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Simon Boardman

Do Nice Guys Finish Last?

Updated: Apr 16, 2021


Can Nice Guys still win, or is success reserved for the psychopaths and obsessives these days?

Nice guys are always good, and good guys are always nice. At least most of us grew up with that stereotype. Phrases like nice guys don't win or nice guys finish last have also become popular. As we look at the psychology of success, mass culture presents us with something of a dilemma. For years it's the good guy, who always triumphed and vanquished the villain. In more recent popular culture, we notice that the not so nice guy seems to have been doing better lately, contributing to the establishment of this notion that you must be wicked to win.

Popular culture always has an influence, particularly in the world of the anti-hero in commerce. Commerce is supposedly where bad guys can perpetrate victim-less crimes. Being nasty and winning, but not harming anyone in the process. Bankrupting people, bullying them in boardrooms and ruining their careers and lives doesn't count. Think Gordon Gekko and Jordan Belfort. Remember the movie Wall Street? From that point on, greed was good. In real life, we made heroes of sociopaths like Neutron Jack Welch and Chainsaw Al Dunlap. Business became less obscure and made it to the front page, accompanied by the rise of the celebrity CEO. It's enough to make you get all nostalgic for the good old days with good old boring CEOs. In short, the belief that you had to be selfish to succeed had arrived.

Clichés and Stereotypes and Why They Matter

We have already been throwing around a bunch of vague words…like nice. Before exploring and then pronouncing a judgment, let's make sure we know what we mean. The origin of the word (500 years ago) explains the modern way most people use it, and it's not as complimentary as one might think. According to Google (where else do you go for at least the first search and definition?), it means: "…pleasant; agreeable; satisfactory (e.g., "we had a nice time")." Synonyms include; enjoyable, pleasant, pleasurable, agreeable, delightful, satisfying, gratifying, acceptable, to one's liking, entertaining, amusing, diverting, marvelous, good. Note the final synonym…good. We'll come back to it.

Again, according to Google; "Word History Five hundred years ago, when nice was first used in English, it meant "foolish or stupid." The word came through early French from the Latin nescius, meaning "ignorant." That explains the pause people often use before they describe someone as "nice" as well as the sideways glance. According to the Merriam-Webster Dictionary, Nice has a shocking number of meanings. Is that why it seems so meaningless? Merriam-Webster then has a detailed description with examples of what they mean by this. It becomes clear that if you use some of these definitions, then the cliché nice guys finish last begins to look less unreasonable.

So, why is this important? Why should we care? We care because as we consider a recipe for success, we think the effect of being nice or good is misunderstood. We fear that this leads to learning the wrong lesson. In this case, if nice guys don't win, then to win, people conclude that they need to be the opposite of whatever nice is. It's a great example of us thinking in extremes again. For instance, if black represent nice, then I need to be white as that is the opposite. We don't detect the grey areas, believing we need to be one (or all) of the following: disagreeable, irksome, troublesome, annoying, irritating, vexatious, displeasing, uncomfortable, distressing, nasty, horrible, appalling, terrible, awful, dreadful, hateful, detestable, miserable, abominable, execrable, odious, invidious, objectionable, offensive, obnoxious, repugnant, repulsive, repellent, revolting, disgusting, distasteful, nauseating, unsavory, unpalatable, ugly…

Do you see what I mean? The inability to detect these subtleties is why such a simple idea is misunderstood and explains why it's such a jungle out there. A simple misunderstanding has contributed to the belief that to succeed; I must be the opposite of nice – which is mean and multiplied by many people, that's a lot of meanness in the world. So maybe the word we need to use is not nice, but good.

Bad Guys on Top

We mentioned earlier that the not so nice guys seem to have been doing rather well lately, promoted by Hollywood and celebrated as rock star CEOs since the 1980s. Maybe, once more, we're victims of the blanket of media coverage that exists today. In other words, the take no prisoners bad guys always did well, it just barely made the front page.

There's certainly plenty of evidence which suggests spectacularly successful companies are run by people who would never win a Nobel Prize for being "an all-round great guy." Think Jobs at Apple, Ellison at Oracle, and we already mentioned Dunlap and Welch. Include Walmart's Doug McMillon, Virgin's Richard Branson (he's not as nice as you think) and IBM's Ginny Rometty and we have a real shark tank. They are one in a million – Apple, Oracle, Facebook, G.E., IBM, H.P., Microsoft, Amazon – exceptional companies run by extraordinary people (extraordinary doesn't necessarily mean good by the way). We use them as examples because they stand out, but they're not always illustrative of the point we should be making. We confuse correlation and causation, chicken, and egg. We connect the most famously successful companies, with their famously unsavory leaders and conclude that "if I want to succeed, I just need to copy those leaders." Unsavoriness and all.

There are plenty of successful companies who serve their customers and provide a pleasurable work environment. Where the bosses don't shout and scream and throw things around ('cos they care so much) and mistreat and bully people. However, we never hear of these companies, 'cos they won't be the next Google. But not to overstate it; they are still thriving. There is way more of these companies than there are the next Googles. They are vitally important to the economy, and there are just as many valuable lessons to learn from them.

The original question in this section was, "have bad guys always done better?" Maybe, maybe not. A better question would be whether that behavior was a determining factor in the company's success? Did Apple become an iconic company because Steve Jobs was obnoxious? Did it become iconic despite Steve Jobs being obnoxious? Alternatively, did Steve Jobs become obnoxious because Apple became iconic? We don't know. We do know that were many, many contributing factors to Apple's success. Steve Jobs' hard drive, uncompromising, and demanding obnoxiousness was probably one (or three) of them, but it wasn't all of them, which means it doesn't have to be all of you.

What do Mr Spock and Mork Have in Common?

Neither of them got humor, but it's worth briefly talking about humor, or the lack of it these days, and the impact this has on good, bad, nice, mean and success. I might be biased, but I think a sense of humor is important for a variety of reasons. People who take themselves too seriously are overly ambitious, continually trying to prove their superiority and leadership prowess. Their pursuit of prestige means they have no time for you, or anyone else.

That's a mistake. Humor has a role in leadership. Dwight Eisenhower said, "A sense of humor is part of the art of leadership, of getting along with people, of getting things done." If Dwight D. Eisenhower, the second least naturally funny President after Franklin Pierce, thought humor was necessary to beat Nazis, build highways, and warn against the military-industrial complex, then you better learn it too." (Joel Stein in Humor Is Serious Business - Insights by Stanford Business, July 11, 2017). Despite Eisenhower's observation, it doesn't seem like people take humor seriously. The research concludes that we're unhappier, more stressed, and the anxiety index is at an all-time high. Alison Beard claims in the Harvard Business Review from May 2014 …" as the MBA candidate Eric Tsytsylin recently put it in a video presentation featured on the Stanford website; working adults are "in the midst of a laughter drought." Babies laugh, on average, 400 times a day; people over 35, only 15. A recent study of Gallup data for the U.S. found that we laugh significantly less on weekdays than we do on weekends. Work is a sober endeavor."

Nice guys and good guys usually have a reasonable sense of humor, and as we repeat over and over its all about finding the balance. We don't need to be a clown all the time, making light of serious situations inappropriately. Neither do we need to fall victim to the belief that to be taken seriously, we need to be serious all the time. Despite research pointing to the general benefits of humor, there doesn't appear to be much evidence of its acceptance as a positive force in business. These days it's all big stick and stack ranking rather than whoopee cushions and exploding cigars. Yes, that's a real shame, but it doesn't have to be that way.

Men Behaving Badly

In our blog article from November 2017, we discuss the idea of a quality we called P.Q. It's like I.Q., and E.Q. but the political equivalent that's useful for successfully negotiating the shark-infested waters of the corporate world. That's an interesting idea, but the real question we're asking is whether you can scale the greasy corporate ladder without permanently corroding your soul. To successfully climb those corporate poles, you must hire people, fire people, intimidate, encourage, motivate, fulfill, praise, and punish. You've got to stroke egos, over-achieve goals (by crushing it) and everyone has to try harder. You must work at weekends and evenings being totally committed. Careers seem to turn on whether your boss likes you today or not. Sound familiar? Sooner or later, people will draw that line never to be crossed, saying, "I can't do that, or I won't do that," as Meatloaf famously said! Then we do whatever that is. We are now a different person from the one we used to be. We crossed that line. Don't underestimate the power of this. While I accept that some of these situations might be more profound than others, once you have crossed that line, you and your life cannot be the same as it was before. You are no longer the person you were.

Human beings can justify just about anything, whether through dissonance, or rationalization. We are quite capable of justifying someone's firing, or the closing of a plant with the loss of 200 jobs, or some shouting and screaming in the conference room. No problem. The real question becomes "how much suffering are we prepared to inflict (or tolerate), and how much will we compromise our own beliefs, our decency, and our integrity? Once we've crossed a line, can we ever go back or have we permanently polluted our personality? In our article called the Politics of Dancing, we use Club Politique as a fictional night club symbolizing the discotheque of corporate politics. Here you need to dance to the rhythm of the prevailing political beat. Club Politique is where we do our corporate politicking, dancing being the political behavior we indulge in. We adopt different rhythms and adapt to varying beats in order to survive and prosper. Sometimes we lead, and sometimes we follow. We reference the metaphor of leaving one's hat and coat at the coat check on the way into Club Politique. Your hat and coat might be metaphors for your soul, your humanity, your empathy. The question we ask is whether you can check those in (leave them at the door temporarily) thereby liberating you from the shackles of decency, allowing you to dance along, compromising as you go and impacting the lives of others as you try to master the politics of the dance and scale the greasy pole of the corporate hierarchy. You may not be able to reclaim that hat and coat (your soul & compassion) on your way out, OR you might. That's the chance you take. Maybe everyone deserves at least one shot at redemption….maybe.

Barking Up the Right Tree

Despite a sojourn into the importance of humor, we seem to be describing a "mean old scene" for the good guys. But not so fast there all you corporate tough guys, its Eric Barker to the rescue. He is the creator of the book and blog Barking Up the Wrong Tree, which presents "science-based answers and expert insight on how to be awesome at life".

Barker is excellent at getting to the heart of the matter. He can draw what's practical from all the advice and examples that are floating around out there. He references some great stories and research when talking about whether nice guys can win. Most of it is oriented around the psychology experiment called the Prisoner's Dilemma.

This dilemma is a standard example in game theory. It shows why two entirely rational individuals might not cooperate, even if it appears that it is in their best interests to do so. It was initially framed by Merrill Flood and Melvin Dresher while working at the RAND Corporation in 1950. Feel free to research it. If you spend any time reading psychological texts around decision making and human behavior, you'll at least be aware of it. The reason I mention it here is that the conclusion of the prisoner's dilemma game is also the same recommendation Barker comes up with. It validates a thought that's as old as the hills and is known in game theory circles as "tit-for-tat." In other words, treat people how they treat you. Do unto others how they do unto you. That phrase has been around longer than the Prisoner's Dilemma and Game Theory, so it seems like these ideas go to prove an older and simple idea. I'll treat you how you treat me.

The Verto Verdict

We're dealing with the age-old problem here of learning the wrong lesson. We interpret what is really a light-hearted, humorous statement like nice guys finish last too literally. We end up doing this 'cos we fall foul of pop culture (where it's more fun to be nasty than nice), and we glorify the wrong people while only superficially understanding their circumstances. Unsurprisingly we then reach the wrong conclusion. Nice guys can win. Good guys can win. Bad guys can win. Mean guys can win. The question we asked is can nice guys win? Implying the opposite; that only the beastly benefit in the modern world. The answer is that you don't have to be a monster to make it. It's a choice.

So here's our advice:

  • We have popularized bad behavior, glorified meanness, trivialized inhumanity, and made it seem like it's more fun and more rewarding to be selfish. Nice guys are characterized as saps who deserve to get run over on the super-highway of success. It doesn't have to be that way. You choose how you want to behave. Don't blame anyone else, and please don't tell me, "it's the way of the world."

  • People misbehave for a few reasons:

    • They believe they can achieve success more easily and faster if they behave badly (although they won't admit to it that way.) This has become fashionable thinking, and we always encourage people to challenge fashionable thinking. So challenge it... please.

    • It is easier - While that might seem counter-intuitive extreme behaviors are easier for humans. They minimize the need to reflect. People can adopt the black or white approach, ignoring the grey areas – the middle ground, which demands contemplation and thoughtfulness.

    • Some people like being mean. There's plenty of psychopaths out there.

    • For many reasons, human beings can justify virtually anything. There's nothing wrong with striving to achieve comfort and security until it becomes extreme. Then it turns into being hateful and odious as the result of greed where the premium is too often the suffering of others.


  • As Barker shows – you can be nice and treat people how they treat you. Nice is probably the wrong word. You can be fair and decent if you treat people pretty much the way they treat you. There's a ton of small things you can do to test this out. For example, buy them lunch. A good sign would be that they insist on splitting the bill, keeping things even, OR the next time they remember that you purchased the previous lunch and insist on paying. If they forget, then make sure you remember. Beware those repeat offenders.


  • When you get into tight spots, realize that this is where the rubber meets the road. It's where you find out who you are. It's inadequate to behave poorly and then use trite justifications. Phrases such as "it was a tough decision," or "I did what I thought was the best at the time" are all cheap words. Think about how you would want to be treated, like not firing someone in the pub – a la Jerry Maguire. It's when you get presented with the tough decision that you need to see it for what it is - the opportunity to be the person you always wanted to be. Don't let yourself down.

Final Thought

Once more, it's about finding and maintaining balance, while challenging conventional thought, learning the right lessons, and persevering to avoid the extremes. The search for truth goes on. In this case, it's the truth around whether you can be good, decent and virtuous and still win? Does winning demand an obsessive focus? Does it mean we have to exclude others and their feelings? Will we have to compromise those most prized qualities of honesty, integrity, and trustworthiness?

A nice person in this context is synonymous with a good person. One we would view as fair, trustworthy, honest, reliable, balanced, virtuous, kind, good, considerate, helpful, polite, thoughtful, and decent. That's quite a job description. But before you become overly intimidated, remember our guiding principle of balance? We live in the grey area, away from the extremes. We must accept, therefore, that we cannot possess all of these virtues, fully, all of the time. Life does get in the way and presents us with difficult decisions. However, we argue that we must have guiding principles. The best word of all the synonyms for nice is one that was not originally on the list and which we added. It is decency. A word that is notoriously hard to define, but we all kind of know what we mean. Wasn't that what someone once said about pornography? "I can't describe it, but I know it when I see it." The same description works for decency. We know it when we see it. And we know it when we don't.


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