’t delusion or an unhealthy obsession?

This is a bit harder, as we can often only really tell someone’s healthy/unhealthy relationship to their pursuit after the consequences have fallen. But I’ll say this: if you find your physical or mental health deteriorating, your relationships suffering (not just things being hard because you’re busy sometimes, real relational strain), and your finances or life balance falling out of sync, that might mean that you’re getting too obsessed.

Maybe that seems contradictory to the article above, but a balanced person is far more effective than an exhausted one. Joe Rogan, in that same podcast I linked above, mentions that sometimes a fighter can overtrain for a fight, and then they’re not loose or capable of adapting enough to the actual fight when it happens.

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