Don’t Turn Losing into Failure: The Power of Counterfactual Thinking

“Losing is a fact, it’s something that happens. Whereas failure is an interpretation of what happened.”

Sam Weinman is the digital editor of Golf Digest and an award-winning sports journalist whose work has appeared in USA Today, ESPN the Magazine, Sports Illustrated, and more. He is the author of the new book, Win at Losing: How Our Biggest Setbacks Can Lead to Our Greatest Gains. Recently, he joined Heleo’s Editorial Director Panio Gianopoulos for a Heleo Conversation on the difference between losing and failing, the power of counterfactual thinking, and the best way to teach kids to lose gracefully.

This conversation has been edited and condensed.

Panio: You make a distinction between losing and failure. How are they different, and what’s the significance of that?

Sam: It’s funny because when I first started writing the book, I used those two words interchangeably. I still slip into that trap sometimes, but they’re not the same thing. The best way it was described to me is that losing is a fact, it’s something that happens. Whereas failure is an interpretation of what happened.

The best way to make the distinction is that you can lose and it can be something that is completely outside of your control. It is not necessarily a referendum on something you did, whereas a failure is. It’s something where you didn’t execute or had some flaw in the execution.

Panio: It’s very much about perspective, your judgment of the situation.

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Sam: Exactly. Sometimes the best way to get over a loss—not always, but sometimes—is to recognize that it was outside of your control. It was just an event that happened, and you move on. Whereas, the opportunities to learn from things often stem from failures. “Oh I did this thing wrong. As a result of that failure, I’m going to analyze the mistakes I made to hopefully extract something positive from it.”

Panio: The tricky thing is assuming too much control over events. With a lot of the sports that you reference—golf or speed skating, it’s just you. If you’re on a team sport, however, the responsibility gets shared.

“If you have a little bit of humility, you also recognize that certain things are outside of your control, and as a result you can’t take the blame for everything.”

Sam: Yeah. I talk a lot about humility, but humility can work both ways. You can be very arrogant in assuming the mistakes weren’t yours, and the fault lies with everyone else, and as a result you should be absolved of the blame. [But] there’s also the arrogance of saying, “It was all my fault. I did all of these things wrong, and as a result we lost.” If you have a little bit of humility, you also recognize that certain things are outside of your control, and as a result you can’t take the blame for everything.

Panio: One of the things that resonated with me was the concept of counterfactual thinking, where you focus on what might have been. That’s why, if you get a silver medal, you [often] feel worse than the person that got the bronze. What did your research show you about that phenomenon, and how to avoid that problem?

Sam: It’s funny because, as you said, so much of this is about perspective. There’s good counterfactual thinking and there’s bad counterfactual thinking. The good counterfactual thinking—when I say good, I mean how we can use it in a positive way to help us—would be the bronze medalist thinking, “Oh well, at least I won a medal. It could have been a lot worse than this. As a result of it I should be thankful for the outcome I had.” You could apply that line of thinking to a lot of things. “I wish I made more money, but at least I have this job. I’m not working for minimum wage.” Or “At least I have a house.”

Those are examples of positive counterfactual thinking, but then there’s also negative counterfactual thinking, which is the silver medal way: “Oh, I could have won gold,” or “This person makes more money than me, this person has more success than me, that could have been me if not for x, y, and z.” It’s all a testament to the mental gymnastics that we go through. We can use perspective in a healthier way to help us look at events more positively.

Panio: It seems like a real [challenge,] because you have to be pretty ambitious to want to become an Olympian in the first place, right? You’ve got to be driven. To have passion. But at the same time, you have to be able to step back if you don’t get the gold and somehow be okay with that.

Sam: You’re right, and I think that’s applicable to any high achiever. There’s a certain amount of singular focus you need to reach a certain level. You’re able to shut off a lot of doubts, where other people might have them.

The other way of thinking is that you’re defining yourself by these singular moments. By that measure, if that happens, if you lose an election, or you don’t get the job you want, or don’t win the game, you are much more likely to define yourself as a failure. It’s an interesting paradox.

Panio: The line between resignation and resilience is blurry sometimes.

Sam: Very much so. Like with startups—there’s so much to be said for the persistence of really seeing an idea through, but there’s also a great value in pulling up stakes and abandoning it. There’s resilience in that as well.

Panio: You see that in other industries as well. Take publishing. As a writer, you hear those stories of books rejected 40 times. The Sheltering Sky, which is a classic, everybody turned it down. Then there are books that get sent out and get rejected for good reason—because they’re terrible.

Sam: Right.

Panio: When you’re on the other side of it, as a creator or athlete or whatever, you can’t help but think sometimes, “Am I deluded, or am I persistent?”

“If you’re going to use perspective in a convenient way to make yourself feel better, that has real limits. So you have to be really honest with yourself, because the objective is not to make yourself feel better, it’s to gain utility from whatever the setback is.”

Sam: It all speaks to that idea of we can do so much with our interpretation of things. If you have your book rejected you can tell yourself, “Oh well, a lot of great books get rejected, so I can’t take this too personally and my book is still great.” Then there’s the other way of looking at it, “Well maybe that’s a testament to the fact it’s just not good enough.” That’s why I go back to honesty: ultimately you probably know, deep down, which it is. If you’re going to use perspective in a convenient way to make yourself feel better, that has real limits. So you have to be really honest with yourself because that’s not the objective. The objective is not to make yourself feel better, it’s to gain utility from whatever the setback is.

Panio: One thing that I found inspiring is you talked about focusing on the process, as opposed to the goal. When people choke, it’s because at that moment, they’re worried, thinking, “Oh if I don’t get this point I’m going to lose.” Or “If I get this point, I’m going to win the game.” Of course, that’s when you miss.

Sam: Yes, we suddenly start thinking about the result far more than we should. I’m the living example of that. I do it all the time, especially in my own very small, pathetic athletic existence. I start thinking, “Oh my god if I lose this game, I’m going to lose the match” and how embarrassing that’s gonna be. Or the other way, which is, “Oh if I win this I’m going to win the match and how cool is that going to be?” It’s just a terrible way to think. There are all kinds of studies about how any kind of focus on the self is really counter productive. Ultimately you want to have an external focus on a goal.

Any time you start internalizing your objectives and make it about all the things that you want because it’ll be good for you or bad for you or whatever, that’s when you get yourself into real trouble.

Panio: Also when it gets tied to identity. You think, “Okay well if I make that, then I will be good. It will prove that I’m actually very skilled at this.” Which is a weird pressure and not necessarily indicative of your overall ability.

Sam: And it’s a trap everyone falls into. You look at whatever it is you’re doing as a reflection of your self worth. “If we get to the count, I am obviously really smart and good at my job, and therefore worthwhile.” As opposed to thinking, “I’m going to put my energy into doing this as well as I can, and if I don’t get it I’m going to learn from that and embrace the lessons that come from it.”

It’s just a healthier way to live, for starters.

Panio: A lot of the impetus for the book came from wanting to teach your kids how to be better sports. This weekend I took my seven-year-old daughter bowling and I was faced with the question of, “Do I let her win?” So I thought, “I’ll try a different technique, the spin, which I never do. Then she’ll just naturally beat me because I’ll do so badly.” But what happened was, I started getting strike after strike. The spin worked. I just annihilated her in the first game. She looked really upset, but I could see her thinking, “Okay, well I’m gonna beat him in the second game.” Usually I’ll throw a game and let her win one.

But when the second game came around I just couldn’t do it. I had a hot hand. Strikes, spares, I was just going and going, doubling, then tripling her score.

She was so upset. I thought, “Am I a terrible parent or have I stumbled into being a good one?” Because now she’s going to have to confront this idea, “I don’t always win. Sometimes I lose everything. That’s just the way it is.” What did you find out in your research? Am I a bad dad?

Sam: No, you’re not a bad dad. You could make the argument that age five, six, and seven, it’s a little early to hammer home this idea that we learn from losses and we can grow from them. But it’s not too early to introduce the idea, “Listen, you’re not going to win every time, be aware that this is going to happen, and it’s not the end of the world when it does.” If we perpetuate this myth, even at a young age, “Oh, you’ll always win,” it becomes much more of a slap in the face when they do have to lose, and suddenly they are ill equipped to deal with it.

I’ve certainly been on your side of it too—I’ll let them win because I don’t want to deal with them. But they have to see that it’s not always going to work out in their favor, they’re going to need some basic coping skills.

Panio: I think that’s one of the innate tensions of modern parenting. It used to be that parents weren’t responsible for entertaining or pleasing their children, it was just about preparing them for the world. You were a deliberately slight buffer. And now it’s become, “I want to protect my kids and make them happy all the time.”

“My feeling is we shouldn’t be insulating our kids from these sensations of failure, because they should learn how to deal with it.”

Sam: I remember playing my parents individually in tennis, and I didn’t beat my dad until I was 16 or 17. Those felt like valid wins, they felt good because I earned them. The “pain of not winning” was offset by the satisfaction that come from genuinely getting over that hump.

Panio: The win is so sweet that it makes up for all the crappy losses you had to take before you got there. It’s something that you lose with participation culture, kids getting trophies for just showing up.

Sam: It devalues the actual successes that we have. If I finish first place—it’s a cliché by now—but if I finish in first place, and I get a trophy, and I look over my shoulder and the kid that finished in sixth place got the same trophy, it doesn’t feel as worthwhile. Similarly, if I finished in eighth place and got a trophy, then two weeks later I finished in first place and got the same trophy, that feels kind of lame.

My feeling is we shouldn’t be insulating our kids from these sensations of failure, because they should learn how to deal with it. I’m also a big believer that if you want to give trophies out to kids for being the most improved, or best attendance, a tangible acknowledgement of the “process”, that can be worthwhile as well.

Panio: That’s also specific to something they did achieve. When you compliment something a child does, you’re supposed to be specific. Not just, “Oh that’s a beautiful painting, you’re a genius.” Instead, “I like how you changed the color halfway up.” I think we underestimate children’s subtle ability to tell when they’re being patronized.

Sam: Totally. When we reward things in a very abstract and vague way, then you’re leaving them no breadcrumbs for how to do it the next time. The whole point is, “Oh I like the way you do that.” So they go, “Oh, okay, I know what that is so I can try to replicate it.” As opposed to an abstract, “I want to paint another great painting.” You don’t know exactly what you’re looking for.

It goes back to the idea that we shouldn’t lose sight of what exactly makes us successful when we are successful.